A new oleanane glycoside from the roots ofAstragalus caprinus

2006

A novel oleanane-type triterpene saponin (1) together with two known molecules, soyasapogenol B and astragaloside VIII were isolated from the roots of Astragalus caprinus. Their structural elucidation was performed mainly by 2D NMR techniques (COSY, TOCSY, NOESY, HSQC, HMBC) and mass spectrometry. Compound 1 was determined as 3-O-[alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucuronopyranosyl]-22-O-beta-D-apiofuranosyl-soyasapogenol B.

Triterpene saponins from Schefflera abyssinica

2006

Saponins from the Roots of Nylandtia spinosa

2007

From the roots of Nylandtia spinosa, four new triterpene saponins, 3- O-beta- d-glucopyranosylpresenegenin 28- O-beta- d-galactopyranosyl-(1-->4)-[alpha- l-arabinopyranosyl-(1-->3)]-beta- d-xylopyranosyl-(1-->4)-[beta- d-apiofuranosyl-(1-->3)]-alpha- l-rhamnopyranosyl-(1-->2)-beta- d-fucopyranosyl ester ( 1), 3- O-beta- d-glucopyranosylpresenegenin 28- O-beta- d-galactopyranosyl-(1-->4)-[alpha- l-arabinopyranosyl-(1-->3)]-beta- d-xylopyranosyl-(1-->4)-alpha- l-rhamnopyranosyl-(1-->2)-beta- d-fucopyranosyl ester ( 2), 3- O-beta- d-glucopyranosylpresenegenin 28- O-beta- d-apiofuranosyl-(1-->4)-[beta- d-galactopyranosyl-(1-->2)]-beta- d-xylopyranosyl-(1-->4)-alpha- l-rhamnopyranosyl-(1-->2)-be…

New Acylated Presenegenin Saponins from Two Species ofMuraltia

2004

Six new acylated bisdesmosidic triterpene glycosides 1–6 were isolated from the roots of Muraltia heisteria (L.) DC., as three inseparable mixtures 1/2, 3/4, and 5/6 of the (E)- and (Z)-3,4,5-trimethoxycinnamoyl derivatives. The compound pair 1/2 along with four known saponins were also isolated from the roots of Muraltia satureioides DC. Their structures were elucidated mainly by spectroscopic experiments including 2D-NMR techniques as 3-O-(β-D-glucopyranosyl)presenegenin 28-{O-β-D-apiofuranosyl-(13)-O-[β-D-xylopyranosyl-(14)]-O-α-L-rhamnopyranosyl-(12)-O-[6-O-acetyl-β-D-galactopyranosyl-(13)]-4-O-[(E)-3,4,5-trimethoxycinnamoyl]-β-D-fucopyranosyl} ester (1) and its (Z)-isomer 2, 3-O-(β-D-g…

Secondary metabolites from polar fractions of Piper umbellatum.

2012

Seven known secondary metabolites were isolated from the methanol extract of the branches of Piper umbellatum. The identification of these compounds was mainly achieved by 2D NMR spectroscopic techniques and FAB-MS. Among them, the known cepharadiones A and B can be considered as chemotaxonomic markers of the genus Piper.

Steroidal glycosides from Ornithogalum dubium Houtt

2018

The phytochemical study of Ornithogalum dubium Houtt. (Asparagaceae) led to the isolation of five undescribed steroidal glycosides together with two known ones. Their structures were established by using NMR analysis and mass spectrometry as (25R)-3β-hydroxyspirost-5-en-1β-yl O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranoside, (25S)-3β-hydroxyspirost-5-en-1β-yl O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside, (22S)-16β-[(α-L-rhamnopyranosyl)oxy]-22-hydroxycholest-5-en-3β-yl O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranoside, (22S,23S)-1β,3β,11α,16β,23-pentahydroxy-5α-cholest-24-en-22β-yl β-D-glucopyranoside, (22S,23S)-3β-[(β-D-glucopyranosyl)oxy]-22,23-dihydroxy-5α-cholest-24-en-16β-yl O-α-…

New terpenoid glycosides from Eriocoelum microspermum

2017

Ursane-Type Triterpene Saponins fromZygophyllum geslini

2007

Four new ursane-based triterpene glycosides, compounds 1–4, as well as the known glycosides zygophylosides E, G, and H, and 3-O-(β-D-quinovopyranosyl)quinovic acid 28-(O-β-D-glucopyranosyl) ester, were isolated from the BuOH-soluble fraction of the MeOH/H2O 7 : 3 extracts of Zygophyllum geslini (roots or aerial parts). Their structures were established mainly by 1D- and 2D-NMR techniques, in combination with HR-MS analysis and acid hydrolysis.

Cycloartane Glycosides from Three Species of Astragalus (Fabaceae)

2011

Nine cycloartane-type glycosides were isolated from three species of the genus Astragalus (Fabaceae): From the aerial parts of A. cicer L., two new saponins, cicerosides A and B (1 and 2, resp.), i.e., a tetradesmosidic and tridesmosidic cycloartane-type glycosides besides one known compound, from the roots of A. sempervirensLam., one known saponin, and from the roots of A. ptilodesBoiss. var. cariensisBoiss., five known compounds. Their structures were established mainly by 600-MHz 2D-NMR techniques (1H,1H-COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectroscopy.

Novel Acylated Triterpene Glycosides from Muraltia heisteria

2002

Four new acylated triterpene glycosides (1-4) have been isolated as two inseparable mixtures of the trans- and cis-3,4,5-trimethoxycinnamoyl derivatives (1,2 and 3,4) from the roots of Muraltia heisteria. The structures of these compounds were elucidated by various 1D and 2D NMR techniques, including (1)H and (13)C, COSY, NOESY, HSQC, TOCSY, and HMBC experiments and FABMS. Compounds 3 and 4 were shown to be cytotoxic in a human colon cancer cell line but did not show any ability to potentiate in vitro cisplatin cytotoxicity.

Two new biologically active triterpene saponins from Acanthophyllum squarrosum.

2000

Two novel triterpenoid saponins (1 and 2) have been isolated from the roots of Acanthophyllum squarrosum. The structures were established mainly by a combination of 2D NMR techniques as 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-be ta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3 )-b eta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L- rhamnopyranosyl-(1-->3)]-beta-D-fucopyranoside (1) and 3-O-beta-D-glucopyranosylgypsogenin-28-O-alpha-L-rhamnopyranosyl-( 1-- >2)-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->6 )]- beta-D-glucopyranoside (2). Compound 1 showed a moderate concentration-dependent immunomodulatory effect …

Steroidal saponins from the fruits of Solanum torvum

2013

Abstract Seven steroidal glycosides have been isolated from the fruits of Solanum torvum Swartz. Their structures were established by 2D NMR spectroscopic techniques ( 1 H, 1 H-COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry as (25 S )-26-(β- d -glucopyranosyloxy)-3-oxo-5α-furost-20(22)-en-6α-yl- O -β- d -xylopyranoside ( 1 ), (25 S )-26-(β- d -glucopyranosyloxy)-3-oxo-22α-methoxy-5α-furostan-6α-yl -O -β- d -xylopyranoside ( 2 ), (25 S )-26-(β- d -glucopyranosyloxy)-3β-hydroxy-22α-methoxy-5α-furostan-6α-yl- O -α- l -rhamnopyranosyl-(1 → 3)-β- d -glucopyranoside ( 3 ), (25 S )-3β-hydroxy-5α-spirostan-6α-yl- O -β- d -xylopyranoside ( 4 ), (25 S )-3-oxo-5α-spirostan-6α-yl- O -β- d -x…

Structural analysis of oleanane-type saponins from the roots of Wisteria frutescens

2016

Structure elucidation of new oleanane-type glycosides from three species of Acanthophyllum

2010

From the roots of three species of Acanthophyllum (Caryophyllaceae), two new gypsogenic acid glycosides, 1 and 2, were isolated, 1 from A. sordidum and A. lilacinum, 2 from A. elatius and A. lilacinum, together with three known saponins, glandulosides B and C, and SAPO50. The structures of 1 and 2 were established mainly by 2D NMR techniques as 23-O-β-D-galactopyranosylgypsogenic acid-28-O-β-D-glucopyranosyl-(13)-[β-D-glucopyranosyl-(16)]-β-D-galactopyranoside (1) and gypsogenic acid-28-O-β-D-glucopyranosyl-(13)-[β-D-glucopyranosyl-(16)]-β-D-galactopyranoside (2). The cytotoxicity of several of these saponins was evaluated against two human colon cancer cell lines (HT-29 and HCT 116). Copyr…

Cycloartane-type saponins from astragalus tmoleus var. tmoleus

2016

Five known cycloartane-type glycosides were isolated from the roots of A. tmoleus Boiss. var. tmoleus. The identification of these compounds was mainly achieved by 1D and 2D NMR spectroscopic techniques and FABMS. The results of our studies confirm that triterpene saponins with the cycloartane-type skeleton might be chemotaxonomically significant for the genus Astragalus.

Triterpene Saponins from the Fruits of Phytolacca rugosa (Phytolaccaceae)

2010

Four known serjanic acid glycosides were isolated from the fruits of Phytolacca rugosa and characterized mainly by 2D NMR spectroscopy and mass spectrometry. This aglycon has a chemotaxonomic significance for the genus Phytolacca.

