Two new triterpenoids from the resin of Boswellia carterii

Two new triterpenoids, 3-oxotirucalla-7,9(11),24-trien-21-oic acid (1) and 18Hα,3β,20β-ursanediol (2), along with 15 known triterpenes, α-amyrin, α-boswellic acid, β-boswellic acid, acetyl α-boswellic acid, acetyl β-boswellic acid, 9,11-dehydro-β-boswellic acid, 9,11-dehydro-α-boswellic acid, acetyl 11α-methoxy-β-boswellic acid, 11-keto-β-boswellic acid, acetyl 11-keto-β-boswellic acid, acetyl α-elemolic acid, 3β-hydroxytirucalla-8,24-dien-21-oic acid, elemonic acid, 3α-hydroxytirucalla-7,24-dien-21-oic acid, and 3α-hydroxytirucall-24-en-21-oic acid, were isolated from the resin of Boswellia carterii Birdw.     

Two new triterpenoids from the resin of Styrax tonkinensis

Two new triterpenoids, 3β,6β-dihydroxy-12-oxo-13Hα-olean-28,19β-olide (1) and 3-oxo-olean-11,13(18)-dien-28,19β-olide (2) were isolated from the resin of Styrax tonkinensis (Pier.) Craib. The structures of both triterpenoids were determined by physicochemical and spectroscopic methods. Compound 1 is the second triterpene found with cis-fused C/D ring from the resin, which is rarely observed in oleanane-type triterpenes.     

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.     

A new chromone and a new aliphatic ester isolated from Daldinia eschscholtzii

Abstract

A new chromone and a new aliphatic ester were isolated from the EtOAc extract of myceliums of Daldinia eschscholtzii. Their structures were elucidated as (R)-5-hydroxy-8-methoxy-2-methylchroman-4-one (1) and (E)-6-(non-3-en-1-yl) -2H-pyran-2-one (2) by interpretation of the spectroscopic evidence.     

A new gymnomitrane-type sesquiterpenoid from the liverwort Cylindrocolea recurvifolia

A novel gymnomitrane-type alcohol was identified from the liverwort Cylindrocolea recurvifolia. The structure of this new compound was confirmed by X-ray analysis. This is the first report on the chemical constituents of this genus.     

Screening of Plumbago Species for the Bio-active Marker Plumbagin

Three locally available Plumbago species (Plumbago auriculata, Plumbago rosea and Plumbago zeylanica) have been quantitatively screened for the bioactive marker plumbagin by high performance thin layer chromatography. In general, the root parts were found to be the rich sources for plumbagin. Most significantly, P. rosea was found to accumulate maximum plumbagin in the roots. In contrast, P. auriculata and P. zeylanica are high yielding species for the leaf and stem parts, respectively. Studies have also been extended to evaluate some P. rosea samples collected from southern India and a traditional medicine, Chitrakadi vati, which contains P. zeylanica as the major constituents.     

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).     

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.     

A new anti-HIV lupane acid from Gleditsia sinensis Lam.

A new lupane acid, 2β-carboxyl,3β-hydroxyl-norlupA (1)-20 (29)-en-28-oic acid (1), together with five known lupane acid derivatives (2-6), were isolated from the stings of Gleditsia sinensis Lam.. Their structures were elucidated on the basis of 1D and 2D NMR techniques. All these known compounds were isolated from this genus for the first time. The new compound 1 showed strong anti-HIV activity.     

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.     

Antifungal Activity of the Essential Oils of Nine Zingiberaceae Species

The rhizome oils of nine Zingiberaceae species [Zingiber officinale Rosc., Z. cassumunar Roxb., Z. zerumbet Smith, Curcuma aeruginosa Roxb., C. mangga Valeton and van Zyp, C. xanthorrhiza Roxb., Kaempferia galanga Linn., Alpinia galanga Swartz and Boesenbergia pandurata (Roxb.) Schlecht] were investigated for their antifungal activities against five dermatophytes (Trichophyton mentagrophytes, T. rubrum, Microsporum canis, M. nanum and Epidermophyton floccosum), three filamentous fungi (Aspergillus niger, A. fumigatus and Mucor sp.) and five strains of yeast (Saccharomyces cerevisiae, Cryptococcus neoformans, Candida albicans, Ca. tropicalis and Torulopsis glabrata). The antifungal testing was carried out by using the broth microdilution and the disc gel diffusion methods. Amongst the essential oils studied, only the oil of B. pandurata was effective against all the fungi, exhibiting the lowest MIC values of 0.63µgµl -1 to Mucor sp., 1.25µgµl -1 to both A. niger and A. fumigatus, and 2.5µgµl -1 to both T. rubrum and E. floccosum, and the highest inhibition zone diameter of 20.6mm against S. cerevisiae. The essential oil of K. galanga showed selective toxicity against A. fumigatus with a MIC value of 0.63µgµl -1, while the essential oils of Z. officinale and Z. cassumunar exhibited high activity against the yeasts (11.7-15.7mm). The chemical composition of the active essential oils was investigated by GC and GC-MS.     

