Two new phenol derivatives from Stereum hirsutum FP-91666

Two new phenol derivatives, 2-(3-methyl-2-buten-1-yl)-4-methoxyethyl-phenol (1) and 5-hydroxy-4-(hydroxymethyl)-2-(3-methylbut-2-en-1-yl)cyclohex-4-en-1-one (2), together with eight known compounds consisting of phenol derivatives (3 and 4), niacinamide (5), and five ergosta type compounds (6–10), were isolated from solid fermentation products of Stereum hirsutum FP-91666. Two new structures were elucidated by extensive spectroscopic methods, including 1D NMR and 2D NMR, and HR-EI-MS experiments.     

Two new monoterpenoid glycosides from Mentha spicata L.

Two new monoterpenoid glycosides, spicatoside A and spicatoside B, were isolated from the whole herbs of Mentha spicata L. which have anti-inflammatory and hemostatic activities. Their structures have been determined on the basis of spectral and chemical analysis. They are (+)-5-[1-(g -D-glucopyranosyloxymethyl)ethenyl]-2-methyl-2-cyclohexen-1-one (1), and (m )-5-{[2-( g -D-glucopyranosyloxy)-1-hydroxy-1-methyl]ethyl}-2-methyl-2-cyclohexen-1-one (2).     

A new dicoumarinoid glycoside from Daphne giraldii

A new dicoumarinoid glycoside, named giraldoid A (1), has been isolated from Daphne giraldii Nitsche. The structure of 1 was determined as 7-O-β-glucosyl-8-(7-hydroxy-2H-1-benzopyran-2-one-8-)yl-2H-1-benzopyran-2-one on the basis of chemical reactions and spectroscopic methods.     

A new isopimarane-type diterpene and a new natural atisane-type diterpene from Excoecaria agallocha

From the woods of Excoecaria agallocha, a new isopimarane-type diterpene, 3α,11β-dihydroxy-ent-isopimara-8(14),15-dien-2-one (1) and a new natural atisane-type diterpene, 16β-hydroxy-ent-atisan-3-one (2) were isolated together with three known compounds, ribenone (3), ent-labda-8(17),13E-diene-3β,15-diol (4), and ent-3β-hydroxybeyer-15-ene-2,12-dione (5). Their structures were determined by spectral data and x-ray crystallography evidence.     

Two new triterpenoids from the leaves and stems of Fritillaria hupehensis

Two new cycloartane-type triterpenoids 25-hydroxyl-9,19-cycloart-22-ene-3-one (1) and (23Z)-9,19-cycloart-23-ene-3α,25-diol (2) along with 9,19-cycloart-25-ene-3β, 24ξ-diol (3) and cycloeucalenol (4) have been isolated from the leaves and stems of Fritillaria hupehensis Hsiao et K.C. Hsia. Their structures were elucidated on the basis of spectroscopic analysis.     

Six compounds from marine fungus Y26-02

Two new compounds, together with four known compounds, have been isolated from the ethyl acetate extract of the fermentation broth of the marine fungus Y26-02. Their structures were elucidated, respectively, as 5-(ethynyloxy)-3-hydroxy-3,6-dihydro-2H-pyran-2-one (1), 4-(butoxymethyl)benzene-1,2-diol (2), 4-(methoxymethyl)benzene-1,2-diol (3), 2-acetoxymethylphenol (4), N-(2-phenylethyl)acetamide (5), and 4-hydroxyphenethyl acetate (6) on the basis of their spectroscopic and physico-chemical properties.     

Two new aromatic compounds from the resin of Styrax tonkinensis (Pier.) Craib

Two new aromatic compounds, trans-(tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-5-oxofuran-3-yl)methyl benzoate (1), 3-(4-hydroxy-3-methoxyphenyl)-2-oxopropyl benzoate (2) and one new natural product, 4-((E)-3-ethoxyprop-1-enyl)-2-methoxyphenol (3) together with five known aromatic compounds have been isolated from the resin of Styrax tonkinensis (Pier.) Craib. Their structures were determined by physical and spectroscopic methods.     

A novel sulphur glycoside from the seeds of Descurainia sophia (L.)

A new sulphur glycoside, named descurainoside (1), and the known compound sinapic acid (2) have been isolated from the seeds of Descurainia sophia (L.) Webb ex Prantl. The structure of 1 has been identified as (1R,6S,8R,9S,10S)-9,10-dihydroxy-4-[(4-hydroxy-3,5-dimethoxyphenyl)methylene]-8-(hydroxymethyl)-2,7-dioxa-5-thiabicyclo[4.4.0]decan-3-one by means of physico-chemical properties and spectroscopic methods (1D and 2D NMR, HRMS, ESI-MS).     

Two new flavonoid alkaloids from Senecio argunensis

Two new flavonoid alkaloids, 8-(2″-pyrrolidinone-5″-yl)-quercetin (1) and 8-(2″-pyrrolidinone-5″-yl)-isorhamnetin (2), were isolated from the herb of Senecio argunensis. Their structures were elucidated by spectral analysis.     

Note: A new compound from Rhododendren anthopogonosides maxim

A new compound, (2R)-4-phenyl-2-O-[β-d-xylopyranosyl(1→6)-β-d-glucopyranosyl]butane (1), has been isolated from the aerial parts of Rhododendren anthopogonoides, together with two known compounds, fraxin (2), and lyoniside (3). Their structures were determined by means of physico-chemical evidence and spectral analyses, including UV, IR, HR-FABMS, ¹H and ¹³C NMR, and 2D NMR data.     

