A new acetylenic compound from the rhizomes of Atractylodes chinensis and its absolute configuration

A new acetylenic compound "atractyloyne", (3S,4E,6E,12E)-1-isovaleryloxy-tetradeca-4,6,12-triene-8,10-diyne-3,14-diol (1) was isolated from the rhizomes of Atractylodes chinensis (Compositae) together with a known compound (4E,6E,12E)-3-isovaleryloxy-tetradeca-4,6,12-triene-8,10-diyne-1,14-diol (2). These structures were determined on the basis of the spectroscopic data and chemical evidence, and the absolute configuration of 1 was established by the modified 2-methoxy-2-trifluoromethylphenylacetic acid (MTPA) method.     

Antiallergic agents from natural sources. 3. Structures and inhibitory effects on nitric oxide production and histamine release of five novel polyacetylene glucosides from Bidens parviflora WILLD

Five new polyacetylene glucosides, bidensyneosides A1, A2, B, C (1-4), and 3-deoxybidensyneoside B (5), have been isolated from the air-dried whole plant of Bidens parviflora WILLD. The structures were identified based on spectroscopic analysis, physicochemical properties, and application of the modified Mosher method to be 3(R),8(E)-8-decene-4,6-diyne-1,3-diol 1-O-beta-D-glucopyranoside (1), deca-3(R),8(Z) 8-decene-4,6-diyne-1,3-diol 1-O-beta-D-glucopyranoside (2), 3(R)-deca-4,6,8-triyne-1,3-diol 1-O-beta-D-glucopyranoside (3), 3(R),8(E)-8-decene-4,6-diyne-1,3,10-triol 1-O-beta-D-glucopyranoside (4), and 8(E)-8-decene-4,6-diyne-1,10-diol 1-O-beta-D-glucopyranoside (5), respectively. These compounds inhibited nitric oxide (NO) production in lipopolysaccharide and interferon-gamma activated murine macrophages (RAW264.7) and also inhibited histamine release from rat mast cells stimulated by the antigen-antibody reaction.     

Glycosides of Atractylodes ovata

A new coumarin glycoside and a new glycoside of an acetylene derivative were isolated from the water-soluble portion of the methanolic extract of Atractylodes ovata rhizome together with eight known compounds. Their structures were characterized as scopoletin beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside and (2E)-2-decene-4,6-diyne-1,8-diol 8-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside, respectively, based on chemical and spectroscopic investigations. A comparison of the polar constituents among Atractylodes japonica, Atractylodes lancea, and A. ovata is led to the conclusion that A. ovata is distinguishable from A. lancea and A. japonica, as also shown by phylogenetic analysis.     

Polyacetylene glycosides from Gymnaster koraiensis

Two polyacetylene glycosides, gymnasterkoreasides A and B, were isolated from the roots of Gymnaster koraiensis. Their structures were elucidated to be (3R)-8-decene-4,6-diyne-1,3-diol 1-O-beta-D-glucopyraside and (3R)-8-decene-4,6-diyne-1,3-diol 1-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyraside on the basis of spectroscopic analysis including COSY, HMQC, and HMBC experiments, as well as chemical methods, which confirmed the determination of a chiral center by the modified Mosher's method.     

Ceramide constituents from five mushrooms

Five mushrooms, Panellus serotinus, Lyophyllum connatum, Amanita pantherina, Sarcodon aspratus and Lepista nuda, have been investigated chemically. Two new ceramides, (2S,3R,4E,8E)-N-hexadecanoyl-2-amino-9-methyl-4,8-octadecadiene-1,3-diol (1) and (2S,3R,4E,8E,9'Z,12'Z)-N-9',12'-octadecadienoyl-2-amino-9-methyl-4,8-octadecadiene-1,3-diol (2), have been isolated from Panellus serotinus. Compound 2 was also isolated from Lyophyllum connatum. Two new ceramides, (2S,2'R,3R,4E,8E)-N-2'-hydroxypentadecanoyl-2-amino-9-methyl-4,8-octadecadiene-1,3-diol (4) and (2S,2'R,3R,4E,8E)-N-2'-hydroxytetradecanoyl-2-amino-9-methyl-4,8-octadeca-diene-1,3-diol (5), have been isolated from Amanita pantherina with (2S,2'R,3R,4E,8E)-N-2'-hydroxyhexadecanoyl-2-amino-9-methyl-4,8-octadecadiene-1,3-diol (3), a known synthetic compound. Compounds 3 and 4 were also isolated from Sarcodon aspratus and compound 3 was isolated from Lepista nuda. The structures of the new compounds were elucidated on the basis of their spectral data.     

