Terpenes and sterols from the fruits of Prunus mume and their inhibitory effects on osteoclast differentiation by suppressing tartrate-resistant acid phosphatase activity.
The fruits of Prunus mume are a common commercial product and a valuable source of food and medicinal material in Eastern Asian countries. Our phytochemical investigation of the P. mume fruit led to the isolation of nine terpenes, including three ursane-type triterpenes (1-3), two cycloartane-type triterpenes (4 and 5), and four tocopherols (10-13), as well as four sterols (6-9). Their structures were elucidated based on extensive spectroscopic analysis, including 1D and 2D NMR and ESI-MS, and the majority of these compounds were isolated from this plant for the first time. The anti-osteoporosis activities of 1-13 were evaluated by measuring their inhibitory effects on tartrate-resistant acid phosphatase (TRAP) activity in receptor activator of nuclear factor κB ligand-induced osteoclastic RAW 264.7 macrophage cells. Compounds 2-7 and 9-12 significantly suppressed TRAP activity down to 47.96 ± 2.45-86.45 ± 3.07 % relative to the control at a concentration of 1 μM. These results suggest that the fruits of P. mume could be an excellent source of anti-osteoporosis phytochemicals that may be developed as natural nutraceuticals and functional foods.
College of Pharmacy, Chungnam National University, Daejeon, 305-764, Republic of Korea.
Xi-Tao
XT
Yan
Sang-Hyun
SH
Lee
Wei
W
Li
Hae-Dong
HD
Jang
Young-Ho
YH
Kim
D000135:Acid Phosphatase / Q000037:antagonists & inhibitors*; D000818:Animals; D018929:Cell Culture Techniques; D002454:Cell Differentiation / Q000187:drug effects*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D005638:Fruit / Q000737:chemistry; D007527:Isoenzymes / Q000037:antagonists & inhibitors*; D008264:Macrophages / Q000166:cytology / Q000187:drug effects / Q000201:enzymology; D051379:Mice; D015394:Molecular Structure; D010010:Osteoclasts / Q000166:cytology / Q000187:drug effects* / Q000201:enzymology; D010840:Phytosterols / Q000302:isolation & purification / Q000494:pharmacology*; D027861:Prunus / Q000737:chemistry*; D000071681:Tartrate-Resistant Acid Phosphatase; D013729:Terpenes / Q000302:isolation & purification / Q000494:pharmacology*
D007527:Isoenzymes; D010840:Phytosterols; D013729:Terpenes; D000135:Acid Phosphatase; C000605511:Acp5 protein, mouse; D000071681:Tartrate-Resistant Acid Phosphatase