Beilstein J. Org. Chem.2024,20, 638–644, doi:10.3762/bjoc.20.56
Jia Tang Yixiang Zhang Yudai Matsuda Department of Chemistry, City University of Hong Kong, Tat Chee Avenue, Kowloon, Hong Kong SAR, China 10.3762/bjoc.20.56 Abstract Fungalmeroterpenoids are diverse structurally intriguing molecules with various biological properties. One large group within
secondary metabolites, filamentous fungi stand out as the most prolific producers of meroterpenoids [1][2][3]. Representative fungalmeroterpenoids of medicinal importance include pyripyropene A, a cholesterol acyltransferase inhibitor [4]; fumagillin, an antimicrobial agent [5]; and mycophenolic acid, a
strong inosine 5-monophosphate dehydrogenase inhibitor [6]. The biosynthesis of fungalmeroterpenoids has garnered interest in the organic chemistry field due to their structural complexity and associated intriguing enzymatic reactions and has thus been extensively researched for over a decade, providing
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Graphical Abstract
Figure 1:
Biosynthesis of selected fungal meroterpenoids. (A, B) Dearomatizing prenylation reactions in the b...
Beilstein J. Org. Chem.2024,20, 578–588, doi:10.3762/bjoc.20.50
for the design of biosynthetic machineries to produce a variety of bioactive meroterpenoids.
Keywords: αKG-dependent dioxygenases; enzyme engineering; fungalmeroterpenoids; synthetic biology; terpene cyclases; Introduction
Meroterpenoids are complex natural products with intricate skeletal
structures, and are partially derived from terpenoids [1]. Many fungalmeroterpenoids are composed of polyketide and terpenoid moieties. Examples of fungalmeroterpenoids include mycophenolic acid (Figure 1, 1), which shows immunosuppressive activity and cell differentiation-inducing activity by inhibiting
of acyl-CoA: cholesterol acyltransferase [4]. In this mini-review, we focus on the fungalmeroterpenoids biosynthesis, especially terpenonid cyclizations and post-cyclization modifications, which mostly contribute to the skeletal diversity. Several terpenoid cyclases and αKG-dependent dioxygenases
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Graphical Abstract
Figure 1:
Examples of bioactive fungal meroterpenoids.