Corygaline A, a hexahydrobenzophenanthridine alkaloid with an unusual carbon skeleton from <i>Corydalis bungeana</i> Turcz.

Gao, Chang; Gu, Xiaoting; Wang, Xin; Cao, Huikun; Lin, Bin; Li, Youping; Di, Xin

doi:10.1039/c8ob02194e

Cited by 7 publications

(2 citation statements)

References 19 publications

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“…Similarly, the role of MTs in the many “unusual” BIA branch pathways has not been investigated. This includes pathways biosynthesizing the rhoeadine alkaloids present in P. rheas (Rönsch, 1986), benzylprotoberberines (e.g., Latifolian A) occurring in Gnetum latifolium (Rochfort et al, 2005), hexahydrobenzophenanthridines (e.g., Corygaline A) occurring in Corydalis bungeana (Gao et al, 2018), as well as the dimeric and trimeric BIAs reported in many species (Schiff, 1991). Biosynthesis of aporphine alkaloids in Nelumbo nucifera (Proteales) has recently received some attention; however, most analyses assumed that central BIA biosynthesis is the same as in Ranunculales and, furthermore, that N. nucifera OMT and NMT homologs catalyze the same reactions as reported in other species (Menéndez-Perdomo and Facchini, 2018).…”

Section: Future Directionsmentioning

confidence: 99%

Molecular Origins of Functional Diversity in Benzylisoquinoline Alkaloid Methyltransferases

Morris

Facchini

2019

Front. Plant Sci.

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O - and N -methylations are ubiquitous and recurring features in the biosynthesis of many specialized metabolites. Accordingly, the methyltransferase (MT) enzymes catalyzing these modifications are directly responsible for a substantial fraction of the vast chemodiversity observed in plants. Enabled by DNA sequencing and synthesizing technologies, recent studies have revealed and experimentally validated the trajectories of molecular evolution through which MTs, such as those biosynthesizing caffeine, emerge and shape plant chemistry. Despite these advances, the evolutionary origins of many other alkaloid MTs are still unclear. Focusing on benzylisoquinoline alkaloid (BIA)-producing plants such as opium poppy, we review the functional breadth of BIA N - and O -MT enzymes and their relationship with the chemical diversity of their host species. Drawing on recent structural studies, we discuss newfound insight regarding the molecular determinants of BIA MT function and highlight key hypotheses to be tested. We explore what is known and suspected concerning the evolutionary histories of BIA MTs and show that substantial advances in this domain are within reach. This new knowledge is expected to greatly enhance our conceptual understanding of the evolutionary origins of specialized metabolism.

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Section: Future Directionsmentioning

confidence: 99%

Molecular Origins of Functional Diversity in Benzylisoquinoline Alkaloid Methyltransferases

Morris

Facchini

2019

Front. Plant Sci.

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“…Corygaline A ( 28 ) is capable of inhibiting the NO production in LPS-activated RAW264.7 macrophages with an IC 50 value of 2.9 μM. Moreover, it is independent of dose [ 64 ].…”

Section: Antitumor Activities Of Benzophenanthridine Alkaloids From N...mentioning

confidence: 99%

Insights on Antitumor Activity and Mechanism of Natural Benzophenanthridine Alkaloids

Peng,

Xu,

Xie

et al. 2023

Molecules

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Benzophenanthridine alkaloids are a class of isoquinoline compounds, which are widely found in the plants of papaveraceae, corydalis, and rutaceae. Biological activities and clinical studies have shown that benzophenanthridine alkaloids have inhibitory effects on many cancers. Considering that the anticancer activities and mechanisms of many natural benzophenanthridine alkaloids have been discovered in succession, the purpose of this paper is to review the anticancer effects of benzophenanthridine alkaloids and explore the application potential of these natural products in the development of antitumor drugs. A literature survey was carried out using Scopus, Pubmed, Reaxys, and Google Scholar databases. This review summarizes and analyzes the current status of research on the antitumor activity and antitumor mechanism of natural products of benzophenanthridine from different sources. The research progress of the antitumor activity of natural products of benzophenanthridine from 1983 to 2023 was reviewed. The antitumor activities of 90 natural products of benzophenanthridine and their related analogues were summarized, and the results directly or indirectly showed that natural products of benzophenanthridine had the effects of antidrug-resistant tumor cell lines, antitumor stem cells, and inducing ferroptosis. In conclusion, benzophenanthridine alkaloids have inhibitory effects on a variety of cancers and have the potential to counteract tumor resistance, and they have great application potential in the development of antitumor drugs.

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An integrated investigation of 16S rRNA gene sequencing and proteomics to elucidate the mechanism of Corydalis bungeana Turcz. on dextran sulfate sodium-induced colitis

Gao,

Ni,

et al. 2023

Biomedicine & Pharmacotherapy

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Corygaline A, a hexahydrobenzophenanthridine alkaloid with an unusual carbon skeleton from Corydalis bungeana Turcz.

Abstract: A novel hexahydrobenzophenanthridine alkaloid, corygaline A (1), was isolated from Corydalis bungeana Turcz.

Cited by 7 publications

References 19 publications

Molecular Origins of Functional Diversity in Benzylisoquinoline Alkaloid Methyltransferases

Molecular Origins of Functional Diversity in Benzylisoquinoline Alkaloid Methyltransferases

Insights on Antitumor Activity and Mechanism of Natural Benzophenanthridine Alkaloids

An integrated investigation of 16S rRNA gene sequencing and proteomics to elucidate the mechanism of Corydalis bungeana Turcz. on dextran sulfate sodium-induced colitis

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