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Cited by 22Plant biochemistry and biosynthesisLipid metabolism and biosynthesisBiochemical and biochemical processes

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Synthesis of 4‐methylvaleric acid, a precursor of pogostone, involves a 2‐isobutylmalate synthase related to 2‐isopropylmalate synthase of leucine biosynthesis

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Wang, Chu, Wang, Ying, Chen, Jing, Liu, Lang, Yang, Mingxia, Li, Zhengguo, Wang, Chengyuan, Pichersky, Eran, Xu, Haiyang·2022·New Phytologist
DOI 10.1111/nph.18186

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Abstract

Summary: We show here that the side chain of pogostone, one of the major components of patchouli oil obtained from Pogostemon cablin and possessing a variety of pharmacological activities, is derived from 4‐methylvaleric acid. We also show that 4‐methylvaleric acid is produced through the one‐carbon α‐ketoacid elongation pathway with the involvement of the key enzyme 2‐isobutylmalate synthase (IBMS), a newly identified enzyme related to isopropylmalate synthase (IPMS) of leucine (Leu) biosynthesis. Site‐directed mutagenesis identified Met 132 in the N‐terminal catalytic region as affecting the substrate specificity of PcIBMS1. Even though PcIBMS1 possesses the C‐terminal domain that in IPMS serves to mediate Leu inhibition, it is insensitive to Leu. The observation of the evolution of IBMS from IPMS, as well as previously reported examples of IPMS‐related genes involved in making glucosinolates in Brassicaceae, acylsugars in Solanaceae, and flavour compounds in apple, indicate that IPMS genes represent an important pool for the independent evolution of genes for specialised metabolism.

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Metadata

Authors
Wang, C., Wang, Y., Chen, J., Liu, L., Yang, M., Li, Z., Wang, C., Pichersky, E., & Xu, H.
Affiliations
  • Chongqing University (CN)
  • Chinese Academy of Sciences (CN)
  • University of Michigan (US)
Corresponding author
Xu, Haiyang
ORCID
Venue
New Phytologist
Publisher
Wiley
Published
2022-05-20
Volume
235
Issue
3
Pages
1129-1145
ISSN
  • 0028-646X (ISSN-L)
  • 1469-8137
DOI
10.1111/nph.18186
OpenAlex
W4225973342
Cited by
22
References
2
Citations by year
2026: 7 · 2025: 4 · 2024: 5 · 2023: 5 · 2022: 1
FWCI
1.22
Type
journal article
Language
en
Open access
Licence
onlinelibrary.wiley.com/termsAndConditions#vor (vor)
Locations
  • New Phytologist (publishedVersion)
  • bioRxiv (Cold Spring Harbor Laboratory) (acceptedVersion)
  • PubMed (publishedVersion)
  • Deep Blue (University of Michigan) (submittedVersion)
Funders
  • Chongqing University (0304001104433)
  • National Key Research and Development Program of China (2018YFD1000800)
  • Fundamental Research Funds for the Central Universities (2020CDJQY-A077, 2018YFD1000800)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant biochemistry and biosynthesis
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Lipid metabolism and biosynthesis
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Biochemical and biochemical processes
Keywords
pogostone, patchouli oil, Pogostemon cablin, leucine biosynthesis, enzyme evolution, substrate specificity, glucosinolates, acylsugars, flavor compounds
MeSH terms
Kinetics, Leucine, Oils, Volatile, 2-Isopropylmalate Synthase

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