New Acylated Saponins fromPolygala myrtifolia

2003

The ten new acylated presenegenin (=(2β,3β,4α)-2,3,27-trihydroxyolean-12-ene-23,28-dioic acid) glycosides 1–10 have been isolated by successive MPLC from the roots of Polygala myrtifolia L. as five inseparable mixtures of the trans- and cis-4-methoxycinnamoyl derivatives, i.e., myrtifoliosides A1/A2 (1/2), B1/B2 (3/4), C1/C2 (5/6), D1/D2 (7/8), and E1/E2 (9/10). Their structures were elucidated mainly by extensive spectroscopic experiments, including 2D NMR techniques, as 3-O-(β-D-glucopyranosyl)presenegenin 28-{O-β-D-galactopyranosyl-(13)-O-β-D-xylopyranosyl-(14)-O-[D-apio-β-D-furanosyl-(13)]-O-α-L-rhamnopyranosyl-(12)-O-[α-L-arabinopyranosyl-(13)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopy…

Triterpene saponins of the root bark of Olax obtusifolia De Wild

2018

Abstract Four undescribed triterpenoid saponins together with five known and oleanolic acid were isolated from root bark of Olax obtusifolia De Wild. Their structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments, in combination with mass spectrometry as 3-O-α- l -rhamnopyranosyl-(1→4)-α- l -rhamnopyranosyl-(1→3)-β- d -glucuronopyranosyloleanolic acid, 3-O-α- l -rhamnopyranosyl-(1→4)-α- l -rhamnopyranosyl-(1→3)-β- d -glucuronopyranosyloleanolic acid 28-O-β- d -glucopyranosyl ester, 3-O-α- l -rhamnopyranosyl-(1→3)-β- d -glucopyranosyl-(1→2)-[β- d -glucopyranosyl-(1→3)]-β- d -glucuronopyranosyloleanolic acid and 3-O-α- l -rhamnopyranosyl-(1→3)-β- d -glucopyranos…

Oleanolic acid and hederagenin glycosides from Weigela stelzneri

2015

Four previously undescribed and one known oleanolic acid glycosides were isolated from the roots of Weigela stelzneri, and one previously undescribed and three known hederagenin glycosides were isolated from the leaves. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyloleanolic acid, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyloleanolic acid, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-…

Spirostane-Type Saponins from Dracaena fragrans Yellow Coast

2015

Three steroidal glycosides were isolated from the bark of Dracaena fragrans (L.) Ker Gawl. « Yellow Coast », and a fourth from the roots and the leaves. Their structures were characterized on the basis of extensive 1D and 2D NMR experiments and mass spectrometry, and by comparison with NMR data of the literature. These saponins have the spirostane-type skeleton and are reported in this species for the first time.

ChemInform Abstract: Two New Triterpene Saponins from Acanthophyllum laxiusculum

2015

Two new triterpene glycosides, 1 and 2, together with three known ones, were isolated from roots of Acanthophyllum laxiusculum Schiman-Czeika. The structures of the new compounds were established by extensive 1D- and 2D-NMR spectroscopic experiments and MS analyses as 23-O-β-D-galactopyranosylgypsogenic acid 28-O-{β-D-glucopyranosyl-(1→2)-6-O-[4-carboxy-3-hydroxy-3-methyl-1-oxobutyl]-β-D-glucopyranosyl-(1→6)}-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranosyl ester (1) and gypsogenic acid 28-O-{β-D-glucopyranosyl-(1→2)-6-O-[4-carboxy-3-hydroxy-3-methyl-1-oxobutyl]-β-D-glucopyranosyl-(1→6)}-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranosyl ester (2).

Secondary metabolites from the roots of Paronychia chionaea

2011

Two novel secondary metabolites, compounds (1–2) were isolated from the roots of Paronychia chionaea. On the basis of spectroscopic data including 1D and 2D NMR experiments (COSY, TOCSY, HSQC, and HMBC), and mass spectroscopy, their structures were established as 6- C-[α-L-arabinopyranosyl-(1→2)-β-D-glucopyranosyl]-7- O-[β-D-glucopyranosyl]-luteolin 3′-methyl ether (1), and 2-(methoxy)-2-(3,5-dimethoxy 4-hydroxyphenyl)-ethane-1,2-diol 1- O-β-D-glucopyranoside (2).

Steroidal saponins from Asparagus acutifolius.

2007

Abstract Six new steroidal saponins ( 1 – 6 ) were isolated from the roots of A. acutifolius L., together with a known spirostanol glycoside ( 7 ). Their structures were elucidated mainly by extensive spectroscopic analysis (1D and 2D NMR, FABMS and HRESIMS). Compounds 4 – 7 demonstrated antifungal activity against the human pathogenic yeasts C. albicans , C. glabrata and C. tropicalis with MICs values between 12.5 and 100 μg/ml.

Triterpene Saponins from Cyclamen trocopteranthum

2010

Two new triterpene saponins ( 1- 2) together with three known saponins, deglucocyclamin I ( 3), cyclamin ( 4), and mirabilin ( 5), were isolated from the tubers of Cyclamen trocopteranthum. They were elucidated as 3 beta- O-{4- O-[3-hydroxyl-3-methylglutaryl]- beta-D-xylopyranosyl-(1 --> 2)- beta-D-glucopyranosyl-(1 --> 4)-[ beta-D-glucopyranosyl-(1 --> 2)]- alpha-L-arabinopyranosyl}-16 alpha-hydroxy-13 beta,28-epoxy-oleanan-30-al ( 1) and 3 beta- O-{4- O-[3-hydroxyl-3-methylglutaryl]- beta-D-xylopyranosyl-(1 --> 2)-[ beta-D-glucopyranosyl-(1 --> 6)]- beta-D-glucopyranosyl-(1 --> 4)-[ beta-D-glucopyranosyl-(1 --> 2)]- alpha-L-arabinopyranosyl}-16 alpha-hydroxy-20,30-lactone-olean-12-ene ( 2…

Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum

2013

Abstract A phytochemical analysis of the whole plant of Allium schoenoprasum , has led to the isolation of four spirostane-type glycosides ( 1 – 4 ), and four known steroidal saponins. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20 S ,25 S )-spirost-5-en-3β,12β,21-triol 3- O -α- l -rhamnopyranosyl-(1 → 2)-β- d -glucopyranoside ( 1 ), (20 S ,25 S )-spirost-5-en-3β,11α,21-triol 3- O -α- l -rhamnopyranosyl-(1 → 2)-β- d -glucopyranoside ( 2 ), laxogenin 3- O -α- l -rhamnopyranosyl-(1 → 2)-[β- d -glucopyranosyl-(1 → 4)]-β- d -glucopyranoside ( 3 ), and (25 R )-5α-spirostan-3β,11α-diol 3- O -β- d -glucopyranosyl-(1 → 3)-[β- d -glucopyranosyl-…

Unusual oleanane-type saponins from Arenaria montana

2010

Three oleanane-type saponins, 3-O-β-d-glucopyranosylechinocystic acid 28-O-β-d-xylopyranosyl-(1→4)-[α-l-rhamnopyranosyl-(1→2)]-α-l-rhamnopyranosyl ester (1), 3-O-β-d-glucopyranosylechinocystic acid 28-O-α-l-arabinopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-[α-l-rhamnopyranosyl-(1→2)]-α-l-rhamnopyranosyl ester (2), 3-O-β-d-glucopyranosylcaulophyllogenin 28-O-β-d-apiofuranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-[β-d-apiofuranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-α-l-rhamnopyranosyl ester (3) were isolated from the whole plant of Arenaria montana. Their unusual structures for the Caryophyllaceae family were established mainly by 2D NMR techniques and mass spectrometry.

Glandulosides A-D, triterpene saponins from Acanthophyllum glandulosum.

2004

Four novel triterpenoid saponins, glandulosides A (1), B (2), C (3), and D (4), together with two known saponins (5 and 6) have been isolated from the roots of Acanthophyllum glandulosum. Their structures were elucidated using a combination of homo- and heteronuclear 2D NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FABMS. The new compounds were characterized as 23-O-beta-D-galactopyranosylgypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[beta-d-galactopyranosyl-(1-->6)]-beta-D-galactopyranoside (1), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-l-rhamn…

Steroidal saponins and flavan-3-ol glycosides from Dioscorea villosa

2006

2002

by Mohamed Elbandya), Tomofumi Miyamotob), Cle¬ment Delaudec), and Marie-Aleth Lacaille-Dubois*a) a) Laboratoire de Pharmacognosie, Unite¬ de Mole¬cules d×Inte¬re√ t Biologique (UMIB JE 2244), Faculte¬ de Pharmacie, Universite¬ de Bourgogne, 7 Bd Jeanne d×Arc, BP 87900, F-21079 Dijon Cedex b) Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan c) Centre de Recherche Phytochimique, Universite¬ de Lieige, Institut de Chimie-B6, Sart Tilman B-4000-Lieige I

Glucuronide triterpene saponins from Bersama engleriana

2006

Five 3-O-glucuronide triterpene saponins (1-5) were isolated from the stem bark of Bersama engleriana Gurke along with two known saponins, polyscias saponin C and aralia saponin 15, and one major C-glycoside xanthone, mangiferin. The structures of the saponins were established mainly by means of spectroscopic methods (one- and two-dimensional NMR spectroscopy as well as FAB-, HRESI-mass spectrometry) as 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-betulinic acid (1), 3-O-[beta-D-glucopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosyl]-oleanolic acid (2), 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-…

Phytochemical analysis of two Weigela florida cultivars, “Pink Poppet” and “Jean’s Gold”

2020

Abstract Nine different oleanane-type glycosides were extracted and isolated by various chromatographic methods from two Weigela florida cultivars, “Pink Poppet” and “Jean’s Gold”. From the roots of W. florida “Pink Poppet”, three monodesmosidic oleanolic acid saponins 1, 4, 5 were obtained, together with one hederagenin ester 6 from the leaves, and six bidesmosidic saponins 2, 3, 6-9 were isolated from the leaves of W. florida “Jean’s Gold”. Among compounds 1-9, three were previously undescribed (1-3) and six (4-9) were already published in the literature. Their structures were assigned by spectroscopic analysis mainly 2D NMR and mass spectrometry (ESI-MS). The cytotoxicity of the isolated…

Steroidal saponins from two species of Dracaena.

