Two new bioactive triterpene glycosides from the sea cucumber Pseudocolochirus violaceus

By activity-guided fractionation, two new triterpene glycosides, violaceusides A (1) and B (2), were isolated from the sea cucumber Pseudocolochirus violaceus as active compounds causing morphological abnormality of Pyricularia oryzae mycelia. By extensive 2D NMR techniques and chemical evidence, the structures of the two new glycosides were established as 16β-acetoxy-3-O-[3-O-methyl-β-d-glucopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)-β-d-quinovopyranosyl-(1 → 2)-4-O-sodiumsulphate-β-d-xylopyranosyl]-holosta-7,24-diene-3β-ol (1) and 16β-acetoxy-3-O-[3-O-methyl-β-d-glucopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 2)-4-O-sodiumsulphate-β-d-xylopyranosyl]-holosta-7,24-diene-3β-ol (2), respectively. The two glycosides also exhibited significant cytotoxicity against HL-60 and BEL-7402 cancer cell lines.     

Note: Xanthone glycosides from Swertia franchetiana

A new xanthone glycoside (1) has been isolated from Swertia franchetiana together with five known xanthone glycosides. Their structures were elucidated as 7-O-[β-d-xylopyranosyl-(1→2)-β-d-xylopyranosyl]-1,7,8-trihydroxy-3-methoxyxanthone (1), 7-O-[α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranosyl]-1,7,8-trihydroxy-3-methoxyxanthone (2), 8-O-β-d-glucopyranosyl-1,3,5,8-tetrahydroxyxanthone (3), 1-O-β-d-glucopyranosyl-1-hydroxy-3,7,8-trimethoxyxanthone (4), 1-O-[β-d-xylopyranosyl-(1→6)-β-d-glucopyranosyl]-1-hydroxy-2,3,5-trimethoxyxanthone (5) and 1-O-[β-d-xylopyranosyl-(1→6)-β-d-glucopyranosyl]-1-hydroxy-3,5-dimethoxyxanthone (6) on the basis of spectroscopic evidence.     

Three new steroidal saponins from Fritillaria pallidiflora

Three new steroidal saponins, pallidiflosides A (1), B (2), and C (3), have been isolated from the dry bulbs of Fritillaria pallidiflora Schrenk. Their structures were elucidated as 26-O-β-d-glucopyranosyl-(25R)-furost-5,20(22)-dien-3β,26-diol-3-O-β-d-xylopyranosyl(1 → 4)-[α-l-rhamnopyranosyl(1 → 2)]-β-d-glucopyranoside (1); 26-O-β-d-glucopyranosyl-3β,26-dihydroxyl-20,22-seco-25(R)-furost-5-en-20,22-dione-3-O-α-l-rhamnopyranosyl(1 → 2)-β-d-glucopyranoside (2); and (25R)-spirost-5-ene-3β,17α-diol-3-O-β-d-glucopyranosyl(1 → 4)-β-d-galactopyranoside (3) by spectroscopic techniques and chemical means.     

New steroidal glycosides from Hosta plantaginea (Lam.) Aschers

Four new furostanol glycosides were isolated from the flowers of Hosta plantaginea (Lam.) Aschers. On the basis of spectroscopic methods including 1D and 2D NMR experiments, their structures were elucidated as 26-O-β-d-glucopyranosyl-(25R)-22-O-methyl-5α-furostan-2α,3β,22ξ,26-tetrol 3-O-α-l-rhamnopyranosyl-(1 → 4)-O-β-d-xylopyranosyl-(1 → 3)-[O-β-d-glucopyranosyl-(1 → 2)]-O-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (hostaplantagineoside A, 1), 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-20(22)-ene-2α,3β,26-triol-3-O-β-d-glucopyranosyl-(1 → 2)-[O-β-d-xylopyranosyl-(1 → 3)]-O-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (hostaplantagineoside B, 2), 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-22(23)-ene-2α,3β,20α,26-tetraol-3-O-β-d-glucopyranosyl-(1 → 2)-[O-β-d-xylopyranosyl-(1 → 3)]-O-β-d-glucopyranosyl-(1 → 4)-O-β-d-galactopyranoside (hostaplantagineoside C, 3), 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-20(22)-ene-2α,3β,26-triol-3-O-α-l-rhamnopyranosyl-(1 → 4)-O-β-d-xylopyranosyl-(1 → 3)-[O-β-d-glucopyranosyl-(1 → 2)]-O-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (hostaplantagineoside D, 4).     

