Phytochemistry of Weigela x "kosteriana variegata" (Caprifoliaceae)

International audience; One new triterpene glycoside 3-O-beta-D-xylopyranosyl-(1 -> 4)-[beta-D-glucopyranosyl-(1 -> 3)]-beta-D-xyl opyranosyl-(1 -> 4)-beta-D-xylopyranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-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 H-1- and C-13 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 …

Triterpene glycosides from plants for antibody recognition

A new oleanane glycoside from the roots ofAstragalus caprinus

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

Saponins from the Roots of Nylandtia spinosa

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…

Secondary metabolites from polar fractions of Piper umbellatum.

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

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

New Triterpenoid and Ergostane Glycosides from the Leaves of Hydrocotyle umbellata L.

Two new triterpenoid glycosides, together with two new ergostane glycosides, umbellatosides A–D (1–4, resp.), have been isolated from the leaves of Hydrocotyle umbellata L. Their structures were established by 2D-NMR spectroscopic techniques (1H,1H-COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry as 3β,22β-dihydroxy-3-O-[α-L-rhamnopyranosyl-(12)-β-D-glucuronopyranosyl]olean-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester (1), 3-O-[α-L-rhamnopyranosyl-(12)-β-D-glucuronopyranosyl]oleanolic acid 28-O-β-D-glucopyranosyl ester (2), (3β,11α,26)-ergosta-5,24(28)-diene-3,11,26-triol 3-O-(β-D-glucopyranosyl)-11-O-(α-L-rhamnopyranosyl)-26-O-β-D-glucopyranoside (3), and (3β,11α,21,26)-ergosta…

Ursane-Type Triterpene Saponins fromZygophyllum geslini

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)

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.

New ursolic and betulinic derivatives as potential cytotoxic agents.

Fifteen new ursolic and betulinic triterpenoids, bearing various functionalities at C-3 and C-28 were synthesized as potential cytotoxic agents. All compounds were obtained by a hemisynthetic route via ursolic and betulinic acids. Preliminary screening of these compounds on human HT 29 colon cancer cells revealed inhibitory activity for three of them. Beta-D-Glucopyranosyl-3beta-hydroxyurs-12(13)-en-28-oate 1c, 3beta-3-(3-pyridyl)-prop-2-enoyloxyurs-12(13)-en-28-oic acid 1i and the potassium salt of 3beta-cinnamoyloxylup-20(29)-en-28-oic acid 2d demonstrated cytotoxic activity in the micromolar range: 8.0, 45.0 and 8.0 microM, respectively.

Steroidal saponins from the fruits of Solanum torvum

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

Constituents of the leaves of Eucalyptus saligna

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

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

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)

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.

Triterpene saponins of the root bark of Olax obtusifolia De Wild

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

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

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

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).

Acylated oleanane-type saponins from Ganophyllum giganteum

Abstract Five oleanane-type saponins , 3- O -β- D -glucuronopyranosylzanhic acid 28- O -β- D -xylopyranosyl-(1→3)-[α- L -rhamnopyranosyl-(1→2)]-(4- O -acetyl)-β- D -fucopyranosyl ester ( 1 ), 3- O -β- D -glucopyranosylzanhic acid 28- O -β- D -xylopyranosyl-(1→3)-[α- L -rhamnopyranosyl-(1→2)]-(4- O -acetyl)-β- D -fucopyranosyl ester ( 2 ), zanhic acid 28- O -β- D -xylopyranosyl-(1→3)-[α- L -rhamnopyranosyl-(1→2)]-(4- O -acetyl)-β- D -fucopyranosyl ester ( 3 ), zanhic acid 28- O -α- L -rhamnopyranosyl-(1→2)-4- O -[(3′-hydroxy-2′-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-β- D -fucopyranosyl ester ( 4 ), medicagenic acid 28- O -α- L -rhamnopyranosyl-(1→2)-4- O -[(3′-hydroxy-2′-methyl-…

Triterpene Saponins from Cyclamen trocopteranthum

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…

Two Triterpene Saponins from Achyranthes bidentata.

