Review of cytotoxic cephalostatins and ritterazines: isolation and synthesis

Journal of Natural Products
Bryan R Moser

Abstract

The cephalostatins and ritterazines comprise a family of structurally related natural products reported by Professors G. R. Pettit and N. Fusetani from 1988 -1998. Isolated from the invertebrate marine chordates Cephalodiscus gilchristi and Ritterella tokioka, the cephalostatins and ritterazines exhibit potent cytotoxicity toward the murine P388 lymphocytic leukemia cell line. In fact, cephalostatin 1 ( 1, ED 50 0.1-0.001 pM) proved to be one of the most powerful cancer cell growth inhibitors ever tested by the U.S. National Cancer Institute. The ritterazines and cephalostatins share many common structural features in which two highly oxygenated steroidal units with side chains forming either 5/5 or 5/6 spiroketals are fused via a pyrazine core. Professor P. L. Fuchs and colleagues reported the total syntheses of 1, cephalostatins 7 ( 7), and 12 ( 12), ritterazines K ( 30) and M ( 32), and cytotoxic analogues. The synthesis of 1, described in 1998, required 65 synthetic operations to complete.

References

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Citations

Jan 13, 2012·Journal of the American Chemical Society·Stephen N GreszlerGlenn C Micalizio
Aug 1, 2013·The Journal of Organic Chemistry·Ananda Kumar KanduluruPhilip L Fuchs
Sep 9, 2011·Journal of Natural Products·George R PettitRobin K Pettit
May 23, 2012·Journal of Natural Products·George R PettitFiona Hogan
Sep 15, 2011·Organic Letters·Kanduluru Ananda KumarPhilip L Fuchs
Feb 11, 2014·The Journal of Steroid Biochemistry and Molecular Biology·Bin YuHong-Min Liu
Aug 9, 2011·Nature Chemical Biology·Anthony W G BurgettMatthew D Shair
Dec 10, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Concetta ImperatoreMarialuisa Menna
Apr 26, 2011·Steroids·Mariana Macías-AlonsoMartin A Iglesias-Arteaga
Oct 19, 2010·Steroids·Khaled Q Shawakfeh, Naim H Al-Said
Nov 6, 2010·Current Opinion in Biotechnology·Eric W Schmidt, Mohamed S Donia
Jun 14, 2014·The Journal of Steroid Biochemistry and Molecular Biology·Natalija M KrstićDušan M Sladić
Dec 13, 2016·The Journal of Organic Chemistry·Yong ShiWei-Sheng Tian
Jan 12, 2017·Chembiochem : a European Journal of Chemical Biology·Andrew J AmbroseJames J La Clair
Sep 12, 2015·Organic & Biomolecular Chemistry·Laura K Smith, Ian R Baxendale
Nov 9, 2018·Cancer Chemotherapy and Pharmacology·Sai-Qi WangXiao-Bing Chen
Nov 6, 2018·International Journal of Cancer. Journal International Du Cancer·Prasanta DeyHyung Sik Kim
Jan 30, 2010·Natural Product Reports·John W BluntMichèle R Prinsep
Jul 22, 2010·Natural Product Reports·Jonathan SperryMargaret A Brimble
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Dec 22, 2009·Organic & Biomolecular Chemistry·Jonathan SperryMargaret A Brimble
May 30, 2014·Natural Product Reports·Danielle Skropeta, Liangqian Wei
Feb 19, 2020·Natural Product Reports·Hendrik Luesch, Ville O Paavilainen
Apr 13, 2011·Critical Reviews in Microbiology·K S RajiniCh V Ramana
Feb 18, 2011·Chemistry, an Asian Journal·Yong ShiWeisheng Tian
Oct 20, 2018·Lipids·Emily J KoubekRaymond J Hohl
Dec 11, 2019·Insects·Matteo CalcagnilePietro Alifano
Nov 16, 2012·Natural Product Reports·Jorge A R SalvadorM Luisa Sá e Melo
Sep 4, 2019·Organic & Biomolecular Chemistry·Rachel M Gillard, Margaret A Brimble
Mar 19, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Gabriel Guerrero-LunaJesús Sandoval-Ramírez
Mar 11, 2021·Journal of the American Chemical Society·Yasuaki NakayamaSarah E Reisman
Aug 25, 2009·The Journal of Organic Chemistry·Joseph J TopczewskiDavid F Wiemer
Sep 28, 2010·Bioorganic & Medicinal Chemistry Letters·Natalie C UlrichDavid F Wiemer
Oct 13, 2017·Journal of the American Chemical Society·Lauren C BurrowsKay M Brummond
Jun 5, 2015·Journal of Natural Products·George R PettitNoeleen Melody

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