Anthraquinones from the roots of Prismatomeris malayana

A novel anthraquinone, 1,3-dihydroxy-5,6-dimethoxy-2-methoxymethyl-9,10-anthraquinone (9) and a new natural product, 2-hydroxymethyl-1-methoxy-9,10-anthraquinone (8) were isolated from the roots of Prismatomeris malayana together with seven known anthraquinones, tectoquinone (1), 1-hydroxy-2-methyl-9,10-anthraquinone (2), rubiadin (3), rubiadin-1-methyl ether (4), 1,3-dihydroxy-5,6-dimethoxy-2-methyl-9,10-anthraquinone (5), nordamnacanthal (6), and damnacanthal (7). Their structures were determined on the basis of spectroscopic data. Some of the anthraquinones were tested for anticancer, antifungal, and antimalarial activities.     

Anthraquinones with antiplasmodial activity from the roots of Rennellia elliptica Korth. (Rubiaceae)

Dichloromethane root extract of Rennellia elliptica Korth. showed strong inhibition of Plasmodium falciparum growth in vitro with an IC?? value of 4.04 μg/mL. A phytochemical study of the dichloromethane root extract has led to the isolation and characterization of a new anthraquinone, 1,2-dimethoxy-6-methyl-9,10-anthraquinone (1), and ten known anthraquinones: 1-hydroxy-2-methoxy-6-methyl-9,10-anthraquinone (2), nordamnacanthal (3), 2-formyl-3-hydroxy-9,10-anthraquinone (4), damnacanthal (5), lucidin-ω-methyl ether (6), 3-hydroxy-2-methyl-9,10-anthraquinone (7), rubiadin (8), 3-hydroxy-2-methoxy-6-methyl-9,10-anthraquinone (9), rubiadin-1-methyl ether (10) and 3-hydroxy-2-hydroxymethyl-9,10-anthraquinone (11). Structural elucidation of all compounds was accomplished by modern spectroscopic methods, notably 1D and 2D NMR, IR, UV and HREIMS. The new anthraquinone 1, 2-formyl-3-hydroxy-9,10-anthraquinone (4) and 3-hydroxy-2-methyl-9,10-anthraquinone (7) possess strong antiplasmodial activity, with IC?? values of 1.10, 0.63 and 0.34 μM, respectively.     

Anthraquinones from the roots of Prismatomeris tetrandra

Three new anthraquinones, 1-hydroxy-2,3-dimethoxy-7-methyl-9,10-anthraquinone, 1,3-dihydroxy-5,6-dimethoxy-2-methyl-9,10-anthraquinone, and 3-hydroxy-1,5,6-trimethoxy-2-methyl-9,10-anthraquinone, along with five known anthraquinones were isolated from the roots of Prismatomeris tetrandra. Their structures were determined on the basis of spectroscopic data.     

Studies on the constituents of Anaxagorea luzonensis A. GRAY

Five new xanthones, 1,3,6-trihydroxy-5-methoxy-4-prenylxanthone (1), 1,3,5-trihydroxy-6-methoxy-2-prenylxanthone (2), 1,3,5-trihydroxy-4-(3-hydroxy-3-methylbutyl) xanthone (3), 1,3,6-trihydroxy-4-prenylxanthone (4), 3,6-dihydroxy-1,5-dimethoxyxanthone (5) and one new flavonoid, 3,5,7,4'-tetrahydroxy-2'-methoxyflavone (6) along with seven known xanthones and seven known flavonoids were isolated from the bark of Anaxagorea luzonensis A. GRAY and their chemical structures were determined by means of chemical and spectral studies. Almost all flavonoids and one xanthone (13) showed antioxidant activity.     

Lignans and anthraquinones from the fruits of Morinda citrifolia

Two new anthraquinones, 1,6-dihydroxy-5-methoxy-2-methoxymethylanthraquinone (1) and 1,5,7-trihydroxy-6-methoxy-2-methoxymethylanthraquinone (2), and one new lignan isoamericanoic acid A (3) were isolated from the fruits of Morinda citrifolia along with 11 known compounds scopoletin, luteolin, americanin A, americanin D, 3,3'-bisdemethylpinoresinol, p-cresol, p-hydroxybenzoic acid, p-hydroxybenzaldehyde, 4-hydroxy-3-methoxybenzaldehyde, 4-hydroxy-3-methoxycinnamaldehyde, and 2,5-dihydroxy-4-methoxybenzaldehyde. The structures of all compounds were elucidated by spectroscopic analysis.     

Two New Antibacterial Anthraquinones from Cultures of an Endophytic Fungus Phomopsis sp.

