NOVEL ALKALOID FROM<i>Rauvolfia capixabae</i>(APOCYNACEAE)

Carlos, Lanamar de Almeida; Mathias, Lêda; Braz-Filho, Raimundo; Vieira, Ivo José Curcino

doi:10.5935/0100-4042.20160002

Cited by 3 publications

(2 citation statements)

References 2 publications

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“…Rauvolfia vomitoria (Apocynaceae) is widely distributed in the tropical regions of Africa and Asia, and has been used in traditional folk medicine to treat a variety of ailments including fever, general weakness, gastrointestinal diseases, liver diseases, psychosis, pain, and cancers . We performed a phytochemical investigation on the aerial parts of Rauvolfia vomitoria to afford two new monoterpenoid indole alkaloids rauvomine A ( 1 ) and rauvomine B ( 2 ).…”

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confidence: 99%

Rauvomines A and B, Two Monoterpenoid Indole Alkaloids from Rauvolfia vomitoria

et al. 2017

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Two unusual normonoterpenoid indole alkaloids rauvomine A (1) and rauvomine B (2), together with two known compounds peraksine (3) and alstoyunine A (4), were isolated from the aerial parts of Rauvolfia vomitoria. The structures with absolute configurations of 1 and 2 were elucidated by spectroscopic analysis, single-crystal X-ray diffraction, and electronic circular dichroism (ECD) calculations. Compound 2 is a novel C normonoterpenoid indole alkaloid with a substituted cyclopropane ring that forms an unusual 6/5/6/6/3/5 hexcyclic rearranged ring system. The plausible biogenetic pathways of 1 and 2 were proposed. Compound 2 exhibited significant anti-inflammatory activity.

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confidence: 99%

Rauvomines A and B, Two Monoterpenoid Indole Alkaloids from Rauvolfia vomitoria

et al. 2017

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“…The structures of the five compounds (3-7) from fraction 7, and 14 compounds (8-21) from other fractions were determined by comparing their MS, UV, and NMR data with those reported in the literature. The known compounds were β-carboline (3) (Bratchkova et al, 2012), 1-methyl-β-carboline 4) (Bratchkova et al, 2012), sarpagine (5) (Rukachaisirikul et al, 2017), lochnerine (6) (Kam et al, 1999), vellosiminol (7) (Mbeunkui et al, 2012), tetrahydroalstonine (8) (Achenbach et al, 1997), isoreserpiline (9) (Gupta et al, 2012), 10-methoxytetrahydroalstonine (10) (Gupta et al, 2012), carapanaubine (11) (Khatoon et al, 2022), isocarapanaubine (12) (Ahmad et al, 2010), N a -methylrauflorine (13) (Carlos et al, 2016), venoterpine (14) (Rukachaisirikul et al, 2017), mitoridine (15) (Kumara et al, 2019), yohimbine (16) (Zhan et al, 2020b), ajmaline (17) (Lim et al, 2014), vinmajorine D (18) (Zhang et al, 2016), 17-epivinmajorine D (19) (Zhang et al, 2016), peraksine (20) (Gao et al, 2015), and 17-epi-peraksine (21) (Arthur et al, 1968).…”

Section: Isolation and Structural Elucidation Of The Active Compounds...mentioning

confidence: 99%

Identification of chemosensitizing agents of colorectal cancer in Rauvolfia vomitoria using an NMR-based chemometric approach

et al. 2023

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Searching for new adjuvants of conventional chemotherapeutic approaches against colorectal cancer cells is extremely urgent. In current research, a non-targeted analytical approach was established by combining proton nuclear magnetic resonance spectroscopy with a chemometrics data mining tool to identify chemosensitizing agents from Rauvolfia vomitoria. This approach enabled the identification of potential active constituents in the initial fractionation process and provided their structural information. This strategy was validated by its application to Rauvolfia vomitoria extract exhibiting chemosensitizing activity on 5-fluorouracil against colorectal cancer cells. After the workflow, the biochemometrics analysis showed that at least 15 signals (Variable influence on projection (VIP) > 1) could have contributions in the differentiation of various fractions. Through systematic literature and database searches, we found that the most active fraction (fraction 7) exhibited the highest presence of sabazin-type and armaniline-type alkaloids, which were potential chemosensitizers as previously reported. To validate the results of the strategy, the effect of 5-FU and compounds isolated from fraction seven incubation on HCT-8 and LoVo cell vialibilty were evaluated. These results evidenced that compound β-carboline (3), 1-methyl-β-carboline (4), and lochnerine (6) could enhance the cytotoxicity of 5-fluorouracil against to Colorectal cancer cells. Besides, 21 compounds including two new compounds were isolated from Rauvolfia vomitoria. The experimental results verify the reliability of the method, and this approach provides a new and efficient tool to overcome some of the bottlenecks in natural products drug discovery.

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The C-19 methyl substituted sarpagine-macroline-ajmaline alkaloids: Diversity, occurrence, bioactivity, and synthesis

Rahman

Cook

2020

Bioactive Natural Products

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NOVEL ALKALOID FROMRauvolfia capixabae(APOCYNACEAE)

Cited by 3 publications

References 2 publications

Rauvomines A and B, Two Monoterpenoid Indole Alkaloids from Rauvolfia vomitoria

Rauvomines A and B, Two Monoterpenoid Indole Alkaloids from Rauvolfia vomitoria

Identification of chemosensitizing agents of colorectal cancer in Rauvolfia vomitoria using an NMR-based chemometric approach

The C-19 methyl substituted sarpagine-macroline-ajmaline alkaloids: Diversity, occurrence, bioactivity, and synthesis

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