Four new triterpenoid glycosides from the seed residue of Hippophae rhamnoides subsp. sinensis

Four new triterpenoid saponins (1–4) were isolated from the seed residue of Hippophae rhamnoides subsp. sinensis, named 3-O-[β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl-(1 → 3)]-[α-l-rhamnopyranosyl-(1 → 2)]-α-l-arabinopyranosyl-13-ene-19-one-28-oic acid 28-O-β-d-glucopyranosyl ester (1), 3-O-[β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl-(1 → 3)]-[α-l-rhamnopyranosyl-(1 → 2)]-α-l-arabinopyranosyl-13-ene-19-one-30-hydroxyolean-28-oic acid 28-O-β-d-glucopyranosyl ester (2), 3-O-[β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl-(1 → 3)]-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranosyl-13-ene-19-one-28-oic acid 28-O-β-d-glucopyranosyl ester (3), and 3-O-[β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl-(1 → 3)]-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranosyl-13-ene-19-one-30-hydroxyolean-28-oic acid 28-O-β-d-glucopyranosyl ester (4), and their structures were elucidated on the basis of spectroscopic and chemical methods.     

Flavonoids from Camptosorus sibiricus Rupr.

Three new flavonol glycosides, kaempferol-3-O-(6-trans-caffeoyl)-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranoside (1), kaempferol-3-O-(6-trans-caffeoyl)-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranoside-7-O-β-d-glucopyranoside (2), and kaempferol-3-O-(6-trans-p-coumaroyl)-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranoside-7-O-β-d-glucopyranoside (3), were isolated from the aerial part of Camptosorus sibiricus. Their structures were elucidated by spectroscopic methods, including 2D NMR spectral techniques.     

A new triterpenoid saponin from the stem of Akebia trifoliata var. australis

A new triterpene glycoside mutongsaponin F (1), together with five known saponins and two known lipids, was isolated from the 70% ethanol extract of the stems of Akebia trifoliata (Thunb.) Koidz. var. australis (Diels) Rehd. Their structures were elucidated on the basis of the spectroscopic analysis and physicochemical properties as 3-β-[(β-d-glucopyranosyl-(1 → 2)-O-[β-d-glucopyranosyl-(1 → 3)-O-]-α-l-arabinopyranosyl)oxy]-30-norolean-12-en-28-oic acid α-l-rhamnopyranosyl-(1 → 4)-O-β-d-glucopyranosyl-(1 → 6)-O-β-d-glucopyranosyl ester (1), 3-β-[(β-d-glucopyranosyl-(1 → 2)-O-[β-d-glucopyranosyl-(1 → 3)-O-]-α-l-arabinopyranosyl)oxy]-30-norolean-12-en-28-oic acid (2), leonticin E (3), collinsonidin (4), arjunolic acid 28-O-glucopyranoside (5), asiatic acid 28-O-glucopyranoside (6), soya-cerebroside I (7), and 1-O-α-l-galactosyl-(1 → 6)-O-β-d-galactosyl-3-O-hexadecanoyl-glycerol (8), respectively.     

Chemical constituents from the roots of Biondia chinensis

Two new triterpenoid saponins, biondianosides F and G, together with 13 known compounds, were isolated from the ethanolic extract of the roots of Biondia chinensis Schltr. (Asclepiadaceae). Their structures were characterized as 3-O-β-d-glucopyranosyl-2α,3β-dihydroxyurs-12-en-28-oic acid-β-d-glucopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 6)]-β-d-glucopyranosyl ester (biondianoside F) (14) and 3-O-β-d-glucopyranosyl-2α,3β,23-trihydroxyolean-12-en-28-oic acid-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (biondianoside G) (15) by spectral and chemical evidence.     

New cycloartane glycosides from Camptosorus sibiricus Rupr

Three new cycloartane glycosides were isolated from the whole herbs of Camptosorus sibiricus Rupr. By means of chemical and spectroscopic methods (IR, 1D, and 2D NMR, HR-MS, ESI-MS), the structures were established as (24R)-3β,7β,24,25, 30-pentahydroxycycloartane-3-O-β-d-glucopyranosyl-(1 → 4)-[α-l-arabinopyranosyl-(1 → 2)-β-d-glucopyranosyl]-24-O-β-d-glucopyranoside (1), (24R)-3β,7β,24,25,30-pentahydroxycycloartane-3-O-β-d-glucopyranosyl-(1 → 4)-[β-d-galactopyranosyl-(1 → 2)-β-d-glucopyranosyl]-24-O-β-d-glucopyranoside (2), (24R)-3β,7β,24,25,30-pentahydroxycycloartane-30-O-coumaroyl-3-O-β-d-glucopyranosyl-24-O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranoside (3). At the same time, the new compounds were tested for their cytotoxicities in vitro against human tumor cell lines (A375-S2, Hela) using MTT method.     

