A new bisabolane sesquiterpenoid from Euphorbia chrysocoma

The new sesquiterpenoid (6R)-2-chloro-6-[(1S)-1,5-dimethylhex-4-en-1-yl]-3-methylcyclohex-2-en-1-one (1), together with ten known compounds, (6R)-6-[(1S)-1,5-dimethylhex-4-en-1-yl]-3-methylcyclohex-2-en-1-one (2), bauerenol acetate (3), lupenone (4), α-amyrenone (5), β-sitosterol (6), stigmasterol (7), β-amyrin (8), ursolic acid (9), betulinic acid (10), scopolin (11), have been isolated from the roots of Euphorbia chrysocoma Lévl. et Vant. Their structures have been elucidated by spectroscopic data.     

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.     

群海绵Agelas sp.的化学成分研究

目的 研究海绵Agelas sp.的化学成分。方法 运用乙醇提取、硅胶、Sephadex-LH₂₀色谱柱、HPLC等多种方法进行分离和纯化,根据理化性质和波谱数据进行结构鉴定。结果 分离得到9个化合物,经结构鉴定分别为4,5-二溴吡咯-2-甲酰胺（1）、4,5-二溴吡咯-2-甲酸（2）、4,5-二溴吡咯-2-甲酸甲酯（3）、N-（4,5-二溴-2-吡咯甲酰基）甘氨酸甲酯（4）、1-（4,5-二溴-2-吡咯甲酰胺基）丙酸甲酯（5）、1-（4,5-二溴-2-吡咯甲酰胺基）丙酸乙酯（6）、异吲哚-1,3-二酮（7）、2（3H）-苯并噻唑酮（8）和manzacidin C（9）。结论 化合物4~9为首次从该属海绵中分离得到,其中化合物4~6为新天然产物。     

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.     

Aromatic acid derivatives from the lateral roots of Aconitum carmichaelii

Seven new aromatic acid derivatives (1–7), together with five known analogs, were isolated from the lateral roots of Aconitum carmichaelii. Structures of the new compounds were determined by spectroscopic and chemical methods as 4-methyl ( ? )-(R)-hydroxyeucomate (1), 4-butyl ( ? )-(R)-hydroxyeucomate (2), 4-butyl-1-methyl (+)-(R)-2-O-(4′-hydroxy-3′-methoxybenzoyl)malate (3), 1-butyl-4-methyl (+)-(R)-2-O-(4′-hydroxy-3′-methoxybenzoyl)malate (4), dimethyl (+)-(R)-2-O-(4′-hydroxy-3′-methoxybenzoyl)malate (5), dimethyl (+)-(R)-2-O-(4′-hydroxybenzoyl)malate (6), and methyl ( ± )-3-(4′-hydroxy-3′-methoxyphenyl)-3-sulfopropionate (7), respectively. Compounds 1 and 2 are 2-benzylmalates (eucomate derivatives), 3–6 belong to 2-O-benzoylmalates, and 7 is a rare phenylpropionate containing a sulfonic acid group. The absolute configurations of eucomate derivatives were confirmed by X-ray crystallographic analysis of 4-methyl eucomate (11).     

Parathesilactones and Parathesiquinones from Branches of Parathesis amplifolia.

Abstract

Three new lactone derivatives, (3E.)-5,6-dihydroxy-3-(3-hydroxy-4-nonyl-5-oxofuran-2(5H.)-ylidene)-7-nonyl-1-benzofuran-2(3H.)-one (1), (3E.)-5,6-dihydroxy-3-(3-hydroxy-4-decyl-5-oxofuran-2(5H.)-ylidene)-7-decyl-1-benzofuran-2(3H.)-one (2), and (3E.)-5,6-dihydroxy-3-(3-hydroxy-4-undecyl-5-oxofuran-2(5H.)-ylidene)-7-undecyl-1-benzofuran-2(3H.)-one (3), denominated as parathesilactones A, B, C, respectively, and two new quinone derivatives, (2,7,8-trihydroxy-3,6-didecyldibenzo[b,d.]furan-1,4-dione (4) and (2,7,8-trihydroxy-3,6-dinonyldibenzo[b,d.]furan-1,4-dione) (5), denominated as parathesiquinones A, B, respectively, were isolated from the branches of Parathesis amplifolia. Lund. (Myrsinaceae). In addition, three known triterpenes, α.-amyrin (6), β.-amyrin (7), and bauerenol (8), and four known alkenylresorcinols, 5-pentadec-8-enyl resorcinol (9), 5-pentadec-10-enyl resorcinol (10), 5-heptadec-8-enyl resorcinol (11), and 5-heptadec-10-enyl resorcinol (12), were also isolated. The structure elucidation was achieved by means of MS, GC-MS, IR, ¹H, ¹³C spectroscopy including Heteronuclear Multiple Quantum Coherence (HMQC), and Heteronuclear Multiple Bond Correlation (HMBC) techniques.     