Chemistry of Natural Compounds - Two new anthraquinones, 3-hydroxy-6-hydroxymethyl-2,5-dimethylanthraquinone (1) and 6-hydroxymethyl-3-methoxy-2,5-dimethylanthraquinone (2), were isolated from the...     

New stilbenoids from Pholidota yunnanensis and their inhibitory effects on nitric oxide production

Six new stilbenoids, a (bibenzyldihydrophenanthrene) ether designated phoyunnanin D (1), a bis(dihydrophenanthrene) ether designated phoyunnanin E (2), and four stilbenes designated phoyunbene A-D (3-6), were isolated from the air-dried whole plant of Pholidota yunnanensis ROLFE. The new compounds were identified as 7-[2-(3-hydroxyphenethyl)-4-hydroxy-6-methoxyphenoxy]-4-hydroxy-2-methoxy-9,10-dihydrophenanthrene (1), 1-[(9,10-dihydro-4-hydroxy-2-methoxy-7-phenanthrenyl)oxy]-4,7-dihydroxy-2-methoxy-9,10-dihydrophenanthrene (2), trans-3,3'-dihydroxy-2',4',5-trimethoxystilbene (3), trans-3,4'-dihydroxy-2',3',5-trimethoxystilbene (4), trans-3,3'-dihydroxy-2',5-dimethoxystilbene (5), and trans-3-hydroxy-2',3',5-trimethoxystilbene (6) based on spectroscopic evidence. Furthermore, the inhibitory effects of compounds 1-6 on nitric oxide production in a murine macrophage-like cell line (RAW 264.7) activated by lipopolysaccharide and interferon-gamma were examined.     

Two new compounds from Dendrobium candidum

Two new compounds were isolated from the stems of Dendrobium candidum: (R)-3,4-dihydroxy-5,4',alpha-trimethoxybibenzyl (1), named dendrocandin A; and 4-[2-[(2S,3S)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-hydroxymethyl-8-methoxy-2,3-dihydrobenzo[1,4]dioxin-6-yl]ethyl]-1-methoxyl benzene (2), dendrocandin B. Five previously known bibenzyls were also identified: 4,4'-dihydroxy-3,5-dimethoxybibenzyl (3), 3,4-dihydroxy-5,4'-dimethoxybibenzyl (4), 3-O-methylgigantol (5), dendrophenol (6), and gigantol (7).     

Separation and determination of the anthraquinones in Xanthophytum attopvensis pierre by nonaqueous capillary electrophoresis

A nonaqueous capillary electrophoresis (NACE) method with direct on-column UV detection has been developed for the separation of the pharmaceutically important anthraquinones from the total grass of Xanthophytum attopvensis pierre extract. The separation of three main anthraquinones (1-hydroxy-2-methoxy-3-hydroxymethyl-9, 10-anthraquinone-1-O-β-d-glucoside (1), rubiadin- 1-methylether (2) and 1-methoxy-2-formyl-3-hydroxy-9, 10-anthraquinone (3)) was optimized with respect to concentration of sodium cholate (SC) and acetic acid, addition of acetonitrile (ACN), and applied voltage. Baseline separation was obtained for the three analytes within 5 min using a running buffer containing 50 mM sodium cholate (SC), 1.0% acetic acid and 40% ACN in methanol. The method of NACE for the separation and determination of bioactive ingredient in traditional Chinese medicines was discussed.     

Constituents of Roots of Rubia Lanceolata Hayata

A naphthohydroquinone and eight anthraquinones were isolated from the roots of Rubia lanceolata Hayata. Their structures were assigned as mollugin ( 1 ), l-hydroxy-2-methyl-9,10-anthraquinone ( 2 ), 2-methylquinizarin ( 3 ), 3-carbomethoxy-l-hydroxy-9,10-anthraquinone ( 4 ), lucidin ethyl ether ( 5 ), rubiadin ( 6 ), alizarin ( 7 ), ω-hydroxypachybasin ( 8 ) and digiferruginol ( 9 ) on the basis of spectral evidence. Among them, compounds 8 and 9 were isolated for the first time from Rubia species.     

Antifungal agent and other constituents from Cynanchum otophyllum

Seven constituents were isolated from the ethyl acetate extract of the rhizome of Cynanchum otophyllum Schneid (Asclepiadaceae). Their structures were determined as 1-(4-methoxy-3-(6-methoxy-3-acetylphenylperoxy)phenyl)ethanone (1), 1-(3-hydroxy-7-acetylnaphthalen-2-yl)ethanone (2), 1-(3,4-dihydroxyphenyl)ethanone (3), 1-(2,4-dihydroxyphenyl)ethanone (4), 1-(3-(3,6-dihydroxy-2-methylbenzoyl)-2,4-dihydroxyphenyl)ethanone (beishouwubenzophenone) (5), N,N-dimethylethanamine (6), and 2-oxo-2-phenylacetic acid (7), respectively, by spectral methods. Among them, 1 and 2 were new compounds; 1 had antifungal activity.     

