Phytolacacinoside A,a new triterpenoid saponin from Phytolacca acinosa Roxb

Phytolacacinoside A (1), a novel triterpenoid saponin, together with the seven known compounds, was isolated from 75% ethanol extract of the root of Phytolacca acinosa Roxb (Phytolaccaceae). Their structures were elucidated on the basis of analysis of spectroscopic data and physicochemical properties as 3-O-β-[(β-d-glucopyranosyl-(1 → 4)-O-β-d-xylopyranosyl)]-11β-methoxy-jaligonic acid 30-methyl ester 28-O-β-d-glucopyranoside (1), 3-O-β-[(β-d-glucopyranosyl-(1 → 4)-O-β-d-xylopyranosyl)]-jaligonic acid 30-methyl ester 28-O-β-d-glucopyranoside (2, esculentoside G), 3-O-β-[(β-d-glucopyranosyl-(1 → 4)-O-β-d-xylopyranosyl)]-jaligonic acid 30-methyl ester (3, phytolaccoside E), 3-O-β-d-xylopyranosyl-jaligonic acid 30-methyl ester (4, phytolaccoside B), hypaphorine (5), palmitic acid monoglyceride (6), β-sitosterol (7), and daucosterol (8).     

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 new anthraquinone glycosides from the roots of Rheum palmatum

Two new anthraquinone glycosides, named 1-methyl-8-hydroxyl-9,10-anthraquinone-3-O-β-d-(6′-O-cinnamoyl)glucopyranoside (1) and rhein-8-O-β-d-[6′-O-(3″-methoxyl malonyl)]glucopyranoside (2), have been isolated from the roots of Rheum palmatum, together with seven known compounds, rhein-8-O-β-d-glucopyranoside (3), physcion-8-O-β-d-glucopyranoside (4), chrysophanol-8-O-β-d-glucopyranoside (5), aleo-emodin-8-O-β-d-glucopyranoside (6), emodin-8-O-β-d-glucopyranoside (7), aleo-emodin-ω-O-β-d-glucopyranoside (8), and emodin-1-O-β-d-glucopyranoside (9). Their structures were elucidated on the basis of chemical and spectral analysis.     

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.     

Three new isoflavone glycosides from Tongmai granules

Three new isoflavone glycosides, 3′-methoxydaidzein-7,4′-di-O-β-d-glucopyranoside (1), biochanin A-8-C-β-d-apiofuranosyl-(1 → 6)-O-β-d-glucopyranoside (2), daidzein-7-O-β-d-glucopyranosyl-(1 → 4)-O-β-d-glucopyranoside (3), and a new natural isoflavone glycoside, daidzein-7-O-α-d-glucopyranosyl-(1 → 4)-O-β-d-glucopyranoside (4) were isolated along with 18 known isoflavones from the EtOAc and n-BuOH fractions of the aqueous extraction of Tongmai granules. All the isoflavones were obtained and determined for the first time from Tongmai granules. The structures of these compounds were elucidated by spectral methods. It was confirmed that the compounds 1–4 were originally from Puerariae Lobatae Radix based on HPLC-DAD analysis of the crude drug extract. The isoflavones isolated were tested for their antioxidative activities by measuring the capacities of scavenging the 2,2′-diphenyl-1-picrylhydrazyl radical.     

New sesquiterpenoid glycoside and phenylpropanoid glycosides from the tuber of Ophiopogon japonicus

A new sesquiterpenoid glycoside, cryptomeridiol 11-O-β-d-xylopyranosyl-(1→6)-β-d- glucopyranoside (1), two new phenylpropanoid glycosides, 3,4-dihydroxy-allylbenzene 3-O-β-d-glucopyranosyl-4-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (2), and 3,4,5-trihydroxy-allylbenzene 3-O-β-d-glucopyranosyl-4-O-β-d-glucopyranoside (3), along with four known phenylpropanoid glycosides (4–7), were isolated from the tuber of Ophiopogon japonicus. Compounds 4–7 were obtained from the genus Ophiopogon for the first time. Their structures were elucidated by spectroscopic methods, including 1D and 2D NMR and HR-ESI-MS.     

New phenolic glycosides from Pilea cavaleriei

Five new phenolic glycosides, 2-hydroxy-(2′E)-prenyl benzoate-2,4′-di-O-β-d-glucopyranoside (1), 2-hydroxy-(2′E)-prenyl benzoate-2-O-α-l-arabinopyranosyl-(1 → 6)-β-d-glucopyranoside (2), 4-methylphenol-1-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside (3), 4-methylphenol-1-O-α-l-arabinopyranosyl-(1 → 6)-β-d-glucopyranoside (4), and 3,5-dimethoxyphenol-1-O-β-d-apiofuranosyl-(1 → 2)-β-d-glucopyranoside (5), together with six known glycosides (6–11), were isolated from the n-BuOH fraction of the EtOH extract of Pilea cavaleriei Levl subsp. cavaleriei. Their structures were elucidated by extensive spectroscopic analysis, including 1D and 2D NMR spectroscopy as well as HR-ESI-MS, and chemical evidences. All these compounds were isolated from the genus Pilea for the first time.     

