Flavonoids from the leaves of Pleioblastus argenteastriatus

A new flavonoid, 5,7,3′-trihydroxy-6-C-β-d-digitoxopyranosyl-4′-O-β-d-glucopyranosyl flavonoside (1), along with four known flavonoids 5,7,4′-trihydroxy-3′,5′-dimethoxy flavone (2), 5,3′,4′-trihydroxy-7-O-β-d-glucopyranosyl flavonoside (3), 5,4′-dihydroxy-3′,5′-dimethoxy-7-O-β-d-glucopyranosyl flavonoside (4), 5,3′,4′-trihydroxy-6-C-[β-d-glucopyranosyl-(1 → 6)]-β-d-glucopyranosyl flavonoside (5) were isolated from 95% EtOH extract of the leaves of Pleioblastus argenteastriatus. Their structures were determined on the basis of spectroscopic techniques and chemical methods.     

Two novel furostanol saponins from Ophiopogon japonicus

Two novel furostanol saponins were isolated from the fresh tubers of Ophiopogon japonicus. Comprehensive spectroscopic analysis allowed the chemical structures of the compounds to be assigned as (25R)-26-[(O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-22α-hydroxyfurost-5-ene-3-O-β-d-xylopyranosyl-(1 → 4)-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside (1, ophiopogonin F) and (25R)-26-[(O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl)]-22α-hydroxyfurost-5-ene-3-O-β-d-xylopyranosyl-(1 → 4)-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside (2, ophiopogonin G). The rare furostanol saponins with two glucosyl residues at C-26 position were isolated from the natural source for the first time.     

Two new steroidal saponins from Tribulus terrestris

Two new steroidal saponins and two known flavonoid glycosides were isolated from the fruits of Tribulus terrestris. Their structures were assigned by spectroscopic analysis and chemical reaction as 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-12-one-3β,22α,26-triol-3-O-β-d-glucopyranosyl (1 → 2)-β-d-glucopyranosyl(1 → 4)-β-d-galactopyranoside (1), 26-O-β-d-glucopyranosyl-(25S)-5α-furostan-22-methoxy-2α,3β,26-triol-3-O-β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl(1 → 4)-β-d-galactopyranoside (2), kaempferol-3-gentiobioside (3), and isorhamnetin-3-gentiobioside (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.     

Triterpenoid glycosides from Stauntonia chinensis

A new bidesmoside triterpenoid saponin, named stauntoside C1 (1), along with three known saponins (2–4) was isolated from Stauntonia chinensis DC. (Lardizabalaceae). Their structures were established by means of spectral and chemical methods as 3-O-β-d-xylopyranosyl-(1 → 2)-O-β-d-xylopyranosyl-(1 → 3)-O-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl oleanolic acid 28-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (1), scabiosaponin E (2), sieboldianoside B (3), and kizutasaponin K₁₂ (4).     

Two new furostanol saponins from the fibrous root of Ophiopogon japonicus

Two new furostanol saponins ophiopogonins J (1) and K (2) were isolated from the fibrous roots of Ophiopogon japonicus. The structures of 1 and 2 were established as (25R)-26-O-[(β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-14-hydroxy-furost-5,20(22)-diene 3-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside (1), and (25R)-26-O-[(β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-furost-5,20(22)-diene 3-O-α-l-rhamnopyranosyl-(1 → 2)[(β-d-xylopyranosyl-(1 → 4)-β-d-glucopyranoside)] (2) on the basis of spectroscopic means including HRESIMS, 1D, and 2D NMR experiments.     

New oleanane-type triterpenoid saponins isolated from the seeds of Celosia argentea

Three new oleanane-type triterpenoid saponins named celosins H (1), I (2), and J (3) were isolated from the seeds of Celosia argentea L. Their structures were characterized as 3-O-β-d-xylopyranosyl-(1 → 3)-β-d-glucuronopyranosyl-polygalagenin 28-O-β-d-glucopyranosyl ester, 3-O-β-d-glucuronopyranosyl-medicagenic acid 28-O-β-d-xylcopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-β-d-fucopyranosyl ester, and 3-O-β-d-glucuronopyranosyl-medicagenic acid 28-O-α-l-arabinopyranosyl-(1 → 3)-[β-d-xylcopyranosyl-(1 → 4)]-α-l-rhamnopyranosyl-(1 → 2)-β-d-fucopyranosyl ester by NMR, MS, and chemical evidences, respectively. In our opinion, celosins H–J could be used as chemical markers for the quality control of C. argentea seeds.     

