Steroidal saponins of Asparagus adscendens

From the methanol extract of the fruits of Asparagus adscendens sitosterol-β-d-glucoside, two spirostanol glycosides (asparanin A and B) and two furostanol glycosides (asparoside A and B) were isolated and characterized as 3-O-[β-d-glucopyranosyl (1→2)-β-d-glucopyranosyl]-(25S)-5β-spirostan-3β-ol, 3-O-{[β-d-glucopyranosyl(1→2)][α-l-rhamnopyranosyl(1→4)]-β-d-glucopyranosyl}-(25S)-5β-spirostan-3β-ol,3-O-{[β-d-glucopyranosyl(1→2)][α-l-rhamnopyranosyl(1→4)]-β-d-glucopyranosyl|} -26-O-(β- d-glucopyranosyl)-22α-methoxy-(25S)-5β-furostan-3β,26-diol and 3-O-{[β-d-glucopyranosyl(1→2)][α-l-rhamnopyranosyl(1→4)]-β-d-glucopyranosyl}-26-O-(β-d-glucopyranosyl)- 25S)-5β-furostan-3β,22α, 26-triol, respectively.     

Steroidal saponins of Yucca filamentosa: Yuccoside C and protoyuccoside C

Two new saponins, yuccoside C and protoyuccoside C, have been isolated from the methanolic extract of Yucca filamentosa root and their structures elucidated. Yuccoside C is 3-O-[α-d-galactopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranosyl]-(25S)-5β-spirostan-3β-ol, whereas protoyuccoside C is 3-O-[α-d-galactopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranosyl]-26-O-[β-d-glucopyranosy]-(25S)-5β-furostan-3β,22α,26-triol.     

Spirostanol glycosides from Asparagus plumosus

Three spirostanol glycosides were isolated from a methanol extract of the leaves of Asparagus plumosus and characterized.     

New steroidal saponins of Agave americana

Two new saponins, agavasaponin E and agavasaponin H have been isolated from the methanolic extract of Agave americana leaves and their structures elucidated. Agavasaponin E is 3-O-[β-d-xylopyranosyl-(1→2glc1)-α-l-rhamnopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→3glc 1)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranosyl-(1→4)-α-d-galactopyranosyl]-(25R)-5α-spirostan-12-on-3β-ol, whereas agavasaponin H is 3-O-[β-d-xylopyranosyl-(1→2 glc 1)-α-l-rhamnopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→3 glc 1)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranosyl-(1→4)-β-d-galactopyranosyl]-26-O-[β-d-glucopyranosyl]-(25R)-5α-furostan-12-on-3β,22α,26-triol.     

Oligofurostanosides from Solanum nigrum

One spirostanol glycoside and two furostanol glycosides have been isolated from a methanol extract of the stems and roots of Solanum nigrum and ide     

Oligofuro- and spiro-stanosides of Asparagus adscendens

Two oligofurostanosides and two spirostanosides, isolated from a methanol extract of Asparagus adscendens (leaves), were characterized as 3-O-[{α-l-rhamnopyranosyl (1 → 4)} {α-l-rhamnopyranosyl (1 → 6)}-β-d-glucopyranosyl]-26-O-[β-d-glucopyranosyl]-22α-methoxy-(25S)-furost-5-en-3β,26-diol (Adscendoside A), 3-O-[{α-l-rhamnopyranosyl (1 → 4)} {α-l-rhamnopyranosyl (1 → 6)}-β-d-glucopyranosyl]-26-O-[β-d-glucopyranosyl]-(25S)-furost-5-en-3β,22α,26-triol-(Adscendoside B), 3-O-[{α-l-rhamnopyranosyl (1 → 6)}-β-d-glucopyranosyl]-(25S)-spirostan-5-en-3β-ol (Adscendin A) and 3-O-[{α-l-rhamnopyranosyl (1 → 4)} {α-l-rhamnopyranosyl (1 → 6)}-β-d-glucopyr anosyl]-(25S)-spirostan-5-en-3β-ol (Adscendin B), respectively. Adscendin B and Adscendoside A are the artefacts of Adscendoside B formed through hydrolysis and methanol extraction respectively.bl]     

Novel steroidal saponins from Dioscorea esculenta (Togedokoro)

Fifteen steroidal saponins 1–15, which include 4 furostanol glycosides 1–3 and 15, and 11 spirostanol glycosides 4–14, were isolated from the tubers and leaves of lesser yam (Dioscorea esculenta, Togedokoro). Their structures were identified by nuclear magnetic resonance and liquid chromatography mass spectroscopy. Four steroidal saponins 9, 11, 14, and 15 were found to be novel compounds.     

