New bioactive clerodane diterpenoids from the bark of Casearia grewiifolia

• Published in: Journal of natural products (Washington, D.C.) Vol. 68; no. 2; pp. 183 - 188
• Main Authors: Kanokmedhakul, S, Kanokmedhakul, K, Kanarsa, T, Buayairaksa, M
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.02.2005; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; Antibacterial agents; antibacterial properties; Antibiotics. Antiinfectious agents. Antiparasitic agents; anticarcinogenic activity; antimalarials; Antimalarials - chemistry; Antimalarials - isolation & purification; Antimalarials - pharmacology; Antineoplastic agents; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Antiparasitic agents; Biological and medical sciences; caseargrewiins; Casearia; Casearia - chemistry; casearia grewiifolia; Cell Line, Tumor; cell lines; chemical structure; Chemistry, Medicinal; clerodane diterpenoids; cytotoxicity; Diterpenes, Clerodane - chemistry; Diterpenes, Clerodane - isolation & purification; Diterpenes, Clerodane - pharmacology; diterpenoids; Drug Screening Assays, Antitumor; General aspects; General pharmacology; Humans; Life Sciences & Biomedicine; Medical sciences; Molecular Structure; Mycobacterium tuberculosis; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; phytochemicals; Plant Bark - chemistry; plant extracts; Plant Sciences; Plants, Medicinal - chemistry; Plasmodium falciparum; Science & Technology; spectral analysis; stereochemistry; Stereoisomerism; Thailand; Thailand; Asia; CORYMBOSA; LEAVES; CONFIGURATION; ANTITUMOR PRINCIPLES; SYLVESTRIS SW FLACOURTIACEAE; TWIGS; MEMBRANACEA; DERIVATIVES; CONSTITUENTS; Antineoplastic agent; Antimalarial; Bark; Cytotoxicity; Extract; Medicinal plant; Antiprotozoal agent; Folk medicine; Dicotyledones; Angiospermae; Flacourtiaceae; Antituberculous agent; Tumor cell; Terpenoid; Pharmacognosy; In vitro; Biological activity; Cell line; Absolute configuration; Plant origin; Diterpene; Parasiticide; Spermatophyta; Antibacterial agent; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np049757k

Bioactivity-guided fractionation of hexane and dichloromethane extracts of the bark of Casearia grewiifolia afforded four new clerodane diterpenes, caseargrewiins A-D (1-4), and two known clerodane diterpenes, rel-(2S,5R,6R,8S,9S,10R,18S,19R)-18,19-diacetoxy-18,19-epoxy-6-methoxy-2-(2-methylbutanoyloxy)cleroda-3,13(16),14-triene (5) and rel-(2S,5R,6R,8S,9S,10R,18S,19R)-18,19-diacetoxy-18,19-epoxy-6-hydroxy-2-(2-methylbutanoyloxy)cleroda-3,13(16),14-triene (6). The structures of 1-4 were established on the basis of the interpretation of their 1D and 2D NMR spectral data. The absolute configuration of 4 was determined by the modified Mosher's method. All compounds exhibited promising antimalarial and antimycobacterial activities but also cytotoxicity against three cancer cell lines.