Structures of two diterpenoid dimers from bulbs of Fritillaria ebeiensis

A new ent-kaurane diterpenoid dimer, fritillebinide C (1) together with one known diterpenoid dimer fritillebinide B (2) were isolated from the bulbs of Fritillaria ebeiensis G.D. Yu et G.Q. Ji. Compound 1 has been determined to be ent-3β-acetoxy-kauran-16β, 17-acetal entβ-kauran-17(S)-aldehyde (1) by means of spectral analysis and chemical evidence.     

Structural elucidations of two ent-kaurane dimers from bulbs of Fritillaria ebeiensis var. purpurea

A novel ent-kaurane diterpenoid dimer, fritillebinide B (1) together with one known diterpenoid dimer fritillebinide A (2) were isolated from the bulbs of Fritillaria ebeiensis var. purpurea G.D. Yu et P. Li. Compound 1 has been established to be ent-3β-acetoxy-kauran-16β,17-acetal ent-16β-kauran-17(R)-aldehyde (1) by means of spectral analysis and chemical evidence.     

Two new diterpenoid dimers,fritillebinide D and E,from bulbs of Fritillaria ebeiensis

Two new ent-kaurane diterpenoid dimers, fritillebinide D (1) and fritillebinide E (2), were isolated from bulbs of Fritillaria ebeiensis G.D. Yu et G.Q. Ji. Their structures have been determined to be ent-3g -acetoxy-kauran-16g , 17-acetal ent-3g -acetoxy-16g -kauran-17(R)-aldehyde (1) and ent-3g -acetoxy-kauran-16g ,17-acetal ent-3g -acetoxy-16g -kauran-17(S)-aldehyde (2) by means of spectral analysis.     

ent-Kaurenoids from the roots of Cacalia pilgeriana

Two new ent-kaurenoids,19-acetoxyl-ent-3β,17-dihydroxykaur-15-ene (1), 19-acetoxyl-ent-3β-hydroxykaur-15-en-17-al (2), together with seven known ent-kaurenoids: ent-kaur-16-en-19-al (3), ent-kaur-16-en-19-oic acid (4), ent-kauran-16β,17-diol (5), ent-15β, 16β-epoxy-17-hydroxykauran-19-oic acid (6),19-acetyl-ent-3β-hydroxyl-kaur-16-ene (7), ent-3β,19-dihydroxykaur-16-ene (8), ent-17-hydroxykaur-15-ene (9), were isolated from Cacalia pilgeriana. Their structures were elucidated by spectroscopic methods including 2D NMR spectral analysis.     

Structures of Two Diterpenoid Dimers from Bulbs of Fritillaria ebeiensis

Abstract

A new ent-kaurane diterpenoid dimer, fritillebinide C (1) together with one known diterpenoid dimer fritillebinide B (2) were isolated from the bulbs of Fritillaria ebeiensis G.D. Yu et G.Q. Ji. Compound 1 has been determined to be ent-3β-acetoxy-kauran-16β, 17-acetal entβ-kauran-17(S)-aldehyde (1) by means of spectral analysis and chemical evidence.     

Structural Elucidations of Two Ent-Kaurane Dimers from Bulbs of Fritillaria ebeiensis var. purpurea

Abstract

A novel ent-kaurane diterpenoid dimer, fritillebinide B (1) together with one known diterpenoid dimer fritillebinide A (2) were isolated from the bulbs of Fritillaria ebeiensis var. purpurea G.D. Yu et P. Li. Compound 1 has been established to be ent-3β-acetoxy-kauran-16β,17-acetal ent-16β-kauran-17(R)-aldehyde (1) by means of spectral analysis and chemical evidence.     

Structural elucidation of fritillahupehin from bulbs of Fritillaria hupehensis Hsiao et K.C. Hsia

A novel diterpenoid ester, fritillahupehin (1) and three known fatty acids, palmitic acid (2), lignoceric acid (3) and azelaric acid (4), have been isolated from the bulbs of Fritillaria hupehensis Hsiao et K.C. Hsia. The structure of fritillahupehin has been established to be ent-kauran-16β-yl lignocerate by means of spectroscopic and chemical evidence. Compounds 2-4 were isolated from Fritillaria sp. for the first time.     