Isolation and structure determination of two new constituents from the fruits of Morinda citrifolia Linn

Studies on the chemical constituents of the fruits of Morinda citrifolia Linn. have led to the isolation of two new compounds, morinaphthalene (=1,3,6,7-tetrahydroxy-2-hydroxymethyl-1,2,3,4-tetrahydronaphthalene, (1); and morindafurone (=5-hydroxy-1,10b-dihydro-6H-anthra [1,9-bc] furan-6-one, (2); as well as two known constituents, 1,8-dihydroxy-6-methoxy-3-methyl-9-anthrone (3) and 2,4-dimethoxy-9-anthrone (4). Their structures were elucidated by spectral analysis including 2D NMR techniques.     

Isolation of four new flavonoids from Melicope triphylla

Four new flavonoids, 3,5-dihydroxy-7,8-dimethoxy-3',4'-methylenedioxyflavone (1), 3,5-dihydroxy-7-methoxy-3',4'-methylenedioxyflavone (2), 3,5-dihydroxy-7-isopentenyloxy-8-methoxy-3',4'-methylenedioxyflavone (3) and 5-hydroxy-3-isopentenyloxy-7-methoxy-3',4'-methylenedioxyflavone (4), were isolated from the leaves of Melicope triphylla. In addition, two known flavonoids were detected including 5-hydroxy-3,7-dimethoxy-3',4'-methylenedioxyflavone (5) and 5-hydroxy-7-isopentenyloxy-3,8-dimethoxy-3',4'-methylenedioxyflavone (6). The structures of the new compounds were established by spectroscopic methods.     

Tautomerism of anthraquinones: VIII. Tautomerism and conformations of 1,4-diamino-9,10-anthraquinone

The compound widely known as 1,4-diamino-9,10-anthraquinone is in fact an equilibrium mixture of 4,9-diamino-1,10-anthraquinone and tautomeric imino forms, 10-amino-9-hydroxy-1,4-anthraquinone 1-imine and its conformer, and 4-amino-1-hydroxy-9,10-anthraquinone 9-imine or 4,9-dihydroxy-1,10-anthraquinone diimine. Amino-imino tautomerism and rotational isomerism are responsible for fine structure of the π_l,π*-absorption of the title compound.     

Two new benzaldehyde derivatives from mangrove endophytic fungus (No. ZZF 32)

Two new benzaldehyde derivatives, 6-ethyl-2-hydroxy-4-methoxy-3-methylbenzaldehyde (1), 6-ethyl-2,4-dihydroxy-3-methylbenzaldehyde (2), together with 2, 4-dihydroxy-3,6-dimethylbenzaldehyde (3) were isolated from mangrove fungus (No. ZZF 32#) from the South China Sea. The structures of compounds 1 and 2 were established by comprehensive analysis of the spectral data, especially 2D NMR spectral results.     

Studies on the constituents of Broussonetia species VIII. Four new pyrrolidine alkaloids, broussonetines R, S, T, and V and a new pyrroline alkaloid, broussonetine U, from Broussonetia kazinoki Sieb

Four new pyrrolidine alkaloids, broussonetines R, S, T, and V and a new pyrroline alkaloid, broussonetine U were isolated from the branches of Broussonetia kazinoki SIEB. (Moraceae) in low yield. Broussonetines R, S and T were formulated as (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(1R)-1-hydroxy-3-[6-(4-hydroxybutyl)-cyclohexy-2-on-1(6)-enyllpropyl] pyrrolidine (1), (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(1R,10S)-1,10,13-trihydroxytridecyl] pyrrolidine (2), (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(1R,5S)-1,5, 13-trihydroxy-10-oxo-tridecyl] pyrrolidine (3). And broussonetines U and V were proposed to be (2S,3S,4S)-2-hydroxymethyl-3, 4-dihydroxy-5-(9-oxo-13-hydroxytridecyl)-5-pyrroline (4), (2R,3S,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(E)-9-oxo-13-hydroxy-3-tridecenyl] pyrrolidine (5), respectively, by spectroscopic and chemical methods.     