2010

Four new steroidal saponins (1-4) were isolated from the stem and bark of two species of Dracaena: deistelianosides A and B (1 and 2) from D. deisteliana and arboreasaponins A and B (3 and 4) from D. arborea. Six known saponins and one known sapogenin were also isolated. The structures of 1-4 were established as diosgenin 3-O-[3-O-sulfate-alpha-l-rhamnopyranosyl-(1-->4)]-beta-d-glucopyranoside (1), 1-O-beta-d-xylopyranosyl-(1-->2)-[alpha-l-rhamnopyranosyl-(1-->3)]-beta-d-fucopyranosyl(23S,24S)-spirosta-5,25(27)-diene-1beta,3beta,23alpha,24alpha-tetrol 24-O-alpha-l-arabinopyranoside (2), pennogenin-3-O-alpha-l-rhamnopyranosyl-(1-->2)-[alpha-l-rhamnopyranosyl-(1-->3)]-[6-O-acetyl]-beta-d-gluc…

A New Aromatic Compound from the Stem Bark of Terminalia catappa

2015

A new aromatic compound 3,4,5-trimethoxyphenyl-1- O-(4-sulfo)-β-D-glucopyranoside (1), in addition to two triterpenoid saponins (chebuloside II, arjunoglucoside II), two triterpenes (arjunolic acid and 3-betulinic acid) and sitosterol-3- O-β-D-glucopyranoside have been isolated from the barks of Terminalia catappa. Their structures have been established on the basis of spectroscopic techniques (1D/2D NMR) and MS. Their cytotoxicity and anti-inflammatory activity, together with the antioxidant capacity of compound 1 were also evaluated.

New Triterpenoidal Saponins fromGypsophila repens

2007

Six new triterpene glycosides, repensosides A–F (1–6, resp.), were isolated from the roots of Gypsophila repens L. Their structures, established by extensive 1D- and 2D-NMR spectroscopic experiments as well as MS analyses, were found to be based on gypsogenic acid (or gypsogenin) as aglycone, with three to nine branched or unbranched sugar moieties.

New Acylated Preatroxigenin Saponins from Atroxima congolana

2003

Eight new acylated preatroxigenin saponins 1–8 were isolated as four inseparable mixtures of the trans- and cis-4-methoxycinnamoyl derivatives, atroximasaponins A1/A2 (1/2), B1/B2 (3/4), C1/C2 (5/6) and D1/D2 (7/8) from the roots of Atroxima congolana. These compounds are the first examples of triterpene saponins containing preatroxigenin (=(2β,3β,4α,22β)-2,3,22,27-tetrahydroxyolean-12-ene-23,28-dioic acid as aglycone. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR studies and FAB-MS as 3-O(β-D-glucopyranosyl)preatroxigenin 28-{O-β-D-xylopyranosyl-(14)-O-α-L-rhamnopyranosyl-(12)-O-[O-β-D-glucopyranosyl-(13)-β-D-glucopyranosyl-(13)]-4-O-(trans-4-methoxycinnamoyl)-β…

Two new triterpene saponins from Eryngium campestre.

2005

Two new triterpene saponins, 3-O-beta-D-glucopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucuronopyranosyl-22-O-angeloyl-R1-barrigenol (1) and 3-O-beta-D-glucopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucuronopyranosyl-22-O-beta,beta-dimethylacryloyl-A1-barrigenol (2), were isolated from the roots of Eryngium campestre (Apiaceae). Their structures were established mainly by 2D NMR techniques and mass spectrometry.

Triterpenoid saponins from Polycarpaea corymbosa Lamk. var. eriantha Hochst.

2013

Abstract Four triterpenoid saponins (1–4) were isolated from Polycarpaea corymbosa Lamk. var. eriantha Hochst along with the known apoanagallosaponin IV (5). Their structures were elucidated by spectroscopic data analysis. Among the compounds 1, 3–5 which were evaluated for their cytotoxicity against three tumor cell lines (SW480, DU145 and EMT6), compound 1 exhibited cytotoxicity with IC50 values ranging from 4.61 to 22.61 μM, which was greater than that of etoposide. Compound 2 was tested only against SW480 and a cardiomyoblast cell line (H9c2), and was inactive.

New Acylated Triterpene Saponins from Silene fortunei that Modulate Lymphocyte Proliferation

2002

Three new acylated triterpene saponins 1-3, with a quillaic acid as aglycon, were isolated from the roots of Silene fortunei together with a known phytoecdysteroid (20-hydroxyecdysone). The compounds were characterized mainly by a combination of 2D NMR techniques, mass spectrometry, and chemical methods. Saponins 1-3, jenisseensosides C and D (4, 5), and 6 (deacylated form of 2/3 and 4/5) were found to stimulate the proliferation of the Jurkat tumor cell lines at low concentration. At high concentration, 2/3 and 4/5 inhibited the proliferation of the cells and suggested the induction of apoptosis.

Steroidal Saponins from the Fruits of Cestrum ruizteranianum

2011

Seven spirostane and furostane-type glycosides were isolated from the aqueous methanolic extract of the fruits of Cestrum ruizteranianum and characterized mainly by 2D NMR spectroscopy and mass spectrometry. These known saponins belong to the Δ5-spirostene and Δ5-furostene series and are reported in this species for the first time.

Acylated triterpene saponins from the roots of Securidaca longepedunculata.

2009

Abstract Four triterpene saponins , 3- O -β- d -glucopyranosylpresenegenin 28- O -β- d -apiofuranosyl-(1 → 3)-β- d -xylopyranosyl-(1 → 4)-[β- d -apiofuranosyl-(1 → 3)]-α- l -rhamnopyranosyl-(1 → 2)-{4- O -[( E )-3,4,5-trimethoxycinnamoyl]}-β- d -fucopyranosyl ester, 3- O -β- d -glucopyranosylpresenegenin 28- O -β- d -apiofuranosyl-(1 → 3)-β- d -xylopyranosyl-(1 → 4)-[β- d -apiofuranosyl-(1 → 3)]-α- l -rhamnopyranosyl-(1 → 2)-[(6- O -acetyl)-β- d -glucopyranosyl-(1 → 3)]-{4- O -[( E )-3,4,5-trimethoxycinnamoyl]}-β- d -fucopyranosyl ester, 3- O -β- d -glucopyranosylpresenegenin 28- O -β- d -apiofuranosyl-(1 → 3)-β- d -xylopyranosyl-(1 → 4)-[β- d -apiofuranosyl-(1 → 3)]-α- l -rhamnopyranosyl-(…

Pursaethosides A-E, triterpene saponins from Entada pursaetha.

2005

Five new triterpenoid saponins, pursaethosides A-E (1-5), were isolated from the n-BuOH extract of the seed kernels of Entada pursaetha along with the known phaseoloidin. The structures of 1-5 were elucidated mainly by spectroscopic data interpretation and chemical degradation. Pursaethosides C-E (3-5) possess as a common structural feature entagenic acid as aglycon, which is rare among triterpene saponins. Compounds 2-4 and phaesolidin were found to be not cytotoxic when tested against HCT 116 and HT-29 human colon cancer cells.

New Triterpenoidal Saponins Acylated with Monoterpenic Acid fromAlbizia adianthifolia

2004

Four new triterpenoidal saponins acylated with monoterpenic acid, i.e., adianthifoliosides C, D, E, and F (1–4), besides the two known julibroside III and the monodesmonoterpenyl elliptoside A, were isolated from the roots of Albizia adianthifolia. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR studies and mass spectrometry as 3-O-{O-α-L-arabinopyranosyl-(12)-O-β-d-fucopyranosyl-(16)-O-[β-d-glucopyranosyl-(12)]-β-d-glucopyranosyl}-21-O-{(2E,6S)-6-{{4-O-[(2E,6S)-2,6-dimethyl-6-(β-D-quinovopyranosyloxy)octa-2,7-dienoyl]-β-d-quinovopyranosyl}oxy}-2-(hydroxymethyl)-6-methylocta-2,7-dienoyl}acacic acid 28-{O-α-L-arabinofuranosyl-(14)-O-[β-d-glucopyranosyl-(13)]-O-α-L-r…

Antifungal steroid saponins from Dioscorea cayenensis.

