STRUCTURE ACTIVITY STUDIES OF BIOLOGICALLY ACTIVE NATURAL PRODUCTS

Important note: Information in this article was accurate in 1992. The state of the art may have changed since the publication date.

STRUCTURE ACTIVITY STUDIES OF BIOLOGICALLY ACTIVE NATURAL PRODUCTS

Diss Abstr Int [B]; 51(12):5879 1991. Unique Identifier : AIDSLINE ICDB/92677050
Van Wagenen BC; Montana State Univ.

Abstract: Investigation of the ichthyotoxic plant Lomatium dissectum resulted in the isolation of a mixture of tetronic acids (17), which were responsible for the ichthyotoxicity, antimicrobial and antineoplastic activity of the organic soluble extracts. Fourteen analogs of 17 were prepared and evaluated for their antimicrobial, antineoplastic, and anti-inflammatory properties. From the insecticidal organic extract of the marine sponge Ulosa ruetzleri two novel metabolites, creatine dimethylphosphate (67) and 1-methyl-2-(methylphosphatoxy)-(5-H)imidazolin-4-one (68), were isolated. Of these, 68 was found to be toxic to the tobacco hornworm, Manduca sexta, and a powerful inhibitor of acetylcholinesterase. Substantial investigations into the total synthesis of 68 resulted in only mono- and di-alkyl phosphate esters of 1-methyl-4-(phosphatoxy)-(5-H)imidazolin-2-one. Recently developed methodologies involving the silver ion-mediated cyclization of alpha-keto imidoyl chlorides was applied toward the total synthesis of four natural products, eudistomins H, I, S, and T (110, 113, 127, 128), originally isolated from the marine tunicate Eudistoma olivaceum. Eudistomin T was tested for cytotoxicity, phytotoxicity, and insecticidal activity. The natural products and the three analogs 129, 130, and 164 were also evaluated against the human immunodeficiency virus. (Full text available from University Microfilms International, Ann Arbor, MI, as Order No. AAD91-12646).

Keywords: Antineoplastic Agents, Phytogenic/*PHARMACOLOGY Furans/*PHARMACOLOGY HIV/DRUG EFFECTS Insecticides/*PHARMACOLOGY Plant Extracts/*PHARMACOLOGY Structure-Activity Relationship THESIS
920228
M9220888

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