Two new furostanol saponins from the seeds of Trigonella foenum-graecum

Two new furostanol saponins, together with two known steroidal saponins, were isolated from the seeds of Trigonella foenum-graecum L. The structures of the new compounds were determined by detailed analysis of 1D NMR, 2D NMR, MS spectra and chemical evidences as 26-O-β-d-glucopyranosyl-(25S)-5-en-furost-3β,22α,26-triol 3-O-α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl-(1 → 3)-β-d-glucopyranosyl-(1 → 4)]-β-d-glucopyranoside (1) and 26-O-β-d-glucopyranosyl-(25R)-5-en-furost-3β,22α,26-triol 3-O-α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 6)]-β-d-glucopyranosyl-(1 → 3)-β-d-glucopyranosyl-(1 → 4)]-β-d-glucopyranoside (2).     

Two new triterpenoid saponins from Ardisia crenata

Two new triterpenoid saponins, ardisicrenoside K (1) and ardisicrenoside L (2), have been isolated from the roots of Ardisia crenata Sims. Their structures have been determined as 3β-O-{α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-[β-d-glucopyranosyl-(1 → 2)]-α-l-arabinopyranosyl}-13β,28-epoxy-16-oxo-30,30-dimethoxyoleanane and 3β-O-{β-d-xylopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-[β-d-glucopyranosyl-(1 → 2)]-α-l-arabinopyranosyl}-13β,28-epoxy-16α,20-dihydroxyoleanane by means of chemical evidences and spectral analysis. Their weak anti-fungal activity against the plant pathogenic fungus Pyricularia oryzae was evaluated in vitro.     

New steroidal glycosides from the rhizome of Anemarrhena asphodeloides

Two new steroidal saponins, timosaponin X (1) and timosaponin Y (2), and one new pregnane glycoside, timopregnane B (3), were isolated from the rhizomes of Anemarrhena asphodeloides, as well as three known compounds 25S-timosaponin BII (4), protodesgalactotigonin (5), and timosaponin BII-a (6) isolated from this plant for the first time. By the detailed analysis of 1D, 2D NMR, MS spectra, and chemical evidences, the structures of new compounds were elucidated as 26-O-β-d-glucopyranosyl-(25S)-5β-22-methoxy-furost-3β,26-diol 3-O-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranoside (1), 5β-pseudo-spirost-3β,15α,23α-triol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-galactopyranoside (2), (5β,17α)-Δ¹⁶⁽¹⁷⁾-20-one-pregn-2β,3β-diol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-galactopyranoside (3).     

Three new flavonoid glycosides from Urena lobata

Three new flavonoid glycosides, kaempferol-3-O-β-d-apiofuranosyl(1 → 2)-β-d-glucopyranosyl-7-O-α-l-rhamnopyranoside (1), kaempferol-4′-O-β-d-apiofuranosyl-3-O-β-d-glucopyranosyl-7-O-α-l-rhamnopyranoside (2), and 5,6,7,4′-tetrahydroxy-flavone-6-O-β-d-arabinopyranosyl-7-O-α-l-rhamnopyranoside (3), were isolated from the aerial parts of Urena lobata L., along with 10 known compounds (4–13). Their structures were determined based on spectroscopic methods including 1D and 2D NMR spectroscopy as well as HR-ESI-MS.     

Triterpenoid saponins from the rhizome of Polygonatum sibiricum

Three new triterpenoid saponins, polygonoides C (1), D (2), and E (3), were obtained from the ethanolic extract of the rhizome of Polygonatum sibiricum Redoute. On the basis of NMR and ESI-MS spectra, and chemical evidence, the structures of the three new compounds were elucidated as 3-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-3β,7β,22β-trihydroxy-oleanolic acid (1), 3-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-3β,7β,22β-trihydroxy-oleanolic acid methyl ester (2), and 3-O-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 4)-[α-L-rhamno-pyranosyl-(1 → 2)]-β-D-glucopyranosyl-3β,21β-dihydroxy-oleanolic acid 28-O-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranoside (3).     