2004

From the rhizomes of Dioscorea cayenensis Lam.-Holl (Dioscoreaceae), the new 26- O- beta- D-glucopyranosyl-22-methoxy-3 beta,26-dihydroxy-25( R)-furost-5-en-3- O- alpha- L-rhamnopyranosyl-(1-->4)- alpha- L-rhamnopyranosyl-(1-->4)-[ alpha- L-rhamnopyranosyl-(1-->2)]- beta- D-glucopyranoside ( 1) was isolated together with the known dioscin ( 2) and diosgenin 3- O- alpha- L-rhamnopyranosyl-(1-->4)- alpha- L-rhamnopyranosyl-(1-->4)-[ alpha- L-rhamnopyranosyl-(1-->2)]- beta- D-glucopyranoside ( 3). Their structures were established on the basis of spectral data. Compound 2 exhibited antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata and C. tropicalis (MICs of …

Anti-phytopathogen terpenoid glycosides from the root bark of Chytranthus macrobotrys and Radlkofera calodendron

2020

Abstract Chytranthus macrobotrys and Radlkofera calodendron are two Sapindaceae characterized by a lack of phytochemical data. Both root barks from the two Sapindaceae species were processed by ethanol extraction followed by the isolation of their primary constituents by liquid chromatography. This process yielded four previously undescribed terpenoid glycosides together with eight known analogues. Extracts and isolated compounds from C. macrobotrys and R. calodendron were then screened for antimicrobial activity against fifteen phytopathogens. The biological screening also involved extracts and pure compounds from Blighia unijugata and Blighia welwitschii, two Sapindaceae previously studie…

New pregnane and phenolic glycosides from Solenostemma argel.

2016

Abstract From the aerial parts, pericarps and roots of Solenostemma argel, three new pregnane glycosides (1–3) with two known ones and a new phenolic glycoside (4) have been isolated. Their structures were established by extensive 1D – and 2D NMR and mass spectroscopic analysis. The cytotoxicity of all compounds was evaluated against two human tumor cell lines (SW 480, MCF-7), but none of them was active in the concentration range 0.9–59.0 μM. Compounds 2 and the known argeloside F at non toxic concentrations for the PBMCs (27.3 μM and 27.6 μM, respectively) significantly decreased the Il-1β production by LPS-stimulated PBMCs. All isolated compounds showed a significant antioxidant potentia…

A new ecdysteroid and other constituents from two Dioscorea species

2008

Phytochemical investigation of the rhizome of Dioscorea dumetorum has led to the isolation by several chromatographic steps on normal and reversed phase silica gel of a new ecdysteroid, (20R)-5β,11α,20-trihydroxyecdysone (1), and two known ecdysteroids, ajugasterone C (2) and herkesterone (3). Their structures were determined by spectroscopic methods including 1D- and 2D-NMR (COSY, TOCSY, HSQC and HMBC). This is the first report on the occurrence of phytoecdysteroids in the Dioscoreaceae family. These compounds were devoid of antifungal activity against three Candida species (Candida albicans, Candida glabrata and Candida tropicalis, MIC > 200 μg/ml).

Furostane-Type Steroidal Saponins from the Roots ofChlorophytum borivilianum

2008

Four new furostanol steroid saponins, borivilianosides A–D (1–4, resp.), corresponding to (3β,5α,22R,25R)-26-(β-D-glucopyranosyloxy)-22-hydroxyfurostan-3-yl O-β-D-xylopyranosyl-(13)-O-β-D-glucopyranosyl-(14)-O-[α-L-rhamnopyranosyl-(12)]-β-D-galactopyranoside (1), (3β,5α,22R,25R)- 26-(β-D-glucopyranosyloxy)-22-methoxyfurostan-3-yl O-β-D-xylopyranosyl-(13)-O-β-D-glucopyranosyl-(14)-O-[α-L-rhamnopyranosyl-(12)]-β-D-galactopyranoside (2), (3β,5α,22R,25R)-26-(β-D-glucopyranosyloxy)-22-methoxyfurostan-3-yl O-β-D-xylopyranosyl-(13)-O-[β-D-glucopyranosyl-(12)]-O-β-D-glucopyranosyl-(14)-β-D-galactopyranoside (3), and (3β,5α,25R)-26-(β-D-glucopyranosyloxy)furost-20(22)-en-3-yl O-β-D-xylopyranosyl-(13…

Triterpenoid saponins from Hydrocotyle bonariensis Lam

2011

Abstract Phytochemical investigation of the under-ground parts of Hydrocotyle bonariensis led to the isolation of five oleanane-type triterpenoid saponins, 3- O -{β- d -glucopyranosyl-(1 → 2)-[α- l -arabinopyranosyl-(1 → 3)]-β- d -glucuronopyranosyl}-21- O -(2-methylbutyroyl)-22- O -acetyl-R 1 -barrigenol, 3- O -{β- d -glucopyranosyl-(1 → 2)-[α- l -arabinopyranosyl-(1 → 3)]-β- d -glucuronopyranosyl}-21- O -(2-methylbutyroyl)-28- O -acetyl-R 1 -barrigenol, 3- O -{β- d -glucopyranosyl-(1 → 2)-[α- l -arabinopyranosyl-(1 → 3)]-β- d -glucuronopyranosyl}-21- O -acetyl-R 1 -barrigenol, 3- O -{β- d -glucopyranosyl-(1 → 2)-[α- l -arabinopyranosyl-(1 → 3)]-β- d -glucuronopyranosyl}-R 1 -barrigenol, a…

Solanum incanum and S. heteracanthum as sources of biologically active steroid glycosides: Confirmation of their synonymy

2012

A new spirostanol saponin (1), along with four known saponins, dioscin (2), protodioscin (3), methyl-protodioscin (4), and indioside D (5), and one known steroid glycoalkaloid solamargine (6) were isolated from the two synonymous species, Solanum incanum and S. heteracanthum. The structure of the new saponin was established as (23S,25R)-spirost-5-en-3β,23-diol 3-O-{β-D-xylopyranosyl-(1→2)-O-α-L-rhamnopyranosyl-(1→4)-[O-α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside}, by using a combination of 1D and 2D NMR techniques including (1)H, (13)C, COSY, TOCSY, NOESY, HSQC and HMBC experiments and by mass spectrometry. The compounds 1, 3, 4 and 5 were evaluated for cytotoxicity against five cancer c…

Triterpene glycosides from Blighia welwitschii and evaluation of their antibody recognition capacity in multiple sclerosis

2020

Multiple sclerosis (MS) in a multifactorial autoimmune disease in which reliable biomarkers are needed for therapeutic monitoring and diagnosis. Autoantibodies (autoAbs) are known biomarker candidates although their detection in biological fluids requires a thorough characterization of their associated antigens. Over the past twenty years, a reverse chemical-based approach aiming to screen putative autoantigens has underlined the role of glycans, in particular glucose, in MS. Despite the progress achieved, a lack of consensus regarding the nature of innate antigens as well as difficulties proposing new synthetic glucose-based structures have proved to be obstacles. Here is proposed a strate…

Spirostane and cholestane glycosides from the bulbs of Allium nigrum L

2011

Abstract A phytochemical investigation of the fresh bulbs of Allium nigrum L. led to the isolation of new spirostane-type glycosides as two inseparable isomer mixtures, nigrosides A1/A2 (1a/1b) and nigrosides B1/B2 (2a/2b), two new cholestane-type glycosides, nigrosides C and D (3 and 4), together with the known compounds, 25(R,S)-5α-spirostan-2α,3β,6β-trio1-3-O-β- d -glucopyranosyl-(1 → 2)-O-[β- d -xylopyranosyl-(1 → 3)]-O-β- d -glucopyranosyl-(1 → 4)-β- d -galactopyranoside (5a/5b) and 25(R,S)-5α-spirostan-2α,3β,6β-trio1 3-O-β- d -glucopyranosyl-(1 → 2)-O-[4-O-(3S)-3-hydroxy-3-methylglutaryl-β- d -xylopyranosyl-(1 → 3)]-O-β- d -glucopyranosyl-(1 → 4)-β- d -galactopyranoside (6a/6b), isola…

Supporting information - Supplemental material for Triterpenoid Saponins From the Stem Bark of Pentaclethra eetveldeana

2019

Supplemental material, Supporting information for Triterpenoid Saponins From the Stem Bark of Pentaclethra eetveldeana by David Pertuit, Mpuza Kapundu, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Clément Delaude, and Marie-Aleth Lacaille-Dubois in Natural Product Communications

Ursane-type saponins from Zygophyllum cornutum

2013

Seven known ursane-type saponins were isolated from the methanolic extract of the whole plant of Zygophyllum cornutum Coss, and identified by 2D NMR spectroscopy and FAB-mass spectrometry. They are reported in this species for the first time and might be chemotaxonomically significant for the genus Zygophyllum.

Oleanane-type glycosides from the roots of Weigela florida “rumba” and evaluation of their antibody recognition

2018

Three triterpene glycosides were isolated from the roots of Weigela florida "rumba" (Bunge) A. DC.: two previously undescribed 3-O-β-d-xylopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→4)]-β-d-xylopyranosyl-(1→4)-β-d-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyloleanolic acid (1) and 3-O-β-d-xylopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-β-d-xylopyranosyl-(1→4)-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyloleanolic acid (2), and one isolated for the first time from a natural source 3-O-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyloleanolic acid (3). Their structures were elucidated mainly by 2D NMR spectroscopic analysis (COSY, …

Cytotoxic Acacic Acid Glycosides from the Roots of Albizia coriaria

2009

Two new oleanane-type saponins, coriariosides A (1) and B (2), along with a known saponin, gummiferaoside C (3), were isolated from the roots of Albizia coriaria. Their structures were established by extensive analysis of 1D and 2D NMR experiments (COSY, ROESY, TOCSY, HSQC, and HMBC) and mass spectrometry. Compounds 1 and 3 when tested for cytotoxicity against two colorectal human cancer cells showed activity against the HCT 116 (IC50 4.2 microM for 1 and 2.7 microM for 3) and HT-29 (IC50 6.7 microM for 1 and 7.9 microM for 3) cell lines.

