A New Flavanone and a New Flavanone Glycoside from Scutellaria baicalensis

A new flavanone (2S)-5, 7, 2',5'-tetrahydroxy-flavanone 1 together with a new flavanone glycoside (2S)-5, 7, 2',5'-tetrahydroxy-flavanone 7-O-β-D-glucopyranoside 2, were isolated from the dry roots of Scutellaria baicalensis. Their structures were elucidated on the basis of spectroscopic data.     

Constituents from Aerial Parts of Bidens ceruna L. and Their DPPH Radical Scavenging Activity

A new chalcone glycoside,butein-4-methoxyl-4'-O-(6-O-acetyl)-β-D-glucopyranoside(2),along with seven known compounds,namely,quercitrin(1),luteolin-7-O-β-D-glucopyranoside(3),butein-4'-O-β-D-glucopyra-noside(4),butein-4-methoxyl-4'-O-β-D-glucopyranoside(5),butin-7-O-β-D-glucopyranoside(6),isoquercitrin(7),and sulfurein(8) was isolated from aerial parts of Bidens ceruna L. Their structures were elucidated on the basis of spectroscopic studies. Compounds 1―8 were tested for their DPPH radical scavenging activi...     

New flavone and isoflavone glycoside from Belamcanda chinensis

The new flavone, 5,4'-dihydroxy-6,7-methylenedioxy-3'-methoxyflavone, and one new isoflavone glycoside, 3',5'-dimethoxy irisolone-4'-O-β-D-glucoside were isolated from the rhizomes of Belamcanda chinensis. Their structures were established based on the spectroscopic methods.     

Studies on the Syntheses of the Side Chains of Brassinolide and Dolicholide

(4R,5S)-2,2-Dimethyl-4-(1',2'-dimethylpropyl)-5-(1'-bromoethyl)--1,3-dioxolane(15) with the side chain of brassinolide and (4R, 5S)--2, 2-dimethyl-4-(l'-methylene-2'-methylpropyl)-5-(1'-bromoethyl) 1,3-dioxolane(14) with the side chain of dolicholide were first synthesized through 11 and 10 stepes from D-mannitol respectively. All of the intermediates 7-13 were first synthesized too.     

ABSOLUTE CONFIGURATION OF (-)ANISODINE (A NEW GANGLIO BLOCKING AGENT) AND (-)ANISODINIC ACID

A new tropane alkaloid, (-)anisodlne (Ⅰ), was isolated from the plant of Anisodus tanguticus. It is a novel ganglio blocking agent. The absolute configuration of (-)anisodinic acid (Ⅶ), which-is the side chain of (-)anisodine, was determined by chemical correlation with (R) (-)-2-phenyl-1, 2-propanediol (Ⅳ) and (R) (-)-2-hydroxy-2-phenylpropionic acid (Ⅵ). Thereby (-)anisodine with the absolute configuration shown as (Ⅰ) is 6β, 7β-epoxy-1αH, 5αH-tropan-3α-ol (S) 2'-phenyl-2', 3'-dihydroxypropionate. Two new tropane alkaloids: 6β, 7β-epoxy-1αH, 5αH-tropan-3α-ol 2',3'-epox-ypropionate (Ⅲ) and 2'-phenyl-2'-hydroxypropionate (Ⅴ) were prepared and its physical constant is reported in this paper.     

Dracaenoside A and B, New C-22 Steroidal Lactone Glycosides from the Stem of Dracaena cochinchinensis

Two new C-22 steroidal lactone glycosides, named dracaenoside A and B were isolated from the methanol extract of the fresh stem of Dracaena cochinchinensis. Their structures were established as (20S)3β,14α,16β-trihydroxy pregn-5-ene-22-carboxylic acid (22,16)-lactone 3-O-α-L-rhamnopyranosyl (1→2)[ α-L-rhamnopyranosyl (l→4)]-β-D-glucopyranoside and (20S)3β, 14α,16β-trihydroxy pregn-5-ene-22-carboxylic acid (22,16)-lactone 3-O-α-L-rhamnopyranosyl (1→2)[β-D-glucopyranosyl(1→3)]-β-D-glucopyranoside by means of 2D NMR spectral and chemical methods. It is the first time that steroidal lactone glycosides were isolated from the genus Dracaena.     

Two New Spirostanol Steroidal Sapogenins form Fermented Leaves of Agave americana

Two new spirostanol sapogenins named agavegenin A and B were isolated from the fermentted leaves of Agave americana L.Their structures were elucidated as (23S,25R)-5α-spirostan-3β,6α,23-tetraol(1)and (23S,25S)-5α-spirostan-3β,23,27-triol(2) by spectral methods.     