Bidentatoside II (1) and chikusetsusaponin V methyl ester (2) are two further triterpene saponins isolated from the roots of Achyranthes bidentata. Chemical and homo and heteronuclear two-dimensional (2D) NMR techniques have led to the structural elucidation of 1 which is a new seco-glycoside of oleanolic acid and the full 1H- and 13C-NMR assignments of 2. These compounds did not show any potentiation of the in vitro cytotoxicity of cisplatin in the HT 29 human colon cancer cell line.

Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum

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

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.

New Steroidal Alkaloids from Solanum Hypomalacophyllum

Two new steroidal alkaloids (1-2) have been isolated from the leaves and roots of Solanum hypomalacophyllum Bitter, respectively. Their structures have been elucidated as deacetoxysolaphyllidine-3- O-β-D-glucopyranoside (1) and 4-keto-5,6-dihydro-(20 S)-verazine (2). Furthermore, two known steroidal alkaloids, 20 R-verazine and 20 S-verazine, and the common secondary metabolites oleanolic acid and β-sitosterol were isolated from the roots, whereas deacetoxysolaphyllidine was obtained from the leaves.

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

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…

Two new triterpenoid saponins fromPittosporum senaciaPutterlick (Pittosporaceae)

From the branches of Pittosporum senacia Putterlick (Pittosporaceae), two new triterpenoid saponins, senaciapittosides A and B (1, 2), were isolated. Their structures were elucidated by extensive analysis of one- and two-dimensional nuclear magnetic resonance spectroscopy, high-resolution electrospray ionization mass spectrometry (HR-ESIMS) and chemical evidence as 3-O-[β-d-glucopyranosyl-(1  2)]-[α-l-arabinopyranosyl-(1  3)]-[α-l-arabinofuranosyl-(1  4)]-β-d-glucuronopyranosyl oleanolic acid 28-O-β-d-glucopyranosyl ester (1) and 3-O-[β-d-glucopyranosyl-(1  2)]-[α-l-arabinopyranosyl-(1  3)]-[α-l-arabinofuranosyl-(1  4)]-β-d-glucuronopyranosyl-22-O-α-l-arabinopyranosyl-21-acetoxy R1-barrigen…

ChemInform Abstract: Two Triterpene Saponins from Achyranthes bidentata.

Bidentatoside II (1) and chikusetsusaponin V methyl ester (2) are two further triterpene saponins isolated from the roots of Achyranthes bidentata. Chemical and homo and heteronuclear two-dimensional (2D) NMR techniques have led to the structural elucidation of 1 which is a new seco-glycoside of oleanolic acid and the full 1H- and 13C-NMR assignments of 2. These compounds did not show any potentiation of the in vitro cytotoxicity of cisplatin in the HT 29 human colon cancer cell line.

A New Aromatic Compound from the Stem Bark of Terminalia catappa

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.

Two new triterpene saponins from Eryngium campestre.

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 the roots of Spergularia marginata.

Phytochemical investigations of the roots of Spergularia marginata had led to the isolation of four previously undescribed triterpenoid saponins, a known one and one spinasterol glycoside. Their structures were established by extensive NMR and mass spectroscopic techniques as 3-O-β-D-glucuronopyranosyl echinocystic acid 28-O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L- arabinopyranosyl ester, 3-O-β-D-glucopyranosyl-(1 → 3)-β-D-glucuronopyranosyl echinocystic acid 28-O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)- α-L-arabinopyranosyl ester, 3-O-β-D-glucopy…

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

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.

Steroidal Saponins from the Fruits of Cestrum ruizteranianum

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.

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-(…

A review of natural and modified betulinic, ursolic and echinocystic acid derivatives as potential antitumor and anti-HIV agents.

The aim of this review is to update current knowledge on the betulinic, ursolic and echinocystic acids and their natural and semisynthetic analogs, focussing on their cytotoxic and anti-HIV activities. Then, the last results of the authors' team on unusual semisynthetic derivatives of these triterpenoids will be presented in order to establish structure/activity relationships.

Constituents isolated from Polyscias fulva

Cytotoxic steroidal glycosides from Allium flavum.