Two New Triterpene Saponins fromAcanthophyllum laxiusculum

2015

Two new triterpene glycosides, 1 and 2, together with three known ones, were isolated from roots of Acanthophyllum laxiusculum Schiman-Czeika. The structures of the new compounds were established by extensive 1D- and 2D-NMR spectroscopic experiments and MS analyses as 23-O-β-D-galactopyranosylgypsogenic acid 28-O-{β-D-glucopyranosyl-(1→2)-6-O-[4-carboxy-3-hydroxy-3-methyl-1-oxobutyl]-β-D-glucopyranosyl-(1→6)}-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranosyl ester (1) and gypsogenic acid 28-O-{β-D-glucopyranosyl-(1→2)-6-O-[4-carboxy-3-hydroxy-3-methyl-1-oxobutyl]-β-D-glucopyranosyl-(1→6)}-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranosyl ester (2).

Oleanane-type glycosides from Pittosporum tenuifolium “variegatum” and P. tenuifolium “gold star”

2017

Abstract The phytochemical study of two cultivars of Pittosporum tenuifolium Banks & Sol. ex Gaertn, “variegatum” and “gold star”, led to the isolation of eight oleanane-type glycosides: seven previously undescribed and a known one. Their aglycons are oxygenated oleanane derivatives as barringtogenol C, camelliagenin A, hederagenin, and 22α-hydroxyoleanolic acid. Their structures were established by 2D NMR spectroscopic techniques and mass spectrometry as 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl-21-O-angeloyl-22-O-acetylbarringtogenol C, 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl-21,22-di-O-angeloylbar…

Acylated Preatroxigenin Glycosides from Atroxima congolana

2003

Six new acylated bisdesmosidic preatroxigenin saponins named atroximasaponins E1, E2 (1, 2), F1, F2 (3, 4), and G1, G2 (5, 6) were isolated as three inseparable mixtures of the trans- and cis-p-methoxycinnamoyl derivatives, from the roots of Atroxima congolana. Their structures were established through extensive NMR spectroscopic analysis as 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-xylopyranosyl-(1--4)-alpha-L-rhamnopyranosyl-(1--2)-[beta-D-glucopyranosyl-(1--3)]-[4-O-trans-p-methoxycinnamoyl]-beta-D-fucopyranoside (atroximasaponin E1, 1), and its cis-isomer, atroximasaponin E2 (2), 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-xylopyranosyl-(1--4)-alpha-L-rhamnopyranosyl-(…

Triterpene Saponins from Cyclamen persicum

2010

A new triterpene saponin 3- O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl-16α-hydroxy-13β,28-epoxy-oleanan-30-al (1), along with four known triterpene glycosides (2-5) were isolated from Cyclamen persicum. Their structures were characterized by a combination of 1D- and 2D-NMR (1H-1H COSY, TOCSY, NOESY, HSQC, and HMBC) and MS spectrocopic data. The cytotoxicity of compounds 2 and 4 was evaluated using two human colon cancer cell lines HT-29 and HCT 116.

Triterpene Saponins from Four Species of the Polygalaceae Family

2005

Twelve triterpene saponins were isolated by successive MPLC over silica gel from four species of Polygalaceae: From Polygala ruwenzoriensis, five new saponins 1–5 of which 1–4 as two pairs of (E)/(Z)-isomers, together with the four known compounds tenuifoline, (E)- and (Z)-senegasaponin b, (E)- and (Z)-senegin II, and polygalasaponin XXVIII, from the genus Carpolobia, one new saponin 6 from C. alba and the known arilloside (11) from C. lutea, and another new triterpene glycoside 7 from Polygala arenaria. Their structures were established mainly by 600-MHz 2D-NMR techniques (1H,1H-COSY, TOCSY, NOESY, HSQC, HMBC) as 3-O-(β-D-glucopyranosyl)presenegenin 28-{O-α-L-arabinopyranosyl-(1  4)-O-β-D-…

Three New Medicagenic Acid Saponins from Polygala micranthaGuill. & Perr.

2011

Three new medicagenic acid saponins, micranthosides A–C (1–3), were isolated from the roots of Polygala micranthaGuill. & Perr., along with six known presenegenin saponins. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR experiments (1H, 13C, DEPT, COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry as 3-O-β-D-glucopyranosylmedicagenic acid 28-[O-β-D-galactopyranosyl-(14)-O-β-D-xylopyranosyl-(14)-O-α-L-rhamnopyranosyl-(12)-β-D-fucopyranosyl] ester (1), 3-O-β-D-glucopyranosylmedicagenic acid 28-[O-6-O-acetyl-β-D-galactopyranosyl-(14)-O-β-D-xylopyranosyl-(14)-O-α-L-rhamnopyranosyl-(12)-β-D-fucopyranosyl] ester (2), and 3-O-{O-β-D-glucopyranosyl-(13)-O-[β-D-gluc…

Steroidal saponins from Smilax medica and their antifungal activity.

2005

Three new steroidal saponins (1-3) were isolated from the roots of Smilax medica, together with the known disporoside A (4). The structures of the new compounds were elucidated mainly by extensive spectroscopic analysis (1D and 2D NMR, FABMS, and HRESIMS). Compounds 1, 2, and 4 demonstrated weak antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata, and C.tropicalis, with MIC values between 12.5 and 50 microg/mL.

Triterpene saponins from the roots of Bupleurum spinosum Gouan

2020

Abstract Three previously undescribed triterpene saponins, and four known ones, were isolated from the EtOH/H2O extract of the roots of Bupleurum spinosum. Their structures were characterized using spectroscopic techniques including 1D and 2D NMR (1H, 13C, COSY, TOCSY, ROESY, HSQC, and HMBC) experiments and mass spectrometry as 3-O-β-D-glucopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→2)]-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl-3β,16β,23,28-tetrahydroxyolean-12-ene, 3-O-β-D-glucopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→2)]-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl-3β,16β,28-trihydroxy-23-oxoolean-12-ene, 3-O-β-D-glucopyranosyl-(1→6)-[α-L-rhamnopyranosyl(1→4)]-β-D-glucopyranosyl-3β,16β,2…

Activation of a Sweet Taste Receptor by Oleanane-Type Glycosides from Wisteria sinensis

2022

The phytochemical study of Wisteria sinensis (Sims) DC. (Fabaceae), commonly known as the Chinese Wisteria, led to the isolation of seven oleanane-type glycosides from an aqueous-ethanolic extract of the roots. After successive purifications by various chromatographic methods, like solid/liquid chromatographic methods, vacuum liquid chromatography (VLC), medium pressure liquid chromatography (MPLC), on normal and reverse phase (RP-18 silica gel), and size exclusion chromatography on Sephadex L, their structures were elucidated by an extensive 600 MHz NMR analysis including 1D and 2D NMR experiments as well as ESI-MS. Among the seven isolated saponins, two have never been reported before : 3…

Steroidal glycosides from the Vietnamese cultivar Cordyline fruticosa “Fairchild red”

2021

Abstract A phytochemical study of Cordyline fruticosa “Fairchild red” (Asparagaceae) from Vietnam, led to the isolation of fourteen steroidal glycosides, including twelve previously undescribed along with two known ones. Ten compounds were obtained by successive solid/liquid chromatographic methods from an aqueous-ethanolic extract of the roots, and four from the aerial parts. Their structures were elucidated mainly by spectroscopic analysis 2D NMR and mass spectroscopy (ESI-MS), as spirostanol glycosides, 5α-spirost-25(27)-ene-1β,3β,4α-triol 1-O-β-D-fucopyranoside, 5α-spirost-(25)27-ene-1β,3β,4α-triol 1-O-β-D-xylopyranoside, 5α-spirost-(25)27-ene-1β,3β,4α-triol 1-O-α-L-rhamnopyranosyl-(1 →…

Three new acylated triterpene saponins from Acanthophyllum squarrosum.

2001

Three new triterpenoid saponins, 1-3, were isolated from the roots of Acanthophyllum squarrosum. Their structures were established mainly by 2D NMR techniques as 3-O-beta-D-galactopyranosyl-(1--2)-[beta-D-xylopyranosyl-(1--3)]-beta-D-glucuronopyranosyl-gypsogenin-28-O-beta-D-xylopyranosyl-(1--3)-beta-D-xylopyranosyl-(1--4)-beta-D-xylopyranosyl-(1--4)-3-O-acetyl-alpha-L-rhamnopyranosyl-(1--2)-3,4-di-O-acetyl-beta-D-fucopyranoside (1), 3-O-beta-D-galactopyranosyl-(1--2)-[beta-D-xylopyranosyl-(1--3)]-beta-D-glucuronopyranosyl-gypsogenin-28-O-beta-D-xylopyranosyl-(1--4)-alpha-L-rhamnopyranosyl-(1--2)-[5-O-acetyl-alpha-L-arabinofuranosyl-(1--3)]-4-O-acetyl-beta-D-fucopyranoside (2), and 3-O-beta…

Triterpenoid Saponins From the Root Bark of Haplocoelum congolanum

2019

Two undescribed triterpenoid saponins together with 5 known ones were isolated from the root bark of Haplocoelum congolanum Hauman. Their structures were elucidated by spectroscopic methods including one-dimensional and two-dimensional nuclear magnetic resonance experiments in combination with mass spectrometry as 3- O-(4- O-[3-hydroxy-3-methylglutaryl])-α-l-arabinopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-α-l-arabinopyranosyloleanolic acid and 3- O-α-l-arabinofuranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-α-l-arabinopyranosyloleanolic acid.