Synthesis and Biological Activity of Novel 2,3-Dihydro-2-phenylsulfonylhydrazono-3-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)thiazoles

A series of novel 2,3-dihydro-2-phenylsulfonylhydrazono-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl) thiazoles were designed and synthesized via the reaction of thiosemicarbazide with chloroaldehyde.Their chemical structures were characterized by 1H and 13C NMR spectroscopy and elemental analysis.The bioassay results indicate that some of these compounds exhibit moderate fungicidal and herbicidal activities.     

Two New Furostanol Glycosides from Asparagus cochinchinensis

Two new furostanol oligoglycosides named as aspacochioside A(1)and B(2) were isolated from the roots of Asparagus cochinchinensis (Lour.)Merr..Their structures were clucidated to be 3-O-[{α-L-rhamnopyranosyl-(1→4）}{β-D-glucopyranosyl}]-26-O-[β-D-glucopy-ranosyl]-(25S)-5β-furostane-3β，22α，26-triol 1 and 3-O-[{α-L-rhamnopyranosyl-(1→4）}{β-D-glu-copyeransoyl}]-26-O-[β-D-glucopyranosyl]-22α-methoxy-(25S)-5β-furostane-3β，26-diol 2 on the basis of spectroscopic techniques and chemical methods.     

Two New Isobutyltartrate Monoester from Coeloglossum viride （L.） Hartm.var.bracteatum（Willd.） Richter

Two new isobutyltartrate monoesters,coelovirin A (1) and B(2),were isolated from the rhizomes of Coeloglossum viride (L.) Hartm. var. bracteatum (Willd.) Richter (Orchidaceae). Their structures were elucidated as (2R,3S)-2-isobutyltartrate-1-(4-β-D-glucopyranosyloxybenzyl) ester 1 and (2R,3S)-2-isobutyltartrate-4-(4-β-D-glucopranosyloxybenzyl) ester 2 on the basis of physical constants and spectroscopic methods including 2D NMR techniques.     

Studies on the constituents of Scutellaria species (XXII). Constituents of the roots of Scutellaria amabilis HARA

From the roots of Scutellaria amabilis HARA, eleven new flavonoids, 5,7,2'-trihydroxy-8-methoxyflavone 7-O-beta-D-glucopyranoside, 5,7,2'-trihydroxy-8-methoxyflavone 2'-O-beta-D-glucopyranoside, 5,7-dihydroxy-8,2'-dimethoxyflavone 7-O-beta-D-glucopyranoside, 5,7,2'-trihydroxyflavone 2'-O-beta-D-glucopyranoside, 5,7,2',5'-tetrahydroxyflavone 7-O-beta-D-glucuronopyranoside, (2S)-5,7,2',5'-tetrahydroxyflavanone, (2S)-5,7,2',5'-tetrahydroxyflavanone 7-O-beta-D-glucopyranoside, (2S)-5,7,2',5'-tetrahydroxyflavanone 7-O-beta-D-glucuronopyranoside, (2S)-7,2'-dihydroxy-5-methoxyflavanone 7-O-beta-D-glucuronopyranoside, (I-2S)-I-5,II-5,I-7,II-7,I-2',II-2',II-5'-heptahydroxy-[I-6,II-6']-flavanonylflavone and (I-2S)-I-5,II-5,I-7,II-7,I-2',II-2',I-5',II-5'-octahydroxy-[I-6,II-6']-flavanonylflavone, were isolated, together with ten known flavonoids, wogonin (5,7-dihydroxy-8-methoxyflavone), 5,7-dihydroxy-8,2'-dimethoxyflavone, (2S)-5,7,2'-trihydroxyflavanone, scutevulin (5,7,2'-trihydroxy-8-methoxyflavone), 5,7,4'-trihydroxy-8-methoxyflavone, alpinetin ((2S)-7-hydroxy-5-methoxyflavanone), 5,7,2'-trihydroxyflavone, 5,7,2',5'-tetrahydroxyflavone, (2S)-7,2'-dihydroxy-5-methoxyflavanone and 5,7-dihydroxy-8,2'-dimethoxyflavone 7-O-beta-D-glucuronopyranoside. The structures were determined on the basis of chemical and spectral data.     

Flavonoids from Andrographis viscosula

Phytochemical investigation of the whole plant of Andrographis viscosula has led to the isolation of three new 2'-oxygenated flavonoids, (2R)-5-hydroxy-7,2',3'-trimethoxyflavanone (1), 7,2',5'-trimethoxyflavone (2), 5,7,2',3'-tetramethoxyflavone (3), and eight known flavones, 5,7,2'-trimethoxyflavone (4), 5,7,2',4',5'-pentamethoxyflavone (5), echioidinin (6), 5,2',6'-trihydroxy-7-methoxyflavone (7), 5-hydroxy-7,2'-dimethoxyflavone (8), echioidin (9), echioidinin 5-O-glucoside (10), and 5,2',6'-trihydroxy-7-methoxyflavone 2'-O-glucoside (11). The structures of 1-11 were elucidated by physical and spectral methods, including extensive 2D NMR studies. The presence of 2'-oxygenated flavonoids is apparently restricted to Andrographis species in Acanthaceae. Therefore, 2'-oxygenated flavonoids are regarded as chemotaxonomic markers of Andrographis genus in the Acanthaceae family.     

