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Gut Metabolism of Furanocoumarins: Proposed Function of Co O-Methyltransferase
ACS Omega ( IF 3.7 ) Pub Date : 2020-11-17 , DOI: 10.1021/acsomega.0c04879 Steven Ryan Susanto Tan 1 , Bekir E Eser 2 , Jaehong Han 1
ACS Omega ( IF 3.7 ) Pub Date : 2020-11-17 , DOI: 10.1021/acsomega.0c04879 Steven Ryan Susanto Tan 1 , Bekir E Eser 2 , Jaehong Han 1
Affiliation
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Gut metabolism of natural products is of great interest due to the altered biological activity of the metabolites. To study the gut metabolism of the dietary furanocoumarins, the biotransformation of Angelica dahurica was studied with human gut microbiota. The major components of Avenula dahurica, including xanthotoxin (1), bergapten (2), imperatorin (3), isoimperatorin (4), oxypeucedanin (5), and byakangelicol (6), were all metabolized by the human fecal sample, and each furanocoumarin was also biotransformed by Blautia sp. MRG-PMF1 responsible for intestinal O-demethylation. Oxypeucedanin (5) and byakangelicol (6) were converted to oxypeucedanin hydrate (9) and desmethylbyakangelicin (12), respectively. The gut microbial conversion of xanthotoxin (1) and bergapten (2) with the MRG-PMF1 strain resulted in the production of xanthotoxol (7) and bergaptol (8), respectively, due to the methyl aryl ether cleavage by O-methyltransferase. Unexpectedly, the biotransformation of prenylated furanocoumarins, imperatorin (3), and isoimperatorin (4) resulted in the corresponding deprenylated furanocoumarins of xanthotoxol (7) and bergaptol (8), respectively. The cleavage of the prenyl aryl ether group by gut microbiota was unprecedented metabolism. Our data presented the first deprenylation of prenylated natural products, presumably by the anaerobic prenyl aryl ether cleavage reaction catalyzed by Co-corrinoid enzyme.
中文翻译：
呋喃香豆素的肠道代谢：Co O-甲基转移酶的拟议功能
由于代谢物的生物活性改变，天然产物的肠道代谢引起了极大的兴趣。为了研究膳食呋喃香豆素的肠道代谢，我们利用人类肠道微生物群研究了白芷的生物转化。白藜芦醇的主要成分包括黄毒素( 1 )、佛手柑内酯( 2 )、欧前胡素( 3 )、异欧前胡素( 4 )、氧化前胡素( 5 )和白当归醇( 6 )，均由人体粪便样本代谢，并且各成分呋喃香豆素也被Blautia sp. 生物转化。 MRG-PMF1 负责肠道O-去甲基化。氧化前胡素( 5 )和白当归醇( 6 )分别转化为氧化前胡素水合物( 9 )和去甲基白当归素( 12 )。由于O-甲基转移酶对甲基芳基醚的裂解，MRG-PMF1 菌株的肠道微生物对花椒毒素 ( 1 ) 和香柠檬烯 ( 2 ) 的转化分别导致产生花椒毒素 ( 7 ) 和香柠檬醇 ( 8 )。出乎意料的是，异戊二烯化呋喃香豆素、欧前胡素 ( 3 ) 和异欧前胡素 ( 4 ) 的生物转化分别产生了相应的去异戊二烯化呋喃香豆素花椒毒素 ( 7 ) 和香柠檬醇 ( 8 )。肠道微生物群对异戊二烯芳基醚基团的裂解是前所未有的代谢。我们的数据展示了异戊二烯化天然产物的首次去异戊二烯化，推测是通过辅类咕啉酶催化的厌氧异戊烯基芳基醚裂解反应实现的。
更新日期：2020-12-01
中文翻译：
呋喃香豆素的肠道代谢：Co O-甲基转移酶的拟议功能
由于代谢物的生物活性改变，天然产物的肠道代谢引起了极大的兴趣。为了研究膳食呋喃香豆素的肠道代谢，我们利用人类肠道微生物群研究了白芷的生物转化。白藜芦醇的主要成分包括黄毒素( 1 )、佛手柑内酯( 2 )、欧前胡素( 3 )、异欧前胡素( 4 )、氧化前胡素( 5 )和白当归醇( 6 )，均由人体粪便样本代谢，并且各成分呋喃香豆素也被Blautia sp. 生物转化。 MRG-PMF1 负责肠道O-去甲基化。氧化前胡素( 5 )和白当归醇( 6 )分别转化为氧化前胡素水合物( 9 )和去甲基白当归素( 12 )。由于O-甲基转移酶对甲基芳基醚的裂解，MRG-PMF1 菌株的肠道微生物对花椒毒素 ( 1 ) 和香柠檬烯 ( 2 ) 的转化分别导致产生花椒毒素 ( 7 ) 和香柠檬醇 ( 8 )。出乎意料的是，异戊二烯化呋喃香豆素、欧前胡素 ( 3 ) 和异欧前胡素 ( 4 ) 的生物转化分别产生了相应的去异戊二烯化呋喃香豆素花椒毒素 ( 7 ) 和香柠檬醇 ( 8 )。肠道微生物群对异戊二烯芳基醚基团的裂解是前所未有的代谢。我们的数据展示了异戊二烯化天然产物的首次去异戊二烯化，推测是通过辅类咕啉酶催化的厌氧异戊烯基芳基醚裂解反应实现的。
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