9, 10-Dihydrophenanthrene derivatives from Pholidota yunnanensis and scavenging activity on DPPH free radical

Three new 9,10-dihydrophenanthrene derivatives named phoyunnanins A-C, together with six known 9,10-dihydrophenanthrene constituents, 4,4',7,7'-tetrahydroxy-2,2'-dimethoxy-9,9',10,10'-tetrahydro-1,1'-biphenanthrene (4), lusianthridin (5), eulophiol (6), 2,4,7-trihydroxy-9,10-dihydrophenanthrene (7) and imbricatin (8), were isolated from the 60% ethanolic extract of air-dried whole plant of Pholidota yunnanensis Rolfe. The structures of phoyunnanins A-C were established as 6-[2'-(3',3'-dihydroxy-5'-methoxybibenzy)]-4,7-dihydroxy-2-methoxy-9,10-dihydrophenanthrene (1), 6-[6'-(trans-3',3'-dihydroxy-5'-methoxystilbeny)]-4,7-dihydroxy-2-methoxy-9,10-dihydrophenanthrene (2) and 4,4',7,7'-tetrahydroxy-2,2'-dimethoxy-9,9',10,10'-tetrahydro-1,6'-biphenanthrene (3), respectively, on the basis of the spectroscopic analysis. All eight compounds (1-8) were found to show the DPPH free radical scavenging activity with EC₅₀ from 8.8 to 55.9 μM.     

Studies on the alkaloid constituents of Evodia rutaecarpa (Juss) Benth var. bodinaieri (Dode) Huang and their acute toxicity in mice

Six alkaloids (1-6) have been isolated from the fruits of Evodia rutaecarpa (Juss) Benth var. bodinaieri (Dode) Huang, two of which are new compounds, identified as 2-undecyl-4(1H)-quinolone (4) and 1-methyl-2-undecanone-10'-4(1H)-quinolone (5); the known compounds were identified as rutaecarpine (1), evodiamine (2), 1-methyl-2-undecyl-4(1H)-quinoline (3) and 2-undecanone-10'-4(1H)-quinolone (6). Compounds 1-5 were evaluated for their acute toxicity.     

Phenolic glycosides from leaves of Hopiciopsis lobata

A new phenolic glycoside, 6'-[(E)-2'-hydroxymethyl, 2'-butenoyl] arbutin (1), and two known phenolic glycosides, 6'-[(E)-4'-hydroxycinnamoyl] arbutin (2) and 6'-[(E)-3',4'-dihydroxycinnamoyl] arbutin (3), were isolated from the leaves of Heliciopsis lobata (Merr.) Sleum. Their structures were elucidated by various spectroscopic methods including 2D NMR spectroscopy.     

New flavonoids and other constituents from Lespedeza cuneata

Two new flavonoids, 6,8,3',4'-tetrahydroxy-2'-methoxy-7-methylisoflavanone (1) and 6,8,3',4'-tetrahydroxy-2'-methoxy-6'-(1,1-dimethylallyl)-isoflavone (2), were isolated from the 95% ethanolic extract of the dried roots of Lespedeza cuneata together with betulinic acid (3), β-sitosterol (4), hexacosanoic acid 2,3-dihydroxy-propyl ester (5), which were isolated from this plant for the first time. Their structures were elucidated by spectral analysis.     

Two new bioactive prenylated dihydroflavanoids from the medicinal plant Dolichos tenuicaulis (Baker) Craib

Two new prenylated dihydroflavanoids have been isolated from the medicinal plant of Dolichos tenuicaulis (Baker) Craib. Their structures were elucidated as (2S)-5,2',6'-trihydroxy-8-prenyl-6,7-(3-prenyl-2,2-dimethylpyrano)-3',4'-(2,2-dimethyl-1-keone-cyclohexadiene)-flavanone (1) and (2S)-5,2',6'-trihydroxy-8-prenyl-6,7-(3-prenyl-2,2-dimethyl-1-keone-cyclohexadiene)-flavanone (2) on the basis of spectroscopic analysis.     

Antibacterial constituents from Stemona sessilifolia

Bioassay-guided fractionation led to the isolation of eight compounds from Stemona sessilifolia. Of the eight isolates, three new bibenzyls, stilbostemins M-O (1-3), and a new tocopherol, 6-methoxy-3,4-dehydro-δ-tocopherol (4) were revealed together with four known compounds 3,5-dihydroxy-2'-methoxy bibenzyl (5), 3,5-dihydroxy bibenzyl (6), β-tocopherol (7), and γ-tocopherol (8). Compounds 5, 6, and 8 exhibited strong antibacterial activities against Staphylococcus aureus and S. epidermidis.     

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.     

Japonicins A and B from the flowers of Inula japonica

Two new flavonols japonicins, A (1) and B (2), along with nine known flavonoids were isolated from an antidepressant fraction, which was separated from the 70% alcohol extract of the flowers of Inula japonica Thumb. The structures of compounds 1 and 2 were determined as 3,3',4',5,9,10-hexahydroxy-12-methylchroman[2,3-h]flavone and 8-(1-(3,4-dihydroxyphenyl)ethyl)-3,3',4',5,7-pentahydroxyflavone by the analyses of physical constants and spectral data. The special flavonoid structure having the substituent 1-phenylethyl at C-8 position was discovered for the first time.     

A new amide from Asarum forbesii Maxim

A highly unsaturated new amide, (2E,4Z,8Z,10Z)-N-isobutyl-2,4,8,10-dodecatetraenamide (1), was isolated in very small quantities from the whole plant of Asarum forbesii Maxim. together with four known compounds, (2E,4E,8Z,10E)-N-isobutyl-2,4,8,10-dodecatetraenamide (2), (-)-sesamin (3), (-)-asarinin (4) andE)-asarone5). The Z/E isomers, 1 and 2, were separated successfully by developed silver-ion medium-pressure liquid chromatography (SIMPLC). Compound 2 and the two diastereoisomers, 3 and 4, were isolated from this plant for the first time. The characterization of these compounds was achieved by various spectroscopic methods.     

A New Bicoumarin from Stellera Chamaejasme L

Thirteen compounds were isolated from roots of Stellera chamaejasme L. (Thymelaeaceae). They are β-sitosterol (2), simplexin (3), pimelea factor P2 (4), daucosterol (5), (+)-3-hydroxy-1,5-diphenyl-1-pentanone (6), 4-ethoxy-benzoic acid (7), 2,4,6-Trimethoxy-benzoic acid (8), (+)-afzelechin (9), fumaric acid (10), N,N-dimethyl-L-aspartic acid (11), umbelliferone (12), daphniretin (13) and a novel bicoumarin named bicoumastechamin (1). Among the known compounds, 7, 8, 9, 10 and 11 were first isolated from this plant, and 6 was first isolated from the natural resources. Their structures have been elucidated on the basis of spectral data. In vitro bioassays showed that 4 inhibited cancer cell growth, 13 exhibited immunomodulatory activity, and 6 exhibited both immunomodulatory and anti-tumor activity.     

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.     

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.     

Further flavonol and iridoid glycosides from Ajuga remota aerial parts

Five new iridoid glycosides characterised as 6-keto-8-acetylharpagide (1), 6,7-dehydro-8-acetylharpagide (2), 7,8-dehydroharpagide (3), 8-acetylharpagide-6-O-β-glucoside (4), harpagide-6-O-β-glucoside (5) together with three flavonol glycosides, myricetin 3-O-rutinoside-4'-O-rutinoside (6), myricetin 3-O-rutinoside-3'-O-rutinoside (7) and isorhamnetin 3-O-rutinoside-7-O-rutinoside-4'-O-β-glucoside (8) have been isolated from the aerial parts of Ajuga remota. Also isolated were two known compounds ajugarin IV and ajugarin V. Their structures were established using spectroscopic methods including UV, IR, FAB-MS, HR-MS, 1D and 2D NMR techniques.     

Harzianums A and B produced by a fungal strain, Hypocrea sp. F000527, and their cytotoxicity against tumor cell lines

A new compound, harzianum B (1), was isolated from the culture broth of a fungal strain, Hypocrea sp. F000527, together with a known trichothecene, harzianum A (2). Its structure was determined by spectroscopic analyses including HRFAB-MS and various ¹H NMR and ¹³C NMR spectral data. Harzianum B (1) was characterised as (E,Z,E)-2', 4', 6'-octatriendioic acid esterified on the 4β-hydroxyl group of trichodermol. Harzianums A (2) and B (1) showed cytotoxicity against several human cancer cell lines.     

A new triterpenoid from Entodon okamurae Broth

One new triterpenoid, entokamurol (1), was isolated from Entodon okamurae Broth, together with other nine compounds, namely dryocrassol (2), chrysophamol (3), physcion (4), 10-nonacosamnol (5), n-hexadecanol (6), phthalic acid isodibutyl ester (7), curcumol (8), β-sitosterol (9) and daucosterol (10). Their structures were elucidated on the basis of extensive NMR (DEPT, DQF-COSY, HMQC, HMBC and NOESY), IR and MS studies. All the compounds were isolated and identified from the genus of Entodon for the first time, and it is also the first report of a guaiane-type sesquiterpenoid and compounds with anthraquinone skeleton in mosses.     

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.     

Heteroclitin H, a new lignan from Kadsura heteroclita

A new dibenzocyclooctadiene lignan, heteroclitin H (1), was isolated together with seven known compounds, heteroclitin D (2), interiorin B (3), interiorin (4), neokasuranin (5), interiotherin C (6), gomisin J (7) and (+)-anwulignan (8), from the stems of Kadsura heteroclita. Their structures were elucidated by spectroscopic methods. This is the first report of the isolation of compounds 3, 5, 6, 7 and 8 from K. heteroclita.     

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.     

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.     

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.