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 metabolites from the mangrove endophytic fungus No. 2524

Two new metabolites, the cyclo-(l-Phe-l-Leu¹-l-Leu²-l-Leu³-l-Ile) (1) and (3S,4R)-dihydroxy-(6S)-undecyl-α-pyranone (2) have been produced by the endophytic fungus no. 2524 isolated from a seed of mangrove Avicennia marina in Hong Kong. The structures have been elucidated by spectra including two-dimensional NMR, ESI tandem mass spectrometry and CD. These compounds show no activity toward human cancer cell lines Bel-7402, NCI-4460 and the normal human cell lines L-02.     

Two new 5,8-quinoflavans from the leaf of Ilex centrochinensis

Two new 5,8-quinoflavans were isolated from the leaf of Ilex centrochinensis, and their structures were elucidated as (2R)-7,3′,4′-trimethoxy-5,8-quinoflavan and (2S)-7-methoxy-4′-hydroxy-5,8-quinoflavan on the basis of spectroscopic methods, especially 1D and 2D NMR, CD, and mass spectral analyses. Both of them exhibited weak cytotoxic activity against HuH7 cell lines and no cytotoxic activity against CaCO-2 cell lines.     

Two novel sesquiterpenoids from Ainsliaea fragrans Champ.

A new sesquiterpene lactone, 3β-O-β-d-glucopyranosyl-8α-hydroxy-11α,13-dihydrozaluzanin C (1), and a novel trinorguaiane-type sesquiterpene, 4β,10α-dimethyl-1β,5α-bicycle[3,5,0]dec-6-en-4α,10β-diol (2), together with three known compounds, glucozaluzanin C (3), 11α,13-dihydrozaluzanin C (4), and 8α-hydroxy-11α,13-dihydrozaluzanin C (5), were isolated from the whole plant of Ainsliaea fragrans Champ. The structures of 1 and 2 were elucidated on the basis of detailed spectral analysis. Structures of the known compounds were identified by comparison of its spectral data with those values in the literature.     

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.     

Two new sesquiterpenoids from the fungus Ceriporia alachuana

Two new sesquiterpenoids, tremulenolide D (1) and muurolane-10β,15-diol (2), together with four known sesquiterpenoids, tremulenediol A (3), 2β-hydroxy-α-candinol (4), epicubenol (5), and 3β-hydroxy-δ-candinol (6), were isolated from cultures of the fungus Ceriporia alachuana. The structures of new compounds were determined by extensive spectroscopic analyses. Structurally, compounds 1 and 3 are tremulane-type sesquiterpenoids with an unusual perhydroazulene carbon skeleton.     

A new gymnomitrane-type sesquiterpenoid from the liverwort Cylindrocolea recurvifolia

A novel gymnomitrane-type alcohol was identified from the liverwort Cylindrocolea recurvifolia. The structure of this new compound was confirmed by X-ray analysis. This is the first report on the chemical constituents of this genus.     

Two new phenols from Lysimachia patungensis

Two new phenols, methyl 3-(2-O-β-d-glucopyranosyl-3-hydroxy-5-methoxyphenyl) propionate (1) and myricetin-3,3′,5′-tri-O-α-l-rhamnopyranoside (2), together with six known phenols compounds (3–8), were isolated from the whole plant of Lysimachia patungensis Hand.-Mazz. Their structures were elucidated on the basis of the interpretation of spectroscopic data, viz., ESI-MS, HR-TOF-MS, UV, IR, and NMR. All the known phenols were isolated from the genus Lysimachia for the first time. A preliminary bioassay revealed that compounds 3 and 7 exhibited significant protective effects against hydrogen peroxide-induced damage in human retinal endothelial cells (HRECs) with the concentration of 10 μM, respectively. Compound 1 showed moderate activity against the HRECs damage at 100 μM.     

氧甲氢龙合成中伴生副产物2-(2-羟基乙氧基)-17β-羟基-2,17α-二甲基-A-失碳-5α-雄甾烷的鉴定与合成

目的为改进氧甲氢龙的合成工艺及提高产率提供实验依据。方法通过柱色谱、重结晶等方法分离纯化合成氧甲氢龙过程中发现的副产物,经IR、1H-NMR、13C-NMR、MS、元素分析、X-单晶衍射实验等分析手段确证副产物的化学结构;推测副产物的形成机制并按此机制合成该副产物。结果与结论鉴定副产物为2-（2-羟基乙氧基）-17β-羟基-2,17α-二甲基-A-失碳-5α-雄甾烷,其形成机制可能是格氏试剂形成的甲基负离子在进攻中间体（7）17位的羰基碳的同时,一部分的甲基负离子从甾体平面结构的下方进攻了2位的乙缩酮的碳原子进而生成该副产物。准确分析出副产物的化学结构及形成机制。