Biologically active indolizidine alkaloids

Zhang, Junmin; Morris‐Natschke, Susan L.; Ma, Di; Shang, Xiaofei; Yang, Chen-Jie; Liu, Ying‐Qian; Lee, Kuo‐Hsiung

doi:10.1002/med.21747

Cited by 59 publications

(38 citation statements)

References 200 publications

(211 reference statements)

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“…[4g] Both pyrrolidine and indolizidine motifs are widely presented in anumber of natural alkaloids. [21] Scheme 3. Scope of the reactions leading to (E)-cinnamylpyrrolines.…”

Section: Synthetic Applicationmentioning

confidence: 99%

Diastereoselective and Stereodivergent Synthesis of 2‐Cinnamylpyrrolines Enabled by Photoredox‐Catalyzed Iminoalkenylation of Alkenes

et al. 2021

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A photoredox‐catalyzed iminoalkenylation of γ‐alkenyl O‐acyl oximes has been developed. Readily available alkenylboronic acids serve as alkenylation reagents, leading to densely functionalized pyrrolines. Both (E)‐ and (Z)‐cinnamylpyrrolines are accessible depending on the reaction solvent. In dichloromethane, (E)‐cinnamylpyrrolines are produced through a photoredox‐mediated single‐electron‐transfer process. In tetrahydrofuran, (Z)‐cinnamylpyrrolines are generated by photocatalytic contra‐thermodynamic E‐to‐Z isomerization of (E)‐cinnamylpyrrolines though an energy‐transfer pathway. Two stereocenters are established with complete diastereoselectivity and only one diastereomer is isolated.

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“…[4g] Both pyrrolidine and indolizidine motifs are widely presented in anumber of natural alkaloids. [21] Scheme 3. Scope of the reactions leading to (E)-cinnamylpyrrolines.…”

Section: Synthetic Applicationmentioning

confidence: 99%

Diastereoselective and Stereodivergent Synthesis of 2‐Cinnamylpyrrolines Enabled by Photoredox‐Catalyzed Iminoalkenylation of Alkenes

et al. 2021

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“…Alkaloids form a large class of heterocyclic nitrogen organic compounds, with over 10,000 isolated to date. Given their antitumor, antibacterial, and anti-inflammatory activities, alkaloids have been widely used for the production of medications (Jain et al, 2019;Zhang et al, 2021). Depending on their biosynthetic pathways and chemical structures, alkaloids are classified into five groups: terpene indole, benzylisoquinoline, tropine, purine, and pyrrolizidine alkaloids (Bhambhani et al, 2021).…”

Section: Main Secondary Metabolites In Medicinal Plantsmentioning

confidence: 99%

Effects of Light on Secondary Metabolite Biosynthesis in Medicinal Plants

Zhang

Zou

et al. 2021

Front. Plant Sci.

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Secondary metabolites (SMs) found in medicinal plants are one of main sources of drugs, cosmetics, and health products. With the increase in demand for these bioactive compounds, improving the content and yield of SMs in medicinal plants has become increasingly important. The content and distribution of SMs in medicinal plants are closely related to environmental factors, especially light. In recent years, artificial light sources have been used in controlled environments for the production and conservation of medicinal germplasm. Therefore, it is essential to elucidate how light affects the accumulation of SMs in different plant species. Here, we systematically summarize recent advances in our understanding of the regulatory roles of light quality, light intensity, and photoperiod in the biosynthesis of three main types of SMs (polyphenols, alkaloids, and terpenoids), and the underlying mechanisms. This article provides a detailed overview of the role of light signaling pathways in SM biosynthesis, which will further promote the application of artificial light sources in medicinal plant production.

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“…They are produced by various organisms, including bacteria, fungi, plants, and animals, and show versatile bioactivities such as antibacterial, antifungal, and phytotoxic activities (Figure 1). [1] Many approaches for synthesizing indolizidine alkaloids have been developed from the perspective of their interesting structural features and attractive bioactivities [2] . However, biosynthetic pathways have been studied for only a few indolizidine alkaloids, mostly from fungi.…”

Section: Introductionmentioning

confidence: 99%

Identification and Analysis of the Biosynthetic Gene Cluster for the Indolizidine Alkaloid Iminimycin in Streptomyces griseus

et al. 2021

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Indolizidine alkaloids, which have versatile bioactivities, are produced by various organisms. Although the biosynthesis of some indolizidine alkaloids has been studied, the enzymatic machinery for their biosynthesis in Streptomyces remains elusive. Here, we report the identification and analysis of the biosynthetic gene cluster for iminimycin, an indolizidine alkaloid with a 6‐5‐3 tricyclic system containing an iminium cation from Streptomyces griseus. The gene cluster has 22 genes, including four genes encoding polyketide synthases (PKSs), which consist of eight modules in total. In vitro analysis of the first module revealed that its acyltransferase domain selects malonyl‐CoA, although predicted to select methylmalonyl‐CoA. Inactivation of seven tailoring enzyme‐encoding genes and structural elucidation of four compounds accumulated in mutants provided important insights into iminimycin biosynthesis, although some of these compounds appeared to be shunt products. This study expands our knowledge of the biosynthetic machinery of indolizidine alkaloids and the enzymatic chemistry of PKS.

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Biologically active indolizidine alkaloids

Cited by 59 publications

References 200 publications

Diastereoselective and Stereodivergent Synthesis of 2‐Cinnamylpyrrolines Enabled by Photoredox‐Catalyzed Iminoalkenylation of Alkenes

Diastereoselective and Stereodivergent Synthesis of 2‐Cinnamylpyrrolines Enabled by Photoredox‐Catalyzed Iminoalkenylation of Alkenes

Effects of Light on Secondary Metabolite Biosynthesis in Medicinal Plants

Identification and Analysis of the Biosynthetic Gene Cluster for the Indolizidine Alkaloid Iminimycin in Streptomyces griseus

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