Cytotoxic sesquiterpene lactones from Eupatorium lindleyanum

Three new germacrane sesquiterpenes, eupalinolides C-E (1-3), along with three known germacrane sesquiterpenes, eupalinolide A (4), eupalinolide B (5), and 3β-acetoxy-8β-(4'-hydroxytigloyloxy)-14-hydroxycostunolide (6), were isolated from Eupatorium lindleyanum. They were tested for cytotoxicity against A-549, BGC-823, SMMC-7721, and HL-60 tumour cell lines. The results showed that these compounds demonstrated potent cytotoxicity. The structures of the compounds were elucidated by means of ¹H and ¹³C NMR spectroscopic analysis, including 2D NMR experiments.     

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.     

鄂贝缩醛A的结构解析与合成

目的：研究民间药鄂北贝母Fritillaria ebeiensis G.D.Yu et G.Q.Ji鳞茎的非生物碱成分。方法：用MeOH提取,反复硅胶柱色谱分离与纯化,经理化常数测定、波谱解析、化学合成及降解反应,确定其结构。结果：从乙酸乙酯萃取物中分离鉴定了1个二萜,其结构为ent-kauran-16β,17-acetal ent-16β-kauran-17(S)-aldehyde (1)。结论：化合物1为新的对映-贝壳杉烷型缩醛聚合二萜,命名为鄂贝缩醛A(fritillebinide A)。     

Rearranged abietane diterpenoids from Clerodendrum mandarinorum

Five new abietane derivatives which have a commonly rearranged abietane skeleton contained a 17(15 → 16),18(4 → 3)-diabeo-abietane framework, mandarones D-H, were isolated from the stem of Clerodendrum mandarinorum Diels (Verbenaceae). The structures were characterized as (16S)-12,16-epoxy-11-hydroxy-17(15 → 16),18(4 → 3)-diabeo-abieta-3,5,8,11,13-pentaene-7-one (mandarone D, 1), 12,16-epoxy-11,14-dihydroxy-17(15 → 16),18(4 → 3)-diabeo-abieta-3,5,8,11,13,15-hexaene-7-one (mandarone E, 2), 12,16-epoxy-6,11,14-trihydroxy-17(15 → 16),18(4 → 3)-diabeo-abieta-3,5,8,11,13,15-hexaene-7-one (mandarone F, 3), 12,16-epoxy-11,14-dihydroxy-6-methoxy-17(15 → 16),18(4 → 3)-diabeo-abieta-3,5,8,11,13,15-hexaene-2,7-dione (mandarone G, 4) and 12,16-epoxy-11,14-dihydroxy-17(15 → 16),18(4 → 3)-diabeo-abieta-3,5,8,11,13,15-hexaene-1,7-dione (mandarone H, 5) respectively, mainly based on the spectral analysis and by comparison with those of closely related compounds.     

Microbial hydroxylation of cinobufagin by Mucor spinosus

Mucor spinosus has been employed for the biotransformation of cinobufagin (1) to afford three metabolites. On the basis of their physico-chemical data, the structures of the transformation products have been characterized as 1β-hydroxy-cinobufagin (2), 12β-hydroxy-cinobufagin (3) and 1β,12β-dihydroxy-cinobufagin (4), of which metabolites 2 and 4 are new compounds. In vitro cytotoxic activities of the biotransformation products and the substrate-cinobufagin have been assayed against four tumor cell lines of Bel 7420, BGC 823, HeLa and HL 60; they all showed cytotoxic activities.     

Arylglycerol glucosides from Dracocephalum forrestii

Three new arylglycerol glucosides, threo-guaiacylglycerol 3-O-(6-O-p-hydroxybenzoyl)-β-D-glucopyranoside (1), threo-guaiacylglycerol 3-O-[6-O-(E)-p-coumaroyl]-β-D-glucopyranoside (2) and threo-guaiacylglycerol 3-O-[6-O-(Z)-p-coumaroyl]-β-D-glucopyranoside (3), together with seven known compounds were isolated from the whole plants of Dracocephalum forrestii and their structures were determined on the basis of spectroscopic evidences.     