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.     

Furostanol oligoglycosides from Asparagus cochinchinensis

Three new furostanol oligoglycosides, named aspacochioside A (1), B (2) and C (3), together with the known compound 3-O-[{α-l-rhamnopyranosyl-(1→4)}{β-d-glucopyranosyl}]-26-O-[β-d-glucopyranosyl]-(25S)-5β-spirostane-3β-ol were isolated from the roots of Asparagus cochinchinensis. Their structures were elucidated by spectroscopic techniques (IR, HR-ESIMS, ESIMS/MS, 1D and 2D NMR) and chemical methods as 3-O-[{α-l-rhamnopyranosyl-(1→4)}{β-d-glucopyranosyl}]-26-O-[β-d-glucopyranosyl]-(25S)-5β-furostane-3β,22α,26-triol (1), 3-O-[{α-l-rhamnopyranosyl-(1→4)}{β-d-glucopyranosyl}]-26-O-[β-d-glucopyranosyl]-22α-methoxy-(25S)-5β-furostane-3β,26-diol (2), and 3-O-[{α-l-rhamnopyranosyl-(1→4)}{β-d-glucopyranosyl}]-26-O-[β-d-glucopyranosyl]-(25S)-5β-furost-20(22)-en-3β,26-diol (3).     

Three new C-flavonoids from Corallodiscus flabellata

Three new C-glycosylflavones, named 5,7,4′-trihydroxy-6-methoxy-8-C-[β-d-xylopyranosyl- (1 → 2)]-β-d-glucopyranosyl flavonoside (1), 5,7,4′-trihydroxy-8-methoxy-6-C-[β-d-xylopyranosyl-(1 → 2)]-β-d-glucopyranosyl flavonoside (2), and 5,3′,4′-trihydroxy-7,8-dimethoxy-6-C-[β-d-xylopyranosyl-(1 → 2)]-β-d-glucopyranosyl flavonoside (3), along with two known compounds 5,4′-dihydroxy-7-methoxy-6-C-glucopyranosyl-flavonoside (4), 3-methoxy-4-hydroxymethyl benzoate (5) were isolated from 70% acetone extract of Corallodiscus flabellata. Their structures were identified on the basis of spectroscopic techniques and chemical methods.     

Two new isoflavone triglycosides from the small branches of Sophora japonica

Two new isoflavone triglycosides, genistein 4′-O-(6″-O-α-l-rhamnopyranosyl)-β-sophoroside (1), and genistein 4′-O-(6?-O-α-l-rhamnopyranosyl)-β-sophoroside (2), together with five known compounds, namely, sophorabioside, genistin, rutin, quercetin 3-O-β-d-glucopyranoside, and kaempferol 3-O-β-d-glucopyranoside, were isolated from the small branches of Sophora japonica L. Their structures were elucidated on the basis of spectroscopic analyses and chemical evidence.     

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.     

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.     

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.     

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.     

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).     

Two new compounds from the leaves of Indocalamus latifolius

Two new compounds, erythro-syringylglycerol-9-O-trans-4-hydroxycinnamate 7-O-β-d-glucopyranoside (1) and indocalatin A (2), together with three known ones, 5,7,3′-trihydroxy-6-C-β-d-digitoxopyranosyl-4′-O-β-d-glucopyranosyl flavonoid (3), 5,4′-dihydroxy-3′,5′-dimethoxy-7-O-[β-d-apiose-(1→2)]-β-d-glucopyranosyl flavonoid (4), and tricin-6-C-β-boivinopyranosyl-8-C-β-glucopyranoside (5), were isolated from the 95% EtOH extract of Indocalamus latifolius leaves. Their molecular structures were determined by UV, IR, HRESIMS, CD, and 1D and 2D NMR data analyses.     

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.     

Two new lignan glycosides from the seeds of Cuscuta chinensis

Two new lignan glycosides, 2′-hydroxyl asarinin 2′-O-β-D-glucopyranoside (cuscutoside C, 1) and 2′-hydroxyl asarinin 2′-O-β-D-apiofuranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranoside (cuscutoside D, 2), were isolated from the seeds of Cuscuta chinensis Lam., along with six known compounds, 2′-hydroxyl asarinin 2′-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside (3), 2′-hydroxyl asarinin 2′-O-β-D-apiofuranosyl-(1 → 2)-β-D-glucopyranoside (cuscutoside A, 4), kaempferol 3,7-di-O-β-D-glucopyranoside (5), 5-caffeoyl quinic acid (6), 4-caffeoyl quinic acid (7), and cinnamic acid (8). Their structures were elucidated on the basis of spectroscopic analyses including HR-ESI-MS, ESI-MS/MS, ¹H and ¹³C NMR, HSQC, HMBC, and TOCSY.     

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.