Prev. Article Next Article Table of Contents

Article

Probing the Bioactive Constituents from Chemotypes of the Sponge Psammocinia aff. bulbosa

Supporting Info

Sarah J. Robinson,^† Karen Tenney,^† Desiree F. Yee,^† Lizabeth Martinez,^† Joseph E. Media,^‡ Frederick A. Valeriote,^‡ Rob W. M. van Soest,^§ and Phillip Crews*^†

Department of Chemistry and Biochemistry and Institute for Marine Sciences, University of California, Santa Cruz, Santa Cruz, California 95064, Josephine Ford Cancer Center, Henry Ford Health System, Detroit, Michigan 48202, and Zologisch Museum, University of Amsterdam, P.O. Box 94766, 1090 GT, Amsterdam, The Netherlands

J. Nat. Prod., 2007, 70 (6), pp 1002–1009

DOI: 10.1021/np070171i

Publication Date (Web): June 9, 2007

†

University of California, Santa Cruz.

‡

Josephine Ford Cancer Center.

University of Amsterdam.

To whom correspondence should be addressed. Tel: 831-459-2603. Fax: 831-459-2935. E-mail: phil@chemistry.ucsc.edu.

Abstract

Since the report of (+)-psymberin (2) in 2004, many synthetic groups have pursued the synthesis of this compound, and our group has further collected Psammocinia aff. bulbosa to successfully isolate more 2. With more (+)-psymberin (2) in hand, additional clonogenic studies, a therapeutic efficacy assessment, and the hollow fiber assay have been completed. The inconsistent production of (+)-psymberin (2) and the classification of six Psammocinia species are further discussed herein. The most recent of these six collections resulted in the isolation of a new brominated cyclic peptide, (−)-psymbamide A (4), which is the first report of a Psammocinia-derived compound in this peptide class. The planar structure was solved via dereplication with Marinlit, HRESIMS, and 1D and 2D NMR techniques, and the absolute configuration determined using Marfey's method.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue June 22, 2007
Received April 13, 2007

Recommend & Share

Related Content

Serinocyclins A and B, Cyclic Heptapeptides from Metarhizium anisopliaeJournal of Natural Products
- Serinocyclins A and B, Cyclic Heptapeptides from Metarhizium anisopliae
  Stuart B. Krasnoff, Ivan Keresztes, Richard E. Gillilan, Doletha M. E. Szebenyi, Bruno G. G. Donzelli, Alice C. L. Churchill and Donna M. Gibson
  Journal of Natural Products 2007 70 (12), pp 1919–1924
  Abstract: Two new cyclic heptapeptides, serinocyclins A (1) and B (2), were isolated from conidia of the entomopathogenic fungus Metarhizium anisopliae. Structures were elucidated by a combination of mass spectrometric, NMR, and X-ray diffraction techniques. ...
  Abstract | Full Text HTML | Hi-Res PDF
Aerucyclamides A and B: Isolation and Synthesis of Toxic Ribosomal Heterocyclic Peptides from the Cyanobacterium Microcystis aeruginosa PCC 7806Journal of Natural Products
- Aerucyclamides A and B: Isolation and Synthesis of Toxic Ribosomal Heterocyclic Peptides from the Cyanobacterium Microcystis aeruginosa PCC 7806
  Cyril Portmann, Judith F. Blom, Karl Gademann and Friedrich Jttner
  Journal of Natural Products 2008 71 (7), pp 1193–1196
  Abstract: Two new modified hexacyclopeptides, aerucyclamides A and B, were isolated from the toxic freshwater cyanobacterium Microcystis aeruginosa PCC 7806. The constitution was assigned by spectroscopic methods, and the configuration determined by chemical ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Psymberin, A Potent Sponge-Derived Cytotoxin from Psammocinia Distantly Related to the Pederin FamilyOrganic Letters
- Psymberin, A Potent Sponge-Derived Cytotoxin from Psammocinia Distantly Related to the Pederin Family
  Robert H. Cichewicz, Frederick A. Valeriote, and Phillip Crews
  Organic Letters 2004 6 (12), pp 1951–1954
  Abstract: Bioassay-guided fractionation of the sponge Psammocinia sp. afforded psymberin (1) possessing 5S,8S,9S,11R,13R,15S,16R,17R stereochemistry. Psymberin exhibits structural similarities to the pederin family metabolites. The potent cytotoxicty and unique ...
  Abstract | Full Text HTML | Hi-Res PDF

Article

Probing the Bioactive Constituents from Chemotypes of the Sponge Psammocinia aff. bulbosa

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Serinocyclins A and B, Cyclic Heptapeptides from Metarhizium anisopliae

Aerucyclamides A and B: Isolation and Synthesis of Toxic Ribosomal Heterocyclic Peptides from the Cyanobacterium Microcystis aeruginosa PCC 7806

Psymberin, A Potent Sponge-Derived Cytotoxin from Psammocinia Distantly Related to the Pederin Family

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES