A New Ajmaline-type Alkaloid from the Roots of Rauvolfia serpentina

Abstract

A new ajmaline-type alkaloid, 21-O-methylisoajmaline (1), together with twenty-one known compounds, a mixture of -sitosterol (2) and stigmasterol (3), reserpinine (4), tetrahydroalstonine (5), reserpine (6), venoterpine (7), yohimbine (8), 6'-O-(3,4,5-trimethoxybenzoyl)glomeratose A (9), isoajmaline (10), 3-epi--yohimbine (11), methyl 3,4,5-trimethoxy-trans-cinnamate (12), a mixture of -sitosterol 3-O--D-glucopyranoside (13) and stigmasterol 3-O--Dglucopyranoside (14), rescidine (15), 7-deoxyloganic acid (16), ajmaline (17), suaveoline (18), (+)-tetraphyllicine (19), loganic acid (20), 3-hydroxysarpagine (21), and sarpagine (22), were isolated from the roots of Rauvolfia serpentina. Their structures were elucidated by spectroscopic data analysis and comparison with literature data. Compounds 11, 12 and 15 were for the first time identified from the genus Rauvolfia and 5, 7, 11, 12, 15, 18 and 22 were found from R. serpentina for the first time. Compound 11 showed moderate anticholinesterase activity with IC 50 value of 15.58 M, whereas 6 exhibited strong vasorelaxant activity with the EC 50 value of 0.05 M.

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).…”

The Hypotensive Activity of Diferent Fractions of the Extracts From Tissue Culture Biomass of Rauwolfia Serpentina Benth

“…148,1±1,1* *Р < 0,05 порівняно з початковим значенням; **Р < 0,05 порівняно з дозою 0,0028 мг/кг; ***Р < 0,05 порівняно з дозою 0,028 мг/кг; ♯ порівняно з дозою 0,28 мг/кг. систему, мають м'яку гіпотензивну, адренолітичну, седативну дію, що зумовлено переважно специфічними властивостями суми індольних алкалоїдів та їх похідних, наявних у рослинній біомасі [11,12]. Зокрема, аймаліцин має симпатолітичну активність, блокує α-рецептори, посилює мозковий кровообіг, входить до складу гіпотензивних препаратів [3].…”

An Update on Cyclohepta[b]indoles

“…In 2017, the acetylcholinesterase inhibiting oktahydrocyclohepta[b]indole alkaloid 8 was isolated by Rukachaisirikula et al from Rauwolfia serpentina (Figure 3). [15] 21-O-Methylisoajmaline ( 8) is derived from the vincamaginine core carbon structure.…”

“…from Rauwolfia serpentina (Figure 3). [15] 21‐ O ‐Methylisoajmaline ( 8 ) is derived from the vincamaginine core carbon structure.…”