Cyclization of All-E- and 2Z-Geranylfarnesols by a Bacterial Triterpene Synthase: Insight into Sesterterpene Biosynthesis in Aleuritopteris Ferns
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概要
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Aleuritopteris ferns produce triterpenes and sesterterpenes with tricyclic cheilanthane and tetracyclic 18-episcalarane skeletons. The structural and mechanistic similarities between both classes of fern terpene suggest that their biosynthetic enzymes may be closely related. We investigate here whether a triterpene synthase is capable of recognizing geranylfarnesols as a substrate, and is able to convert them to cyclic sesterterpenes. We found that a bacterial triterpene synthase converted all-E-geranylfarnesol (1b) into three scalarane sesterterpenes with 18αH stereochemistry (5, 7 and 8), as well as mono- and tricyclic sesterterpenes (6 and 9). In addition, 2Z-geranylfarnesol (4) was converted into an 18-episcalarane derivative (10), whose skeleton can be found in sesterterpenes isolated from Aleuritopteris ferns. These results provide insight into sesterterpene biosynthesis in Aleuritopteris ferns.
著者
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Masuda Kazuo
Showa College Of Pharmaceutical Sciences
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Ebizuka Yutaka
Graduate School Of Pharmaceutical Sciences The University Of Tokyo
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Shibuya Masaaki
Faculty Of Pharmaceutical Sciences The University Of Tokyo
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Shinozaki Junichi
Showa Pharmaceutical University
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