Two new and four known polyphenolics obtained as new cell-cycle inhibitors from Rubus aleaefolius poir

Two new polyphenolics, rubuphenol (1) and sanguiin H-2 ethyl ester (2), were isolated together with ellagic acid (3), ethyl gallate (4), 1,2,3,4,6-penta-O-galloyl-g -D-glucopyranose (5) and 1,2,3,6-tetra-O-galloyl-g -D-glucopyranose (6) as new cell-cycle inhibitors from Rubus aleaefolius by bioassay-guided separation procedure and the structures of 1 and 2 were elucidated by spectroscopic method. Compounds 1 - 6 inhibited the cell cycle progression of tsFT210 cells at the G₀/G₁ phase with the MIC values of 14.6 w M (1), 22.1 w M (2), 10.3 w M (3), 7.8 w M (4), 7.9 w M (5) and 6.6 w M (6).     

Antioxidative iridoid glycosides and phenolic compounds from <Emphasis Type="Italic">Veronica peregrina</Emphasis>

Eight iridoid glycosides and four phenolic compounds were isolated from the EtOAc soluble fraction of Veronica peregrina MeOH extract as the radical scavengers for antioxidant activity. The compounds were identified as protocatechuic acid (1), luteolin (2), veronicoside (3), minecoside (4), specioside (5), amphicoside (6), catalposide (7), 6-O-cis-p-coumaroyl catalpol (8), p-hydroxy benzoic acid methyl ester (9), verproside (10), verminoside (11), and chrysoeriol 7-glucuronide (12) by spectroscopic analysis. All compounds except for 1 and 2 were isolated for the first time from this plant. The antioxidant activity was evaluated by the ORAC(Oxygen Radical Absorbance Capacity) assay, which measures scavenging activity against peroxy radicals induced by 2,2′-azobis (2-methoxypropion-amidine) dihydrochloride, and the ORAC value is expressed as relative trolox equivalent. Compounds 2, 4, 5, 6, 8, and 12 exhibited potent antioxidant activity, and compounds 1, 11 had similar activity with trolox, whereas the other compounds showed weaker activity than trolox.     

One new pregnane glycoside from the seeds of cultivated <Emphasis Type="Italic">Brucea javanica</Emphasis>

A new pregnane glycoside, named (20R)-O-(3)-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl-pregn-5-en-3β,20-diol (1), and seven known compounds, brusatol (2), bruceine B (3), bruceine D (4), yadanziolide A (5), bruceine E (6), yadanzioside G (7), and yadanzioside B (8), were isolated from the cultivated dry seeds of Brucea javanica. The structure of 1 was elucidated on the basis of 1D- and 2D-NMR spectroscopic analyses. Their inhibitory effects on tumor cells were also tested. Compound 1 was slightly active against HL-60, SMMC-7721, A-549, and MCF-7 tumor cells. Compounds 2 and 3 demonstrated significant inhibitory activities against all tested cells. These results indicate that cultivated B. javanica could replace the wild plant as an antitumor plant resource.     

Caragasinin C: a new oligostilbene from the roots of Caragana sinica

A new oligostilbene, caragasinin C (1), and seven known compounds, betulinic acid (2), 4-hydroxybenzaldehyde (3), (?)-medicarpin (4), wistin (5), (2E,4S)-4-hydroxy-2-nonenoic acid (6), pallidol (7), and (+)-α-viniferin (8), were isolated from the roots of Caragana sinica. The structure of caragasinin C was established on the basis of spectroscopic techniques, including HRESIMS, 1D and 2D-NMR.     

Seven new dammarane triterpenes from the floral spikes of Betula platyphylla var. japonica

Seven new dammarane-type triterpenoids, including two 20(S)-hydroxy-25-methoxy-dammar-23-enes (1 and 2), two 20(S),24(R)-epoxydammaranes (3 and 4), a cabralealactone (5), and two 20(S),25-epoxydammaranes (6 and 7), together with seven known triterpenes (8–14), were isolated from the floral spikes of Betula platyphylla var. japonica. The structures for all compounds were elucidated by the analyses of extensive spectroscopic data, as well as chemical examinations.     

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.     

A new cerebroside from Uvaria tonkinensis var. subglabra

A new cerebroside, subglain A (1), together with five known compounds (2–6) have been isolated from the stems of Uvaria tonkinensis var. subglabra. The structure of 1 has been determined to be 1-O-β-D-glucopyranosyl-(2S,3S,4R,8Z,2′R)-2-[N-(2′-hydroxytetracosanyl)-N-(1″,2″-dihydroxyethyl)-amide]-8-tetradecene-1,3,4-triol by spectroscopic evidence. The known compounds were identified as schisandriside (2), erythritol (3), β-D-glucopyranose (4), kaempferol-3,7-O-α-L-dirhamnoside (5), and (+)-lyoniresinol (6).     

Phenolic compounds from the aqueous extract of Acacia catechu

Two new phenolic compounds, 5-hydroxy-2-[2-(4-hydroxyphenyl) acetyl]-3-methoxylbenzoic acid (1) and (2S,3S)-3,7,8,3′,4′-pentahydroxyflavane (2), were obtained from the aqueous extract of Acacia catechu, along with four known compounds identified as rhamnetin (3), 4-hydroxyphenyl ethanol (4), 3,3′,5,5′,7-pentahydroxyflavane (5), and fisetinidol (6). Their structures were determined on the basis of spectroscopic analysis. Free radical-scavenging activities of the new compounds were evaluated.     

