1994 Fiscal Year Final Research Report Summary
COMPREHENSIVE RESEARCH TOWARD THE ELUCIDATION OF BIOLOGICAL ACTIVITIES OF NATURAL ORGANIC COMPOUNDS
| Project/Area Number |
05303018
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| Research Category |
Grant-in-Aid for Co-operative Research (A)
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| Allocation Type | Single-year Grants |
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| Research Field |
Bioorganic chemistry
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| Research Institution | OSAKA CITY UNIVERSITY |
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Principal Investigator |
ISOE Sachihiko OSAKA CITY UNIVERSITY FACULTY OF SCIENCE PROFESSOR, 理学部, 教授 (90046946)
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| Co-Investigator(Kenkyū-buntansha) |
KUSUMOTO Shoichi OSAKA UNIVERSITY FACULTY OF SCIENCE PROFESSOR, 理学部, 教授 (30028253)
YAMADA Kiyoyuki NAGOYA UNIVERSITY FACULTY OF SCIENCE PROFESSOR, 理学部, 教授 (90022540)
TACHIBANA Kazuo TOKYO UNIVERSITY FACULTY OF SCIENCE PROFESSOR, 理学部, 教授 (70142081)
HIRAMA Masahiro TOHOKU UNIVERSITY FACULTY OF SCIENCE PROFESSOR, 理学部, 教授 (30165203)
MURAI Akio HOKKAIDO UNIVERSITY FACULTY OF SCIENCE PROFESSOR, 理学部, 教授 (20000838)
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| Project Period (FY) |
1993 – 1994
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| Keywords | Terpenoid Dialdehyde / Marine Natural Product / Carcinogenic Substance / DNA Cleavage Mechanism / Antitumor Compound / Defensive Substance / Glycolipid / 複合糖質 |
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| Research Abstract |
1. The broad diversity of both structure and biological activity exhibited by terpenoids having dialdehyde functionality has generated much interest for their synthesis. We were especially attracted to the polyfunctional iridoids and marine di- and sester terpenoids structurally related to the iridoid since these terpenoids exhibit cytotoxic, antileukemic, antimicrobial, antifungal, antiviral and anti-inframmatory activities. In this project we acoomplished the synthesis of halitunal, a novel 10 pi-heteroaromatic diterpene isolated from marine algae Halimeda tuna. 2. A number of marine cyclic bromo-ethers having straight C15-chained skeletones have benn isolated from red algae. First synthesis of laurencin, a representative natural product of this class, was accomplished from laurediol. 3. Stereoselective synthesis of AB ring fragments of ciguatoxin and gambiertoxin was accomplished and the absolute configuration of C2 was determined. Albumin conjugates for anti-ciguatoxin antibody, wa
… More
s also synthesized. 4. A lipophilic ichthyotoxin from the defensive mucous skin secretion of soapfish, named lipo-grmmistin-A was isolated and chemically characterized. Lipogrammistin-A is the first example of a macrocyclic polyamine lactam found in the animal kingdam. 5. Ptaquilosin, the final carcinogenic substance isolated from bracken fern was synthesized. The mechanism of DNA cleavage of this compound was elucidated. Aplyronine, a potent antitumor macrolide from the sea hare Aplysia kurodai was synthesized. Doliculide a potent cytotoxic cyclodepsipeptide from sea hare Dolabella auricularia was also synthesized. 6. Thioglycosides, which can be used as the protecting group at the anomeric position but can be used as efficient glycosyl donors through activation with appropriate thiophilic reagents, have been widely used for the synthesis of complex carbohydrates. In the present study two novel glycosylation reaction using thioglycosides were developed and successfully applied for the synthesis of glycolipids. Less
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