Biosynthesis of Antroquinonol and 4-Acetylantroquinonol B via a Polyketide Pathway Using Orsellinic Acid as a Ring Precursor in Antrodia cinnamomea
In: Journal of Agricultural and Food Chemistry, Jg. 65 (2016-12-21), S. 74-86
Online
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Zugriff:
Antroquinonol (AQ) and 4-acetylantroquinonol B (4-AAQB), isolated from the mycelium of Antrodia cinnamomea, have a similar chemical backbone to coenzyme Q (CoQ). Based on the postulation that biosynthesis of both AQ and 4-AAQB in A. cinnamomea starts from the polyketide pathway, we cultivated this fungus in a culture medium containing [U-13C]oleic acid, and then we analyzed the crude extracts of the mycelium using UHPLC-MS. We found that AQ and 4-AAQB follow similar biosynthetic sequences as CoQ. Obvious [13C2] fragments on the ring backbone were detected in the mass spectrum for [13C2]AQ, [13C2]4-AAQB, and their [13C2] intermediates found in this study. The orsellinic acid, formed from acetyl-CoA and malonyl-CoA via the polyketide pathway, was found to be a novel benzoquinone ring precursor for AQ and 4-AAQB. The identification of endogenously synthesized farnesylated intermediates allows us to postulate the routes of AQ and 4-AAQB biosynthesis in A. cinnamomea.
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Biosynthesis of Antroquinonol and 4-Acetylantroquinonol B via a Polyketide Pathway Using Orsellinic Acid as a Ring Precursor in Antrodia cinnamomea
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Autor/in / Beteiligte Person: | Wu, Hsiang-Lin ; Chiang, Been-Huang ; Sheu, Fuu ; Chang, Tsu-Liang ; Kevin Chi-Chung Chou ; Chen, Kai-Hsien ; Lin, Pei-Yin ; Yang, Shang-Han |
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Zeitschrift: | Journal of Agricultural and Food Chemistry, Jg. 65 (2016-12-21), S. 74-86 |
Veröffentlichung: | American Chemical Society (ACS), 2016 |
Medientyp: | unknown |
ISSN: | 1520-5118 (print) ; 0021-8561 (print) |
DOI: | 10.1021/acs.jafc.6b04346 |
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