Isolation of tuberospironine A, a novel croomine derivative from Stemona tuberosa Lour.

Pudjiastuti, Pratiwi; Pyne, Stephen G.; Sugiyanto, .; Lie, Wilford

doi:10.1016/j.phytol.2012.03.001

Cited by 10 publications

(2 citation statements)

References 11 publications

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“…The crude alkaloid was separated using column chromatography under silica gel as stationary phase and DCM-methanol as mobile phase with polarity gradient elution. The alkaloids were purified using preparative chromatography to give tuberostemonine, croomine, and epi -croomine ( epi -10-hydroxycroomine or 3- epi -tuberospironine A) [ 19 ].…”

Section: Methodsmentioning

confidence: 99%

Inhibitory Activity and Docking Analysis of Antimalarial Agents from Stemona sp. toward Ferredoxin-NADP+ Reductase from Malaria Parasites

Pudjiastuti

Puspaningsih

Siswanto

et al. 2018

Journal of Parasitology Research

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Ferredoxin-NADP+ reductases (FNRs, EC 1.18.1.2) were found in the plastids of Plasmodium and have been considered as a target for the development of new antimalarial agents. Croomine, epi-croomine, tuberostemonine, javastemonine A, and isoprotostemonine are isolated alkaloids from the roots of Stemona sp. and their inhibitory effect on FNRs from Plasmodium falciparum (PfFNR) was investigated. Croomine showed the highest level of inhibition (33.9%) of electron transfer from PfFNR to PfFd, while tuberstemonine displayed the highest level of inhibition (55.4%) of diaphorase activity of PfFNR. Docking analysis represented that croomine is located at the middle position of PfFNR and PfFd. Croomine from S. tuberosa appeared to have potential as an antimalarial agent.

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Section: Methodsmentioning

confidence: 99%

Inhibitory Activity and Docking Analysis of Antimalarial Agents from Stemona sp. toward Ferredoxin-NADP+ Reductase from Malaria Parasites

Pudjiastuti

Puspaningsih

Siswanto

et al. 2018

Journal of Parasitology Research

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“…collected from Seram Island, Moluccas Province, Indonesia (Figure 5). 72 Stemona-lactams R ( 137 ) with a hydroxy group at C10 was obtained from the roots of Stemona tuberosa (Figure 5). 26 Yuea et al 27 found 9 a - epi -tuberospironine ( 138 ) from the roots of Stemona tuberosa (Figure 5).…”

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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Structural classification and biological activities of Stemona alkaloids

Greger

2019

Phytochem Rev

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Stemona alkaloids represent a unique class of natural products exclusively known from the three genera Stemona, Stichoneuron, and Croomia of the monocotyledonous family Stemonaceae. Structurally they are characterized by a central pyrroloazepine core usually linked with two butyrolactone rings. The great diversity, comprising 215 derivatives, is created by the formation of additional CC linkages and oxygen bridges together with ring cleavages and eliminations of the lactone rings. Based on biosynthetic considerations they can be grouped into three structural types represented by the croomine, stichoneurine, and protostemonine skeleton. Due to the formation of characteristic terminal lactone rings and the central pyrrolidine ring pandanamine and pandamarilactonine, isolated from Stichoneuron calcicola, were suggested to represent biogenetic precursors. The taxonomically complex S. tuberosa group can be clearly segregated by the formation of stichoneurines, while the other Stemona species are characterized by protostemonine derivatives. Croomine derivatives are more widespread found in both groups and in the genus Croomia. Of chemotaxonomic significance are the different transformations of protostemonine into stemofolines with a cage-type structure or into pyridoazepines characterized by a six-membered piperidine ring. Stimulated by the great interest in the antitussive activity of Stemona alkaloids, differences in transport mechanisms and potencies via different administrative routes were investigated. Follow-up studies on the significant insecticidal activities focused on the mode of action by using biochemical and electrophysiological approaches. Screening for acetylcholinesterase inhibitory properties revealed a much higher potency for stemofoline derivatives compared to pyridoazepines, but showed also significant activity for isomers of stenine with a stichoneurine skeleton. Evaluating synergistic growth inhibitory effects with cancer chemotherapeutic agents stemofoline exhibited the most potent effect in the reversal of permeability glycoprotein-mediated multidrug resistance. The anti-inflammatory activity of some derivatives was identified as an inhibition of the expression of inflammatory mediators. Comparing the diverse bioactivities of Stemona alkaloids stemofoline-type derivatives are the most versatile compounds representing promising lead structures for further development as commercial agents in agriculture and medicine.

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Isolation of tuberospironine A, a novel croomine derivative from Stemona tuberosa Lour.

Cited by 10 publications

References 11 publications

Inhibitory Activity and Docking Analysis of Antimalarial Agents from Stemona sp. toward Ferredoxin-NADP+ Reductase from Malaria Parasites

Inhibitory Activity and Docking Analysis of Antimalarial Agents from Stemona sp. toward Ferredoxin-NADP+ Reductase from Malaria Parasites

Isolation and Bioactivities of Stemona Alkaloid: A Review

Structural classification and biological activities of Stemona alkaloids

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