Cytotoxic and anti-HIV-1 constituents from leaves and twigs of Gardenia tubifera

• Published in: Tetrahedron Vol. 60; no. 7; pp. 1517 - 1523
• Main Authors: Reutrakul, Vichai, Krachangchaeng, Chongkon, Tuchinda, Patoomratana, Pohmakotr, Manat, Jaipetch, Thaworn, Yoosook, Chalobon, Kasisit, Jittra, Sophasan, Samaisukh, Sujarit, Kulawee, Santisuk, Thawatchai
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 09.02.2004; Elsevier
• Subjects: Anti-HIV activity; Chemistry; Chemistry, Organic; Cytotoxic activity; Flavones; Octanolide; Physical Sciences; Ring-A seco-cycloartane; Science & Technology; Anti-HIV activity; Octanolide; Flavones; Ring-A seco-cycloartane; Cytotoxic activity; octanolide; ring-A seco-cycloartane; NIGRANOIC ACID; flavones; PLANTS; TANZANIA; cytotoxic activity; INHIBITORS; anti-HIV activity; MEDICINE; DERIVATIVES
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2003.12.010

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. 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. Two new natural cycloartanes 1 and 2 , together with the known 3 and 4 have been isolated from leaves and twigs of Gardenia tubifera. In addition, a new flavone 5 , five known flavones and hexacosyl 4′-hydroxy- trans-cinnamate were also obtained from the same source. All isolated constituents were evaluated for cytotoxic and anti-HIV-1 activities.