Citation: Desen Li, Minjie Yang, Rongfang Mu, Shihong Luo, Yuegui Chen, Wenyuan Li, An Wang, Kai Guo, Yan Liu, Shenghong Li. Characterization of two chimeric sesterterpene synthases from a fungal symbiont isolated from a sesterterpenoid-producing Lamiaceae plant Leucosceptrum canum[J]. Chinese Chemical Letters, ;2023, 34(1): 107469. doi: 10.1016/j.cclet.2022.04.067 shu

Characterization of two chimeric sesterterpene synthases from a fungal symbiont isolated from a sesterterpenoid-producing Lamiaceae plant Leucosceptrum canum

Desen Li ^{a, d, 1} ,
Minjie Yang ^{a, 1} ,
Rongfang Mu ^{a, d} ,
Shihong Luo ^c ,
Yuegui Chen ^{a, d} ,
Wenyuan Li ^a ,
An Wang ^a ,
Kai Guo ^b ,
Yan Liu ^{a, b, *,} ,
Shenghong Li ^{a, b, *,}

a.
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China
b.
State Key Laboratory of Southwestern Chinese Medicine Resources, and Innovative Institute of Chinese Medicine and Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China
c.
College of Bioscience and Biotechnology, Shenyang Agricultural University, Shenyang 110866, China
d.
University of Chinese Academy of Sciences, Beijing 100049, China

liuyan@cdutcm.edu.cn

shli@mail.kib.ac.cn

Received Date: 10 February 2022
Revised Date: 22 April 2022
Accepted Date: 24 April 2022
Available Online: 28 April 2022

Figures(4)

Two chimeric sesterterpene synthases (AaTPS1 and AaTPS2) were functionally characterized from Alternaria alternata MB-30 isolated from the leaves of a sesterterpenoid-producing Lamiaceae plant Leucosceptrum canum. AaTPS1 generated a 5/8/6/5 tetracyclic sesteraltererol (1) and its absolute stereochemistry was determined by X-ray crystallographic analysis of its derivative 10, 11-epoxysesteraltererol (2), which enabled revision of the absolute configuration of C7 of sesterfisherol produced by NfSS and PTTS014 characterized previously and its derivative 10, 11-epoxysesterfisherol. AaTPS2 produced a 5/15 bicyclic preterpestacin I (3). Site-directed mutagenesis suggested that F192 in AaTPS1 was likely involved in controlling of the hydroxylation of C12, and eight amino acids were important for the enzyme activity of AaTPS1 and AaTPS2. The engineered Escherichia coli and Saccharomyces cerevisiae strains were constructed for the productions of compounds 1 and 3, and the highest titer of compound 1 reached 62.3 mg/L in shake-flask culture. Both compounds 1 and 2 showed anti-adipogenic activity.
- Sesterterpenoids,
- Chimeric sesterterpene synthases,
- Plant symbiotic fungi,
- Alternaria alternata,
- Leucosceptrum canum,
- Anti-adipogenic activity
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