Structural diversity, evolutionary origin, and metabolic engineering of plant specialized benzylisoquinoline alkaloids

Tian, Ya; Kong, Lingzhe; Li, Qi; Wang, Yifan; Wang, Yongmiao; An, Zhoujie; Ma, Yuwei; Tian, Lixia; Duan, Baozhong; Sun, Wei; Gao, Ranran; Chen, Shilin; Xu, Zhichao

doi:10.1039/d4np00029c

Nat. Prod. Rep.

2024

DOI: 10.1039/d4np00029c

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Structural diversity, evolutionary origin, and metabolic engineering of plant specialized benzylisoquinoline alkaloids

Ya Tian,

Lingzhe Kong,

Qi Li

et al.

Abstract: This review explores structures, classifications, and distributions of benzylisoquinoline alkaloids (BIAs) and summarizes their biosynthetic pathway, enzymatic catalysis, origin, evolution, and metabolic engineering.

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Remarkable diversity of alkaloid scaffolds inPiper fimbriulatum

Damiani,

Smith,

Hebra

et al. 2024

Preprint

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SummaryThe Piperaceae plant family is known for its special phytochemistry and is widely recognized as a rich source of bioactive natural products. Piperaceae plants, especially from thePipergenus, have been extensively investigated in the past decades; yet, new alkaloids are still regularly reported from this genus. Here, we investigated the alkaloid diversity ofPiper fimbriulatumusing a metabolomics workflow that combines untargeted LC-MS/MS analysis with a range of recently developed computational tools. In particular, we leverage open libraries of MS/MS spectra and metabolomics data repositories for metabolite annotation and to direct isolation efforts towards structurally-novel compounds (i.e., dereplication). We identified several alkaloids belonging to 5 different classes and isolated one novelseco- benzylisoquinoline alkaloid with a linear quaternary amine nitrogen. Notably, many of the identified compounds were never reported in Piperaceae plants. Our findings expand the known alkaloid diversity of the Piperaceae family, and demonstrate the potential of revisiting well-studied plant families using state-of-the-art computational metabolomics workflows to uncover previously overlooked chemodiversity. Finally, we contextualized our findings in a broader evolutionary framework by mapping literature reports for the identified alkaloid scaffolds onto the angiosperm tree of life, which highlighted the remarkable alkaloid diversity in thePipergenus.Significance StatementWe leveraged untargeted metabolomics with a range of recently developed computational tools to uncover a remarkable diversity of alkaloid scaffolds inPiper fimbriulatum. Our findings demonstrate the potential of revisiting well-studied plant families using state-of-the-art computational metabolomics workflows to uncover previously overlooked chemodiversity.

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Remarkable diversity of alkaloid scaffolds inPiper fimbriulatum

Damiani,

Smith,

Hebra

et al. 2024

Preprint

View full text Add to dashboard Cite

show abstract

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Structural diversity, evolutionary origin, and metabolic engineering of plant specialized benzylisoquinoline alkaloids

Abstract: This review explores structures, classifications, and distributions of benzylisoquinoline alkaloids (BIAs) and summarizes their biosynthetic pathway, enzymatic catalysis, origin, evolution, and metabolic engineering.

Cited by 1 publication

References 159 publications

Remarkable diversity of alkaloid scaffolds inPiper fimbriulatum

Remarkable diversity of alkaloid scaffolds inPiper fimbriulatum

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