Glycosides of Atractylodes lancea

Five sesquiterpenoid glycosides (two guaiane-type glycosides and three eudesmane-type glucosides) and a glucoside of an acetylene derivative were newly isolated from the water-soluble portion of the methanolic extract of Atractylodes lancea rhizome together with 26 known compounds. Their structures were characterized as atractyloside A 14-O-beta-D-fructofuranoside, (1S,4S,5S,7R,10S)-10,11,14-trihydroxyguai-3-one 11-O-beta-D-glucopyranoside, (5R,7R,10S)-isopterocarpolone beta-D-glucopyranoside, cis-atractyloside I, (2R,3R,5R,7R,10S)-atractyloside G 2-O-beta-D-glucopyranoside, and (2E,8E)-2,8-decadiene-4,6-diyne-1,10-diol 1-O-beta-D-glucopyranoside on the basis of chemical and spectroscopic investigation. The presence of six characteristic guaiane-type glucosides in both rhizomes of A. lancea and Atractylodes japonica suggested a close chemotaxonomic relationship between them.     

红树植物海杧果内生真菌Penicillium sp.中的抗菌活性成分

对红树植物海杧果内生真菌Penicillium sp.发酵液的乙酸乙酯提取物进行了柱层析分离, 得到3个化合物, 经MS, NMR, 1H-1H COSY, HMQC和HMBC等鉴定, 分别为4-(3-hydroxybutan-2-yl)-3,6-dimethylbenzene-1,2-diol(1), 4-(3-hydroxybutan-2-yl)-3-methyl-6-acetylbenzene-1,2-diol(2)和3,4,5-trimethyl-1,2-benzenediol(3). 其中化合物1和2为新化合物, 化合物3为新的天然产物. 抗菌活性测试结果表明, 化合物1和3均具有抗耐甲氧西林金黄色葡萄球菌的活性, 化合物2则未显示此活性.     

A new polyacetylene glycoside from the rhizomes of Atractylodes lancea

<正>A new polyacetylene glycoside,(1,3Z,11E)-tridecatriene-7,9-diyne-5-hydroxyl-6-O-β-D-glucopyranoside,was isolated from the rhizomes of Atractylodes lancea(Thunb.) DC.Its structure was elucidated on the basis of spectral analysis.     

Chemical composition and antioxidant activity of Campanula alliariifolia

In this study, the chemical constituents of Campanula alliariifolia Willd. (Campanulaceae) are being investigated for the first time with the aid of this article. Five known compounds, which were quercetin-3-O-glucoside, quercetin-3-O-rutinoside, kaempferol-3-O-glucoside, lobetyolin (9-O-beta-D-glucopyranosyl-2,10-tetradecadien-4,6-diyne-8,14-diol) and lobetyol (2,10-tetradecadien-4,6-diyne-8,9,14-triol), were isolated from the methanol extract. The antioxidant activity of the methanol extract and the purified compounds of the plant was investigated with DPPH (1,1-diphenyl-picrilyhydrazyl) (free radical scavenging activity) and reducing power methods. The methanol extract has antioxidant capacity according to the mentioned methods. Lobetyol and lobetyolin showed significant antioxidant activity more than both methanol extract and other purified compounds.     

3-epicabraleahydroxylactone and other triterpenoids from camellia oil and their inhibitory effects on Epstein-Barr virus activation

The structure of a triterpenoid isolated from the nonsaponifiable lipid (NSL) of the seed oil of the camellia (Camellia japonica L.; Theaceae) was established to be (20S)-3beta-hydroxy-25,26,27-trisnordammaran-24,20-olide (1; 3-epicabraleahydroxylactone) on the basis of spectroscopic and chemical methods. Six other triterpenoids isolated from the NSL were identified as 3-epicabraleadiol (2), ocotillol II (3), ocotillol I (4), dammarenediol II (5), (20R)-taraxastane-3beta,20-diol (6), and lupane-3beta,20-diol (7). Upon evaluation of the seven triterpenoids (1-7) with respect to their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, three compounds (5-7) showed potent inhibitory effects against EBV-EA induction (IC(50) values of 277-420 mol ratio/32 pmol TPA).     