Steroidal saponins and ecdysterone from Asparagus filicinus and their cytotoxic activities

Two new spirostanoides, filiasparosides E (1) and F (2), one new furostanoside, filiasparoside G (3), and one new ecdysterone, stachysterone A-20, 22-acetonide (4), together with six known steroidal saponins, asparagusin A (5), filiasparoside A (6), filiasparoside B (7), aspafilioside A (8), aspafilioside B (9), and filiasparoside C (10) were isolated from the roots of Asparagus filicinus Buch.-Ham. Their structures were elucidated on the basis of spectroscopic and chemical evidence. Compounds 1-10 were investigated for their cytotoxicities against human breast adenocarcinoma MDA-MB-231 cell line and compounds 8-10 exhibited cytotoxic activities with IC₅₀ values ranging from 3.4 to 6.6 μM.     

A saponin from Asparagus gonocladus

The ethanolic extract of the aerial part of Asparagus gonocladus yielded a new saponin. It was identified as lup-20(29)-en-28-oic-3-O-α-l-rhamnopyranosyl-(2 → 1)-O-β-d-glucopyranoside.     

Steroidal saponins from Asparagus acutifolius

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 microg/ml.     

Diosgenin saponins from Dioscorea floribunda

Five spirostanol glycosides and two furostanol glycosides were isolated from Dioscorea floribunda. In addition to the IR spectra of the free glycosides and the MS of the peracetates and permethyl ethers, the most effective method for structural determination proved to be the NMR spectra of the free saponins in pyridine-d₅.     

Beshornin and beshornoside,steroidal saponins of Beshorneria yuccoides

Two new saponins beshornin and beshornoside have been isolated from the methanolic extract of Beshorneria yuccoides leaves and their structures elucidated. Beshornin is 3-O-[α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl- (1 → 2)-[α-l-rhamnopyranosyl-(1 -+ 4)-P-D-glucopyranosyl-(1 → 3)]-β-d-glucopyranosyl-(1 → 4)-β-d- galactopyranosyl-(25R)-5α-spirostan-3β-ol, whereas beshornoside is 3-O-[α-l-rhamnopyranosyl-(1 → 4)- β-d)-glycopyranosyl-(1 → 2)]-[α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 3)]-β-d-glucopyranosyl- (1 → 4)-β-d-galactopyranosyl 26-O-[β-d]-glucopyranosyl-(25R)-5α-furostan-3β,22α,26-triol.     

Melongosides n,o and p: steroidal saponins from seeds of solanum melongena

Three new saponins, melongosides N, O and P, have been isolated from the methanolic extract of seeds of Solanum melongena and their structures elucidated. Melongoside N is 3-O-[β-D-glucopyranosy l-(1 → 2)-β-D-glucopyranosyl]-26-O-(β-D-glucopyranosyl)-(25R)-5α-furostan-3β,22 α,26-triol, whereas melongoside O is 3-O-[β-D-glucopyranosyl-(1 → 2)β-D-glucopyranosyl]- 26-O-(β-D-glucopyranosyl)-(25R)-furost-5-en-3β,22α,26-triol and melongoside P is 3-O- [β-D-glucopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 3)]-β-D-glucopyranosyl)-26-O- (β-D-glucopyranosyl)-(25 R)-5α-furostan-3β,22α,26-triol.     

Steroidal saponins from Dioscorea floribunda: Structures of floribundasaponins A and B

Two steroidal saponins, floribundasaponins A and B isolated from the yams of Dioscorea floribunda, have been characterized as pennogenin-3-O-β-d-glucopyranoside and pennogenin-3-O-α-l-rhamnopyranosyl(1→4)-β-d-glucopyranoside.     

Steroidal saponins from the leaves of Beaucarnea recurvata

Thirteen steroidal saponins were isolated from the leaves of Beaucarnea recurvata Lem. Their structures were established using one- and two-dimensional NMR spectroscopy and mass spectrometry. Six of them were identified as: 26-O-β-d-glucopyranosyl (25S)-furosta-5,20(22)-diene 1β,3β,26-triol 1-O-α-l-rhamnopyranosyl-(1 → 2) β-d-fucopyranoside, 26-O-β-d-glucopyranosyl (25S)-furosta-5,20(22)-diene 1β,3β,26-triol 1-O-α-l-rhamnopyranosyl-(1 → 2)-4-O-acetyl-β-d-fucopyranoside, 26-O-β-d-glucopyranosyl (25R)-furosta-5,20(22)-diene-23-one-1β,3β,26-triol 1-O-α-l-rhamnopyranosyl-(1 → 2) β-d-fucopyranoside, 26-O-β-d-glucopyranosyl (25S)-furosta-5-ene-1β,3β,22α,26-tetrol 1-O-α-l-rhamnopyranosyl-(1 → 4)-6-O-acetyl-β-d-glucopyranoside, 26-O-β-d-glucopyranosyl (25S)-furosta-5-ene-1β,3β,22α,26-tetrol 1-O-α-l-rhamnopyranosyl-(1 → 2) β-d-fucopyranoside, and 24-O-β-d-glucopyranosyl (25R)-spirost-5-ene-1β,3β,24-triol 1-O-α-l-rhamnopyranosyl-(1 → 2)-4-O-acetyl-β-d-fucopyranoside. The chemotaxonomic classification of B. recurvata in the family Ruscaceae was discussed.     

