Halenaquinone, a pentacyclic polyketide from a marine sponge

Roll, Deborah M.; Scheuer, Paul J.; Matsumoto, Gayle K.; Clardy, Jon

doi:10.1021/ja00357a049

Cited by 109 publications

(76 citation statements)

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“…A hexacyclic alkaloid, exiguamine A (22), was isolated from Neopetrosia exigua collected in Papua New Guinea (Brastianos et al, 2006). Two polycyclic alkaloids, (Roll et al, 1983). Halenaquinol (49) was reported from N. Sapra and N. seriata (Petrosia seriata) (Gorshkova et al, 1999).…”

Section: -Alkylpyridine Alkaloidsmentioning

confidence: 99%

“…In a screening of crude extracts of 6 species of sponges for their antifouling activity, Limna Mol and co-authors (2010) ,8alpha-epidioxy-24alpha -ethylcholestrol-6-en-3-ol (70) exigua) was reported with antibacterial activity against Staphylococcus aureus and Bacillus subtilis (Roll et al, 1983). (+)-Araguspongine C (7) was reported with antituberculosis activity with MIC 3.9 µM (Orabi et al, 2002).…”

Section: Antimicrobial Antifouling and Anti-hiv Activitiesmentioning

confidence: 99%

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Chemical and bioactive diversities of marine sponge Neopetrosia

Qaralleh

2016

Bangladesh J Pharmacol

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The marine sponge Neopetrosia contains about 27 species that is highly distributed in Indian Ocean, Atlantic Ocean (Caribbean Sea) and Pacific Ocean. It has proven to be valuable to the discovery of medicinal products due to the presence of various types of compounds with variable bio-activities. More than 85 compounds including alkaloids, quinones, sterols and terpenoids were isolated from this genus. Moreover, the crude extracts and the isolated compounds revealed activities such as antimicrobial, anti-fouling, anti-HIV, cytotoxic, anti-tumor, anti-oxidant, anti-protozoal, anti-inflammatory. Because only 9 out of 27 species of the genus Neopetrosia have been chemically studied thus far, there are signiﬁcant opportunities to ﬁnd out new chemical constituents from this genus.

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Section: -Alkylpyridine Alkaloidsmentioning

confidence: 99%

Section: Antimicrobial Antifouling and Anti-hiv Activitiesmentioning

confidence: 99%

Chemical and bioactive diversities of marine sponge Neopetrosia

Qaralleh

2016

Bangladesh J Pharmacol

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“…Halenaquinone, Fig. (4), is a pentacyclic polyketide first isolated from a marine sponge (Xestospongia exigua) collected in Palau [69]. Halenaquinone was later isolated from an Okinawan X. exigua and found to induce apoptosis in PC-12 cells (EC 50 = 10 μM), while the closely related compound xestoquinone was inactive [70].…”

Section: Apoptosismentioning

confidence: 99%

Mechanism Targeted Discovery of Antitumor Marine Natural Products

Nagle¹,

Zhou²,

Mora³

et al. 2004

Current Medicinal Chemistry

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Antitumor drug discovery programs aim to identify chemical entities for use in the treatment of cancer. Many strategies have been used to achieve this objective. Natural products have always played a major role in anticancer medicine and the unique metabolites produced by marine organisms have increasingly become major players in antitumor drug discovery. Rapid advances have occurred in the understanding of tumor biology and molecular medicine. New insights into mechanisms responsible for neoplastic disease are significantly changing the general philosophical approach towards cancer treatment. Recently identified molecular targets have created exciting new means for disrupting tumor-specific cell signaling, cell division, energy metabolism, gene expression, drug resistance, and blood supply. Such tumor-specific treatments could someday decrease our reliance on traditional cytotoxicity-based chemotherapy and provide new less toxic treatment options with significantly fewer side effects. Novel molecular targets and state-of-the-art molecular mechanism-based screening methods have revitalized antitumor research and these changes are becoming an ever-increasing component of modern antitumor marine natural products research. This review describes marine natural products identified using tumor-specific mechanism-based assays for regulators of angiogenesis, apoptosis, cell cycle, macromolecule synthesis, mitochondrial respiration, mitosis, multidrug efflux, and signal transduction. Special emphasis is placed on natural products directly discovered using molecular mechanism-based screening.

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“…Chemistry/bioactivity: the structure of halenaquinone 196 was determined by single crystal X-ray analysis, 149 and the compound exhibited modest in vitro activity versus S. aureus and B. subtilis.…”

Section: Xestospongia Exiguamentioning

confidence: 99%