Glycosylated constituents of iris fulva and Iris brevicaulis

The major constituents of leaf extracts of Iris fulva KER GAWL. comprised a known flavone C-glycoside, 5,4'-dihydroxy-7-methoxyflavone-6-C-(6?-O-(E)-p-coumaroyl-β-glucopyranosyl)(1?→2″)-β-glucopyranoside (1) and the new monoterpene glycoside, linalyl-6'-O-(3″-hydroxy-3″-methylglutaroyl)-β-D-glucopyranoside (2), both of which were prominent components of Iris brevicaulis RAF. leaf extracts. The structure of a new polyacylated sucrose derivative (3a) obtained from the rhizomes of I. fulva was elucidated as 3-O-(E)-p-coumaroyl-β-D-fructofuranosyl-(2?1')-[2″,4″,6″-tri-O-acetyl-β-D-glucopyranosyl-(1″→3')-(2',6'-di-O-acetyl-4'-O-(E)-p-coumaroyl-α-D-glucopyranoside)]. Selective hydrolysis of the 4″-O-acetyl moiety of the terminal β-glucopyranosyl residue of 3a occurred after several hours in solution giving 3-O-(E)-p-coumaroyl-β-D-fructofuranosyl-(2?1')-[2″,6″-di-O-acetyl-β-D-glucopyranosyl-(1″→3')-(2',6'-di-O-acetyl-4'-O-(E)-p-coumaroyl-α-D-glucopyranoside)] (3b), which subsequently underwent further deacetylation.     

Inhibitory effects of constituents from Euphorbia lunulata on differentiation of 3T3-L1 cells and nitric oxide production in RAW264.7 cells

A new flavonol galactopyranoside, myricetin 3-O-(2',3'-digalloyl)-β-D-galactopyranoide (1), and 23 known constituents, including myricetin 3-O-(2'-galloyl)-β-D-galactopyranoide (2), myricitrin (3), myricetin (4), quercetin 3-O-(2', 3'-digalloyl)-β-D-galactopyranoide (5), quercetin 3-O-(2'-galloyl)-β-D-galactopyranoide (6), hyperin (7), isoquercetrin (8), quercetin (9), kaempferol (10), apigenin (11), luteolin (12), 3-O-methylquercetin (13), 5,7,2',5'-tetrahydroxyflavone (14), 1,3,4,6-tetra-O-galloyl-β-D-glucose (15), 1,2,6-tri-O-galloyl-β-D-glucose (16), 1,3,6-tri-O-galloyl-β-D-glucose (17), gallic acid (18), protocatechuic acid (19), 3,4,5-trimethoxybenzoic acid (20), 2,6-dihydroxyacetophenone (21), 3,3'-di-O-methylellagic acid (22), ellagic acid (23) and esculetin (24) were isolated from Euphorbia lunulata Bge. Their structures were determined by spectroscopic analysis. Isolated hydrolysable tannins, flavonoids, and flavonol galactopyranoside gallates showed significant inhibition of the differentiation of 3T3-L1 preadipocytes and triglyceride accumulation in maturing adipocytes, and nitric oxide production in RAW 264.7 cells.     

New flavan and unusual chalcone glycosides from Drypetes parvifolia

Two new compounds 7-hydroxy-5-O-（β-D-glucopyranoside） flavan （1） and （Z）-4＇,6＇-dihydroxy-2＇-O-（β-D-glucopyranoside） chalcone （2）, along with eight known compounds, were isolated from the stem bark of Drypetes parvifolia （Euphorbiaceae）. Their structures were established on the basis of spectroscopic analysis and chemical evidence.     

Microbial metabolism. Part 12. Isolation, characterization and bioactivity evaluation of eighteen microbial metabolites of 4'-hydroxyflavanone