Chemical constituents of Pseudopterogorgia species of the Indian ocean

A new ceramide, (2S,3R,4E)-1,3-dihydroxy-2-[(hexadecanoyl)amino]-nonadeca-4-ene (1), cholest-5-en-3β,7β,19-triol (2), identified as its, peracetyl derivative (3), and batyl alcohol (4) were isolated from Pseudopterogorgia species. 1 exhibited antibacterial activity against Gram-positive and Gram-negative bacteria.     

Triterpenes from Campanula lactiflora

One new triterpene compound, 3β-acetoxylup-20(30)-en-29-al (1) and two known 3-acetylptiloepoxide (2) and 3β-acetoxylup-20(29)-ene (3) were isolated for the first time from the leaves of Campanula lactiflora and their structures were deduced by high field 1D and 2D 400 MHz NMR, EI-MS and (+) LC-MS/MS spectra.     

Studies on chemical constituents from Ilex pubescens

Two new phenolic glycosides, ilexpubsides A and B, along with four known lignan glycosides were isolated from the roots of Ilex pubescens. By spectral evidence, the structures of the new compounds were elucidated as 4-O-β-D-[6'-O-(4'-O-β-D-glucopyranosylvanilloyl)glucopyranosyl] vanillic acid (1) and syringinic 6'-O-β-D-xylopyranoside (2). The known compounds were identified to be liriodendrin (3), (-)-olivil (4), tortoside A (5) and (+)-cyclo-olivil (6). All compounds were first isolated from Ilex pubescens.     

A new sesquiterpene lactone glucoside with inhibitory effect on K562 cells from Ixeris sonchifolia (Bge) Hance

A new minor sesquiterpene lactone glucoside, ixerin Z_A (1), together with 16 known compounds, were isolated from the whole plants of Ixeris sonchifolia (Bge) Hance. The structure of 1 was elucidated as 1(10),3,11(13)-guaiatriene-12,6-olide-2-one-3-O-[6'-(p-metheoxyphenylacetyl)]-β-glucopyranoside on the basis of spectroscopic and chemical evidence. Compound 1 exhibited an inhibitory effect on K₅₆₂ cells.     

Chemical Constituents from the Leaves of Magnolia Denudata

20 compounds were isolated from the leaves of Magnolia denudata including 16 lignans, which belong to 6 structural types. Except for (7R, 8S, 1'S) -δ^8' - 1', 4' - dihydro - 5'- methoxy - 3, 4 -methylenedioxy - 4' - oxo -7.O.2', 8.1' - neolignan (6), magliflonenone (9), 2,5' - diene-2', 8'- epoxy - 5' - methoxy - 8 - methyl - 4' - oxo - 3,4-methylenedioxy - spiro (5,5) - undecane (10), veraguensin (16) and β-sitosterol (20), the other 15 compounds were obtained from this species for the first time. The absolute configurations of 3 compounds (1,4,10) were determined by CD spectroscopy for the first time. The anti-inflammatory activities of compounds 1, 2 and 16 were assessed and 2 was shown to have significant inhibition effect on mice hind-paw edema induced by carrageenan.     

Oleanane-type triterpenes from Ludwigia octovalvis

Two new oleanane-type triterpenes, (23Z)-feruloylhederagenin (1) and (23E)-feruloylhederagenin (2), together with two known oleanane-type triterpenes, β-amyrin acetate and β-amyrin palmitate, have been isolated from the whole plant of Ludwigia octovalvis. The structures of 1 and 2 were characterised on the basis of spectral evidence.     

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-β-D-glucopyranose (5) and 1,2,3,6-tetra-O-galloyl-β-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 μM (1), 22.1 μM (2), 10.3 μM (3), 7.8 μM (4), 7.9 μM (5) and 6.6 μM (6).