New flavonoids with 2BS cell proliferation promoting effect from the seeds of <Emphasis Type="Italic">Trigonella foenum</Emphasis>-<Emphasis Type="Italic">graecum</Emphasis> L.

Ten flavonoids were isolated from the ethyl acetate-soluble fraction of the ethanolic extract of the seeds of Trigonella foenum-graecum and their structures were elucidated on the basis of spectroscopic methods to be 5,7,3′-trihydroxy-5′-methoxylisoflavone (1), biochanin A (2), formononetin (3), irilone (4), tricin (5), daidzein (6), calycosin (7), orientin-2″-O-p-trans-coumarate (8), vitexin-2″-O-p-trans-coumarate (9), and tricin-7-O-β-d-glucopyranoside (10). Compounds 1 and 8 are new flavonoids, and 8 and 9 strongly promoted 2BS cell proliferation induced by H₂O₂.     

Three new alkaloids from the seeds of Nigella glandulifera

Three new alkaloids namely 8-(4-hydroxyphenyl)-6-methoxy-3,4-dihydroisoquinolin-1(2H)-one (1), 4-aminonigellidine (2), and N-[(4-hydroxy-2-isopropyl-5-methyl)]phenylurea (3), along with six known ones (4–9), were isolated from the seeds of Nigella glandulifera. The structures of 1–3 were determined through spectroscopic analyses (HRESIMS, 1D/2D NMR). Compound 1 was a rare isoquinolinone alkaloid with phenyl substituted at C-8.     

Phenolic constituents of <Emphasis Type="Italic">Acorus gramineus</Emphasis>

The purification of a MeOH extract from the rhizome of Acorus gramineus (Araceae) using column chromatography furnished two new stereoisomers of phenylpropanoid, acoraminol A (1) and acoraimol B (2). It also furnished 17 known phenolic compounds, β-asarone (3), asaraldehyde (4), isoacoramone (5), propioveratrone (6), (1′R,2′S)-1′,2′-dihydroxyasarone (7), (1′S,2′S)-1′,2′-dihydroxyasarone (8), 3′,4′-dimethoxycinnamyl alcohol (9), 3′,4′,5′-trimethoxycinnamyl alcohol (10), kaempferol 3-methyl ether (11), 2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-1,3-propanediol (12), hydroxytyrosol (13), tyrosol (14), (2S,5S)-diveratryl-(3R,4S)-dimethyltetrahydrofuran (15), (7S,8R)-dihydrodehydrodiconiferyl alcohol (16), 7S,8S-threo-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8-O-4′-neolignan (17), 7S,8R-erythro-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8-O-4′-neolignan (18), and dihydroyashsbushiketol (19). The structures of the new compounds were elucidated by analysis of spectroscopic data including 1D and 2D NMR data. The absolute configurations of 1 and 2 were determined using the convenient Mosher ester procedure. Compounds 5–19 were isolated for the first time from this plant source. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamine B (SRB) bioassay.     

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).     

A new ferulic acid ester and other constituents from Dracocephalum peregrinum

A new ferulic acid ester, 1′-methyl-2′-hydroxyethyl ferulate (1), together with methylcaffeate (2), 4-hydroxy cinnamic acid (3), ferulic acid (4), caffeic acid (5), diosmetin (6), luteolin (7), 5,3′,4′-trihydroxy-3,7-dimethoxyflavone (8), eriodictyol (9), kaempferol (10), quercetin (11), acacetin-7-O-glcopyranoside (12), 4-(β-glucopyranosyloxy) benzoic acid (13), luteolin-7-O-(6″-feruloyl) glucopyranoside (14), luteolin-7-O-glucopyranoside (15), kaempferide-3-O-rhamnopyranoside (16), quercitrin (17), kaempferol-3-O-glucopyranoside (18), prunasin (19), quercetin-7-O-glucopyranoside (20), quercetin-3-O-glucopyranoside (21), plantaginin (22), linarin (23), luteolin-7-O-rutinoside (24), and chlorogenic acid (25) were isolated from the aerial parts of Dacocephalum peregrinum. The structure of 1 was elucidated on the basis of spectroscopic and HR-ESI-MS analyses. In addition, compound 1 exhibited mild inhibitory effect on NO production in LPS-stimulated RAW264.7 cells.     

Four new compounds from the rhizome of Aristolochia championii

Three new flavonoid glycosides (1–3) and one new aristololactam N-glycoside (4) were isolated from the rhizome of Aristolochia championii. The structures of compounds 1–4 were elucidated on the basis of their spectroscopic data and chemical evidence (UV, IR, HR-ESI-MS, 1D and 2D NMR). Their structures were determined as 8-(5-formyl-2-furanmethyl)-isorhamentin 3-O-robinobioside (1), 8-(5-methyl-2-furanoyl)-isorhamentin 3-O-robinobioside (2), 8-formylisorhamentin 3-O-robinobioside (3), and N-β-D-glucopyranosylaristololactam V (4), respectively.