Fermentation of 4'-hydroxyflavanone (1) with fungal cultures, Beauveria bassiana (ATCC 13144 and ATCC 7159) yielded 6,3',4'-trihydroxyflavanone (2), 3',4'-dihydroxyflavanone 6-O-β-D-4-methoxyglucopyranoside (3), 4'-hydroxyflavanone 3'-sulfate (4), 6,4'-dihydroxyflavanone 3'-sulfate (5) and 4'-hydroxyflavanone 6-O-β-D-4-methoxyglucopyranoside (7). B. bassiana (ATCC 13144) and B. bassiana (ATCC 7159) in addition, gave one more metabolite each, namely, flavanone 4'-O-β-D-4-methoxyglucopyranoside (6) and 6,4'-dihydroxyflavanone (8) respectively. Cunninghamella echinulata (ATCC 9244) transformed 1 to 6,4'-dihydroxyflavanone (8), flavanone-4'-O-β-D-glucopyranoside (9), 3'-hydroxyflavanone 4'-sulfate (10), 3',4'-dihydroxyflavanone (11) and 4'-hydroxyflavanone-3'-O-β-D-glucopyranoside (12). Mucor ramannianus (ATCC 9628) metabolized 1 to 2,4-trans-4'-hydroxyflavan-4-ol (13), 2,4-cis-4'-hydroxyflavan-4-ol (14), 2,4-trans-3',4'-dihydroxyflavan-4-ol (15), 2,4-cis-3',4'-dihydroxyflavan-4-ol (16), 2,4-trans-3'-hydroxy-4'-methoxyflavan-4-ol (17), flavanone 4'-O-α-D-6-deoxyallopyranoside (18) and 2,4-cis-4-hydroxyflavanone 4'-O-α-D-6-deoxyallopyranoside (19). Metabolites 13 and 14 were also produced by Ramichloridium anceps (ATCC 15672). The former was also produced by C. echinulata. Structures of the metabolic products were elucidated by means of spectroscopic data. None of the metabolites tested showed antibacterial, antifungal and antiprotozoal activities against selected organisms.     

Two new iridoid glycosides from the root barks of Sambucus williamsii Hance

Two new iridoid glycosides, named williamsoside C (1) and williamsoside D (2) were isolated from the root barks of Sambucus williamsii Hance. Their structures were established on the basis of extensive spectroscopic analysis (1D, 2D NMR and HRESIMS) and chemical studies as α-D-glucopyranosyl (1→2)-β-D-fructofuranosyl (4→6)-β-morroniside (1) and 7β-O-ethyl morroniside-(6'-O-7')-β-morroniside (2), respectively.     

Isolation of sesquiterpenoids from sponge Dysidea avara and chemical modification of avarol as potential antitumor agents

The marine sponge Dysidea avara contained avarol (1) and avarone (2). Avarol on acylation yielded 2',5'-O-dibenzoylavarol (3); 2,5'-O-(4-chlorobenzoyl)avarol (4); 2,5'-O-dicinnamoylavarol (5); 2,5'-O-(4-bromobenzoyl)avarol(6); 2',5'-O-dioctanoylavarol (7); 2',5'-O-(4-fluorobenzoyl)avarol (8) and diacetylavarol (9). The structural elucidation of all the compounds 1-9 have been done by spectral analysis. The cytotoxicity of these compounds were also determined and evaluated. Compounds 6 and 9 showed selective cytotoxicity against Hepa (human hepatoma) and KB cell lines respectively.     

A new homostilbene and two new homoisoflavones from the bulbs of Scilla scilloides

A new homostilbene, named scillabene A (2), and two new homoisoflavones, named scillavones A (3) and B (4), were isolated from the bulbs of Scilla scilloides DRUCE (Liliaceae) along with 13 known compounds comprising a homostilbene, seven homoisoflavones, a xanthone, a lignan, and three nortriterpenes. The structures of 2-4 were characterized as 3,5,4'-trihydroxy-3'-methoxy-4-methyl-trans-stilbene, (3R)-5,7,2'-trihydroxy-3',4'-dimethoxyspiro{2H-1-benzopyran-7'-bicyclo[4,2,0]octa[1,3,5]-trien}-4-one and (3S)-3-(3,4-dihydroxybenzyl)-5-hydroxy-6,7-dimethoxychroman-4-one, respectively, on the basis of spectroscopic data and X-ray crystallographic analysis.     

Cytotoxic and antimicrobial aporphine alkaloids from Fissistigma poilanei (Annonaceae) collected in Vietnam

Two new aporphine alkaloids: 8-hydroxy-9-methoxy-1,2-methylenedioxyaporphine (1) and 8-hydroxy-3,9-dimethoxy-1,2-methylenedioxyaporphine (2) were isolated from the ethyl acetate extract of Fissistigma poilanei along with five known compounds: oxocrebanine (3), kuafumine (4), (2R,3R)-3',4',5,7-tetrahydroxydihydroflavonol-3-O-α-L-rhamnopyranoside (5), (+)-catechin 3-O-α-L-rhamnopyranoside (6) and quercetine 3,7-dimethoxy-3'-O-α-L-rhamnopyranosyl-(1?→?2)-β-D-glucopyranoside (7). These two new aporphine alkaloids exhibited a moderate cytotoxic activity against four human cancer cell lines (KB, Hep-G2, MCF-7, LU) as well as antimicrobial activity against Lactobacillus fermentum, Enterococcus faecium, Staphylococcus aureus and Bacillus subtillis.