Dihydrobenzofurans as cannabinoid receptor ligands from Cordyceps annullata,an entomopathogenic fungus cultivated in the presence of an HDAC inhibitor |
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Authors: | Teigo Asai Dan Luo Yutaro Obara Tohru Taniguchi Kenji Monde Kouwa Yamashita Yoshiteru Oshima |
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Institution: | 1. Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba-yama, Aoba-ku, Sendai 980-8578, Japan;2. Faculty of Advanced Life Science, Frontier Research Center for Post-Genome Science and Technology, Hokkaido University, Kita 21 Nishi 11, Sapporo 001-0021, Japan;3. Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan |
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Abstract: | The secondary metabolite production of Cordyceps annullata, an entomopathogenic fungus, was clearly enhanced by the addition of suberoyl bis-hydroxamic acid (SBHA), a histone deacetylase (HDAC) inhibitor, to the culture medium. Four new 2,3-dihydrobenzofurans, annullatins A–D (1–4), and a new aromatic polyketide, annullatin E (5) were isolated from the culture medium, and the structures, including the absolute stereochemistries, were determined by spectroscopic analysis, vibrational circular dichroism (VCD), and chemical transformations. Annullatin A (1) exhibited potent agonistic activity toward the cannabinoid receptors CB1 and CB2. Annullatin B (2) and D (4) displayed CB1 agonistic activity and CB2 inverse agonistic activity. |
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