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 triterpenoid saponins from the seeds of Aesculus turbinata

Three new triterpenoid saponins, named isoescins VIIa (1), VIa (2), and VIIIa (3), were isolated from the seeds of Aesculus turbinata and identified by spectroscopic analysis and chemical hydrolysis. Their structures were established as 21β-O-tigloyl-28-O-acetylprotoaescigenin 3β-O-[β-d-galactopyranosyl(1 → 2)][β-d-glucopyranosyl(1 → 4)]-β-d-glucopyranosiduronic acid (Isoescin VIIa, 1), 21β-O-(2-methylbutyryl)-28-O-acetylprotoaescigenin 3β-O-[β-d-glucopyranosyl(1 → 2)] [β-d-glucopyranosyl(1 → 4)]-β-d-glucopyranosiduronic acid (Isoescin VIa, 2), and 21β-O-angeloyl-28-O-acetylbarringtogenol C 3β-O-[β-d-glucopyranosyl(1 → 2)] [β-d-glucopyranosyl(1 → 4)]-β-d-glucopyranosiduronic acid (Isoescin VIIIa, 3).     

New dianthramide and cinnamic ester glucosides from the roots of Aconitum carmichaelii

Four new compounds N-salicyl-3-hydroxyanthranilic acid methyl ester (1), N-(2′-dehydroxysalicyl)-3-hydroxyanthranilic acid methyl ester (2), methyl-4-β-D-allopyranosyl-ferulate (3), and methyl-4-β-D-gulopyranosyl-cinnamate (4), along with six known compounds (5–10), were isolated from the roots of Aconitum carmichelii Debx. Their structures were elucidated on the basis of spectral data analysis, including 1D, 2D-NMR, and HR-ESI-MS. Compounds 1 and 2 showed the inhibition of nitric oxide (NO) production with IC₅₀ values of 9.13 and 19.94 μM, respectively.     

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.     

Sesquiterpenoids and other constituents from the flower buds of Tussilago farfara

One new norsesquiterpenoid, namely tussfarfarin A (1), and four new artifacts resulting from extraction procedure, namely tussfarfarin B (2), 6-(1-ethoxyethyl)-2,2-dimethylchroman-4-ol (3), 5-ethoxymethyl-1H-pyrrole-2-carbaldehyde (4), and 3β-hydroxy-7α-ethoxy-24β-ethylcholest-5-ene (5), along with 18 known compounds, were isolated from the flower buds of Tussilago farfara. Their structures were elucidated by extensive spectroscopic analysis.     

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).     

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.     

Two new sesquiterpene polyol esters from the root barks of Celastrus angulatus

Angulatin F (1) and angulatin I (2), two new sesquiterpene polyol esters, were isolated from the root barks of Celastrus angulatus, together with six known compounds 1β,2β-diacetoxy-4α,6α-dihydroxy-8α-isobutanoyloxy-9β-benzoyloxy-15-(α-methyl) butanoyloxy-β-dihydroagrofuran (3), angulatin A (4), angulatin B (5), celangulatin E (6), 1β,2β,15-triacetoxy-4α,6α-dihydroxy-8α-isobutanoyloxy-9β-benzoyloxy-β-dihydroagrofuran (7), and celangulin I (8). The structures of 1 and 2 were elucidated as 1β,2β,6α,15-tetraacetoxy-4α-hydroxy-8β,9α-difuroyloxy-β-dihydroagrofuran and 1β,2β,6α,8β,15-pentaacetoxy-4α-hydroxy-9β-furoyloxy-β-dihydroagrofuran by spectroscopic means.     

Water-soluble constituents from the leaves of Ilex oblonga

Four new water-soluble constituents, oblongaroside A (1), oblongar ester A (2), oblongaroside B (3), and oblongaroside C (4), were isolated along with four known compounds: 4-O-β-d-glucopyranosyl-3-hydroxybenzalcohol (5), 7-methoxyl-4-O-β-d-glucopyranosyl-3-hydroxybenzalcohol (6), 4-O-β-d-glucopyranosyl-3-hydroxybenzoic acid (7), and 3,4-dihydroxybenzoic acid (8) from the leaves of Ilex oblonga. Identification of their structures was achieved by 1D and 2D NMR experiments, including ¹H–¹H COSY, NOESY, HMQC, and HMBC methods and FAB mass spectral data.     

Antioxidant and α-amylase inhibitory activities of extract and isolates from Zygogynum pancheri subsp. arrhantum

One new sesquiterpenoid (5R^*,8R^*,9R^*,10R^*)-cinnamolide (8), and seven known compounds, 5-hydroxy-7-methoxyflavonone (1), 8-hydroxy-3-(4′-hydroxyphenyl)-6,7-(2″,2″-dimethylchromene)-tetralone (2), 8-hydroxy-3-(3′,4′-dihydroxyphenyl)-6,7-(2″,2″-dimethylchromene)-tetralone (3), 1β-E-O-p-methoxycinnamoyl-bemadienolide (4), 1β-O-(E-cinnamoyl)-6α-hydroxy-9-epi-polygodial (5), 1β-O-(E-cinnamoyl)-6α-hydroxypolygodial (6), and 1β-O-E-cinnamoylpolygodial (7) were isolated from the ethyl acetate extract of barks of Zygogynum pancheri subsp. arrhantum (Winteraceae). The structures of these molecules were assigned predominantly based on spectral data. The structure of compound 8 was confirmed by X-ray crystallographic analysis. Compounds 2 and 3 exhibited significant antioxidant activity, whereas compounds 1 and 4–7 showed significant α-amylase inhibitory activity.     

