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 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…

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.

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…

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-…

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.

Steroidal saponins from two species of Dracaena.

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…

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…

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…

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…

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…

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…

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.

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.

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.

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…

Oleanane-type saponins from the roots of Wisteria floribunda macrobotrys

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…

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…

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…

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…

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.

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.