6-Hydroxy-5,6-seco-stemocurtisine: A novel seco-stemocurtisine-type alkaloid

Mungkornasawakul, Pitchaya; Pyne, Stephen G.; Willis, Anthony C.; Jatisatienr, Arayar; Phuthsuk, Duang; Lie, Wilford

doi:10.1016/j.phytol.2013.07.016

Cited by 8 publications

(5 citation statements)

References 13 publications

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“…Thus indicating hydroxylation is specifically directed at C-6 by substrate orientation in the enzyme active site. Interestingly, in plants the pyrido[1,2a]azepine alkaloid stemocurtisine (4) gives rise to other natural products most likely via hydroxylation and ring opening reactions of the azepine ring at C-6 [21,22]. However, it was found to be inert to biotransformation by C. elegans.…”

Section: Discussionmentioning

confidence: 99%

Oxidative biotransformation of stemofoline alkaloids

Phaya

Chalom

Ingkaninan

et al. 2021

Artificial Cells, Nanomedicine, and Biotechnology

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Biotransformations of stemofoline (1a), (2 0 S)-hydroxystemofoline (2a), (11Z)-1 0 ,2 0-didehydrostemofoline (3a) and stemocurtisine (4) were studied through fermentation with Cunninghamella elegans TISTR 3370. Three new stemofoline derivatives; 6 R-hydroxystemofoline (1b), (2 0 S, 6 R)-dihydroxystemofoline (2b) and (11Z,6R)-1 0 ,2 0-didehydro-6-hydroxystemofoline (3b), together with the known compound 1 0 ,2 0didehydrostemofoline-N-oxide (3c), were produced by C-hydroxylation and N-oxidation reactions. Stemocurtisine was not biotransformed under these conditions. The transformed product 1b was four times more potent (IC 50 ¼ 11.01 ± 1.49 mM) than its precursor 1a (IC 50 ¼ 45.1 ± 5.46 mM) as an inhibitor against acetylcholinesterase.

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Section: Discussionmentioning

confidence: 99%

Oxidative biotransformation of stemofoline alkaloids

Phaya

Chalom

Ingkaninan

et al. 2021

Artificial Cells, Nanomedicine, and Biotechnology

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“…A new Stemona alkaloid, 6-hydroxy-5,6-seco-stemocurtisine ( 246 ) was produced from the aerial parts of Stemona curtisii collected from Trang Province in Thailand and its configuration was determined by single-crystal X-ray crystallographic analysis (Figure 10). 108 Fukaya et al 109 obtained stemona-lactam S ( 247 ) from the roots of Stemona tuberosa and its absolute stereochemistry was elucidated by analysis of X-ray crystallography and vibrational circular dichroism (Figure 10). Stichoneurines F ( 248 ) and G ( 249 ) were achieved from the root extracts of Stichoneuron caudatum (Figure 10).…”

Section: Phytochemistrymentioning

confidence: 99%

Isolation and Bioactivities of Stemona Alkaloid: A Review

Nguyen-Thi,

Vo-Cong,

Giang

et al. 2024

Natural Product Communications

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Objective/Background: In Chinese, Vietnamese, and Thai traditional medicine of Southeast Asian countries, Stemonaceae plants have long been employed. Various studies have proved that these herbal plants contain Stemona alkaloids with valuable medicinal value. Although some review articles on Stemona alkaloids have appeared in the literature, they are quite outdated. The current study offers a comprehensive review of the isolation and bioactivities of Stemona alkaloids. The article might be useful for chemists who work in alkaloid chemistry as well as pharmaceutical areas. Methods: “ Stemona alkaloids” was the most useful keyword to search for literature data. References have been collected from various resources such as Google Scholar, SciFinder, and PubMed. More than 120 electronic publications were obtained from these resources. Results: More than 250 Stemona alkaloids from 8 groups have been isolated and structurally elucidated from Stemonaceae plants. Extracts from these plants as well as isolated compounds possess a wide range of bioactivities, such as antituberculosis, antibacterial, antifungal, and antihelmintic properties activities. Conclusion: In this review article, we have summarized 116 studies on the isolation and bioactivities of Stemona alkaloids in the literature. More than 250 Stemona alkaloid compounds have been isolated and identified. In addition, the article also gives an overview of the bioactivities of Stemona alkaloids.

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“…When the reaction was performed at 50 C, the chemical yield was substantially improved, with virtually maintained stereoselectivities (entry 11). Different solvents were also screened (entries [12][13][14][15][16][17], and toluene remained to the solvent of choice.…”

Section: Construction Of Bicyclic Furofuransmentioning

confidence: 99%

“…Some representative examples are illustrated in Fig. 1 , including asteltoxin, 12 marasmene, 13 6-hydroxy-5,6-seco-stemocurtisine, 14 GRL-0519, 15 tiliifolin A/B, 16 and darunavir. 17 The biological activities of these compounds are often dependent on the substitution pattern of the chiral acetal moiety, thus the asymmetric synthesis of these molecules is highly desirable.…”

Section: Introductionmentioning

confidence: 99%