New Alkaloids of the Sarpagine Group from Rauvolfia serpentina Hairy Root Culture

Abstract

Three new monoterpenoid indole alkaloids, 19(S),20(R)-dihydroperaksine (1), 19(S),20(R)-dihydroperaksine-17-al (2), and 10-hydroxy-19(S),20(R)-dihydroperaksine (3), along with 16 known alkaloids 4-19 were isolated from hairy root culture of Rauvolfia serpentina, and their structures were elucidated by 1D and 2D NMR analyses. Taking into account the stereochemistry of the new alkaloids and results of preliminary enzymatical studies, the putative biosynthetical relationships between the novel alkaloids are discussed.

Three new indole alkaloids from Rauvolfia yunnanensis

“…The UV spectrum showed absorptions at λ max 228, 282, and 303 nm typical of a substituted indole chromophore. 9 The IR spectrum showed absorptions at 3432 and 1628 cm -1 , attributed to hydroxy and olefin groups, respectively. The 1 H NMR spectrum (Table 1) 7), and three methyl groups (δ C 41.5, 29.3, and 13.1).…”

Rauvotetraphyllines A-E, new indole alkaloids from Rauvolfia tetraphylla

“…The isolation and structure elucidation of three indole alkaloids rauvoyunines A, B, and C from the aerial parts of Rauvolfia yunnanensis have been reported earlier. 5 As one part of our ongoing research program exploring bioactive indole alkaloids from Chinese species of Rauvolfia, phytochemical analysis has been carried out on the aerial parts of R. tetraphylla collected from Yunnan Province, with particular attention to the monoterpene indole constituents, and has resulted in the isolation of five new alkaloids, rauvotetraphyllines A-E (1)(2)(3)(4)(5), as well as eight known analogues, alstonine (6), 6 nortetraphyllicine, 7 peraksine, 8 sarpagine, 9 3-hydroxysarpagine, 10 dihydroperaksine, 11 10-hydroxydihydroperaksine, 11 and raucaffricine. 12 The present paper reports the isolation, structure elucidation, and cytotoxic evaluation of the new compounds.…”

Purification, cloning, functional expression and characterization of perakine reductase: the first example from the AKR enzyme family, extending the alkaloidal network of the plant Rauvolfia

“…Sequence analysis groups PR as a novel member of the aldo-keto reductase (AKR) enzyme family. Extensive investigation of the substrate specificity of PR not only points to multi-functionality of the enzyme, which has not been observed for any other Rauvolfia enzyme known to date, but also links and significantly extends the large Rauvolfia alkaloid metabolome to the recently detected novel group of peraksine alkaloids (Sheludko et al 2002).…”