Chemical Constituents of Cocculus carolinus D. C. (Menispermaceae)

Slatkin, David J.; Doorenbos, Norman J.; Knapp, Joseph E.; Schiff, Paul L.

doi:10.1002/jps.2600611132

Cited by 9 publications

(3 citation statements)

References 17 publications

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“…Preliminary screening of the MeOH extract of this plant toward HepG2 cells (human hepatoma cell line, IC 50 )18.2 µg/mL) indicated cytotoxic potential. Using bioactivityguided fractionation methods, 22 compounds, including five bisbenzylisoquinolines, (+)-isotrilobine (1), 10 (+)-coccuorbiculatine A (2), (+)-10-hydroxyisotrilobine (3), (+)-1,2dehydroapateline (4), 11 and (+)-O-methylcocsoline (5); 12 three aporphines, the mixture of (+)-laurelliptinhexadecan-1-one ( 6) and (+)-laurelliptinoctadecan-1-one ( 7) and (+)norboldine; 13 three protoberberines, (-)-4-methoxy-13,14dihydrooxypalmatine ( 8), (-)-4-methoxypalmatine, 14 and oxypalmatine; 15 one oxoaporphine, peruvianine, 16 and one morphinan, (-)-sinococuline (9), 17 were isolated from the MeOH extracts of stems. Compounds 2-3 and 6-8 are new.…”

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New Bisbenzylisoquinolines, Fatty Acid Amidic Aporphines, and a Protoberberine from Formosan Cocculus orbiculatus

Chang

2005

J. Nat. Prod.

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Two new bisbenzylisoquinoline alkaloids, (+)-coccuorbiculatine A (2) and (+)-10-hydroxyisotrilobine (3), two new amidic aporphines, a mixture of (+)-laurelliptinhexadecan-1-one (6) and (+)-laurelliptinoctadecan-1-one (7), and one new protoberberine (-)-4-methoxy-13,14-dihydrooxypalmatine (8) have been isolated from the stems of Taiwanese Cocculus orbiculatus. The structures were established on the basis of extensive analysis of spectroscopic data and by comparison with known related metabolites. Cytotoxicity of the isolated compounds was examined toward HepG2, Hep3B, MCF-7, and MDA-MB-231 cancer cell lines. Alkaloids 1 and (-)-sinococuline (9) showed significant inhibitory activity against the target cell lines.

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confidence: 99%

New Bisbenzylisoquinolines, Fatty Acid Amidic Aporphines, and a Protoberberine from Formosan Cocculus orbiculatus

Chang

2005

J. Nat. Prod.

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“…3 9). 1) and resulted in the following: acid-neutral fraction (Fraction A, 310.2 g), nonquaternary alkaloid fraction (Fraction B, 5.7 g), and quaternary alkaloid chloride fraction (Fraction C, 2.9 9). Fractional crystallization from ethanol-water afforded pure (+)-quercitol (350 mg), Rf 0.30, mp 229-230°, [a]:: + 20.8' (c 1.2, Melting points were determined on a Thomas-Hoover Uni-melt meltingpoint apparatus and are corrected.…”

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confidence: 99%

“…A partition system of petroleum ether (bp 60-90°)-ethylene dichloride-methanol-water (12:3:2:0.4) was established as described previously (2). The purified fraction (3.0 g) was placed on the column (150 g, 3.0 X 60 cm), and alkaloidal bands were observed and collected accordingly.…”

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confidence: 99%