Literature DB >> 35075754

Biosynthesis of Terpenoid-Pyrrolobenzoxazine Hybrid Natural Product CJ-12662.

Wei Cheng1,2, Mengbin Chen1,3, Masao Ohashi1, Yi Tang1,4.   

Abstract

The fungal natural product CJ-12662 is a structurally complex terpene-amino acid hybrid, and is a potent anthelmintic compound. The biosynthetic pathway of CJ-12662 is elucidated based on metabolite analysis from heterologous expression. We demonstrate the terpene portion is derived from successive P450-catalyzed oxidations of amorpha-4,11-diene, while three flavin-dependent enzymes are involved in morphing the esterified tryptophan into a chlorinated pyrrolobenzoxazine, utilizing a cascaded [1,2]-Meisenheimer rearrangement.
© 2022 Wiley-VCH GmbH.

Entities:  

Keywords:  Amorpha-4,11-diene Synthase; Flavoenzymes; Fungal Natural Products; Pyrrolobenzoxazine; [1,2]-Meisenheimer Rearrangement

Mesh：

Substances：

Year:  2022        PMID： 35075754      PMCID： PMC8901528          DOI： 10.1002/anie.202116928

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   16.823


  30 in total

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Review 4.  Enzymatic Cascade Reactions in Biosynthesis.

Authors:  Christopher T Walsh; Bradley S Moore
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-20       Impact factor: 15.336

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Journal:  Planta Med       Date:  2005-01       Impact factor: 3.352

6.  Full stereochemical assignment and synthesis of the potent anthelmintic pyrrolobenzoxazine natural product CJ-12662.

Authors:  Charles Didier; Douglas J Critcher; Nigel D Walshe; Yasuhiro Kojima; Yuji Yamauchi; Anthony G M Barrett
Journal:  J Org Chem       Date:  2004-11-12       Impact factor: 4.354

7.  Assembly of asperlicin peptidyl alkaloids from anthranilate and tryptophan: a two-enzyme pathway generates heptacyclic scaffold complexity in asperlicin E.

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Review 8.  Biosynthesis of fungal meroterpenoids.

Authors:  Yudai Matsuda; Ikuro Abe
Journal:  Nat Prod Rep       Date:  2016-01       Impact factor: 13.423

9.  Convergent biosynthetic transformations to a bacterial specialized metabolite.

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10.  Five New Cytotoxic Metabolites from the Marine Fungus Neosartorya pseudofischeri.

Authors:  Wen-Jian Lan; Sheng-Jiao Fu; Meng-Yang Xu; Wan-Ling Liang; Chi-Keung Lam; Guo-Hua Zhong; Jun Xu; De-Po Yang; Hou-Jin Li
Journal:  Mar Drugs       Date:  2016-01-13       Impact factor: 5.118
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