An Antiproliferative Bis-prenylated Quinone from the New Zealand Brown Alga Perithalia capillaris

• Published in: Journal of natural products (Washington, D.C.) Vol. 70; no. 12; pp. 2042 - 2044
• Main Authors: Sansom, Catherine E, Larsen, Lesley, Perry, Nigel B, Berridge, Michael V, Chia, Elizabeth W, Harper, Jacquie L, Webb, Victoria L
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 01.12.2007; Amer Chemical Soc; American Society of Pharmacognosy; American Chemical Society
• Subjects: algae and seaweeds; Animals; anti-inflammatory activity; anticarcinogenic activity; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Biological and medical sciences; cell proliferation; chemical structure; Chemistry, Medicinal; cultured cells; cytotoxicity; General pharmacology; HL-60 Cells; Humans; Life Sciences & Biomedicine; Marine; Medical sciences; Molecular Structure; neutrophils; Neutrophils - drug effects; New Zealand; Nuclear Magnetic Resonance, Biomolecular; Perithalia capillaris; Phaeophyceae; Phaeophyceae - chemistry; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; phenols; Plant Sciences; quinones; Quinones - chemistry; Quinones - isolation & purification; Quinones - pharmacology; Science & Technology; spectral analysis; Sporochnales; Superoxides - blood; New Zealand; Oceania; PSE, New Zealand; RESPIRATORY BURST; AGENTS; CAUDATA; PHENOL; Antineoplastic agent; Human; Promyelocytic leukemia; Pharmacognosy; Algae; Quinone; Antiinflammatory agent; Isoprenoid; In vitro; Biological activity; HL60 cell line; Medicinal plant; Heterokontophyta; Cell line; Plant origin; Isolation; Superoxide radicals; Neutrophil; Tumor cell; Structural analysis; Phaeophyceae
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np070436t

Bioactivity-directed isolation work on the endemic New Zealand brown alga Perithalia capillaris, seeking anti-inflammatory compounds, led to a new bis-prenylated quinone (4). This compound inhibited superoxide production by human neutrophils in vitro (IC50 2.1 µM), but was more potent at inhibiting proliferation of HL60 cells (IC50 0.34 µM). Two related bis-prenylated phenols were also isolated, one known (2) and one new (5), with weaker biological activities. This report extends the examples of bis-prenylated phenols as chemotaxonomic markers for brown algae of the order Sporochnales.