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Volumn 63, Issue 10, 1998, Pages 3281-3286

Palau'amine and its congeners: A family of bioactive bisguanidines from the marine sponge Stylotella aurantium

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; BIGUANIDE DERIVATIVE; PALAU AMINE; UNCLASSIFIED DRUG;

EID: 0032524819     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971987z     Document Type: Article
Times cited : (183)

References (42)
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    • A preliminary account of part of this work was presented at the Seventh International Symposium on Marine Natural Products, Capri, Italy, July 5-10, 1992; Abstract C7. When it was originally collected and a communication was published, the sponge was identified as S. agminata. (Kinnel, R. B.; Gehrken, H.-P.; Scheuer, P. J. J. Am. Chem. Soc. 1993, 115, 3376-3377). The correct species name is S. aurantium (Kelly-Borges, M.; Bergquist, P. Indo-Malayan Zool. 1988, 5, 121-159).
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  • 2
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    • A preliminary account of part of this work was presented at the Seventh International Symposium on Marine Natural Products, Capri, Italy, July 5-10, 1992; Abstract C7. When it was originally collected and a communication was published, the sponge was identified as S. agminata. (Kinnel, R. B.; Gehrken, H.-P.; Scheuer, P. J. J. Am. Chem. Soc. 1993, 115, 3376-3377). The correct species name is S. aurantium (Kelly-Borges, M.; Bergquist, P. Indo-Malayan Zool. 1988, 5, 121-159).
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    • Brossi, A., Cordell, G. A., Eds.; Academic Press: San Diego, CA, Chapter 2
    • Kobayashi, J.; Ishibashi, M. In The Alkaloids; Brossi, A., Cordell, G. A., Eds.; Academic Press: San Diego, CA, 1992; Vol. 41, Chapter 2.
    • (1992) The Alkaloids , vol.41
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    • For example, in leucodrin tetraacetate, the comparable hydrogens have a coupling constant of 12.4 Hz (Lowry, J. B.; Riggs, N. V. Tetrahedron Lett. 1964, 2911-2914).
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    • note
    • Molecular modeling was carried out with the Discover (BIOSYM) program, using InsightII to construct the models; energy minimization was carried out using the CV force field.
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    • The carboxamide of pyrrole-2-carboxylic acid was reported in: König, G. M.; Wright, A. M. Nat. Prod. Lett. 1994, 5, 141-146. AAPE has been reported in two different sponges: Wright, A. E.; Chiles, S. A.; Cross, S. S. J. Nat. Prod. 1991, 54, 1684-1686.
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    • The carboxamide of pyrrole-2-carboxylic acid was reported in: König, G. M.; Wright, A. M. Nat. Prod. Lett. 1994, 5, 141-146. AAPE has been reported in two different sponges: Wright, A. E.; Chiles, S. A.; Cross, S. S. J. Nat. Prod. 1991, 54, 1684-1686.
    • (1991) J. Nat. Prod. , vol.54 , pp. 1684-1686
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    • We are grateful to a reviewer for suggesting this better alternative to our original proposed biogenetic scheme
    • We are grateful to a reviewer for suggesting this better alternative to our original proposed biogenetic scheme.
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    • Bedoya Zurita, M.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1989, 45 6713-6720. Commercon, A.; Gueremy, C. A. Tetrahedron Lett. 1991, 32, 1419-1422.
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    • note
    • The dust from the dried sponge caused an allergic reaction consisting of severe shortness of breath for about 4 h, which disappeared within 1 day. In addition, some workers also experienced skin rashes from contact with the sponge.


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