Anti-HIV-1 and anti-inflammatory lupanes from the leaves, twigs, and resin of Garcinia hanburyi.

Two new lupanes, 2 alpha-acetoxy-3 beta-hydroxy-19 beta-hydrogen-lup-20(29)-en-28-oic acid (2-acetoxyalphitolic acid) ( 1) and 2 alpha-hydroxy-3 beta-acetoxy-19 beta-hydrogen-lup-20(29)-en-28-oic acid (3-acetoxyalphitolic acid) ( 2), together with the known betulinic acid ( 3), betulin ( 4), and stimasterol-3- O- beta- D-glucopyranoside ( 5), were isolated from the leaves and twigs of GARCINIA HANBURYI. Compounds 1- 3 were also isolated from the resin of this plant. The structure of 2 was confirmed by single-crystal X-ray diffraction analysis. All of the lupanes ( 1- 4) displayed anti-HIV-1 activities in the anti-HIV-1 reverse transcriptase (IC (50) values 16.3-116.9 microg/mL) and syncytium assays (EC (50) 5.6-73.6 microg/mL, SI 1.7-3.3). Moreover compounds 1- 4 exhibited anti-inflammatory activity in an ethyl phenylpropiolate (EPP)-induced ear edema model.

Anti HIV-1 flavonoid glycosides from Ochna integerrima.

Bioassay-guided fractionation of the anti-HIV-1 active EtOAc extract from leaves and twigs of Ochna integerrima led to the isolation of five new flavonoid glycosides 1 - 5, five known flavonoids 6 - 10, and two known flavonoid glycosides 11 and 12. Structures were determined based on spectroscopic analyses. 6- gamma, gamma-Dimethylallyldihydrokaempferol 7- O- beta-D-glucoside (1), 6-gamma, gamma-dimethylallylquercetin 7- O- beta- D-glucoside (3), 6-(3-hydroxy-3-methylbutyl)taxifolin 7- O- beta-D-glucoside (4), 6-(3-hydroxy-3-methylbutyl)quercetin 7- O-beta-D-glucoside (5), and 6-gamma, gamma-dimethylallyltaxifolin 7-O-beta-D-glucoside (11) showed anti-HIV-1 activities in the syncytium assay using the (Delta Tat/rev)MC99 virus and the 1A2 cell line system with EC(50) values ranging from 14.0 - 102.4 microg/mL. Furthermore, ochnaflavone 7''-O-methyl ether (7) and 2'', 3''-dihydroochnaflavone 7''-O-methyl ether (8) were very active; they exerted activities in the syncytium assay with EC(50) values of 2.0 and 0.9 microg/mL, respectively, and likewise inhibited HIV-1 reverse transcriptase (RT) with IC(50) values of 2.0 and 2.4 microg/mL, respectively.

Cytotoxic and anti-HIV-1 caged xanthones from the resin and fruits of Garcinia hanburyi.

Three new caged xanthones, 7-methoxydesoxymorellin (1), 2-isoprenylforbesione (2) and 8,8a-epoxymorellic acid (3), together with nine known caged xanthones were isolated from the EtOAc extracts of resin and fruits of Garcinia hanburyi. The structures were determined by spectroscopic methods. Most of the isolated compounds showed significant cytotoxicities against a panel of mammalian cancer cell lines. Compound 3, together with the known compounds desoxymorellin, morellic acid, gambogic acid, hanburin, forbesione and dihydroisomorellin, exhibited anti-HIV-1 activity in the reverse transcriptase (RT) assay while the known compounds desoxygambogenin and dihydroisomorellin were found moderately active in the syncytium assay. This work represents the first report on the anti-HIV-1 activities of caged xanthones.

Cytotoxic styryl-lactones from the leaves and twigs of Polyalthia crassa.

Four new styryl-lactones, crassalactones A-D (1-4), were isolated from a cytotoxic ethyl acetate-soluble extract of the leaves and twigs of Polyalthia crassa, together with seven known compounds, (+)-3-acetylaltholactone, (+)-altholactone, aristolactam AII, cinnamic acid, (+)-goniofufurone, (+)-goniopypyrone, and (+)-howiinol A. Their structures were determined on the basis of spectroscopic methods. The absolute configuration of 1-3 was established by chemical conversions. Single-crystal X-ray analysis and the Mosher ester method were used to confirm the absolute stereochemistry of 4. Cytotoxic evaluation against several mammalian cancer cell lines was performed on all new isolates, aristolactam AII, and the modified (+)-tricinnamate derivative 11 obtained from 1.

Anti-HIV-1 constituents from leaves and twigs of Cratoxylum arborescens.

