Gynostemosides A-E, megastigmane glycosides from Gynostemma pentaphyllum.
Megastigmane glycosides (1-5) together with seven (6-12) related known compounds were isolated from the whole plants of Gynostemma pentaphyllum. The structures were elucidated by means of spectroscopic methods, including 2D NMR, HR-ESIMS, and circular dichroism (CD), as well as chemical transformations to be (3R,4R,5S,6S,7E)-3,4,6-trihydroxymegastigmane-7-en-9-one-3-O-beta-D-glucopyranoside (gynostemoside A, 1), (3S,4S,5R,6R,7E,9R)-3,4,6,9-tetrahydroxymegastigmane-7-en-3-O-beta-D-glucopyranoside (gynostemoside B, 2), (3S,4S,5S,6S,7E,9R)-3,4,9-trihydroxymegastigmane-7-en-9-O-beta-D-glucopyranoside (gynostemoside C, 3), (3S,4S,5S,6S,7E,9R)-3,4,9-trihydroxymegastigmane-7-en-3-O-beta-D-glucopyranoside (gynostemoside D, 4), and (3S,4S,5S,6S,7E,9R)-3,4,9-trihydroxymegastigmane-7-en-4-O-beta-D-glucopyranoside (gynostemoside E, 5), respectively.
Zhang
Zhen
Z
Department of Natural Products for Chemical Genetic Research, Key Laboratory of Brain Functional Genomics, Ministry of Education, East China Normal University, Shanghai, PR China.
Zhang
Wei
W
Ji
Yan-Ping
YP
Zhao
Yun
Y
Wang
Chuan-Gui
CG
Hu
Jin-Feng
JF
D003512:Cyclohexanones / Q000737:chemistry / Q000302:isolation & purification; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification*; D029774:Gynostemma / Q000737:chemistry*; D015394:Molecular Structure; D045792:Norisoprenoids / Q000737:chemistry / Q000302:isolation & purification*; D010936:Plant Extracts / Q000737:chemistry*
C552328:(3R,4R,5S,6S,7E)-3,4,6-trihydroxymegastigmane-7-en-9-one-3-O-beta-D-glucopyranoside; C552329:(3S, 4S, 5R, 6R, 7E, 9R)-3,4,6,9-tetrahydroxymegastigmane-7-en-3-O-beta-D-glucopyranoside; C552330:(3S, 4S, 5S, 6S, 7E, 9R)-3,4,9-trihydroxymegastigmane-7-en-9-O-beta-D-glucopyranoside; D003512:Cyclohexanones; D005960:Glucosides; D006027:Glycosides; D045792:Norisoprenoids; D010936:Plant Extracts; C413264:megastigmane