Steroidal saponins from the fruits of Asparagus racemosus

Three steroidal saponins, racemosides A (1), B (2) and C (3), were isolated from the methanolic extract of the fruits of Asparagus racemosus, and characterized as (25S)-5beta-spirostan-3beta-ol-3-O-{beta-D- glucopyranosyl (1-->6)-[alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranosyl (1-->4)]-beta-D-glucopyranoside}, (25S)-5beta-spirostan-3beta-ol-3-O-alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranoside and (25S)-5beta-spirostan-3beta-ol-3-O-{alpha-L-rhamnopyranosyl-(1-->6)-[alpha-L-rhamnopyranosyl (1-->4)]-beta-D-glucopyranoside}, respectively, by spectrometric analysis and some chemical strategies.     

黑刺菝葜中的甾体皂苷

从黑刺菝葜(Smitax scobinicaulis C.H.Wringh)根茎中再次分离得到2个新的甾体皂苷化合物,经理化、光谱分析及与标准样品对照,鉴定化合物Ⅲ为(25D)螺甾-5-烯-3β,17α,27-三羟基-3-O-β-D-吡喃葡萄糖-(1→4)-O-[α-L-吡喃阿拉伯糖(1→6)]-β-D-吡喃葡萄糖甙。化合物Ⅳ为(25D)螺甾-3β,17α,27-三羟基-3-O-β-D-吡喃葡萄糖-(1→4)-O-[α-L-吡喃阿拉伯糖(1→6)]-β-D-吡喃葡萄糖甙。     

Triterpenoid saponins from Fatsia japonica

Five triterpenoid saponins isolated from the flowers, the mature fruits and the leaves of Fatsia japonica were identified as 3-O-[β-d-glucopyranosyl(1→4)-β-d-glucopyranosyl]-hederagenin (1), 3-O-[β-d-glucopyranosyl-(1→4)-α-l-arabinopyranosyl]-oleanolic acid (2), 3-O-[α-l-arabinopyranosyl]-hederagenin (3), 3-O-[β-d-glucopyranosyl]-hederagenin (4) and 3-O-[β-d-glucopyranosyl(1→4)-α-l-arabinopyranosyl]-hederagenin (5). The saponins 1 and 2 are new, naturally occurring, triterpenoid saponins. The distribution of the five saponins in three parts of the plant was investigated. Saponins 2, 3 and 5 were present in the flowers, saponins 1, 3, 4 and 5 were in the mature fruits and saponins 2, 3, 4 and 5 were in the leaves.     

Steroidal glycosides from the rhizomes of Ruscus hypophyllum

Seven steroidal glycosides, along with one known glycoside, were isolated from the rhizomes of Ruscus hypophyllum (Liliaceae). Comprehensive spectroscopic analysis, including 2D NMR spectroscopy, and the results of acid hydrolysis allowed the chemical structures of the compounds to be assigned as (23S,25R)-23-hydroxyspirost-5-en-3beta-yl O-alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranoside (1), 1beta-hydroxyspirosta-5,25(27)-dien-3beta-yl O-alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranoside (2), (22S)-16beta,22-dihydroxycholest-5-en-3beta-yl O-alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranoside (3), (22S)-16beta-[(beta-d-glucopyranosyl)oxy]-22-hydroxycholest-5-en-3beta-yl O-alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranoside (4), (22S)-16beta-[(beta-d-glucopyranosyl)oxy]-22-hydroxycholest-5-en-3beta-yl beta-d-glucopyranoside (5), (22S)-16beta-[(beta-d-glucopyranosyl)oxy]-3beta,22-dihydroxycholest-5-en-1beta-yl O-alpha-l-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl-beta-d-xylopyranoside) (6), and (22S)-16beta-[(beta-d-glucopyranosyl)oxy]-3beta,22-dihydroxycholest-5-en-1beta-yl O-alpha-l-rhamnopyranosyl-(1-->2)-O-[beta-d-xylopyranosyl-(1-->3)]-beta-d-xylopyranoside (7), respectively. This is the first isolation of a series of cholestane glycosides from a Ruscus species.