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The structures and cytotoxic properties of polyketide peroxides from a Plakortis sponge.

Abstract
A morphologically distinct Fijian sponge, Plakortis sp., has yielded two new peroxides, plakortolide E [5] and plakoric acid [12]. After standing for approximately one year, plakortolide E rearranged to plakortolide ether [10]. The structures of plakortolide E [5] and plakortolide ether [10] were established from 2D nmr data and by analogy to a known compound, plakortolide [3]. The stereochemistry of the bicyclic ring substituents of 5 was established using nOe and NOESY nmr data along with comparisons to 3. The absolute stereochemistry at the three chiral sites of 5 was assigned by preparing acyclic compounds 6-9, and both 8 and 9 were investigated using the modified Mosher's method. This represents the first absolute stereochemistry determination for a sponge-derived polyketide peroxide. The characterization of plakoric acid [12] was based on spectral analogies to known polyketides such as plakortin. Plakortolide E [5] exhibited selective potency against the melanoma and breast tumor cell lines in the in vitro 60-cell line panel of the National Cancer Institute.
AuthorsM Varoglu, B M Peters, P Crews
JournalJournal of natural products (J Nat Prod) Vol. 58 Issue 1 Pg. 27-36 (Jan 1995) ISSN: 0163-3864 [Print] United States
PMID7760075 (Publication Type: Journal Article, Research Support, U.S. Gov't, Non-P.H.S., Research Support, U.S. Gov't, P.H.S.)
Chemical References
  • Antineoplastic Agents
  • Dioxanes
  • Propionates
  • plakoric acid
  • plakortolide E
  • 4-Butyrolactone
Topics
  • 4-Butyrolactone (analogs & derivatives, chemistry, isolation & purification, pharmacology)
  • Animals
  • Antineoplastic Agents (chemistry, isolation & purification, pharmacology)
  • Dioxanes (chemistry, isolation & purification, pharmacology)
  • Drug Screening Assays, Antitumor
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Porifera (chemistry)
  • Propionates (chemistry, isolation & purification, pharmacology)
  • Stereoisomerism
  • Tumor Cells, Cultured

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