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).     

Ceramides and cerebrosides from the marine bryozoan Bugula neritina inhabiting South China Sea

From the marine bryozoan Bugula neritina inhabiting South China Sea, a new ceramide named (2S,3R,4E)-2-(14′-methyl-pentadecanoylamino)-4-octadecene-l,3-diol (1) and a new cerebroside named 1-O-(β-d-glucopyranosyl)-(2S,3R,4E)-2-(heptadecanoylamino)-4-octadecene-l,3-diol (6), together with one known ceramide (2) and three known cerebrosides (3, 4, and 5), were isolated. Their structures were deduced by extensive spectral analysis and chemical evidences. Compound 1 is branched with a methyl [–CH(CH₃)₂] in the fatty acid moiety, which is a rare structural feature among ceramides. Compound 6 is a new cerebroside with 17 carbons in the fatty acid moiety, while 5 is a new natural product which was isolated from a natural origin for the first time.     

Two new phenolic compounds from the tuber of Sparganium stoloniferum

Two new phenolic compounds, 2-(2-hydroxyphenyl)-4-methoxycarbonyl-5-hydroxybenzofuran (1) and 1-methoxycarbonyl-2, 3-dihydroxydibenzo[b, f]oxepine (2), were isolated from the tuber of Sparganium stoloniferum. The structures of both new compounds were determined on basis of spectroscopic means including HR-ESI-MS, 1D and 2D NMR experiments.     

A new pyrrole alkaloid isolated from<Emphasis Type="Italic">Arum palaestinum</Emphasis> Boiss. and its biological activities

The phytochemical analysis of the ethyl acetate fraction ofArum palaestinum Boiss. (Araceae) led to the isolation and identification of a new polyhydroxy alkaloid compound; (S)-3,4,5-trihydroxy-1H-pyrrol-2(5H)-one (1), and other five known compounds; caffeic acid (2), isoorientin (3), luteolin (4) and vicenin II (5), as well as the rare compound 3,6,8-trimethoxy, 5,7,3′,4′-tetrahydroxy flavone (6). The structural elucidations of all the compounds were based on spectroscopic data (¹H- and¹³C-NMR, DEPT, HSQC, HMBC and NOE difference techniques) and comparison with literature data. Investigation of the antioxidant activity of the ethyl acetate fraction indicated its strong scavenging capacity for 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radicals (SC₅₀ 3.1 ±0.82 μg/mL). Moreover, the treatment of different human cancer cell lines with the ethyl acetate fraction led to dose-dependant suppression in the proliferation of both breast carcinoma cells (MCF-7; IC₅₀ 59.09±4.1 μg/mL) and lymphoblastic leukemia cells (1301; IC₅₀ 53.1±2.9 μg/mL); however, it was found to have no effect on the growth of hepatocellular carcinoma cells (Hep G2).     

Two new triterpenoids from the fungus Perenniporia maackiae

Two new triterpenoids, 3β-(2-methoxy-oxalyloxy)-24-methylene-lanost-8-en-21-oic acid (1) and 3β-(2-methoxy-oxalyloxy)-15α-hydroxy-24-methylene-lanost-8-en-21-oic acid (2), were isolated from cultures of the fungus Perenniporia maackiae, together with two previously known triterpenoids (3 and 4). Their structures were determined by spectroscopic methods, including 1D and 2D NMR, and MS analyses. All compounds were evaluated for their cytotoxic activities on five tumor cell lines.     

Two new 4,6-dimethyl-3,4-dihydrochromen-2-one derivatives from Craterellus odoratus

Two rare types of 4,6-dimethyl-3,4-dihydrochromen-2-one derivatives, named cralactones A and B (1 and 2), were isolated from the culture broth of Craterellus odoratus. The structures of the new ones were established on the basis of extensive spectroscopic analysis, and it was found that the new compounds did not show pancreatic lipase inhibitory activity. Compounds 1 and 2 are the first examples of 4,6-dimethyl-3,4-dihydrochromen-2-one.     

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.     

Two new resorcinols from Sargassum thunbergii

Two new resorcinols, 1-(5-acetyl-2,4-dihydroxyphenyl)-3-methylbutan-1-one (1) and 1-(5-acetyl-2-hydroxy-4-methoxyphenyl)-3-methylbutan-1-one (2), have been isolated from the brown algae Sargassum thunbergii (Mert.) O'Kuntze. Their structures were elucidated on the basis of spectroscopic methods.     

Two novel flavanes from the leaves of Morus alba L.

Two new flavanes, (2R,4S)-2′,4′-dihydroxy-2H-furan-(3″,4″:8,7)-flavan-4-ol (1) and (2S)-2′,4′-dihydroxy-7-methoxyl-8-butyricflavane (2), together with four known flavonoids, were isolated from the leaves of Morus alba L. Their structures were determined on the basis of spectroscopic analysis.     

Enantioselective synthesis of tri-deuterated (–)-geosmin to be used as internal standard in quantitation assays

For the accurate and sensitive quantitation of the off-flavor compound geosmin, particularly in complex matrices, a stable isotopologue as internal standard is highly advantageous. In this work, we present a versatile synthetic strategy leading from (4aR)-1,4a-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one to tri-deuterated (–)-geosmin ((4S,4aS,8aR)-4,8a-dimethyl(3,3,4-²H₃)octahydronaphthalen-4a(2H)-ol). The starting material was readily accessible from inexpensive 2-methylcyclohexan-1-one using previously published procedures.