Polyandrocarpidines: antimicrobial and cytotoxic agents from a marine tunicate (Polyandrocarpa species) from the Gulf of California

Cheng, Michael T.; Rinehart, Kenneth L.

doi:10.1021/ja00491a047

Cited by 37 publications

(10 citation statements)

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“…To the best of our knowledge this study represents only the third report on new chemistry from the ascidian genus, Polyandrocarpa. Previous investigations have reported the isolation of the antimicrobial guanidine-derived metabolites, the polyandrocarpidines, [24][25][26] and the -carbonyl indole-based alkaloids, polyandrocarpamides A-D. 27 This is the first report of 2-aminoimidazolone-derived compounds from this genus. The synthesis of both polyandrocarpamines A (1) and B (2) confirmed the spectroscopically assigned structures.…”

Section: Resultsmentioning

confidence: 79%

The isolation and synthesis of polyandrocarpamines A and B. Two new 2-aminoimidazolone compounds from the Fijian ascidian, Polyandrocarpa sp.

et al. 2002

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Chemical investigation of a Fijian ascidian, Polyandrocarpa sp., has resulted in the isolation of two new 2-aminoimidazolone-derived compounds, polyandrocarpamines A (1) and B (2). The structures of these unique metabolites were determined by the interpretation of spectroscopic data and confirmed by total synthesis. The stereospecific synthesis of 1 was accomplished using aldol condensation chemistry to generate an arylidene thiohydantoin that was subsequently transaminated to yield polyandrocarpamine A. Demethylation of synthetic 1 afforded polyandrocarpamine B. Both the natural product and synthetic polyandrocarpamines were assigned Z geometries about the exocyclic double bond (C-5/C-7) on the basis of 13 C/ 1 H long-range coupling constants, which were measured using a gHSQMBC experiment.

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Section: Resultsmentioning

confidence: 79%

The isolation and synthesis of polyandrocarpamines A and B. Two new 2-aminoimidazolone compounds from the Fijian ascidian, Polyandrocarpa sp.

et al. 2002

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“…We had earlier observed modestantiviral activity in other compound tunicates (Ref. 12,13); thus, the latter observation came as no surprise. Cytotoxicity was widely distributed among the phyla.…”

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confidence: 73%

Marine natural products as sources of antiviral, antimicrobial, and antineoplastic agents

Rinehart¹,

Shaw²,

Shield³

et al. 1981

Pure and Applied Chemistry

153

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Extracts of marine species from Baja California and theCaribbean have been examined on shipboard for a variety of bioactlvities and their constituents studied there by gas chromatography! mass spectrometry. A very high proportion of the extracts has been shown to be cytotoxic, a high proportion to be antibacterial or antifungal and a surprisingly large number to be antiviral. Many of these activities have been confirmed in more extensive assays against tumor cells, pathogenic microorganisms and a battery of viruses. A number of the compounds responsible for the activities have been identified, including several new compounds. Of special current interest are the didemnins, depsipeptides isolated from a didemnid tunicate, which inhibit a number of RNA and DNA viruses and exhibit potent cytotoxicity vs. tumor cell lines.

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“…Polyandrocarpidines I (67, n=5) and 11 (67, n=4) were found in a colonial tunicate, Polyandrocarpa sp. (Cheng and Rinehart, 1978). Their structure was established mainly from mass spectral studies of various pyrimidyl derivatives and that of polyandrocarpidine 11 was indirectly confirmed by synthesis.…”

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confidence: 99%

Natural Guanidino Compounds

Robin¹,

Marescau

1985

Guanidines

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Polyandrocarpidines: antimicrobial and cytotoxic agents from a marine tunicate (Polyandrocarpa species) from the Gulf of California

Abstract: Communications to the Editor 7409 References and Notes(1) This work was performed under the auspices of the Division of Basic Energy Sciences of the U.S. Department of Energy. We also wish to acknowledge the partial support of this collaborative research by the National Science

Cited by 37 publications

References 1 publication

The isolation and synthesis of polyandrocarpamines A and B. Two new 2-aminoimidazolone compounds from the Fijian ascidian, Polyandrocarpa sp.

The isolation and synthesis of polyandrocarpamines A and B. Two new 2-aminoimidazolone compounds from the Fijian ascidian, Polyandrocarpa sp.

Marine natural products as sources of antiviral, antimicrobial, and antineoplastic agents

Natural Guanidino Compounds

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