Chemistry of Trisdecacyclic Pyrazine Antineoplastics: The Cephalostatins and Ritterazines † This review is dedicated to the community of isolation/identification natural product detectives, with special thanks to the groups of Bob Pettit and Nobuhiro Fusatani.

Author:

Lee Seongmin1,LaCour Thomas G.1,Fuchs Philip L.1

Affiliation:

1. Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, and Department of Chemistry, Purdue University, West Lafayette, Indiana 47907

Publisher

American Chemical Society (ACS)

Subject

General Chemistry

Reference118 articles.

1. Antineoplastic agents. 147. Isolation and structure of the powerful cell growth inhibitor cephalostatin 1

2. Corrigendum

3. Isolation and structure of the exceptional Pterobranchia human cancer inhibitors cephalostatins 16 and 171

4. The unavailability of color photographs ofC. gilchristifrom the Pettit collection inspired a thorough web search for closely relatedCephalodiscusspecies. A key paper (Schiaparelli, S., Cattaneo-Vietti, R., and Mierzejewski, P.Polar. Bio. 2004, 27, 813) led us to contact professor Schiaparelli, who graciously provided the first three pictures shown in Chart 1. Comparison of a drawing ofC. gilchristiprovided by Professor Pettit withC. densusphoto 1.3 revealed the minute (3 mm) worms to be nearly identical. Schiaparelli collectedC. densusfrom Terra Nova Bay, Ross Sea, Antarctica, begging the question of whether it also hosts an assortment of trisdecacyclic pyrazines.

5. Ritterazine A, a highly cytotoxic dimeric steroidal alkaloid, from the tunicate Ritterella tokioka

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