New alkaloids of the sarpagine group from Rauvolfia serpentina hairy root culture.
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.
Sheludko
Yuri
Y
Department of Pharmaceutical Biology, Institute of Pharmacy, Johannes Gutenberg-University, Staudinger Weg 5, D-55099 Mainz, Germany.
Gerasimenko
Irina
I
Kolshorn
Heinz
H
Stöckigt
Joachim
J
D002855:Chromatography, Thin Layer; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011926:Rauwolfia / Q000737:chemistry*; D012231:Rhizobium / Q000378:metabolism; D046948:Secologanin Tryptamine Alkaloids / Q000737:chemistry* / Q000302:isolation & purification*; D013237:Stereoisomerism
C465586:10-hydroxy-19(S),20(R)-dihydroperaksine; C465585:19(S),20(R)-dihydroperaksine; C465584:19(S),20(R)-dihydroperaksine-17-al; D026121:Indole Alkaloids; D046948:Secologanin Tryptamine Alkaloids