Identification and biological evaluation of flavonoids from the fruits of Prunus mume.
This Letter describes the identification of potent antioxidant and anti-osteoporosis agents from the fruits of Prunus mume. From the methanol extract, a novel flavan dimer, characterized as 2β,3β-epoxy-5,7,4'-trihydroxyflavan-(4α→8)-epicatechin (1), was isolated along with five known flavonoids (2-6). Their structures were determined based on extensive spectroscopic analysis, including IR, HRESIMS, 1D- and 2D-NMR, and CD spectra. The antioxidant activities of compounds 1-6 were evaluated in terms of their peroxyl radical-scavenging (Trolox equivalent) and reducing capacities. All isolates showed potent peroxyl radical-scavenging and reducing activities at concentrations of 1-10 μM. Among them, compounds 1 and 2 were the most active at 1 μM. Anti-osteoporosis activities were investigated using both murine osteoblastic MC3T3-E1 cells and osteoclastic RAW 264.7 cells. Compounds 2, 3, and 6 significantly stimulated the differentiation of osteoblastic MC3T3-E1 cells to increase collagen synthesis or mineralization functions of osteoblasts. Compounds 1, 3, 4, and 6 significantly suppressed tartrate-resistant acid phosphatase (TRAP) activity in receptor activator of nuclear factor-κB ligand (RANKL)-induced osteoclastic RAW 264.7 macrophage cells.
College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.
Xi-Tao
XT
Yan
College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.
Wei
W
Li
College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.
Ya-Nan
YN
Sun
College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.
Seo-Young
SY
Yang
Department of Food and Nutrition, Hannam University, Daejeon 305-811, Republic of Korea.
Sang-Hyun
SH
Lee
College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea; College of Pharmacy, Korea University, Chungnam 339-700, Republic of Korea.
Jian-Bo
JB
Chen
Department of Food and Nutrition, Hannam University, Daejeon 305-811, Republic of Korea. Electronic address: haedong@hnu.kr.
Hae-Dong
HD
Jang
College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea. Electronic address: yhk@cnu.ac.kr.
Young-Ho
YH
Kim
D000135:Acid Phosphatase / Q000378:metabolism; D000818:Animals; D000975:Antioxidants / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D002454:Cell Differentiation / Q000187:drug effects; D002460:Cell Line; D003094:Collagen / Q000096:biosynthesis; D005419:Flavonoids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D005609:Free Radicals / Q000737:chemistry; D005638:Fruit / Q000737:chemistry / Q000378:metabolism; D007527:Isoenzymes / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008968:Molecular Conformation; D027861:Prunus / Q000737:chemistry* / Q000378:metabolism; D053245:RANK Ligand / Q000494:pharmacology; D000071681:Tartrate-Resistant Acid Phosphatase
D000975:Antioxidants; D005419:Flavonoids; D005609:Free Radicals; D007527:Isoenzymes; D053245:RANK Ligand; D003094:Collagen; D000135:Acid Phosphatase; C000605511:Acp5 protein, mouse; D000071681:Tartrate-Resistant Acid Phosphatase
Anti-osteoporosis activity; Antioxidant activity; Flavan dimer; Flavonoid; Prunus mume; Rosaceae