Enantioselective photoconversion of pyridones into β-lactam derivatives in inclusion complexes with optically active host compounds

Irradiation of inclusion complexes of pyridones and optically active host compounds, (R,R)-(-)-1,6-di(o-chlorophenyl)-1,6-diphenylhexa-2,4-diyne-1,6-diol and (R,R)-(-)-trans-4,5-bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxacyclopentane, in the solid state gave optically active β-lactam derivatives.     

Five new sesquiterpenoids and a new diterpenoid from Erigeron annuus (L.) PERS., Erigeron philadelphicus L. and Erigeron sumatrensis RETZ

The aerial parts of Erigeron annuus (L.) PERS., E. philadelphicus L. and E. sumatrensis RETZ. (Compositae) have been investigated chemically. A new sesquiterpenoid, 6beta,14-epoxyeudesm-4(15)-en-1beta-ol (1), and a new diterpenoid, philadelphinone (6), have been isolated from E. philadelphicus. Four new sesquiterpenoids, (7R*)-opposit-4(15)-ene-1beta,7-diol (2), 11-methoxyopposit-4(15)-en-1beta-ol (3), 15-methoxyisodauc-3-ene-1beta,5alpha-diol (4) and 10alpha-hydroxycadin-4-en-15-al (5), have been isolated from E. annuus. Compounds 2 and 4 were also isolated from E. sumatrensis. The structures of the new compounds were elucidated on the basis of their spectral data.     

Synthesis of new trans double-bond sphingolipid analogues: Delta(4,6) and Delta(6) ceramides

Unsaturation was introduced at Delta(4,6) and Delta(6) of the sphingoid chain of naturally occurring ceramide 1 via a beta-keto sulfoxide (12) and sulfone (18) derived from N-Boc-L-serine methyl ester acetonide (9), affording two novel ceramide analogues, (2S,3R)-2-octanoylamidooctadeca-(4E,6E)-diene-1,3-diol (2) and (2S,3R)-2-octanoylamidooctadec-(6E)-ene-1,3-diol (3). After C-alkylation of 12 with (E)-1-bromo-2-tetradecene (8), a trans double bond was installed by elimination of PhS(O)H, providing conjugated dienone oxazolidine 13. Reaction of 18 with 8, followed by desulfonation (Al(Hg)), afforded keto-oxazolidine 20, which bears a (E)-Delta(6) double bond. The syntheses of analogues 2 and 3 from ketones 13 and 20, respectively, were completed by the following sequence of reactions: diastereoselective reduction (NaBH(4)/CeCl(3) or DIBAL-H), hydrolysis of the oxazolidine ring, liberation of the amino group, and installation of the N-amide group.     

Phenolic glycosides from Pyrola japonica

Five new phenolic glycosides, 2-beta-D-glucopyranosyloxy-5-hydroxyphenylacetic acid methyl ester (4), 4-hydroxy-2-[3-hydroxy-3-methylbutyl]-5-methylphenyl beta-D-glucopyranoside (5), 4-hydroxy-2-[(E)-4-hydroxy-3-methyl-2-butenyl]-5-methylphenyl beta-D-glucopyranoside (7), 4-hydroxy-2-[(2E,6Z)-8-beta-D-glucopyranosyloxy-3,7-dimethylocta-2,6-dien-1-yl]-5-methylphenyl beta-D-glucopyranoside (8), and 2,7-dimethyl-1,4-dihydronaphthalene-5,8-diol 5-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranoside (10), were isolated from the whole plants of Pyrola japonica (Pyrolaceae), together with androsin, (-)-syringaresinol glucoside, homoarbutin, pirolatin, hyperin, monotropein and chimaphilin.     

Sesquiterpenes from the secondary metabolites of Streptomyces sp. (YIM 56130)

Three new sesquiterpenes were isolated from the fermentation broth of Streptomyces sp. and their structures were determined as caryolane-1,7α-diol (1), 1,6,11-eudesmanetriol; (1α,6β)-form (2), 11-eudesmene-1,6-diol; (1α,6β)-form (3), together with nine known compounds as caryolane-1,9α-diol (4), 2-methyl-5-nonanol (5), soyasaponin I (6), cyclo (Ala-Leu) (7), homononatinic acid (8), β-sitosteryl glucoside-3'-O-heptadecoicate (9), 2'-deoxythymidine (10), 2'-deoxyuridine (11), trehalose (12). The structures were elucidated by spectral analysis.     

