Structure and biological activity of isolates from Anogeissus acuminata.

Important note: Information in this article was accurate in 1995. The state of the art may have changed since the publication date.

Structure and biological activity of isolates from Anogeissus acuminata.

Diss Abstr Int [B]; 54(12):6218 1994. Unique Identifier : AIDSLINE ICDB/95607141
Rimando AM; Univ. of Illinois at Chicago, Health Sciences Center

Abstract: Phytochemical work on Anogeissus acuminata [(Roxb ex DC) Guill and Perr var lanceolata Wall ex CB Clarke] (Combretaceae) led to the isolation of three new and four known compounds. The new compounds were identified as 2-(2',4'-dihydroxybenzyl)-3-(3',4' methylenedioxybenzyl)-1,3-butadiene, which was given the common name anolignan A; 2,3-bis-(4-hydroxybenzyl)-1,3-butadiene, which was named anolignan B; and 2,3-cis-3,4-cis-4,5-cis-2,5-bis-(4-hydroxyphenyl)-3,4-dimethyltet- rahydrofuran, which was named 2-epi-larreatricin. The four known compounds isolated were (-)-secoisolariciresinol, dihydrodehydrodiconiferyl alcohol, conocarpan, and pterostilbene. The structures of these compounds, including the stereochemistry of 2-epi-larreatricin, were established by various spectroscopic methods including UV, IR, MS, NMR. Through the use of 2D-NMR experiments, revision of the 1H and [13C]-NMR assignments of dihydrodehydrodiconiferyl alcohol, and of the [13C]-NMR assignments of pterostilbene were made. Through bioactivity-guided fractionation, anolignans A and B were identified as the constituents acting together to inhibit HIV-1 reverse transcriptase activity. Anolignan B, which was weakly active by itself, demonstrated higher activity in combination with anolignan A. The activity of anolignan A was also enhanced in the presence of anolignan B. With the exception of (-)-secoisolariciresinol, all the isolates demonstrated cytotoxicity in vitro. Significant cytotoxicity was shown by anolignan A and pterostilbene against breast cancer cell line and by anolignan B against fibrosarcoma cell line. The isolates obtained from this work were the first lignans, neolignans and stilbene isolated from Anogeissus. Anolignans A and B were the first dibenzylbutadiene lignans isolated from a plant. (Full text available from University Microfilms International, Ann Arbor, MI, as Order No. AAD94-14933)

Keywords: Antineoplastic Agents, Phytogenic/*PHARMACOLOGY Breast Neoplasms/PATHOLOGY Butanediols/*CHEMISTRY/PHARMACOLOGY Fibrosarcoma/PATHOLOGY HIV-1/*ENZYMOLOGY Lignin/*CHEMISTRY/PHARMACOLOGY Molecular Structure Plants/*CHEMISTRY RNA-Directed DNA Polymerase/*ANTAGONISTS & INHIB Spectrum Analysis Tumor Cells, Cultured THESIS
950530
M9551039

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