Triterpene constituents from the seedling of Aronia melanocarpa

Two new triterpene saponins, 16-O-acetyl-21-O-angeloyltheasapogenol A 3-O-[β-d-galactopyranosyl(1 → 2)][β-d-xylopyranosyl(1 → 2)-α-l-arabinopyranosyl (1 → 3)]-β-d-glucopyranosiduronic acid (1) and 16,28-O-diacetyl-21-O-tigloyltheasapogenol A 3-O-[β-d-galactopyranosyl(1 → 2)][β-d-xylopyranosyl(1 → 2)-α-l-arabinopyranosyl (1 → 3)]-β-d-glucopyranosiduronic acid (2), together with four known triterpenenes, have been isolated from the dried seedling of Aronia melanocarpa, and their structures established by spectroscopic and chemical evidence.     

Two new furostanol glycosides from the fibrous root of Ophiopogon japonicus (Thunb.) Ker-Gawl

Two new furostanol glycosides, ophiopogonins H (1) and I (2), were isolated from the fibrous root of Ophiopogon japonicus. The structures of 1 and 2 were established as (25R)-26-[(O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-22α-hydroxyfurost-5-ene-3-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside and (25R)-26-[(O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-20α-hydroxyfurost-5,22-diene-3-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside on the basis of spectroscopic means including HR-ESI-MS, 1D and 2D NMR experiments.     

Two new furostanol saponins from Tribulus terrestris

Two new furostanol saponins were isolated from the fruits of Tribulus terrestris L. Their structures were established as 26-O-β-d-glucopyranosyl-(25S)-5α-furost-20(22)-en-3β,26-diol-3-O-α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-galactopyranoside (1) and 26-O-β-d-glucopyranosyl-(25S)-5α-furost-20(22)-en-12-one-3β,26-diol-3-O-β-d-galactopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (2) on the basis of spectroscopic data as well as chemical evidence.     

Two new steroidal glucosides from Tribulus terrestris L.

Two new furostanol saponins, tribufurosides D (1) and E (2), were isolated from the fruits of Tribulus terrestris L. With the help of chemical and spectral analyses (IR, MS, 1D, and 2D NMR), the structures of the two new furostanol saponins were established as 26-O-β-d-glucopyranosyl-(25S)-5α-furost-12-one-2α,3β,22α,26-tetraol-3-O-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (1) and 26-O-β-d-glucopyranosyl-(25R)-5α-furost-12-one-2α,3β,22α,26-tetraol-3-O-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (2).     

Pregnane glycosides from Solanum nigrum

Two new pregnane saponins, solanigroside A (1) and solanigroside B (2), along with two known compounds (3 and 4), were isolated from 60% ethanolic extract of the dried herb of Solanum nigrum L. The structures of 1 and 2 were elucidated as 5α-pregn-16-en-3β-ol-20-one 3-O-β-d-xylopyranosyl-(1 → 3)-O-[α-l-arabinopyranosyl-(1 → 2)]-O-β-d-glucopyranosyl-(1 → 4)-O-[α-l-rhamnopyranosyl-(1 → 2)]-O-β-d-galactopyranoside (1) and 5α-pregn-16-en-3β-ol-20-one 3-O-β-d-glucopyranosyl-(1 → 2)-O-[β-d-glucopyranosyl-(1 → 3)]-O-β-d-glucopyranosyl-(1 → 4)-O-β-d-galactopyranoside (2), respectively, on the basis of extensive spectroscopic analysis as well as comparison with reported spectroscopic data of related compounds. This paper deals with the isolation and structural characterisation of pregnane glycosides from S. nigrum L.     

Triterpene saponins from the leaves of Ilex kudingcha

Three new triterpene saponins, ilekudinosides T–V (1–3), along with six known saponins were isolated from the 70% ethanolic extract of the leaves of Ilex kudingcha. The new saponins were characterized as 3-O-β-d-glucopyranosyl-(1 → 3)-[α-l-rhamnopyranosyl-(1 → 2)]-α-l-arabinopyranosyl-3β,19α-dihydroxy-urs-12(13)-en-28,20β-lactone (1), 3-O-β-d-glucopyranosyl-(1 → 3)-[α-l-rhamnopyranosyl-(1 → 2)]-α-l-arabinopyranosyl-3β,19α-dihydroxy-12-ethoxy-urs-13(18)-ene-28,20β-lactone (2), 3-O-β-d-glucopyranosyl-(1 → 3)-[α-l-rhamnopyranosyl-(1 → 2)]-α-l-arabinopyranosyl-3β,19α-dihydroxy-11-oxo-urs-13(18)-ene-28,20β-lactone (3), respectively. The structures of compounds 1–3 were elucidated on the basis of the chemical and spectroscopic evidence, and the structures of known compounds were identified by comparison of their spectroscopic data with those reported in the literature.