A pair of isomeric saponins with cytotoxicity from Albizzia julibrissin

Two new saponins have been isolated from the stem barks of Albizzia julibrissin Durazz, and their structures identified as 3-O-[β-d-xylopyranosyl-(1 → 2)-β-d-fucopyranosyl-(1 → 6)-β-d-2-deoxy-2-acetoamidoglucopyranosyl]-21-O-{(6S)-2- trans -2-hydroxymethyl-6-methyl-6-O-[4-O-((6S )-2- trans -2-hydroxymethyl-6-hydroxy-6-methyl-2,7-octadienoyl)-β-d-quinovopyranosyl]-2,7-octadienoyl}-acacic acid-28-O-β-d-glucopyranosyl-(1 → 3)-[α-l-arabinofuranosyl-(1 → 4)]-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (1) and 3-O-[β-d-xylopyranosyl-(1 → 2)-β-d-fucopyranosyl-(1 → 6)-β-d-2-deoxy-2-acetoamidoglucopyranosyl]-21-O-{(6S)-2-trans-2-hydroxymethyl-6-methyl-6-O-[3-O-((6S)-2-trans-2-hydroxymethyl-6-hydroxy-6-methyl-2,7-octadienoyl)-β-d-quinovopyranosyl]-2,7-octadienoyl}acacic acid 28-O-β-d-glucopyranosyl-(1 → 3)-[α-l-arabinofuranosyl-(1 → 4)]-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (2), based on chemical and spectral evidences, named as julibroside J₁₉ and julibroside J₁₈, respectively. Both compounds show significant inhibition action against HeLa, Bel-7402 and MDA-MB-435 cancer cell lines in vitro.     

A novel triterpenoid saponin from Polygala tenuifolia Willd.

A new triterpenoid saponin, tenuifoside A, was isolated together with three known triterpenoid saponins 2, 3, and 4 from the roots of Polygala tenuifolia Willd. With the help of chemical and spectral analyses (IR, MS, 1D-NMR, and 2D-NMR), the structure of the new saponin was elucidated as 3-O-β-d-glucopyranosyl presenegenin 28-O-β-d-xylopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)-[β-d-apiofuranosyl-(1 → 3)]-α-l-rhamnopyranosyl-(1 → 2)-[4-O-p-methoxycinnamoyl]-[α-l-rhamnopyranosyl-(1 → 3)]-β-d-fucopyranosyl ester (1). Three known triterpenoid saponins (2–4) were identified on the basis of spectroscopic data.     

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).     

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.     

Two new triterpenoid saponins from Sarcandra glabra

Two new triterpenoid saponins, named sarcandroside A and B, have been isolated from Sarcandra glabra (Thunb) Nakai. Their structures have been established as 3β,19α,20β-trihydroxyurs-11,13 (18)-diene-28,20β-lactone-3-O-β-d-glucopyranosyl (1 → 3)-[α-l-rhamnopyranosyl(1 → 2)]-β-d-xylopyranoside (1) and 3-O-β-d-glucopyranosyl (1 → 3)-[α-l-rhamnopyranosyl(1 → 2)]-β-d-xylopyranosyl-pomolic acid 28-O-β-d-glucopyranosyl ester (2) by means of spectral and chemical methods.     

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.     

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.     

Three triterpenoid saponins acylated with monoterpenic acid from Gymnocladus chinensis

A new triterpenoid saponin acylated with monoterpenic acid, together with two known triterpenoid saponins, has been isolated from the fruit of Gymnocladus chinensis Baill. Their structures were elucidated as 2β,23-dihydroxy-3-O-α-L-rhamnopyranosyl-21-O-{(6S)-2-trans-2,6-dimethyl-6-O-[3-O-(β-D-glucopyranosyl)-4-O-((6S)-2-trans-2,6-dimethyl-6-hydroxy-2,7-octadienoyl)-β-L-arabinopyranosyl]-2,7-octadienoyl}-acacic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 6)]-β-D-glucopyranosyl ester (1), gymnocladus saponin E (2), and gymnocladus saponin F₂ (3).     

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.     

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.     

A new compound from Gentianopsis paludosa

A new compound, named gentianopfluorenone (1), along with three known compounds,1-O-β-d-glucopyranosyl-5-hydroxy-3-methoxyxanthone (2), 1-O-[β-d-xylopyranosyl-(1 → 6)-β-d-glucopyranosyl]-7,8-dihydroxy-3–methoxyxanthone (3), and apigenin (4), were isolated from the whole herb of Gentianopsis paludosa. On the basis of spectral and chemical evidence, the structure of 1 was elucidated as 4,4a,6-trihydroxy-5-methoxy-fluoren-2,9-dione. Compounds 2–4 were isolated from the plant for the first time.     

Two new flavone glycosides from the seeds of Impatiens balsamina L.

Two new flavone glycosides were isolated from the seeds of Impatiens balsamina L. and their structures were determined as quercetin-3-O-[α-l-rhamnose-(1 → 2)-β-d-glucopyranosyl]-5-O-β-d-glucopyranoside (1), and quercetin-3-O-[(6?-O-caffeoyl)-α-l-rhamnose-(1 → 2)-β-d-glucopyranosyl]-5-O-β-d-glucopyranoside (2) on the basis of various spectral and chemical studies.     

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.