Abstract Three new spirostane-type glycosides ( 1 – 3 ) were isolated from the whole plant of Allium flavum . Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20 S ,25 R )-2α-hydroxyspirost-5-en-3β-yl O -β- d -xylopyranosyl-(1 → 3)-[β- d -galactopyranosyl-(1→2)]-β- d -galactopyranosyl-(1→4)-β- d -galactopyranoside ( 1 ), (20 S ,25 R )-2α-hydroxyspirost-5-en-3β-yl O -β- d -xylopyranosyl-(1 → 3)-[β- d -glucopyranosyl-(1→2)]-β- d -galactopyranosyl-(1→4)-β- d -galactopyranoside ( 2 ), and (20 S ,25 R )-spirost-5-en-3β-yl O -α- l -rhamnopyranosyl-(1 → 4)-[β- d -glucopyranosyl-(1→2)]-β- d -glucopyranoside ( 3 ). The three saponins were evaluated f…

Antifungal steroid saponins from Dioscorea cayenensis.

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 …

Four new triterpene saponins from Bupleurum rigidum L.

Abstract Four previously undescribed triterpene saponins (1-4) were isolated from the EtOH/H2O extract of the aerial parts of Bupleurum rigidum, together with a known structural analogue. Their structures were elucidated by analysis of 1D-(1H, 13C) and 2D-NMR (1H-1H COSY, TOCSY, ROESY, HSQC, HMBC) spectroscopic data and mass spectrometry (ESI- and HR-ESI-MS) and by comparison with those of related metabolites. An unusual structure was characterized as 3-O-β-D-glucopyranosyl-(1 → 2)-[ β-D-glucopyranosyl-(1 → 3)]- β-D-fucopyranosyl-21-O-β-D-glucoyranosyl-3β,16β,21β,23-tetrahydroxy-13,28-epoxyolean-11-ene (1). The three other compounds shared the same sugar sequence as 1 and differed by the st…

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

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.

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…

Furostane-Type Steroidal Saponins from the Roots ofChlorophytum borivilianum

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

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

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

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…

Steroidal saponins from Chlorophytum deistelianum.

Abstract Phytochemical investigation of the aerial parts of Chlorophytum deistelianum led to the isolation of four previously undescribed steroidal saponins called chlorodeistelianosides A–D with five known ones. Their structures were established mainly by extensive 1D and 2D NMR spectroscopic techniques and mass spectrometry as (25R)-3β-[(β- d -glucopyranosyl-(1 → 3)-[α- l -rhamnopyranosyl-(1 → 4)]-β- d -xylopyranosyl-(1 → 3)-[β- d -glucopyranosyl-(1 → 2)]-β- d -glucopyranosyl-(1 → 4)-β- d -galactopyranosyl)oxy]-5α-spirostan-12-one, (24S,25S)-24-[(β- d -glucopyranosyl)oxy]-3β-[(β- d -glucopyranosyl-(1 → 2)-[β- d -xylopyranosyl-(1 → 3)]-β- d -glucopyranosyl-(1 → 4)-β- d -galactopyranosyl)ox…

Triterpene Saponins from Wisteria floribunda “macrobotrys” and “rosea”

Five oleanane-type saponins were isolated from two cultivars of Wisteria floribunda (Willd.) DC. (Fabaceae): From the roots of Wisteria floribunda “macrobotrys”, one new oleanane derivative elucidated as 3- O-β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranosyl-22- O-acetyl-3p,22p,24-trihydroxyolean-12-en-30-oic acid, and two known glycosides, and from the roots of Wisteria floribunda “rosea”, two known ones. Their structures were elucidated by a detailed 600 MHz NMR analysis including 1D and 2D NMR (1H, 13C, COSY, TOCSY, ROESY, HSQC, HMBC) experiments and mass spectrometry. Chemotaxonomic conclusions were proposed.

Bioactive aristolactams from Piper umbellatum.

