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.
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Authors | M Varoglu, B M Peters, P Crews |
Journal | Journal of natural products
(J Nat Prod)
Vol. 58
Issue 1
Pg. 27-36
(Jan 1995)
ISSN: 0163-3864 [Print] United States |
PMID | 7760075
(Publication Type: Journal Article, Research Support, U.S. Gov't, Non-P.H.S., Research Support, U.S. Gov't, P.H.S.)
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Chemical References |
- Antineoplastic Agents
- Dioxanes
- Propionates
- plakoric acid
- plakortolide E
- 4-Butyrolactone
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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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