Spectroscopic Analysis of the Interactions of Anthraquinone Derivatives (Alizarin,Alizarin-DA and Alizarin-DA-Fe) with Bovine Serum Albumin (BSA)

In this paper, three anthraquinones (alizarin (1,2-dihydroxy-9,10-anthraquinone), alizarin-DA (1,2-dihydroxy-9,10-anthraquinone-3-aminomethyl-N,N-diacetic acid) and alizarin-DA-Fe (1,2-dihydroxy-9,10-anthraquinone-3-aminomethyl-N,N-diacetate-ferric(III))) with a tricyclic anthraquinone planar structure are used as quenchers, to study their interaction with bovine serum albumin (BSA) molecules by fluorescence spectroscopy. The results show that these three anthraquinones can bind to BSA molecules efficiently but the stabilities decrease in the order alizarin, alizarin-DA and alizarin-DA-Fe. In addition, synchronous fluorescence spectroscopy indicates that the tryptophan (Trp) residues of BSA molecules are more accessible to alizarin and alizarin-DA than the tyrosine (Tyr) residues, but both have similar accessibility to alizarin-DA-Fe.     

Three new phenanthrenes from Monomeria barbata Lindl

<正>Three new monophenanthrene compounds were isolated from an acetone extract of the tubers of Monomeria barbata Lindl. (Orchidaceae).Using spectroscopic methods,the structures of compounds 1-3 were determined as 1,4,7-trihydroxy-2-methoxy- 9,10-dihydrophenanthrene(1),1-(p-hydroxybenzoyl)-2-methoxy-4,7-dihydroxy-9,10-dihydrophenanthrene(2),1,3,8-tri(p-hydroxybenzyl) -4-methoxy-phenanthrene-4,7-diol(3).These compounds showed cytotoxicities on four tumor cell lines(HepG2, HL-60,Skov-3,A431).     

莽吉柿中几种双苯吡酮和蒽醌类成分的分离与鉴定

对莽吉柿(Pericarpium Garciniae Mangostanae)85%乙醇提取物进一步分离,得到8个双苯吡酮类化合物和1个蒽酮类化合物,经理化性质和NMR及MS谱学数据鉴定分别为α-倒捻子素-3,6-二乙酸酯（α-mangostin-3,6-diyl diacetate,Ⅰ）、1,5,8-三羟基-3-甲氧基-2,4-双-（3-甲基丁-2-烯）双苯吡酮（8-hydroxycudraxanthone G,Ⅱ）、1,3-二羟基-6,7-二甲氧基-2,8-双-（3-甲基丁-2-烯基）双苯吡酮（Cowaxanthone B,Ⅲ）、1,6-二羟基-3,5-二甲氧基-2-（3-甲基丁-2-烯基）双苯吡酮（Cowaxanthone A,Ⅳ）、1,5-二羟基-4-（3-甲基丁-2-烯基）-6′,6′-二甲基吡喃[2′,3′:3,2]双苯吡酮（trapezifolixanthone,Ⅴ）、1,6-二羟基-6′,6′-二甲基吡喃[2′,3′:7,8]-6″,6″-二甲基吡喃[2″,3″:3,2-]双苯吡酮（brasilixanthone B,Ⅵ）、1,3,5-三羟基-2-（3-甲基丁-2-烯）-4-（1,1-二甲基-2-烯丙基）双苯吡酮（Allanxanthone A,Ⅶ）、1,3,8-三羟基-5-甲氧基-2,4-双-（3-甲基丁-2-烯）双苯吡酮(2,4-di-(3-methylbut-2-enyl)-1,3,8-trihydroxy-5-methoxyxanthone,Ⅷ)、1,4,8-三羟基-6-甲基-3-甲氧基-9,10-蒽酮(1,4,8-trihydroxy-6-methyl-3-methoxy- 9,10-anthraquinone, Ⅸ）。 其中化合物Ⅰ、Ⅴ、Ⅵ、Ⅶ、Ⅸ为首次从藤黄属植物中分离得到,化合物Ⅱ、Ⅲ、Ⅳ、Ⅷ为首次从该植物中分离得到。     

Antibacterial thymol derivatives isolated from Centipeda minima

Two new monoterpenoids, 8,10-dihydroxy-9(2)-methylbutyryloxythymol (1) and 10-hydroxy-8,9-dioxyisopropylidene-thymol (2), together with five known thymol derivatives: 8,9,10-trihydroxythymol (3), thymol-beta-glucopyranoside (4), 9-hydroxythymol (5), 8,10-dihydroxy-9-isobutyryloxythymol (6), and 8-hydroxy-9,10-diisobutyryloxythymol (7), were isolated from Centipeda minima. Their structures were identified by means of spectroscopic analyses. Interestingly, compound 2 is not an extraction artifact according to a close HPLC examination of material after extraction by analytical MeOH at ambient temperature. The antibacterial activities of compounds 1-7 were evaluated against eight microbial strains by the agar dilution method.