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Constituents of marine invertebrates : chemical and pharmacological properties

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Title: Constituents of marine invertebrates : chemical and pharmacological properties
Authors: Ichiba, Toshio
Keywords: Marine invertebrates -- Composition
Issue Date: 1994
Abstract: Sixteen compounds belonging to seven distinct classes of organic compounds were isolated from a bryozoan and seven sponges; their structures were characterized by a combination of spectroscopic and chemical methods. The classes of compounds are aliphatic amino alcohols, bromotyrosine-derived peptides, a nucleoside, an alkaloid, sesquiterpenes, bromo and peroxy acids. The first chemical study of an Hawaiian bryozoan led to isolation of two new amino alcohols 30 and 31. The extract from a Pohnpei sponge, Aplysinella sp., yielded two new bromotyrosine derivatives, psammaplysins D (46) and E (47), which show antiviral and immunosuppresive activities.[1] An unprecedented alkylated arabinonucleoside, kumusine (52), was found in an Indonesian sponge, Theoneila sp. Kumusine (52) exhibited moderate immunosuppressive activity. A new manzamine, 8-hydroxymanzamine A (78), was isolated from an Indonesian sponge, Pachypellina sp.[2] The compound showed cytotoxicity against tumor cells (KB and LoVo) and a virus (HSY-II). Two thiocyanates, 2-thiocyanatoneopupukeanane (84) and 4-thiocyanatoneopupukeanane (85) were found in two sponges.[3] Both compounds possess the neopupukeanane skeleton; the rare thiocyano group was confirmed by chemical transformation to a thiol. Three unstable fatty acids, (7E, 13E, 15Z)-14, 16-dibromo-hexadeca-7,13, 15-trien-5-ynoic acid (94), (7E ,9E, 13E,15Z)-14,16-dibromohexadeca-7 ,9, 13, 15-tetraen-5ynoic acid (95), (5Z,7E,9E, 13E,15Z)-6,14,16-tribromohexadeca-5,7,9,13,15-pentaenoic acid (96),[4] and two epidioxy acids, epidioxymanadic acids A (105) and B (106), were purified by high speed countercurrent chromatography. Structure determination of the polybrominated acids and the epidioxy acids was carried out mainly by NMR techniques. Absolute stereochemistry of the epidioxy acids was determined on an alcohol derivative of the acid.
Description: Thesis (Ph. D.)--University of Hawaii at Manoa, 1994.
Includes bibliographical references (leaves 97-105).
xiv, 105 leaves, bound ill. 29 cm
Rights: All UHM dissertations and theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission from the copyright owner.
Appears in Collections:Ph.D. - Chemistry

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