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.
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
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.
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Abstract Further phytochemical work on Anogeissus acuminata var. lanceolata (Combretaceae) led to the isolation of pterostilbene (1), dihydrodehydrodiconiferyl alcohol (2), and conocarpan (3). The structure of these compounds were determined by spectroscopic means, mainly through 1D and 2D NMR experiments. A revision of some of the 13C NMR chemical shifts of 1 and 2 were made possible by HETCOR, FLOCK, and selective INEPT experiments. Homonuclear spin-decoupling and 1H-1H COSY experiments also enabled the precise assignment of the 1H NMR chemical shifts of 2. Compounds 1–3 exhibited in vitro cytotoxicity in various cancer cell lines. This is the first isolation of 1–3 from Anogeissus.
A new ring-A secotriterpene, koetjapic acid [1], and five known compounds, 3-oxo-olean-12-en-29-oic acid [2] (a novel natural product), katonic acid [3], (-)-alloaromadendrene, (-)-caryophyllene oxide, and (+)-spathulenol, have been isolated and characterized from a cytotoxic Et2O-soluble extract of Sandoricum koetjape stems. Of these compounds, 2 and 3 demonstrated significant cytotoxic activity against cultured P-388 cells (ED50 values of 0.61 and 0.11 microgram/ml, respectively). Significant, albeit less intense, cytotoxicity was also observed with a variety of cultured human cancer cells. The 13C-nmr chemical shifts of these triterpenes were assigned unambiguously using selective INEPT nmr experiments. Aside from compounds 2 and 3, these substances were not toxic with cultured cells.