Sulfated Lupane Triterpene Derivatives and a Flavone C-Glycoside from Gypsophila repens

2007

A new sulfated lupane triterpene, Gypsophilin (1), and its glucosyl ester, Gypsophilinoside (2) were isolated from the roots of Gypsophila repens whereas a new flavone C-glycoside (3) was obtained from the aerial parts. Their structures were established as (3beta)-3-O-(sulfo)lup-20(29)-en-23,28-dioic acid (1), (3beta)-3-O-(sulfo)lup-20(29)-en-23,28-dioic acid -28-O-beta-D-glucopyranosyl ester (2) and luteolin-7-O-alpha-L-arabinopyranosyl-6-C-beta-glucopyranoside (3) by spectroscopic methods such as 1D and 2D NMR, HR-ESI-MS and FAB-MS.

Triterpenoid saponins from the roots of two Gypsophila species.

2013

Two triterpenoid saponins with two known ones have been isolated from the roots of Gypsophila arrostii var. nebulosa, and two new ones from the roots of Gypsophila bicolor. Their structures were established by extensive NMR and mass spectroscopic techniques as 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosylquillaic acid 28-O-β-d-xylopyranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-β-d-fucopyranosyl ester (1), 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosylgypsogenin 28-O-β-d-xylopyranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-β-d-fuco…

Three New Triterpene Saponins from Two Species of Carpolobia

2002

Three new acetylated triterpene saponins 1-3 were isolated from the roots of Carpolobia alba and C. lutea. Their structures were established mainly by 2D NMR techniques as 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-galactopyranosyl-(1-->4)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl)-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-galactopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->3)]-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl)-beta-D-fucopyranosyl ester, and 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-xylopyranosyl-(1-->4)-[beta-D-apiofuranosyl…

Triterpenoid Saponins From the Stem Bark of Pentaclethra eetveldeana

2019

Two previously undescribed triterpenoid saponins together with 4 known ones were isolated from the stem bark of Pentaclethra eetveldeana De Wild. & Th. Dur. Their structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments in combination with mass spectrometry as 3- O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyloleanolic acid and 3- O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosylhederagenin.

Foetidissimosides C—F, Novel Glycosides from the Roots of Cucurbita foetidissima.

2004

Two novel echinocystic acid (=(3β,16α)-3,16-dihydroxyolean-12-en-28-oic acid) glycosides, foetidissimosides C (1), and D (2), along with new cucurbitane glycosides, i.e., foetidissimosides E/F (3/4) as an 1 : 1 mixture of the (24R)/(24S) epimers, were obtained from the roots of Cucurbita foetidissima. Their structures were elucidated by means of a combination of homo- and heteronuclear 2D-NMR techniques (COSY, TOCSY, NOESY, ROESY, HSQC, and HMBC), and by FAB-MS. The new compounds were characterized as (3β,16α)-28-{[O-β-D-glucopyranosyl-(13)-O-β-D-xylopyranosyl-(14)-O-6-deoxy-α-L-mannopyranosyl-(12)-α-L-arabinopyranosyl]oxy}-16-hydroxy-28-oxoolean -12-en-3-yl β-D-glucopyranosiduronic acid (1…

Sphingolipids and other constituents from Cordia platythyrsa

2005

New Acylated Triterpene Saponins fromPolygala arenaria

2003

Eight new acylated triterpene saponins 1–8 were isolated from the roots of Polygala arenaria as four inseparable (E)/(Z) mixtures of the 4-methoxycinnamoyl and 3,4-dimethoxycinnamoyl derivatives by repeated MPLC over silica gel. Their structures were established mainly by 600-MHz 2D-NMR techniques (1H,1H-COSY, TOCSY, NOESY, HSQC, HMBC) as 3-O-(β-D-glucopyranosyl)presenegenin 28-(O-β-D-galactopyranosyl-(14)-O-[β-D-glucopyranosyl-(13)]-O-β-D-xylopyranosyl-(14)-O-α-L-rhamnopyranosyl-(12)-{4-O-[(E)-4-methoxycinnamoyl]}-β-D-fucopyranosyl) ester and its (Z)-isomer (1/2), 3-O-(β-D-glucopyranosyl)presenegenin 28-(O-β-D-galactopyranosyl-(14)-O-[β-D-glucopyranosyl-(13)]-O-β-D-xylopyranosyl-(14)-O-α-L…

Cytotoxic Spirostane-Type Saponins from the Roots of Chlorophytum borivilianum

2009

Four new spirostane-type saponins named borivilianosides E-H (1-4) were isolated from an ethanol extract of the roots of Chlorophytum borivilianum together with two known steroid saponins (5 and 6). The structures of 1-4 were elucidated using mainly 2D NMR spectroscopic techniques and mass spectrometry. The cytotoxicity of borivilianosides F (2), G (3), and H (4) and three known compounds was evaluated using two human colon cancer cell lines (HT-29 and HCT 116).

New triterpenoid estersaponins from the root barks of Pittosporum verticillatum subsp. verticillatum and evaluation of cytotoxicities

2013

The phytochemical investigation of the root barks of Pittosporum verticillatum Bojer subsp. verticillatum led to the isolation of three new triterpene saponins, 3-O-[β-D-glucopyranosyl-(1→2)]-[α-L-arabinopyranosyl-(1→3)]-[α-L-arabinofuranosyl-(1→4)]-β-D-glucuronopyranosyl-21-O-(2-acetoxy-2-methylbutanoyl)-R1-barrigenol (1), 3-O-[β-D-glucopyranosyl-(1→2)]-[α-L-arabinopyranosyl-(1→3)]-[α-L-arabinofuranosyl-(1→4)]-β-D-glucuronopyranosyl-21-O-(2-acetoxy-2-methylbutanoyl)-28-O-acetyl-R1-barrigenol (2), 3-O-[β-D-glucopyranosyl-(1→2)]-[α-L-arabinopyranosyl-(1→3)]-[α-L-arabinofuranosyl-(1→4)]-β-D-glucuronopyranosyl-21-O-β,β-dimethylacryloyl-22-O-angeloyl-R1-barrigenol (3), and one known saponin sen…

Cycloartane-type Glycosides from Two Species of Astragalus (Fabaceae)

2009

Three known cycloartane-type glycosides were isolated from the roots of two different species of Astragalus, A. glycyphyllos, A. sempervirens. The identification of these compounds were mainly achieved by 2D NMR spectroscopic techniques and FAB-MS. The results of our studies confirm that triterpene saponins from the cycloartane-type skeleton might be chemotaxonomically significant to the genus Astragalus.

Acylated Triterpene Saponins from Atroxima libericaStapf

2011

The four new acylated triterpene saponins 1–4, isolated as two pairs of isomers and named libericosides A1/A2 and B1/B2, one pair of isomers 5/6, the (Z)-isomer libericoside C2 (5) being new, one new sucrose ester, atroximoside (7), and eight known compounds were isolated from the roots of Atroxima liberica by repeated MPLC and VLC on normal and reversed-phase silica gel. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR studies (1H- and 13C-NMR, DEPT, COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry as 3-O-β-D-glucopyranosylpresenegenin 28-{O-α-L-arabinopyranosyl-(13)-O-β-D-xylopyranosyl-(14)-O-α-L-rhamnopyranosyl-(12)-4-O-[(E)-3,4-dimethoxycinnamoyl]-β-D-f…

Triterpenoid saponins from the cultivar “Green Elf” of Pittosporum tenuifolium

2021

Four oleanane-type glycosides were isolated from a horticultural cultivar “Green Elf” of the endemic Pittosporum tenuifolium (Pittosporaceae) from New Zealand: three acylated barringtogenol C glycosides from the leaves, with two previously undescribed 3-O-β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C, 3-O-β-d-galactopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C, and the known 3-O-β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C (Eryngioside L). From the roots, the known 3-O-β-d-glucopyra…

Steroidal saponins from Dioscorea preussii.

