目的 研究山茱萸(Cornus officinalis Sieb. et Zucc.)成熟果实的化学成分及其对缺氧缺糖 (oxygen-glucose deprivation，OGD) 损伤PC12细胞的保护作用。方法 采用大孔吸附树脂、硅胶、ODS、Sephadex LH-20柱色谱和制备HPLC等技术进行分离和纯化，结合理化性质及MS、NMR等波谱方法鉴定化合物的结构，并采用MTT法测定其对OGD损伤的PC12细胞的保护作用。结果 从山茱萸成熟果实水提取物中分离得到8个化合物，分别为6′-O-乙酰基-7β-O-乙基莫诺苷 (1)，金圣草黄素(2)，木犀草素(3)，5-羟甲基糠醛(4)，丁香酸(5)，对羟基苯甲酸(6)，咖啡酸甲酯(7)和没食子酸乙酯(8)。结论 化合物1为新化合物，化合物2， 3， 5， 7为首次从山茱萸植物中分离得到;化合物4在1.0 μmol·L-1的浓度下，对OGD/R损伤的PC12细胞具有一定的保护作用。
Abstract
OBJECTIVE To study the chemical constituents from the ripe fruits of Cornus officinalis Sieb. et Zucc., and evaluate their protection on PC12 cells exposed to oxygen and glucose deprivation.METHODS The compounds were isolated through various chromatographic methods including macroporous adsorption resin, silica gel, ODS, Sephadex LH-20 column chromatography, and preparative HPLC, and their structures were determined through spectroscopic analysis, including 1D and 2D NMR and MS data.RESULTS Eight compounds were isolated from the water extract of the ripe fruits of Cornus officinalis Sieb. et Zucc., and their structures were elucidated as 6′-O-acetyl-7β-O-ethyl morroniside (1), chrysoderol(2), luteolin(3), 5-hydroxymethylfurfural(4), syringate(5),p-hydroxybenzoic acid(6),caffeic acid methyl ester(7), ethyl gallate(8).CONCLUSION Compound 1 is a new iridoid glucoside, and compounds 2, 3, 5, 7 are obtained from Cornus officinalis for the first time. The MTT results show that compound 4 moderately increases the viability of OGD/R treated PC12 cells at the concentration of 1.0 μmol·L-1.
关键词
山茱萸 /
环烯醚萜苷类 /
6′-O-乙酰基-7β-O-乙基莫诺苷 /
PC12细胞
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Key words
Cornus officinalis /
Iridoid glucoside /
6′-O-acetyl-7β-O-ethyl morroniside /
PC12 cell
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中图分类号：
R284
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参考文献
[1] Flora of China editorial committee. Flora of China (中国植物志) . Vol 67. Beijing:Science Press, 1990:56-84.
[2] PANG Y, WANG T S. Summary of the studies of the chemical composition of dogwood fruit . J Nanjing Univ Tradit Chin Med(南京中医药大学学报), 1998, 14(1):61-62.
[3] ZANG L B, ZHENG Y J. The effect of Cornusofficinalis on antioxidant enzyme activity in mice . Chin J Tradit Med Sci Technol(中国中医药科技), 1994, 1(6):34-35.
[4] ZANG L B, ZHENG Y J. Study on anti-aging experiment of Cornus officinalis . J Zhejiang Univ Tradit Chin Med(浙江中医学院学报), 1993,17(5):34.
[5] Ch.P. 2015(Ⅰ)(中国药典2015年版一部) . 2015:27.
[6] CAO G, ZHANG Y, CONG X D,et al. Research progress on the chemical constituents and pharmacological activities of Fructuscorni. J Chin Pharm Sci(中国药学英文版), 2009, 18(3):208-213.
[7] MA W, WANG K J, CHENG C S, et al. Bioactive compounds from Cornus officinalis fruits and their effects on diabetic nephropathy . J Ethnopharmacol, 2014, 153(3):840-845.
[8] ZHAO L H, DING Y X, ZHANG L, et al. Cornel iridoid glycoside improves memory ability and promotes neuronal survival in fimbria-fornix transected rats . Eur J Pharmacol,2010, 647(1-3):68-74.
[9] PARK C H, NOH J S, KIM J H, et al. Evaluation of morroniside, iridoid glycoside from corni fructus, on diabetes-induced alterations such as oxidative stress, inflammation,and apoptosis in the liver of type 2 diabetic db/db mices. Biol Pharm Bull, 2011, 34(10):1559-1565.
LIN M H, LIU H K, HUANG W J, et al. Evaluation of the potential hypoglycemic and beta-cell protective constituents isolated from corni fructus to tackle insulin-dependent diabetes mellitus . J Agric Food Chem, 2011, 59(14):7743-7751.
HU J F, STARKS C M, WILLIAMS R B,et al. Secoiridoid glycosides from the pitcher plant sarraceniaalata. Helv Chim Acta, 2009, 92(2):273-280.
HAN S Y, PAN Y, DING G, et al. The application of 1H-NMR and 13C-NMR in identification of iridoid compounds from Cornus officinalis . Chin Arch Tradit Chin Med (中医药学刊), 2004, 22(1):56-59.
TANAKA T,NAKASHIMA T, UEDA T, et al. Facile discrimination of aldose enantiomers by reversed-phase HPLC . Chem Pharm Bull, 2007, 55:899-901.
REN F C, WANG L X, WANG F, et al. Chemical constituents from Scilla scilloides . Chin Tradit Herb Drugs (中草药), 2014, 45(14):1984-1988.
XU R L, SHI Y P. Chemical constituents from Artemisiae Anomalae Herba . Chin Tradit Herb Drugs (中草药), 2014, 45(11):1521-1525.
LING X N, ZHOU M Y, SHEN P Q, et al. Chemical constituents from Rehmannia glutinosa . Chin J Chin Mater Med (中国中药杂志), 2011, 36(22):3125-3129.
LI W, CHEN F K, YIN X W, et al. Chemical constituents of Folium Isatidis . J Shenyang Pharm Univ(沈阳药科大学学报), 2005, 20(1):15-16.
SHAO J C, HE C H, LI I T, et al. Chemial constituents of Tetrastigma planicauce (Hook. ) Gagnep. Chin Pharm J(中国药学杂志),2011,46(6):414-417.
WANG X S, CHE Q M, LI Y M, et al. A study on chemical constituents in seeds of Crataegus pinnatifida Bge. var. major N. E . Br . Chin J Chin Mater Med (中国中药杂志), 1999, 24(12):739-740.
ZHAO X H, CHEN D H, SI J Y, et al. Studies on the phenolic acid constituents from Chinese medicine “sheng-ma”, rhizome of Cimicifuga foetida L . Acta Pharm Sinica(药学学报), 2002, 37(7):535-538.
HU J, WANG Z Y, KANG M, et al. Chemical constituents of Ardisia faberi . Chin Tradit Herb Drugs(中草药),2015, 46(14):2048-2051.
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脚注
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基金
国家自然科学基金资助项目(81473119, 81473590);北京市科委十病十药研究专项资助(Z171100001717009)
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