Novel Bioactive Clerodane Diterpenoids from the Leaves and Twigs of Casearia sylvestris

• Published in: Journal of natural products (Washington, D.C.) Vol. 65; no. 2; pp. 95 - 99
• Main Authors: Oberlies, Nicholas H, Burgess, Jason P, Navarro, Hernán A, Pinos, Rosa Elena, Fairchild, Craig R, Peterson, Russell W, Soejarto, Djaja D, Farnsworth, Norman R, Kinghorn, A. Douglas, Wani, Mansukh C, Wall, Monroe E
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-02-2002; Glendale, AZ American Society of Pharmacognosy
• Subjects: Antifungal Agents - chemistry; Antifungal Agents - isolation & purification; Antifungal Agents - pharmacology; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Aspergillus niger - drug effects; Biological and medical sciences; Colonic Neoplasms; Diterpenes - chemistry; Diterpenes - isolation & purification; Diterpenes - pharmacology; Drug Screening Assays, Antitumor; Ecuador; Female; General pharmacology; Humans; Inhibitory Concentration 50; KB Cells - drug effects; Lung Neoplasms; Magnoliopsida - chemistry; Medical sciences; Molecular Conformation; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Ovarian Neoplasms; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant Leaves - chemistry; Plant Shoots - chemistry; Plants, Medicinal - chemistry; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet; Spectroscopy, Fourier Transform Infrared; Tumor Cells, Cultured - drug effects; South America; Ecuador; America; Antineoplastic agent; Lung; Cytotoxicity; Oxygen heterocycle; Medicinal plant; Fungi; Ovary; Antifungal agent; Dicotyledones; Acylal; Angiospermae; Conjugated dienic compound; Flacourtiaceae; Fungi Imperfecti; Colon; Secondary alcohol; Acylate; Tumor cell; Thallophyta; Human; Terpenoid; Pharmacognosy; Plant leaf; Tricyclic compound; In vitro; Biological activity; Cell line; Aspergillus niger; KB cell line; Plant origin; Diterpene; Isolation; Spermatophyta; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np010459m

Fractionation of a methanol extract of the leaves and twigs of Casearia sylvestris, as directed by activity against KB cell cytotoxicity, led to the isolation of three novel clerodane diterpenoids, casearvestrins A−C (1−3). The structures of 1−3 were deduced from one- and two-dimensional NMR experiments, including relative stereochemical assignments based on ROESY correlations and COSY coupling constants. All three compounds displayed promising bioactivity, both in cytotoxicity assays against a panel of tumor cell lines and in antifungal assays via the growth inhibition of Aspergillus niger in a disk diffusion assay.