Coronalolide methyl ester

Tetrahedron,2004, 60(7):1517-23.

Cytotoxic and anti-HIV-1 constituents from leaves and twigs of Gardenia tubifera[Reference: WebLink]

METHODS AND RESULTS:
Two new natural cycloartanes, tubiferolide methyl ester (1) and tubiferaoctanolide (2), together with the known coronalolide (3) and Coronalolide methyl ester (4) have been isolated from leaves and twigs of Gardenia tubifera. In addition, a new flavone 5,3′,5′-trihydroxy-7,4′-dimethoxyflavone (5), five known flavones 6–10 and hexacosyl 4′-hydroxy-trans-cinnamate (11) were also obtained from the same source. The structures were assigned on the basis of spectroscopic methods.
CONCLUSIONS:
Compounds 3, 7, 9, and 10 showed significant cytotoxic activities only in P-388 cell line. Compound 1 was cytotoxic against P-388, KB, Col-2 and Lu-1, while 4 was active in P-388 and BCA-1. Compounds 3 and 4 displayed significant anti-HIV activities in the HIV-1RT assay; compound 7 showed moderate activity in this assay. Compounds 5–10 were also found to be active in the ΔTat/RevMC 99 syncytium assay.

Tetrahedron,1997,28(18):529-38.

Novel cytotoxic ring-a seco-cycloartane triterpenes from Gardenia coronaria and G. sootepensis[Reference: WebLink]

METHODS AND RESULTS:
Coronalolide methyl ester (1), coronalolide (2), and coronalolic acid (3) were isolated from the leaves and/or stems of Gardenia coronaria. A further compound, methyl coronalolate acetate (4), was purified from the stems after methylation. The novel compounds 1–4 have the rare ring-A seco-cycloartane carbon skeleton and their structures were assigned on the basis of spectral data and molecular modeling, as well as X-ray crystallography performed on 1.
CONCLUSIONS:
Compounds 1 and 2 were also isolated from the leaves of Gardenia sootepensis and showed broad cytotoxic activity when evaluated against a panel of human cancer cell lines.