Dammarane glycosides from the root of Machilus yaoshansis.
Nine new dammarane triterpene glycosides (1-3 and 8-13) and 12 known analogues have been isolated from an ethanol extract of the roots of Machilus yaoshansis. Compounds 1-7 have an uncommon 20,23-dihydroxydammar-24-en-21-oic acid-21,23-lactone moiety that was previously reported in compounds isolated from Gynostemma pentaphyllum. The configurations of the lactone moieties in 1-3 were determined by comparison of the experimental ECD spectra of 1-3 and the hydrolysates, 1a and 1b, with the corresponding calculated ECD spectra. On the basis of NMR and ECD data analysis of 1-7, the previously reported C-20 and C-23 configurations of 4-7 and related derivatives from Gynostemma pentaphyllum were revised. In addition, the application of NMR data and Cotton effects to the determination of the relative and absolute configurations of the γ-lactone moiety in 3β,20,23-trihydroxydammar-24-en-21-oic acid-21,23-lactone derivatives is discussed.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica,  Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050, People's Republic of China.
Maoluo
M
Gan
Mingtao
M
Liu
Lishe
L
Gan
Sheng
S
Lin
Bo
B
Liu
Yanling
Y
Zhang
Jiachen
J
Zi
Weixia
W
Song
Jiangong
J
Shi
D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D029774:Gynostemma / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018517:Plant Roots / Q000737:chemistry; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1 / Q000037:antagonists & inhibitors; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000097669:Dammaranes
D004365:Drugs, Chinese Herbal; D006027:Glycosides; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1; D014315:Triterpenes; D000097669:Dammaranes