2014

Abstract Three new steroidal saponins, named diospreussinosides A–C (1–3), along with two known ones (4, 5) were isolated from rhizomes of Dioscorea preussii. Their structures were elucidated mainly by 1D and 2D NMR spectroscopic analysis and mass spectrometry as (25S)-17α,25-dihydroxyspirost-5-en-3β-yl-O-α- l -rhamnopyranosyl-(1 → 4)-α- l -rhamnopyranosyl-(1 → 4)-β- d -glucopyranoside (1), (25S)-17α,25-dihydroxyspirost-5-en-3β-yl-O-α- l -rhamnopyranosyl-(1 → 4)-α- l -rhamnopyranosyl-(1 → 4)-[α- l -rhamnopyranosyl-(1 → 2)]-β- d -glucopyranoside (2), and (24S,25R)-17α,24,25-trihydroxyspirost-5-en-3β-yl-O-α- l -rhamnopyranosyl-(1 → 4)-α- l -rhamnopyranosyl-(1 → 4)-[α- l -rhamnopyranosyl-(1 → …

Triterpene Glycosides from the Roots of Astragalus flavescens

2007

Six new triterpene saponins, 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21-epi-kudzusapogenol A (1), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21-epi-kudzusapogenol A (2), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-22-O-beta-D-glucopyranosyl-21-epi-kudzusapogenol A (3), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-22-O-beta-D-glucopyranosyl-21-epi-kudzusapogenol A (4), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-22-O-alpha-L-arabinopyranosyl-21-epi-kudzus…

Arboreasides A−E, Triterpene Saponins from the Bark of Cussonia arborea

2009

Five new triterpene saponins, arboreasides A-E (1-5), and two known saponins, ciwujianoside C(3) and 23-hydroxyursolic acid 28-O-alpha-L-rhamnopyranosyl-(1--4)-beta-D-glucopyranosyl-(1--6)-beta-D-glucopyranosyl ester, were isolated from the bark of Cussonia arborea. The structures were established using extensive 1D and 2D NMR spectroscopic analyses and mass spectrometry.

New Triterpene Saponins fromAcanthophyllum pachystegium

2004

Four new triterpenoid saponins, pachystegiosides A (1), B (2), C (3), and D (4), were isolated from the roots of Acanthophyllum pachystegium K. H. Their structures were elucidated by means of a combination of homo- and heteronuclear 2D-NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FAB-MS. The new compounds were characterized as 3-O-{O-β-D-galactopyranosyl-(12)-O-[β-D-xylopyranosyl-(13)]-β-D-glucuronopyranosyl}quillaic acid 28-{O-β-D-xylopyranosyl-(13)-O-β-D-xylopyranosyl-(14)-O-α-L-rhamnopyranosyl-(12)-O-[3,4-di-O-acetyl-β-D-quinovopyranosyl-(14)]-β-D-fucopyranosyl}ester (1), 3-O-{O-β-D-galactopyranosyl-(12)-O-[β-D-xylopyranosyl-(13)]-β-D-glucuronopyranosyl}quillaic acid 28-{O-…

Two New Triterpene Saponins from Cyclamen africanumBoiss. & Reuter

2012

Two new oleanane-type triterpene saponins, afrocyclamins A and B (1 and 2, resp.), were isolated from a MeOH extract of the roots of Cyclamen africanum Boiss. & Reuter, together with three known triterpenoid saponins, lysikokianoside, deglucocyclamin I, and its dicrotalic acid derivative. The structures were elucidated, on the basis of 1D- and 2D-NMR experiments and mass spectrometry as (3β,20β)-13,28-epoxy-16-oxo-3-{O-β-D-xylopyranosyl-(12)-O-β-D-glucopyranosyl-(14)-O-[β-D-glucopyranosyl-(12)]-α-L-arabinopyranosyl}oxy}oleanan-29-al (1) and (3β,16α,20β)-16,28,29-trihydroxy-olean-12-en-3-yl O-4-O-(4-carboxy-3-hydroxy-3-methyl-1-oxobutyl)-β-D-xylopyranosyl-(12)-O-β-D-glucopyranosyl-(14)-O-[β-…

Glaucasides A-C, three saikosaponins from Atriplex glauca L. var. ifiniensis (Caball) Maire

2011

From the roots of Atriplex glauca L. var. ifiniensis (Caball) Maire (syn. of Atriplex parvifolia Lowe var. genuina Maire), three new saikosaponins designated as glaucasides A-C (1-3) were isolated together with the known 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-galactopyranosyl-saikogenin F (4). The structures of the new compounds were elucidated by extensive analysis of one-dimensional and two-dimensional NMR spectroscopy, FABMS, HR-ESIMS and chemical evidence as 13β,28-epoxy-16β,21β-dihydroxyolean-11-en-3β-yl O-β-D-[2-O-sulfate]-glucopyranosyl-(1 → 2)-α-L-arabinopyranoside (1), 13β,28-epoxy-16β,21β-dihydroxyolean-11-en-3β-yl O-β-D-[2-O-sulfate]-glucopyranosyl-(1 → 2)-α-L-arabinopyranosyl 21-O-{…

Tetrapterosides A and B, two new oleanane-type saponins fromTetrapleura tetraptera

2009

From the stem bark of Tetrapleura tetraptera, two new oleanane-type saponins, tetrapteroside A 3-O-{6-O-[(2E,6S)-2,6-dimethyl-6-hydroxyocta-2,7-dienoyl]-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 3)-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl}-3,27-dihydroxyoleanolic acid (1), and tetrapteroside B 3-O-{ beta-D-glucopyranosyl-(1 --> 2)-6-O-[(E)-feruloyl]-beta-D-glucopyranosyl-(1 --> 3)-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl}-3,27-dihydroxyoleanolic acid (2), were isolated. Further extractions from the roots led to the isolation of four known oleanane-type saponins. Their structures …

Presenegenin Glycosides from Securidaca welwitschii

2010

) Centre de Recherche Phytochimique, Universite´ de Lie`ge, Institut de Chimie-B6, Sart Tilman,B-4000-Lie`ge IThe five new presenegenin glycosides 1–5 were isolated from Securidaca welwitschii, together withone known sucrose diester. Compounds 1–4 were obtained as pairs of inseparable (E)/(Z)-isomers of a3,4-dimethoxycinnamoyl derivative, i.e., 1/2 and 3/4. Their structures were elucidated mainly by 2D-NMR techniques and mass spectrometry as 3-O-(b-d-glucopyranosyl)presenegenin 28-{O-b-d-xylopyr-anosyl-(1!4)-O-a-l-rhamnopyranosyl-(1!2)-O-[b-d-glucopyranosyl-(1!3)]-4-O-[(E)-3,4-dimeth-oxycinnamoyl]-b-d-fucopyranosyl} ester (1) and its (Z)-isomer 2, 3-O-(b-d-glucopyranosyl)presenege-nin 28-{O…

Junceosides A-C, new triterpene saponins from Arenaria juncea.

2002

Three novel triterpenoid saponins, junceosides A (1), B (2), and C (3), together with two known saponins have been isolated from the roots of Arenaria juncea. Their structures were elucidated using a combination of homo- and heteronuclear 2D NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FABMS. The new compounds were characterized as 3-O-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-glucopyranosyl(1-->3)-[beta-D-xylopyranosyl-(1-->4)]-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (1), 3-O-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-x…

Terpenoid glycosides from the root's barks of Eriocoelum microspermum Radlk. ex Engl.

2018

Abstract Eight undescribed triterpenoid saponins together with a known one, and two undescribed sesquiterpene glycosides were isolated from root's barks of Eriocoelum microspermum. Their structures were elucidated by spectroscopic methods including 1D and 2D experiments in combinaison with mass spectrometry as 3-O-α-L-rhamnopyranosyl-(1 → 3)-[α-L-rhamnopyranosyl-(1 → 2)]-α-L-arabinopyranosylhederagenin, 3-O-α-L-rhamnopyranosyl-(1 → 3)-[β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-α-L-arabinopyranosylhederagenin, 3-O-α-L-rhamnopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-α-L-arabinopyranosylhederagenin, 3-O-α-L-rhamnopyranosyl-(1 → 4)-[α-L-rhamnopyrano…

Triterpene saponins from Eryngium kotschyi

2015

Four new oleanane-type saponins 3-O-alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucuronopyranosyl-22-O-beta, beta-dimethylacryloylA1-barrigenol (1), 3-O-alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucuronopyranosyl-22-O-angeloylA1-barrigenol (2), 3-O-beta-D-glucopyranosyl-(1 -> 2)-[beta-D-glucopyranosyl-(1 -> 6)]-beta-D-glucopyranosyl-21,22,28-O-triacetyl-(3 beta,21 beta,22 alpha)-olean-12-en-16-one (3), and 3-O-beta-D-glucopyranosyl-(1 -> 2)-glucopyranosyl-22-O-beta-D-glucopyranosylsteganogenin (4), along with the known 3-O-beta-D-galactopyranosyl-(1 -> 2)-[alpha-L-arabinopyranosyl-(1 -> 3)]-beta-D-glucuronopyranosyl-22-O-angeloylA1-barrigenol and 3-O-alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-gluc…

A New Phenanthrene Glycoside and Other Constituents from Dioscorea opposita

2005

Phytochemical investigation of the rhizome of Dioscorea opposita has led to the isolation of a new phenanthrene glycoside, 3,4,6-trihydroxyphenanthrene-3-O-beta-D-glucopyranoside (1), and five known compounds, soyacerebroside I (2), adenosine (3), beta-sitosterol (4), palmitic acid (5) and palmitoyloleoylphosphatidylcholine (6). Their structures were determined by spectroscopic methods, including 1D- and 2D-NMR. Compounds 1-6 exhibited no antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata and C. tropicalis.

