| Autor: |
Shinozaki J; Showa Pharmaceutical University., Shibuya M, Ebizuka Y, Masuda K |
| Jazyk: |
angličtina |
| Zdroj: |
Bioscience, biotechnology, and biochemistry [Biosci Biotechnol Biochem] 2013; Vol. 77 (11), pp. 2278-82. Date of Electronic Publication: 2013 Nov 07. |
| DOI: |
10.1271/bbb.130543 |
| Abstrakt: |
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. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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