Microbial transformation of deoxyandrographolide by Fusarium graminearum AS 3.4598

Biotransformation of deoxyandrographolide (1) by Fusarium graminearum AS 3.4598 was investigated in this paper. And five transformed products of 1 by F. graminearum AS 3.4598 were obtained. Their chemical structures were characterized as 3-oxo-8α,17β-epoxy-14-deoxyandrographolide (2), 3-oxo-14-deoxyandrographolide (3), 3-oxo-17,19-dihydroxyl-8,13-ent-labdadien-15,16-olide (4), 1β-hydroxyl-14-deoxyandrographolide (5), and 7β-hydroxyl-14-deoxyandrographolide (6) by spectral methods including 2D NMR. Among them, products 2, 4, and 5 are new.     

Anti-emetic Principles of Water Extract of Brazilian Propolis

ABSTRACT

Water extract of Brazilian propolis showed anti-emetic activity on copper sulfate–induced emesis in young chicks. Bioassay-guided fractionation of the extract was carried out, and dehydrohautriwaic acid (1), (E.)-3-(2,2-dimethyl-2H.-1-benzopyran-6-yl)-2-propenoic acid (2), dihydrocinnamic acid (3), (Z.)-3-(2,2-dimethyl-2H.-1-benzopyran-6-yl)-2-propenoic acid (4), aromadendrane-4β,10α-diol (5), and lupeol (6) were isolated as the active components.     

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).     

A new meta-homoisoflavane from the fresh stems of dracaena cochinchinensis

A new meta-homoisoflavane, 10,11-dihydroxydracaenone C (1), together with 7,4′-dihydroxyflavone (2), 7,4′-dihydroxyflavane (3), 4,4′-dihydroxy-2-methoxychalcone (4), 4,4′-dihydroxy-2-methoxydihydrochalcone (5), 7,4′-dihydrohomoisoflavanone (6), 7,4′-homoisoflavane (7), lophenol (8), β-sitosterol (9), stigma-5, 22-diene-3-ol (10), 1-(4′-O-β-d-glucopyranosyl)benzyl-ethan-2-ol (11), 3,4-dihydoxy-1-allylbenezene-4-O-α-l-rhamnopyranosyl-(1 → 6)-O-β-d-glucopyranoside (12), 1-hydroxy-3,4,5-trimethoxybenzene-1-O-α-l-apiopyranosyl-(1 → 6)-O-β-d-glucopyranoside (13), and tachioside (14) have been isolated from the fresh stems of Dracaena cochinchinensis. Their structures have been established by spectroscopic analysis, especially by 2D NMR. This is the first time compounds 11, 13, 14 have been isolated from Dracaena.     

Stilbene C-glucosides from Cissus repens

Four new stilbene C-glucosides, namely trans-3-O-methyl-resveratrol-2-C-β-glucoside (1), cis-3-O-methyl-resveratrol-2-C-β-glucoside (2), trans-3-O-methyl-resveratrol-2-(2-p-coumaric)-C-β-glucoside (cissuside A) (3), and trans-3-O-methyl-resveratrol-2-(3-p-coumaric)-C-β-glucoside (cissuside B) (4), were isolated from the aerial parts of Cissus repens, along with known trans-resveratrol (5), trans-resveratrol-2-C-β-glucoside (6) and cis-resveratrol-2-C-β-glucoside (7). Their structures were established by spectroscopic methods. Stilbene C-glucosides were found in the genus Cissus for the first time.     

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.     

Three new sulfated triterpenoids from the roots of Gypsophila pacifica

Three new sulfated triterpenoids (1–3), along with one known compound (4), were isolated from the roots of Gypsophila pacifica Kom. The structures of the new compounds were established as 3β-O-sulfate gypsogenin 28-O-β-d-glucopyranosyl ester (1), 3β-O-sulfate gypsogenin (2), and 3β-O-sulfate quillaic acid (3) on the basis of 1D, 2D NMR, and HR-ESI-MS methods.     

Biotransformation of oleanolic acid by Alternaria longipes and Penicillium adametzi

Microbial transformation of oleanolic acid (1) was carried out. Six transformed products (2–7) from 1 by Alternaria longipes and three transformed products (8–10) from 1 by Penicillium adametzi were isolated. Their structures were elucidated as 2α,3α,19α-trihydroxy-ursolic acid-28-O-β-d-glucopyranoside (2), 2α,3β,19α-trihydroxy-ursolic acid-28-O-β-d-glucopyranoside (3), oleanolic acid 28-O-β-d-glucopyranosyl ester (4), oleanolic acid-3-O-β-d-glucopyranoside (5), 3-O-(β-d-glucopyranosyl)-oleanolic acid-28-O-β-d-glucopyranoside (6), 2α,3β,19a-trihydroxy-oleanolic acid-28-O-β-d-glucopyranoside (7), 21β-hydroxyl oleanolic acid-28-O-β-d-glucopyranoside (8), 21β-hydroxyl oleanolic acid (9), and 7α,21β-dihydroxyl oleanolic acid (10) based on the extensive NMR studies. Among them, 10 was a new compound and compounds 5 and 8–10 had stronger cytotoxic activities against Hela cell lines than the substrate. At the same time, it was reported for the first time in this paper that the skeletons of compounds 2 and 3 were changed from oleanane to uranane and seven glycosidation products were obtained by biotransformation.     

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.     

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).