Isolation of Antithrombotic Phenolic Compounds from the Leaves of Crataegus pinnatifida

Shao-Jiang Song; Ling-Zhi Li; Pin-Yi Gao; Yan-Qiang Yuan; Ru-Ping Wang; Ke-Chun Liu; Ying Peng

doi:10.1055/s-0032-1327877

Planta Medica, Inhaltsverzeichnis

Planta Med 2012; 78(18): 1967-1971
DOI: 10.1055/s-0032-1327877

Natural Product Chemistry

Letters

Georg Thieme Verlag KG Stuttgart · New York

Isolation of Antithrombotic Phenolic Compounds from the Leaves of Crataegus pinnatifida

Shao-Jiang Song

¹School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, PR China

²State 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, PR China

,

Ling-Zhi Li

¹School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, PR China

²State 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, PR China

,

Pin-Yi Gao

³College of Chemical Engineering, Shenyang University of Chemical Technology, Shenyang, PR China

,

Yan-Qiang Yuan

⁵Biology Institute of Shandong Academy of Sciences, Jinan, PR China

,

Ru-Ping Wang

¹School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, PR China

²State 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, PR China

,

Ke-Chun Liu

⁵Biology Institute of Shandong Academy of Sciences, Jinan, PR China

,

Ying Peng

⁴School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, PR China

› Institutsangaben

Abstract

Four novel phenolic compounds (1–4) were isolated from the leaves of Crataegus pinnatifida, along with three known ones (5–7). Their structures were elucidated as: methyl 4-O-β-D-glucopyranosyl-3-[(2E,6E)-8-O-β-D-glucopyranosyl-3,7-dimethyl-2,6-octadienyl] benzoate (1), biphenyl-5-ol-3-O-β-D-glucoside (2), 3,4′-dimethoxy-biphenyl-5-ol-4-O-β-D-glucoside (3), (E)-6-(benzoyloxy)-1-hydroxyhex-3-en-2-O-β-D-glucoside (4), shanyenoside A (5), eriodectyol (6), and 2″-O-rhamnosyl vitexin (7), using a combination of mass spectroscopy, 1D and 2D NMR spectroscopy, and chemical analysis. The antithrombotic activity of the isolated compounds was investigated on the transgenic zebra fish system. Among them, eriodectyol (6) potently inhibited the production of thrombus.

Key words

Crataegus pinnatifida - Rosaceae - phenolic compounds - antithrombotic activity

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Referenzen

References
1 Liu PZ, Yang BR, Kallio HK. Characterization of phenolic compounds in Chinese hawthorn (Crataegus pinnatifida Bge. var. major) fruit by high performance liquid chromatography–electrospray ionization mass spectrometry. Food Chem 2010; 121: 1188-1197
2 Min BS, Huong HT, Kim JH, Jun HJ, Na MK, Nam NH, Lee HK, Bae K, Kang SS. Furo-1,2-naphthoquinones from Crataegus pinnatifida with ICAM-1 expression inhibition activity. Planta Med 2004; 70: 1166-1169
3 Liu TX, Cao YN, Zhao MM. Extraction optimization, purification and antioxidant activity of procyanidins from hawthorn (C. pinnatifida Bge. var. major) fruits. Food Chem 2010; 119: 1656-1662
4 Ding XP, Wang XT, Chen LL, Qi J, Xu T, Yu BY. Quality and antioxidant activity detection of Crataegus leaves using on-line high-performance liquid chromatography with diode array detector coupled to chemiluminescence detection. Food Chem 2010; 120: 929-933
5 Liu PZ, Kallio HK, Lü DG, Zhou CS, Ou S, Yang B. Acids, sugars, and sugar alcohols in Chinese hawthorn (Crataegus spp.) fruits. J Agric Food Chem 2010; 58: 1012-1019
6 Liu PZ, Kallio HK, Yang B. Phenolic compounds in hawthorn (Crataegus grayana) fruits and leaves and changes during fruit ripening. J Agric Food Chem 2011; 59: 11141-11149
7 Park Y, Choi S, Hwang S, Lee K. Changes of phenolics and antioxidant activity during hawthorn (Crataegus pinnatifida Bunge) fruit ripening. Planta Med 2010; 76: 341
8 Sun YJ, Li ZL, Chen H, Liu XQ, Zhou W, Hua HM. Three new cytotoxic aryltetralin lignans from Sinopodophyllum emodi . Bioorg Med Chem Lett 2011; 21: 3794-3797
9 Mondol MA, Kim JH, Lee HS, Lee YJ, Shin HJ. Macrolactin W, a new antibacterial macrolide from a marine Bacillus sp. Bioorg Med Chem Lett 2011; 21: 3832-3835
10 Wu H, Nakamura H, Kobayashi J, Kobayashi M, Ohizumi Y, Hirata Y. Structures of agelasines, diterpenes having a 9-methyl-adeninium chromophore isolated from the Okinawan marine sponge Agelas nakamurai Hoshino. Bull Chem Soc Jpn 1986; 59: 2495-2504
11 Agrawal PK. NMR Spectroscopy in the structural elucidation of oligosaccharides and glycosides. Phytochemistry 1992; 31: 3307-3330
12 Chen J, Song SJ, He J, Xu SX. A new biphenyl glucoside from the leaves of Crataegus pinnatifida . J Shenyang Pharm Univ 2006; 23: 430-431
13 Liang YH, Ye M, Han J, Wang BR, Guo DA. Lignans and flavonoids from rhizome of Drynaria fortunei . Chin Tradit Herbal Drugs 2011; 42: 25-30
14 Sun JY, Yang SB, Xie HX, Li GH, Qiu HX. Studies on chemical constituents from fruit of Crataegus pinnatifida . Chin Tradit Herbal Drugs 2002; 33: 483-486
15 Finley KR, Zon LI. Zebra fish and stem cell research. In: Lanza R, editor Handbook of stem cells, Vol. 2. Amsterdam: Elsevier; 2004: 677-683
16 Gerlai R, Lahav M, Guo S, Rosenthal A. Drinks like a fish: zebra fish (Danio rerio) as a behavior genetic model to study alcohol effects. Pharm Biochem Behav 2000; 67: 773-782
17 Jagadeeswaran P, Gregory M, Day K, Cykowski M, Thattaliyath B. Zebrafish: a genetic model for hemostasis and thrombosis. J Thromb Haemost 2005; 3: 46-53
18 OʼConnor MN, Salles II, Cvejic A, Watkins NA, Walker A, Garner SF, Jones CI, Macaulay IC, Steward M, Zwaginga JJ, Bray SL, Dudbridge F, Bono BD, Goodall AH, Deckmyn H, Stemple DL, Ouwehand WH. Functional genomics in zebrafish permits rapid characterization of novel platelet membrane proteins. Blood 2009; 113: 4754-4762
19 Zon LI, Peterson RT. In vivo drug discovery in the zebrafish. Nat Rev Drug Discov 2005; 4: 35-44
20 Kurz KD, Main BW, Sandusky GE. Rat model of arterial thrombosis induced by ferric chloride. Thromb Res 1990; 60: 269-280

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