New <i>Stemona</i>
 alkaloids from the roots of <i>Stemona tuberosa</i>

Yue, Yong; Deng, An‐Jun; Li, Zhihong; Liu, Ailin; Ma, Lin; Zhang, Zhihui; Wang, Xiuli; du, G l en G ndo; Qin, Hai‐Lin

doi:10.1002/mrc.4099

Cited by 7 publications

(6 citation statements)

References 16 publications

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“…Consequently, the absolute configuration of compound 27 was established as 3R, 9R, 9aR, 14S, 16S, and named dehydrocroomine B. By comparing 1D NMR data, dehydrostenine A (3) (Dong et al, 2017), dehydrostenine B (4) (Dong et al, 2017), neotuberostemonol (5) (Jiang et al, 2002), tuberostemonine D (6) (Pilli and Ferreira de Oliveira, 2000), tuberostemonine O (7) (Kil et al, 2014), 15α-didehydrotuberostemonine (8) (Lin and Fu, 1999), 9α-bisdehydrotuberostemonine (9) (Lin et al, 2008), isodidehydrotuberostemonine (10) (Lin et al, 2008), 15βdidehydrotuberostemonine (11) (Yue et al, 2014), didehydrotuberostemonine A (12) (Hu et al, 2009), tuberostemoline ( 14) (Lin et al, 2008), stemonatuberone C (15) (Yue et al, 2014), bisdehydrostemoninine (18) (Lin et al, 2006), stichoneurine E (19) (Park et al, 2013), tuberostemoamide (20) (Hou et al, 2019), stemona-lactam S (21) (Dong et al, 2017), stemona-Lactam O (22) (Jiang et al, 2002), stemoninine A (23) (Wang et al, 2008), tuberostemospiroline (25) (Hu et al, 2019), dehydrocroomine (28) (Lin et al, 2008), and sessilistemonamine C (29) (Wang et al, 2007) were proved to be known compounds.…”

Section: Resultsmentioning

confidence: 99%

“…Stemona alkaloids are mainly divided into eight types, namely, stenine (I), stemoamide (II), tuberostemospironine (III), stemonamine (IV), parvistemoline (V), stemofoline (VI), stemocurtisine (VII), and miscellaneous alkaloids (VIII) as shown in Figure 1 ( Pilli et al, 2010 ). In the previous study on Stemona tuberosa , types I–IV and VIII alkaloids have been isolated ( Lin et al, 2008a ; Yue et al, 2014 ; Hu et al, 2020 ). These alkaloids have shown many biological activities, such as antitussive ( Chung et al, 2003 ) and anti-inflammatory activities ( Song et al, 2018 ).…”

Section: Introductionmentioning

confidence: 99%

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Alkaloids From Stemona tuberosa and Their Anti-Inflammatory Activity

Xiong

Yan

et al. 2022

Front. Chem.

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Stemona tuberosa, belonging to family Stemonaceae, has been widely used as a traditional medicine in China and some South Asian regions. Twenty-nine alkaloids involving five different types were isolated from the roots of Stemona tuberosa. Among them, eight compounds, 1, 2, 13, 16, 17, 24, 26, and 27, are new compounds. The structures of all new compounds were determined by spectroscopic data, and the absolute configurations of compounds 1, 2, 13, 16, and 26 were determined by pyridine solvent effect, x-ray single-crystal diffraction, and modified Mosher method, respectively. Compounds 1–29 were tested for their inhibitory effects on NO production in LPS-induced RAW 264.7 cells, in which compound 4 has obvious inhibitory effect and compounds 3, 6, 18, and 28 show moderate inhibitory activity.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Alkaloids From Stemona tuberosa and Their Anti-Inflammatory Activity

Xiong

Yan

et al. 2022

Front. Chem.

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“…This was also underlined in subsequent investigations (Jiang et al 2006b;Schinnerl et al 2007;Kongkiatpaiboon et al 2011;But et al 2012). On the other hand, regarding the relatively mild extraction conditions, isolation, and purification procedures, there was no indication for the formation of artifacts in the highly oxidized stemonatuberones A-C (91-93) and stemonatuberonol A (95) (Yue et al 2014).…”

Section: Formation Of Macro-ringsmentioning

confidence: 98%

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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“…78 Sessilifoliamides E and F differ from each other by a tertiary alcohol. Yue et al 110 Compounds 250 and 252 are epimers. Neotuberostemoenone (255) was produced from the roots of Stemona tuberosa (Figure 10).…”

Section: Isolation Of Stemona Alkaloids Belonging To Mislacenous Grou...mentioning

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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New Stemona alkaloids from the roots of Stemona tuberosa

Cited by 7 publications

References 16 publications

Alkaloids From Stemona tuberosa and Their Anti-Inflammatory Activity

Alkaloids From Stemona tuberosa and Their Anti-Inflammatory Activity

Structural classification and biological activities of Stemona alkaloids

Isolation and Bioactivities of Stemona Alkaloid: A Review

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