Anteaglonialides A鈥揊 and Palmarumycins CE1鈥揅E3 from Anteaglonium sp. FL0768, a Fungal Endophyte of the Spikemoss Selaginella arenicola

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• 作者：Ya-ming Xu ; Jair Mafezoli ; Maria C. F. Oliveira ; Jana M. U鈥橰en ; A. Elizabeth Arnold ; A. A. Leslie Gunatilaka
• 刊名：Journal of Natural Products
• 出版年：2015
• 出版时间：November 25, 2015
• 年：2015
• 卷：78
• 期：11
• 页码：2738-2747
• 全文大小：465K
• ISSN：1520-6025

文摘

Anteaglonialides A鈥揊 (1鈥?b>6), bearing a spiro[6-(tetrahydro-7-furanyl)cyclohexane-1,2鈥?naphtho[1,8-de][1,3]-dioxin]-10-one skeleton, three new spirobisnaphthalenes, palmarumycins CE₁鈥揅E₃ (7鈥?b>9), nine known palmarumycin analogues, palmarumycins CP₅ (10), CP_4a (11), CP₃ (12), CP₁₇ (13), CP₂ (14), and CP₁ (15), CJ-12,371 (16), 4-O-methyl CJ-12,371 (17), and CP₄ (18), together with a possible artifact, 4a(5)-anhydropalmarumycin CE₂ (8a), and four known metabolites, O-methylherbarin (19), herbarin (20), herbaridine B (21), and hyalopyrone (22), were encountered in a cytotoxic extract of a potato dextrose agar culture of Anteaglonium sp. FL0768, an endophytic fungus of the sand spikemoss, Selaginella arenicola. The planar structures and relative configurations of the new metabolites 1鈥?b>9 were elucidated by analysis of extensive spectroscopic data, and the absolute configuration of 1 was determined by the modified Mosher鈥檚 ester method. Application of the modified Mosher鈥檚 ester method combined with the NOESY data resulted in revision of the absolute configuration previously proposed for 10. Co-occurrence of 1鈥?b>6 and 7鈥?b>18 in this fungus led to the proposal that the anteagloniolides may be biogenetically derived from palmarumycins. Among the metabolites encountered, anteaglonialide F (6) and known palmarumycins CP₃ (12) and CP₁ (15) exhibited strong cytotoxic activity against the human Ewing鈥檚 sarcoma cell line CHP-100, with IC₅₀ values of 1.4, 0.5, and 1.6 渭M, respectively.