Vinmajorines C – E, Monoterpenoid Indole Alkaloids from Vinca major

Abstract

Three new monoterpenoid indole alkaloids, vinmajorines C–E (1–3), along with 18 known analogues (4–21), were isolated from the whole plants of Vinca major. The new structures were elucidated as (5α,15β,16R,17α,19β,20α,21β)‐10,17‐dimethoxy‐21‐methyl‐18‐oxa‐5,16‐cycloyohimban‐19‐ol (1), (5α,15β,16R,17α,20α,21β)‐10‐methoxy‐21‐methyl‐18‐oxa‐5,16‐cycloyohimban‐17‐ol (2), and (5α,15β,16R,17α,20α,21β)‐10‐methoxy‐21‐methyl‐18‐oxa‐5,16‐cycloyohimban‐17‐yl acetate (3), respectively, by extensive NMR and MS analysis and comparison with known compounds. Compounds 1–3 were evaluated for their cytotoxic activities against five human cancer cell lines, compounds 1 and 3 showing moderate cytotoxic activities.

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

“…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).…”

Monoterpene Indole Alkaloids with Cav3.1 T-Type Calcium Channel Inhibitory Activity from Catharanthus roseus

“…In recent years, some new and bioactive MIAs were still reported from this plant [11][12][13][14][15][16][17]. In our continuing search for structurally unique and pharmaceutically interesting MIAs from medicinal plants [18][19][20][21][22], a phytochemical study of the twigs and leaves of C. roseus was undertaken and led to the identification of two new MIAs, catharanosines A (1) and B (2), and six known analogues (Figure 1). Compound 2 was found to represent an unprecedented aspidosperma-type alkaloid with a piperidine moiety at C-10.…”