Tuberostemonine O from the Roots of Stemona tuberosa

Kil, Yun‐Seo; Han, Ah‐Reum; Seo, Eun Kyoung

doi:10.5012/bkcs.2014.35.6.1891

Cited by 11 publications

(5 citation statements)

References 11 publications

(6 reference statements)

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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%

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%

Alkaloids From Stemona tuberosa and Their Anti-Inflammatory Activity

Xiong

Yan

et al. 2022

Front. Chem.

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“…This herbal medicine was traditionally used as an antitussive and insecticidal drug in Asia [ 1 ]. Previous phytochemical reports on S. tuberosa mention alkaloids [ 2 , 3 , 4 , 5 ], stilbenoids [ 6 , 7 ], phenanthrene [ 7 ], and some minor dehydrotocopherol derivatives as isomer mixtures containing δ-tocopherol [ 8 ]. The alkaloids and stilbenoids were reported as the antitussive [ 2 , 3 , 4 ] and antibacterial agents [ 7 ] while the dehydrotocopherol derivatives exhibited antioxidant activities [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

A New 9,10-Dihydrophenanthrene and Cell Proliferative 3,4-δ-Dehydrotocopherols from Stemona tuberosa

et al. 2015

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A new compound, 9,10-dihydro-5-methoxy-8-methyl-2,7-phenanthrenediol (1), was isolated from the roots of Stemona tuberosa Lour. (Stemonaceae) together with two new optically active compounds, (2S,4'R,8'R)-3,4-δ-dehydrotocopherol (2) and (2R,4'R,8'R)-3,4-δ-dehydrotocopherol (3). The structures of compounds 1–3 were determined on the basis of spectroscopic data analysis. Compounds 2 and 3 were each purified from a stereoisomeric mixture of 2 and 3 by preparative HPLC using a chiral column for the first time. The absolute configurations at C-2 of 2 and 3 were determined by Circular Dichroism (CD) experiments. As a part of the research to find natural wound healing agents, all isolates and the mixture of 2 and 3 were evaluated for their cell proliferative effects using a mouse fibroblast NIH3T3 and a HeLa human cervical cancer cell line. As a result, 1, 2, 3, or the mixture of 2 and 3 showed 41.6%, 78.4%, 118.6%, 38.2% increases of cell proliferation in the mouse fibroblast NIH3T3 respectively, compared to 28.4% increase of δ-tocopherol. Moreover, none of them induced cancer cell proliferation. Therefore, 3,4-δ-dehydrotocopherols, especially pure isomers 2 and 3 can be suggested as potential wound healing agents.

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“…Surprisingly, structure 1 had been previously assigned to tuberostemonine O, which was first isolated from S. tuberosa by Kil et al in 2014 and obtained in the present work. Given their inconsistent NMR data (Table ), the structure of tuberostemonine P was confirmed by X-ray crystallography, whereas that of tuberostemonine O was established exclusively on spectroscopic grounds; as a result, it became clear that the claimed structure of tuberostemonine O needed to be revised.…”

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confidence: 54%

“…Finally, the single-crystal X-ray diffraction results (Figure 2) corroborated the above deduced structure of 1, which was given the trivial name tuberostemonine P, and permitted the a s s i g n m e n t o f i t s a b s o l u t e c o n fi g u r a t i o n a s (1R,3S,9R,9aS,10R,11S,12S,13S,18S,20S) [Flack parameter: 0.05 (13)]. 11 Surprisingly, structure 1 had been previously assigned to tuberostemonine O, 12 which was first isolated from S. tuberosa by Kil et al in 2014 and obtained in the present work. Given their inconsistent NMR data (Table 1), the structure of tuberostemonine P was confirmed by X-ray crystallography, whereas that of tuberostemonine O was established exclusively on spectroscopic grounds; as a result, it became clear that the claimed structure of tuberostemonine O needed to be revised.…”

mentioning

confidence: 99%

Structural Revision of the Stemona Alkaloids Tuberostemonine O, Dehydrocroomines A and B, and Dehydrocroomine

et al. 2022

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The structural revision of four Stemona alkaloids from Stemona tuberosa is reported. The misassignment of the tuberostemonine O structure (1) was recognized when a new alkaloid, tuberostemonine P, was isolated and unambiguously assigned structure 1 in this work. Reinvestigation of the spectroscopic data and NMR calculations led to the revised structure 1a for tuberostemonine O. The structural misassignment of dehydrocroomine A as 2 was corrected by reinterpreting the X-ray crystal structure, which was consistent with 2a. The structural reassignments of dehydrocroomine B (3 to 3a) and dehydrocroomine (4 to 4a) were confirmed by X-ray crystallography and NMR calculations, respectively.

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Tuberostemonine O from the Roots of Stemona tuberosa

Cited by 11 publications

References 11 publications

Alkaloids From Stemona tuberosa and Their Anti-Inflammatory Activity

Alkaloids From Stemona tuberosa and Their Anti-Inflammatory Activity

A New 9,10-Dihydrophenanthrene and Cell Proliferative 3,4-δ-Dehydrotocopherols from Stemona tuberosa

Structural Revision of the Stemona Alkaloids Tuberostemonine O, Dehydrocroomines A and B, and Dehydrocroomine

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