Four alkaloids named piperumbellactams A-D (1-4) were isolated from branches of Piper umbellatum together with known N-hydroxyaristolam II (5), N-p-coumaroyl tyramine (6), 4-nerolidylcatechol (7), N-trans-feruloyltyramine, E-3-(3,4-dihydroxyphenyl)-N-2-[4-hydroxyphenylethyl]-2-propenamide, beta-amyrin, friedelin, apigenin 8-C-neohesperidoside, acacetin 6-C-beta-d-glucopyranoside, beta-sitosterol, its 3-O-beta-d-glucopyranoside and its 3-O-beta-d-[6'-dodecanoyl]-glucopyranoside. Glycosidase inhibition, antioxidant and antifungal activities of these compounds were evaluated. Compounds 1-3 showed moderate alpha-glucosidase enzyme inhibition with IC50 values 98.07+/-0.44, 43.80+/-0.56 and 29.64…

Triterpene saponins from Billia rosea.

Five previously undescribed triterpene saponins, billiosides A-E, and a known analogue, were isolated from the seeds of Billia rosea (Planch. & Linden) C. Ulloa & P. Jorg. Their structures were elucidated on the basis of extensive 1D and 2D NMR experiments (1H, 13C, DEPT, COSY, TOCSY, NOESY, ROESY, HSQC, and HMBC) and mass spectrometry as (3β,21β,22α)-3-[(2-O-β-D-glucopyranosyl-O-[α-L-arabinopyranosyl-(1 → 4)]-β-D-glucopyranosyl)oxy]-21-[((2E,6S)-2,6-dimethyl-6-hydroxyocta-2,7-dienoyl)oxy]-22-(acetyloxy)-24-hydroxyolean-12-en-28-oic acid, (3β,21β,22α)-3-[(2-O-β-D-galactopyranosyl-β-D-glucopyranosyl)oxy]-21,22-dihydroxyolean-12-en-28-yl O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranoside, (3β…

Cytotoxic glycosides from the roots of Weigela x “Bristol Ruby”

International audience; Seven oleanane-type glycosides were extracted and isolated by various chromatographic methods from the roots of Weigela x "Bristol Ruby" (1-7), six previously undescribed (1-6) and a known one (7). Their structures were assigned by spectroscopic analysis mainly 2D NMR and mass spectrometry (ESIMS). Selected triterpenoid glycosides (1-3, 6, 7) displayed a good cytotoxic activity against a mouse colon cancer cell line CT26.

Ursane-type saponins from Zygophyllum cornutum

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

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

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

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”

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…

Triterpene Saponins from Cyclamen persicum

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

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.

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…

Triterpene saponins from the roots of Bupleurum spinosum Gouan

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…

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

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 →…

Oleanane-type saponins from the roots of Wisteria floribunda macrobotrys

Triterpenoid Saponins From the Root Bark of Haplocoelum congolanum

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.

Triterpenoid saponins from the roots of two Gypsophila species.

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

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…

A review on the phytopharmacological studies of the genus Polygala

Abstract Ethnopharmacological relevance The genus Polygala, the most representative genus of the Polygalaceae family, comprises more than 600 species from all over the world of which around 40 are distributed in China, some of them, being used in the Traditional Chinese Medicine system. Aim of the review We intend to discuss the current knowledge about the traditional uses, and the newest phytochemical and pharmacological achievements with tentative elucidation of the mechanism of action on the genus Polygala covering the period 2013–2019 to provide a scientific support to the traditional uses, and to critically analyze the reported studies to obtain new insights for further researches. Mat…

Triterpenoid Saponins From the Stem Bark of Pentaclethra eetveldeana

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.

Sphingolipids and other constituents from Cordia platythyrsa

New Acylated Triterpene Saponins fromPolygala arenaria

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

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).

Chemical constituents from Phlomis bovei Noë and their chemotaxonomic significance

Abstract A phytochemical investigation of the leaves and roots of Phlomis bovei Noe (Lamiaceae) led to the isolation of sixteen compounds, including iridoids (1, 2, 3), megastigmanes (4, 5), phenylpropanoids (6, 7, 8, 9, 10), lignans (11, 12, 13, 14), a nortriterpene (15), and a phenyl glucoside (16). Compounds (1, 2, 4, 5, 6, 10) were obtained from the leaves and compounds (1, 2, 3, 7, 8, 9, 11, 12, 13, 14, 15, 16) were isolated from the roots. Compounds 1 and 2 were found both in the leaves and in roots. The compounds were identified by analysis of 1D- (1H, 13C), 2D-NMR (1H–1H COSY, TOCSY, ROESY, HSQC, HMBC) spectroscopic data, mass spectrometry (ESI- and HR-ESI-MS), and by comparison wit…

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

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)

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

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

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.