Antibacterial sphingolipid and steroids from the black coral Antipathes dichotoma

From the black coral Antipathies dichotoma, a sphingolipid (2S*,3S*,4E,8E)-2N-[tetradecanoyl]-4(E),8(E)-icosadiene-1,3-diol (1) and a steroid (22E)-methylcholesta-5,22-diene-1α,3β,7α-triol (2) were isolated. Other known compounds, 3β,7α-dihydroxy-cholest-5-ene (3), (22E,24S),5α,8α-epidioxy-24-methylcholesta-6,22-dien-3β-ol (4) and (22E,24S),5α,8α-epidioxy-24-methylcholesta-6,9(11),22-trien-3β-ol (5). The structures were established on the basis of NMR spectroscopic analysis and comparison with literature. The antibacterial activity of five compounds was evaluated.     

Two new phenolic compounds from Ardisia gigantifolia

Two new compounds were isolated from the 60% ethanol extract of the dried rhizome of Ardisia gigantifolia Stapf. The structures were elucidated on the basis of spectroscopic methods as （＋）-5-（1,2-dihydroxypentyl）-benzene- 1,3-diol and （-）-5-（1,2- dihydroxypentyl）benzene- 1,3-diol.     

Two new cucurbitane triterpenoids from Momordica charantia L.

Two new cucurbitane-type triterpenoids,(23E)-5β,19-epoxycucurbita-6,23,25-triene-3β-ol(1) and(19R,23E)-5/β,19-epoxy- 19-ethoxycucurbita-6,23-diene~3β,25-diol(2),together with three known compounds,have been isolated from the fruit of Momordica charantia L.Their structures were determined on the basis of spectral analysis.Their cytotoxic activity was tested on 5 cancer cell lines,MCF-7,HepG2,Dul45,Colon205 and HL-60 by MTT assay.Compounds 1,3 and 4 showed weak cytotoxicity.     

Megastigmane glucosides from Equisetum debile and E. diffusum

A new megastigmane diglucoside, (3S,5R,6S,7E,9S)-megastigman-7-ene-5,6-epoxy-3,9-diol 3,9-O-beta-D-diglucopyranoside (3), was isolated from the aerial portion of Equisetum debile along with macarangioside D (debiloside A), sammangaoside A, (6R,9S)-3-oxo-alpha-ionol 9-O-beta-D-glucopyranoside, debiloside B, kaempferol 3-O-sophoroside, kaempferol 3,7-O-beta-D-diglucopyranoside, kaempferol 3-O-sophoroside-7-O-beta-D-glucopyranoside, phenylethyl O-beta-D-glucopyranoside, (Z)-3-hexenyl O-beta-D-glucopyranoside, (7S,8R)-dehydrodiconiferyl 4-O-beta-D-glucopyranoside, and L-tryptophan. The absolute configuration at C-6 of the original structure of debilo-side A was revised to 6R-configuration, and was identical with macarangioside D (1). From the aerial portion of E. diffusum, four compounds, sammangaoside A, kaempferol 3-O-sophoroside and L-tryptophan and (3S,5R,6S,7E,9S)-megastigman-7-ene-5,6-epoxy-3,9-diol 3-O-beta-D-glucopyranoside were identified. The spectroscopic data of (3S,5R,6S,7E,9S)-megastigman-7-ene-5,6-epoxy-3,9-diol 3-O-beta-D-glucopyranoside (13) were found to be identical with corchoionoside A (9R-isomeric compound). The structure of corchoionoside A was also discussed. Structure determinations were based on physical data and spectroscopic evidence.     

Structure determination of germacrane-type sesquiterpene alcohols from an endophyte Streptomyces griseus subsp

Three germacrane-type sesquiterpene alcohols were isolated from an endophyte of mangrove plant Kandelia candel. Their structures were characterized as 1(10)E,5E-germacradiene-11-ol (1), 1(10)E,5E-germacradiene-3,11-diol (2), 1(10)E,5E-germacradiene-2,11-diol (3) based on the extensive NMR studies. Among them, 2 and 3 are identified as new compounds.