New stemona alkaloids from the roots of Stemona sessilifolia.
From the roots of Stemona sessilifolia, three new stemona-type alkaloids, namely stemosessifoine (1), isooxymaistemonine (2), and isomaistemonine (3), along with eight known alkaloids (bisdehydrostemoninine, isobisdehydrostemoninine, tuberostemonine, bisdehydrotuberostemonine, bisdehydrostemoninine, isobisdehydrostemoninine, stemoninine, and protostemonine), were isolated. Their structures were determined on the basis of extensive 2D-NMR spectroscopic-data analysis and by comparison with reported values in the literature. Compound 1 is a structurally unprecedented alkaloid, and it is depicted to be bioconverted from tuberostemonine as the precursor. Isooxymaistemonine (2) showed a positive effect on the human high-density lipoprotein (HDL) receptor gene CD36 and LIMP II analogous-1 (CLA-1) at the dosage of 10 microg/ml.
Guo
Aobo
A
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100083, P.R. China
Jin
Li
L
Deng
Zhiwei
Z
Cai
Shaoqing
S
Guo
Shunxin
S
Lin
Wenhan
W
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D045744:Cell Line, Tumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification; D006801:Humans; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification*; D008075:Lipoproteins, HDL / Q000187:drug effects; D051907:Lysosomal Membrane Proteins / Q000187:drug effects; D019906:Nuclear Magnetic Resonance, Biomolecular; D018517:Plant Roots / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry / Q000302:isolation & purification*; D018110:Receptors, Lipoprotein / Q000187:drug effects; D051116:Receptors, Scavenger / Q000187:drug effects; D051122:Scavenger Receptors, Class B / Q000096:biosynthesis; D041901:Stemonaceae / Q000737:chemistry*; D015854:Up-Regulation
D000470:Alkaloids; D004365:Drugs, Chinese Herbal; D007783:Lactones; D008075:Lipoproteins, HDL; D051907:Lysosomal Membrane Proteins; D011759:Pyrrolidines; D018110:Receptors, Lipoprotein; D051116:Receptors, Scavenger; C495124:SCARB1 protein, human; C074299:SCARB2 protein, human; D051122:Scavenger Receptors, Class B; C031616:high density lipoprotein receptors; C483261:stemonine