Two new xanthones, 1,3,8-trihydroxy-2,4-dimethoxyxanthone (1) and 1,7-dihydroxy-2,8-dimethoxyxanthone (2), along with twelve known compounds 3 - 14 were isolated from leaves and twigs of Cratoxylum arborescens. Compound 1, euxanthone (4), betulinic acid (8), lup-20(29)-ene-3beta,30-diol (9), 3beta-hydroxylup-20(29)-en-30-oic acid (10) and 3,4-dihydroxybenzoic acid (11) displayed anti-HIV-1 activities in the syncytium assay using (Delta)(Tat/Rev)MC99 virus and the 1A2 cell line system (EC (50) values between 3.9 and 32.2 microg/mL with TI ranging from 1.5 to 11.7), while 1,3,7-trihydroxy-6-methoxy-4,5-diisoprenylxanthone (3), 4, and 8 - 10 inhibited HIV-1 reverse transcriptase with IC (50) values between 8.7 and 84.9 microg/mL.

Cytotoxic arylnaphthalide lignan glycosides from the aerial parts of Phyllanthus taxodiifolius.

The arylnaphthalide lignan glycosides, taxodiifoloside, cleistanthoside A, cleistanthin A and cleistanthin A methyl ether, together with a triterpene, glochidone, have been isolated from the aerial parts of Phyllanthus taxodiifolius. The structures were established using spectral and chemical methods. Compounds and, as well as the derivatives and exhibited potent cytotoxic activities with GI50 values in the range of 10(-7)-10(-9) M in five cultured mammalian cancer cell lines while the new compound showed moderate activity (GI50 in the order of 10(-6) M). Compounds and were inactive in all tested cell lines.

Anti-HIV-1 cycloartanes from leaves and twigs of Gardenia thailandica.

Thailandiol ( 1), gardenolic acid A ( 2), quadrangularic acid E ( 3) and 3beta-hydroxy-5alpha-cycloart-24(31)-en-28-oic acid ( 4) have been isolated from the leaves and twigs of Gardenia thailandica Tirveng (order: Rubiales; family: Rubiaceae). In addition, 5-hydroxy-7,2',3',4',5',6'-hexamethoxyflavone ( 5), 5,7-dihydroxy-2',3', 4',5',6'-pentamethoxyflavone ( 6), 5-hydroxy-7,2',3',4',5'-pentamethoxyflavone ( 7) and 5,7-dihydroxy-2',3',4',5'-tetramethoxyflavone ( 8) were also isolated from the same source. The structures were elucidated by spectroscopic methods. Crude extracts and compounds 1 - 4 displayed anti-HIV-1 activities as determined by using the (Delta)(Tat/Rev)MC99 virus and 1A2 cell line system. The EC (50) values determined by the syncytium assay ranged from < 7.8 to 110 microg/mL. They also exhibited moderate to high activities in reverse transcriptase (RT) assay; the IC (50) values of compounds 1 - 4, ranged from < 22.5 to 156.8 microg/mL.

Cytotoxic coumarins from Mammea harmandii.

Two new naturally occurring coumarins, isomesuol (1) and mammearin A (2), together with nine known Mammea coumarins 3-11 were isolated from the EtOAc extract of the leaves and twigs of Mammea harmandii. Coumarins 1, 3 and 4 showed cytotoxicity against a panel of mammalian cancer cell lines. Their structures were determined by spectroscopic methods. The assignments of 13C-NMR signals of isomesuol (1), which was isolated for the first time as a natural product, have been revised.

Constituents of the leaves and twigs of Ficus hispida.

A new norisoprenoid, ficustriol (1), and the known phenanthroindolizidine alkaloid O-methyltylophorinidine (2), were isolated from a CHCl3 extract of the leaves and twigs of Ficus hispida. O-Methyltylophorinidine showed potent cytotoxic activity when tested against a small panel of human cancer cells, while ficustriol was inactive. The structure and stereochemistry of 1 were determined using chemical and spectral methods.

Anti-inflammatory cyclohexenyl chalcone derivatives in Boesenbergia pandurata.

The cyclohexenyl chalcone derivative [(-)-hydroxypanduratin A], together with the previously known panduratin A, sakuranetin, pinostrobin, pinocembrin, and dihydro-5,6-dehydrokawain were isolated from the chloroform extract of the red rhizome variety of Boesenbergia pandurata (Robx.) Schltr. [currently known as Boesenbergia rotunda (L.) Mansf., Kulturpfl.]. Their structures were assigned on the basis of their spectroscopic data. (-)-Hydroxypanduratin A and (-)-panduratin A showed significant topical anti-inflammatory activity in the assay of TPA-induced ear edema in rats.