Production of an emericellin and its analogues as fungal biological responses for Shimbu-to extract
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This research examined the production of fungal metabolites as a biological response to Kampo medicines. Shimbu-to (SMB) is a Kampo medicine composed of five herbal components: peony root (Shakuyaku), ginger (Shokyo), processed aconite root (Bushi), Poria sclerotium (Bukuryo), and Atractylodes lancea rhizomes (Sojutsu). High-performance liquid chromatography (HPLC) analysis of the fungus Aspergillus nidulans CBS 112.46 incubated in potato dextrose broth supplemented with SMB extract revealed emericellin (2) as the major peak and new xanthone analogues 24-hydroxyshamixanthone (1), shamixanthone (3), epishamixanthone (4), pre-shamixanthone (5), and variecoxanthone A (6) as minor peaks. The structure of 1 was determined by detailed analysis of 1D-NMR, 2D-NMR, and MS data. The results suggest that SMB extract regulates the biosynthesis of emericellin and its analogues in A. nidulans. Further investigations revealed that glucose induces the biosynthesis of emericellin and its analogues in A. nidulans in a concentration-dependent manner.
KeywordsShimbu-to Aspergillus nidulans Xanthone Emericellin Glucose
This study was supported by the Japan Society for the Promotion of Science (JSPS; Grant number 15K08005).
- 3.Zain ME (2009) Effect of olive oil on secondary metabolite and fatty acid profiles of Penicillium expansum, Aspergillus flavus, A. parasiticus and A. ochraceus. Aust J Basic Appl Sci 3:4274–4280Google Scholar
- 4.Yu-Ming C, Chien-Kei W, Da-Wei C, Mohamed E, Chi-Ting H, Teigo A, Yoshiteru O, Tusty-Jiuan H, Tsong-Long H, Yang-Chang W, Fang-Rong C (2013) An epigenetic modifier enhances the production of anti-diabetic and anti-inflammatory sesquiterpenoids from Aspergillus sydowii. Bioorg Med Chem 21:3866–3872CrossRefGoogle Scholar
- 7.Masayoshi I, Takashi H, Yuichi H, Keiichi F, Tomitake T, Yukiteru K (1975) Emericellin, a new metabolite from Aspergillus nidulans. Agric Biol Chem 39:291–292Google Scholar
- 8.Kuldip KC, Christopher F, John SEH, Thomas JS, Kenneth Y (1974) The biosynthesis of fungal metabolites part III structure of shamixanthone and tajixanthone, metabolites of Aspergillus variecolor. J Chem Soc Perkin Trans 1:1584–1593Google Scholar
- 9.Masayoshi I, Takashi H, Yuichi H, Keiichi F, Tomitake T, Yukiteru K (1976) Epishamixanthone, a new metabolite from Aspergillus rugulosus. Agric Biol Chem 40:1051–1052Google Scholar
- 11.Kuldip KC, John SEH, Thomas JS, Kenneth Y (1975) The biosynthesis of fungal metabolites part V structure of variecoxanthones A, B, and C, metabolites of Aspergiiius variecolor; conversion of variecoxanthone A into (±)-De-C-prenylepishamixanthone. J Chem Soc Perkin Trans 1(6):543–548Google Scholar