Structures and Cytotoxic Evaluation of New and Known Acyclic Ene-Ynes from an American Samoa Petrosia sp. Sponge

• Published in: Journal of natural products (Washington, D.C.) Vol. 76; no. 3; pp. 425 - 432
• Main Authors: Mejia, Eric J, Magranet, Lindsay B, De Voogd, Nicole J, TenDyke, Karen, Qiu, Dayong, Shen, Young Yongchun, Zhou, Zhongrui, Crews, Phillip
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 22.03.2013; Amer Chemical Soc
• Subjects: American Samoa; Animals; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Chemistry, Medicinal; Drug Screening Assays, Antitumor; Humans; Life Sciences & Biomedicine; Marine Biology; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Petrosia - chemistry; Pharmacology & Pharmacy; Plant Sciences; Polyynes - chemistry; Polyynes - isolation & purification; Polyynes - pharmacology; Science & Technology; METABOLITES; POLYACETYLENE; ACID; ACETYLENIC ALCOHOLS
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np3008446

Four new compounds, (−)-petrosynoic acids A–D (1–4), and five known congeners, pellynols A (5), C (6), D (7), F (8), and I (9), were isolated from a Petrosia sp. marine sponge collected in American Samoa. Isolation work was guided by cytotoxicity against human lung cancer cells (H460). The structures of the C31–C33 polyacetylenes (1–9) were determined on the basis of 1D- and 2D-NMR analysis, mass spectrometry, and comparison of specific rotation values. Compounds 1–9 were found to be broadly cytotoxic with limited selectivity for cancer cells, as they were all moderately active against the A2058 (melanoma), H522-T1 (lung), and H460 (lung) human cancer cell lines as well as IMR-90 quiescent human fibroblast cells.