Steroidal saponins from Dracaena marginata

2013

Three new steroidal saponins and ten known ones were isolated from the bark of Dracaena marginata, along with two known steroidal saponins from the roots. Their structures were elucidated on the basis of extensive 1D and 2D NMR experiments and mass spectrometry as (25R)-26-(beta-D-glucopyranosyloxy)3beta,22alpha-dihydroxyfurost-5-en-1beta-yl O-alpha-L-rhamnopyranosyl-(1 --> 2)-[alpha-L-rhamnopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (1), (25R)-26-(beta-D-glucopyranosyloxy)-3beta,22alpha-dihydroxyfurost-5-en-1beta-yl O-alpha-L-rhamnopyranosyl-(1 --> 2)-4-O-sulfo-alpha-L-arabinopyranoside (2), and (25S)-3beta-hydroxyspirost-5-en-1beta-yl O-alpha-L-rhamnopyranosyl-(1 --> 2)-4-O-sulfo-alpha-L…

Steroidal saponins from the roots of Smilax aspera subsp. mauritanica

2008

Two new steroidal saponins (1, 2) were isolated from the roots of Smilax aspera subsp. mauritanica (POIR.) ARCANG. (Liliaceae), together with the known curillin G (3), asparagoside E (4), asparoside A (5), asparoside B (6) and the phenolic compound resveratrol (7). Their structures were established mainly on the basis of 600 MHz 2D-NMR spectral data. 3 exhibited antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata and C. tropicalis (minimum inhibitory concentrations of 25, 25 and 50 microg/ml, respectively) whereas the other compounds were inactive.

Phytochemistry of Weigela x “kosteriana variegata” (Caprifoliaceae)

2018

One new triterpene glycoside 3- O-β-D-xylopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→3)]-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyloleanolic acid, was isolated from Weigela x “kosteriana variegata” (Caprifoliaceae), with three known ones. Their structures were characterized by a combination of mass spectrometry and 1D and 2D NMR spectrocopic techniques including 1H- and 13C NMR, COSY, TOCSY, NOESY, HSQC, and HMBC experiments. The toxicological properties of some glycosides were determined with a zebrafish-based assay. The results show that the most active compounds were toxic to the larvae in the range of 1 μM.

Foetidissimosides C–F, Novel Glycosides from the Roots ofCucurbita foetidissima

2004

Two novel echinocystic acid (=(3β,16α)-3,16-dihydroxyolean-12-en-28-oic acid) glycosides, foetidissimosides C (1), and D (2), along with new cucurbitane glycosides, i.e., foetidissimosides E/F (3/4) as an 1 : 1 mixture of the (24R)/(24S) epimers, were obtained from the roots of Cucurbita foetidissima. Their structures were elucidated by means of a combination of homo- and heteronuclear 2D-NMR techniques (COSY, TOCSY, NOESY, ROESY, HSQC, and HMBC), and by FAB-MS. The new compounds were characterized as (3β,16α)-28-{[O-β-D-glucopyranosyl-(13)-O-β-D-xylopyranosyl-(14)-O-6-deoxy-α-L-mannopyranosyl-(12)-α-L-arabinopyranosyl]oxy}-16-hydroxy-28-oxoolean -12-en-3-yl β-D-glucopyranosiduronic acid (1…

Steroidal saponins from Chlorophytum orchidastrum.

2009

Six new spirostane-type saponins (1−6), named orchidastrosides A−F, and chloromaloside D were isolated from an ethanol extract of the roots of Chlorophytum orchidastrum. The saponins have neotigogenin or neogitogenin as the aglycon and oligosaccharidic chains possessing seven to nine sugar units. Their structures were elucidated mainly by 2D NMR spectroscopic analyses (COSY, TOCSY, NOESY, HSQC, and HMBC) and FABMS and HRESIMS. Compounds 1−6 were tested for cytotoxicity against two human colon cancer cell lines, HCT 116 and HT-29.

Bioactive Steroidal Saponins from Smilax medica

2006

Two new spirostanol saponins ( 1 and 2) were isolated from the roots of Smilax medica, together with the known smilagenin 3-O-beta-D-glucopyranoside (3). Their structures were determined by spectroscopic methods including 1D- and 2D-NMR experiments. Compounds 1 and 2 exhibited antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata and C. tropicalis (MICs between 6.25 and 50 microg/mL) whereas 3 was inactive.

A New Steroidal Saponin from Dioscorea cayenensis

2004

The new 26-O-beta-D-glucopyranosyl-3beta,26-dihydroxy-20,22-seco-25(R)-furost-5-en-20,22-dione-3-O-alpha-L-rhamnopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside (1), along with the known methyl protodioscin (2), asperoside (3) and prosapogenin A of dioscin (4) were isolated from the rhizomes of Dioscorea cayenensis LAM.-HOLL (Dioscoreaceae). Their structures were established mainly on the basis of 600 MHz 2D-NMR spectral data. 4 exhibited antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata and C. tropicalis (MICs of 20.8, 6.25, 25 microg/ml, respectively), whereas saponins 1-3 were inactive.

Two new biologically active triterpenoidal saponins acylated with salicylic acid from Albizia adianthifolia

2003

International audience; Two new oleanane-type triterpene saponins, adianthifoliosides A (1) and B (2), were isolated from a 95% ethanolic extract of roots of Albizia adianthifolia. Their structures were elucidated mainly by using a combination of 600 MHz 1D and 2D NMR techniques (COSY, NOESY, TOCSY, HSQC, and HMBC) and by FABMS and HRESIMS. Compounds 1 and 2 were characterized as glycosides of acacic acid acylated by an o-hydroxybenzoyl unit. The crude saponin mixture (CSM), compounds 1 and 2 together with 3 and 4 (prosapogenins obtained from the mild alkaline hydrolysate of the CSM), were evaluated for immunomodulatory activity on the Jurkat T cell line and for hemolytic property against s…

Triterpenoid saponins from Piptadeniastrum africanum (Hook. f.) Brenan

2013

One new triterpenoid saponin, named piptadeniaoside (1), along with two known saponins (2–3) have been isolated from the stem bark of Piptadeniastrum africanum. After previous isolation of flavone derivatives from this plant, new phytochemical investigations were performed for its saponin content. Their structures were established by direct interpretation of their spectral data, mainly HRESIMS, 1D NMR (1H, 13C NMR, DEPT) and 2D NMR (COSY, NOESY, HSQC and HMBC), and by comparison with the literature data.

Isolation and identification of new anthraquinones from Rhamnus alaternus L and evaluation of their free radical scavenging activity

2018

From the butanolic and the ethyl acetate extracts of Rhamnus alaternus L root bark and leaves, three new anthraquinone glycosides, alaternosides A-C (1,4,6,8 tetrahydroxy-3 methyl anthraquinone 1-O-ß-D-glucopyranosyl-4,6-di-O-α-L-rhamnopyranoside (1); 1,2,6,8 tetrahydroxy-3 methyl anthraquinone 8-O-ß-D-glucopyranoside (2) and 1, 6 dihydroxy-3 methyl 6 [2′-Me (heptoxy)] anthraquinone (3)) were isolated and elucidated together with the two known anthraquinone glycosides, Physcion-8-O-rutinoside (4) and emodin-6-O-α-L-rhamnoside (5) as well as with the known kaempferol-7-methylether (6), β-sitosterol (7) and β-sitosterol-3-O-glycoside (8). Their chemical structures were elucidated using spectr…

Chionaeosides A–D, Triterpene Saponins from Paronychia chionaea

2007

Four new triterpenoid saponins, chionaeosides A-D (1-4) were isolated from the roots of Paronychia chionaea. On the basis of their spectroscopic data, the structures of the new saponins were established as 3-O-alpha-L-arabinopyranosylgypsogenic acid 28-O-beta-D-glucopyranosyl-(1--3)-beta-D-glucopyranosyl-(1--6)-beta-D-glucopyranoside (1), 3-O-alpha-L-arabinopyranosylgypsogenic acid 28-O-beta-D-glucopyranosyl-(1--6)-beta-D-glucopyranoside (2), 3-O-alpha-L-arabinopyranosylgypsogenic acid 28-O-beta-D-glucopyranoside (3), and 3-O-alpha-L-arabinopyranosylgypsogenic acid (4).

Hederagenin glycosides from the fruits of Blighia unijugata

2019

Abstract A phytochemical investigation of Blighia unijugata led to the isolation of eleven hederagenin glycosides. Among these compounds, six are previously undescribed, two are described in their native forms for the first time and three are known whereas firstly isolated from Blighia unijugata. The structure of the undescribed compounds was elucidated on the basis of 2D NMR and mass spectrometry analyses as 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-3-O-acetyl-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyr…

Flavonoids from Acacia pennata and their Cyclooxygenase (COX-1 and COX-2) Inhibitory Activities

2007

Two new flavonoids quercetin 4'-O-alpha-L-rhamnopyranosyl-3-O-beta-D-allopyranoside (1) and apigenin 6-C-[2''-O-(E)-feruloyl- beta-D-glucopyranosyl]-8-C-beta-glucopyranoside (2), along with the known isorhamnetin 3-O-alpha-L-rhamnopyranoside (3), kaempferol 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranoside (4), and isovitexin (5) were isolated from the leaves of Acacia pennata Willd. (Mimosaceae) and tested for their anti-inflammatory activity. Their structures were determined by 1D and 2D NMR and mass spectrometry. They were tested for an inhibitory effect on COX-1 and COX-2, showing 60-90% inhibition at 10(-4) g/mL and 5-14% inhibition at 10(-4) g/mL, respectively.