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

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…

Induction of Neuronal Differentiation in Neurosphere Stem Cells by Ellagic Acid Derivatives

A bioassay-guided fractionation of methanol extracts of stem barks, combined with screening based on Epidermal Growth Factor (EGF)-responsive neural stem cells (erNSCs) differentiation assay, has been used. This study resulted in the isolation of 3,3′-di- O-methylellagic acid 1, 3,3′-di- O-methyl ellagic acid-4- O-β-D-xylopyranoside 2, ellagic acid 3, and arjunolic acid 4. Among them, compounds 1 and 2 exhibit potent induction of neuronal differentiation in neurosphere stem cells with no cytotoxic effect. These results indicate that compounds 1 and 2 may be useful as pharmacological agents for the treatment of neurodegenerative diseases. These compounds may account, for the use of T. super…

Two New Triterpene Saponins from Cyclamen africanumBoiss. & Reuter

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-…

Glycoside derivatives of scopoletin and β-sitosterol from Hymenodictyon floribundum

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

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

) 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…

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

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

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…

Bidentatoside I, a New Triterpene Saponin from Achyranthes bidentata

Bidentatoside I (1) is a new triterpene saponin bearing an unusual dioxopropionic acid unit, isolated from the roots of Achyranthes bidentata. Structural elucidation was performed mainly by chemical and homo- and heteronuclear 2D NMR techniques. This compound did not show any potentiation of the in vitro cytotoxicity of cisplatin in the HT 29 human colon cancer cell line.

A New Phenanthrene Glycoside and Other Constituents from Dioscorea opposita

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

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 Chlorophytum deistelianum

Abstract Phytochemical investigation of the aerial parts of Chlorophytum deistelianum led to the isolation of four previously undescribed steroidal saponins called chlorodeistelianosides A–D with five known ones. Their structures were established mainly by extensive 1D and 2D NMR spectroscopic techniques and mass spectrometry as (25R)-3β-[(β- d -glucopyranosyl-(1 → 3)-[α- l -rhamnopyranosyl-(1 → 4)]-β- d -xylopyranosyl-(1 → 3)-[β- d -glucopyranosyl-(1 → 2)]-β- d -glucopyranosyl-(1 → 4)-β- d -galactopyranosyl)oxy]-5α-spirostan-12-one, (24S,25S)-24-[(β- d -glucopyranosyl)oxy]-3β-[(β- d -glucopyranosyl-(1 → 2)-[β- d -xylopyranosyl-(1 → 3)]-β- d -glucopyranosyl-(1 → 4)-β- d -galactopyranosyl)ox…

Phytochemistry of Weigela x “kosteriana variegata” (Caprifoliaceae)

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.

Steroidal saponins from Chlorophytum orchidastrum.

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.

A New Steroidal Saponin from Dioscorea cayenensis

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.

Natural Triterpene Glycosides for Antibody Recognition

Multiple sclerosis is an autoimmune disease that affects the central nervous system. The key role of the glycosylation in disease pathogenesis has been previously studied and the synthetic N-glucosylated peptide CSF114(Glc) proved its efficiency in autoantibody recognition in the sera of multiple sclerosis patients. Herein, pure natural triterpene glycosides containing different glycosyl moieties were isolated and tested in multiple sclerosis patientsʼ sera to better understand the role of glycosylation. They were selected taking into account the nature and complexity of their osidic part. Five triterpene glycosides were isolated from several plants with more than 95 % purity. The interacti…

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

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.

Two New Oleanane-type Saponins from Hydrocotyle multifida

A phytochemical study of a Venezuelan species Hydrocotyle multifida led to the isolation of five oleanane-type glycosides: two previously undescribed and three known ones. 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-glucuronopyranosyloleanolic acid and 3- O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyrano-syloleanolic acid. These results represent a significative contribution to the chemotaxonomy of the Hydrocotyle genus.

Hederagenin glycosides from the fruits of Blighia unijugata

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…