Novel Antimitotic Dibenzocyclo-Octadiene Lignan Constituents of the Stem Bark of Steganotaenia araliacea

• Published in: Journal of natural products (Washington, D.C.) Vol. 56; no. 12; pp. 2083 - 2090
• Main Authors: Wickramaratne, D. B. M, Pengsuparp, T, Mar, W, Chai, H.-B, Chagwedera, T. E, Beecher, C. W. W, Farnsworth, N. R, Kinghorn, A. D, Pezzuto, J. M, Cordell, G. A
• Format: Journal Article
• Language: English
• Published: CINCINNATI American Chemical Society 01.12.1993; AMER SOC PHARMACOGNOSY
• Subjects: AGENTES ANTINEOPLASTICOS; Animals; ANTINEOPLASTIC AGENTS; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; BARK PRODUCTS; Cell Survival - drug effects; CHEMICAL COMPOSITION; Chemistry, Medicinal; COMPOSICION QUIMICA; COMPOSITION CHIMIQUE; CYTOTOXICITY; DRUG PLANTS; Drug Screening Assays, Antitumor; Humans; Leukemia P388 - drug therapy; Life Sciences & Biomedicine; Lignans - isolation & purification; Lignans - pharmacology; LIGNINAS; LIGNINE; LIGNINS; MEDICAMENT CYTOSTATIQUE; MEDICINAL PLANTS; Mice; Microtubules - metabolism; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; Pharmacology & Pharmacy; Plant Sciences; PLANTAS MEDICINALES; PLANTE MEDICINALE; Plants, Medicinal - chemistry; PRODUIT A BASE D'ECORCE; Science & Technology; STEMS; TALLO; TIGE; TOXICIDAD; TOXICITE; TOXICITY; TROZOS DE CORTEZA; Tubulin - biosynthesis; Tumor Cells, Cultured; UMBELLIFERAE; ZIMBABWE; NEOISOSTEGANE; STEGANACIN; LACTONES; INVITRO; HOCHST; ASSIGNMENT; BISBENZOCYCLOOCTADIENOLACTONIC LIGNAN; DIMENSIONAL NMR; POLARIZATION TRANSFER; ANTITUBULIN ACTIVITY
• DOI: 10.1021/np50102a009
• ISSN: 0163-3864

By means of activity-directed chromatographic fractionation using cultured astrocytoma (ASK) cells, six dibenzocyclo-octadiene lignans were isolated from Steganotaenia araliacea stem back. In addition to the most abundant analogue, steganangin [1], two other known compounds, steganacin [3] and steganolide A [6], and three new compounds, episteganangin [2], steganoate A [4], and steganoate B [5], were obtained. Episteganangin [2] was chemically correlated with the known ketone steganone [7]. All of these compounds demonstrated cytotoxic activity when tested against a panel of eleven human tumor cell lines, with the exception of steganoate A [4]. The magnitude of this activity tended to correlate with antimitotic activity observed with the ASK assay and in vitro inhibition of microtubule assembly. Steganacin [3] was less cytotoxic than colchicine, but more active in these latter two assay systems.