Macharistol, a New Cytotoxic Cinnamylphenol from the Stems of Machaerium aristulatum

• Published in: Journal of natural products (Washington, D.C.) Vol. 64; no. 11; pp. 1483 - 1485
• Main Authors: SEO, Eun-Kyoung, KIM, Nam-Cheol, MI, Qiuwen, CHAI, Heebyung, WALL, Monroe E., WANI, Mansukh C., NAVARRO, Hernán A., BURGESS, Jason P., GRAHAM, James G., CABIESES, Fernando, TAN, Ghee T., FARNSWORTH, Norman R., PEZZUTO, John M., KINGHORN, A. Douglas
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.11.2001; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Benzopyrans - chemistry; Benzopyrans - isolation & purification; Benzopyrans - pharmacology; Biological and medical sciences; Chemistry, Medicinal; Fabaceae - chemistry; General pharmacology; Humans; Isoflavones - chemistry; Isoflavones - isolation & purification; Isoflavones - pharmacology; Life Sciences & Biomedicine; Medical sciences; Molecular Structure; Nasopharyngeal Neoplasms; Nuclear Magnetic Resonance, Biomolecular; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Phenols - chemistry; Phenols - isolation & purification; Phenols - pharmacology; Plant Sciences; Plant Stems - chemistry; Plants, Medicinal - chemistry; Pterocarpans; Science & Technology; Structure-Activity Relationship; Tumor Cells, Cultured - drug effects; Tumor Cells, Cultured - enzymology; South America; America; Amazon Basin; DALBERGIA; ISOFLAVONOID CONSTITUENTS; Antineoplastic agent; Intraperitoneal administration; Cytotoxicity; Diphenols; Stem; Medicinal plant; Folk medicine; Dicotyledones; Angiospermae; Human; Pharmacognosy; Rodentia; Malignant tumor; Biological activity; Vertebrata; Chemotherapy; Mammalia; Treatment; Leguminosae; Mouse; Animal; Plant origin; Benzenic compound; Isolation; Spermatophyta; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np0103158

A new cinnamylphenol, macharistol (1), along with a known pterocarpan, (+)-medicarpin (2), were isolated as cytotoxic constituents from the stems of Machaerium aristulatum. In addition, a known pterocarpan, (+)-maackiain (3), and a known isoflavone, formononetin (4), were identified as inactive constituents. Compound 1 was evaluated in the in vivo hollow fiber assay with KB, Col-2, and hTERT-RPE1 cells and found to be inactive at the highest dose (25 mg/kg body weight) tested.