Chemical Constituents of Calophyllum brasiliense. 2. Structure of Three New Coumarins and Cancer Chemopreventive Activity of 4-Substituted Coumarins

• Published in: Journal of natural products (Washington, D.C.) Vol. 66; no. 3; pp. 368 - 371
• Main Authors: Ito, Chihiro, Itoigawa, Masataka, Mishina, Yoshitaka, Filho, Valdir Cechinel, Enjo, Fumio, Tokuda, Harukuni, Nishino, Hoyoku, Furukawa, Hiroshi
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.03.2003; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: anticarcinogenic activity; Anticarcinogenic Agents - chemistry; Anticarcinogenic Agents - isolation & purification; Anticarcinogenic Agents - pharmacology; Antigens, Viral - drug effects; antineoplastic agents; bark; Biological and medical sciences; brasimarins; Brazil; calanolides; Calophyllum; Calophyllum - chemistry; Calophyllum brasiliense; cell lines; Cells, Cultured - drug effects; chemical structure; Chemistry, Medicinal; chemoprevention; coumarins; Coumarins - chemistry; Coumarins - isolation & purification; Coumarins - pharmacology; Drug Screening Assays, Antitumor; General pharmacology; Human herpesvirus 4; Humans; inophyllums; Life Sciences & Biomedicine; Lymphoma, B-Cell; Medical sciences; Nuclear Magnetic Resonance, Biomolecular; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; phenylcoumarin; phytochemicals; Plant Bark - chemistry; plant extracts; Plant Sciences; Plants, Medicinal - chemistry; propylcoumarin; Science & Technology; spectral analysis; stems; Tetradecanoylphorbol Acetate - pharmacology; Brazil; South America; America; TREE; INOPHYLLUM; Pharmacognosy; Coumarine derivatives; Guttiferae; Bark; Lactone; Anticarcinogen; Antitumor promotor; Tricyclic compound; Oxygen heterocycle; In vitro; Biological activity; Stem; Medicinal plant; Ketophenols; Dicotyledones; Angiospermae; Plant origin; Isolation; Spermatophyta; Aromatic compound; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np0203640

Continuing our search for cancer chemopreventive agents from natural sources, we examined constituents of the stem bark of Calophyllum brasiliense. Three new 4-substituted coumarins named brasimarins A (2), B (3), and C (4) were isolated and characterized, along with 11 known coumarins belonging to the calanolides or inophyllums. We also discuss the inhibitory effects of these coumarins on Epstein−Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells.