Acylated phenylethanoid glycosides, echinacoside and acteoside from Cistanche tubulosa, improve glucose tolerance in mice
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- 作者：Toshio Morikawa (1) (2)
Kiyofumi Ninomiya (1) (2)
Mio Imamura (1)
Junji Akaki (1)
Shota Fujikura (1)
Yingni Pan (1) (3)
Dan Yuan (3)
Masayuki Yoshikawa (1)
Xiaoguang Jia (4)
Zheng Li (5)
Osamu Muraoka (1) (2) - 关键词：Echinacoside ; Acteoside ; Glucose tolerance improvement effect ; Aldose reductase inhibitor ; Cistanche tubulosa
- 刊名：Journal of Natural Medicines
- 出版年：2014
- 出版时间：July 2014
- 年：2014
- 卷：68
- 期：3
- 页码：561-566
- 全文大小：
- 参考文献：1. Jiménez C, Riguera R (1994) Phenylethanoid glycosides in plants: structure and biological activity. Nat Prod Rep 11:591-06 CrossRef
2. Fu G, Pang H, Wong YH (2008) Naturally occurring phenylethanoid glycosides: potential leads for new therapeutics. Curr Med Chem 15:2592-613 CrossRef
3. He J, Hu X-P, Zeng Y, Li Y, Wu H-Q, Qiu R-Z, Ma W-J, Li T, Li C-Y, He Z-D (2011) Advanced research on acteoside for chemistry and bioactivities. J Asian Nat Prod Res 13:449-64 CrossRef
4. Stoll A, Renz J, Brack A (1950) Isolierung und konstitution des echinacosids, eines glykosids aus den wurzeln von / Echinacea angustifolia D. C. 6. mitteilung über antibakterielle stoffe. Helv Chim Acta 33:1877-893 CrossRef
5. Becker H, Hsieh WC, Wylde R, Laffite C, Andary C (1982) Structure of echinacoside. Z Naturforsch C: Biosci 37C:351-53
6. Scarpati ML, Dell MF (1963) Isolation from / Verbascum sinuatum of two new glucosides, verbascoside and isoverbascoside. Ann Chim 53:356-67
7. Birkofer L, Kaiser C, Thomas U (1968) Sugar esters. IV. acteoside and neoacteoside, sugar esters from / Syringa vulgaris. Z Naturforsch, B: Chem Sci 23:1051-058
8. Andary C, Wylde R, Laffite C, Privat G, Winternitz F (1982) Structures of varbascoside and orobanchoside, caffeic acid sugar esters from / Orobanche rapum- / genistae. Phytochemistry 21:1123-127 CrossRef
9. Sakurai A, Kato T (1983) A new glycoside, kusaginin isolated from / Clerodendron trichotomum. Bull Chem Soc Jpn 56:1573-574 CrossRef
10. Lee KJ, Woo E-R, Choi CY, Shin DW, Lee DG, You HJ, Jeong HG (2004) Protective effect of acteoside on carbon tetrachloride-induced hepatotoxicity. Life Sci 74:1051-064 CrossRef
11. Jia C, Shi H, Jin W, Zhang K, Jiang Y, Zhao M, Tu P (2009) Metabolism of echinacoside, a good antioxidant, in rats: isolation and identification of its biliary metabolites. Drug Metab Dispos 37:431-38 CrossRef
12. Jia Y, Guan Q, Guo Y, Du C (2012) Echinacoside stimulates cell proliferation and prevents cell apoptosis in intestinal epithelial MODE-K cells by up-regulation of transforming growth factor-β1 expression. J Pharmacol Sci 118:99-08 CrossRef
13. Li F, Yang Y, Zhu P, Chen W, Qi D, Shi X, Zhang C, Yang Z, Li P (2012) Echinacoside promotes bone regeneration by increasing OPG/RANKL ratio in MC3T3-E1 cells. Fitoterapia 83:1443-450 CrossRef
14. Li F, Yang X, Yang Y, Guo C, Zhang C, Yang Z, Li P (2013) Antiosteoporotic activity of echinacoside in ovariectomized rats. Phytomedicine 20:549-57 CrossRef
15. Yoshikawa M, Matsuda H, Morikawa T, Xie H, Nakamura S, Muraoka O (2006) Phenylethanoid oligoglycosides and acylated oligosugars with vasorelaxant activity from / Cistanche tubulosa. Bioorg Med Chem 14:7468-475 CrossRef
16. Morikawa T, Pan Y, Ninomiya K, Imura K, Matsuda H, Yoshikawa M, Yuan D, Muraoka O (2010) Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant / Cistanche tubulosa. Bioorg Med Chem 18:1882-890 CrossRef
17. Pan Y, Morikawa T, Ninomiya K, Imura K, Yuan D, Yoshikawa M, Muraoka O (2010) Bioactive constituents from Chinese natural medicines. XXXVI. Four new acylated phenylethanoid oligoglycosides, kankanosides J1, J2, K1, and K2, from stems of / Cistanche tubulosa. Chem Pharm Bull 58:575-78 CrossRef
18. Xie H, Morikawa T, Matsuda H, Nakamura S, Muraoka O, Yoshikawa M (2006) Monoterpene constituents from / Cistanche tubulosa: chemical structures of kankanosides A-E and kankanol. Chem Pharm Bull 54:669-75 CrossRef
19. Morikawa T, Pan Y, Ninomiya K, Imura K, Yuan D, Yoshikawa M, Hayakawa T, Muraoka O (2010) Iridoid and acyclic monoterpene glycosides, kankanosides L, M, N, O, and P from / Cistanche tubulosa. Chem Pharm Bull 58:1403-407 CrossRef
20. Kobayashi H, Oguchi H, Takizawa N, Miyase T, Ueno A, Usmanghani K, Ahmad M (1987) New phenylethanoid glycosides from / Cistanche tubulosa (Schrenk) Hook. f. I. Chem Pharm Bull 35:3309-314 CrossRef
21. Shimoda H, Tanaka J, Takahara Y, Takemoto K, Shan S-J, Su M-H (2009) The hypocholesterolemic effects of / Cistanche tubulosa extract, a Chinese traditional crude medicine, in mice. Am J Chin Med 37:1125-138 CrossRef
22. Yoshikawa M, Morikwa T, Matsuda H, Tanabe G, Muraoka O (2002) Absolute stereostructure of potent α-glucosidase inhibitor, salacinol, with unique thiosugar sulfonium sulfate inner salt structure from / salacia reticulata. Bioorg Med Chem 10:1547-554 CrossRef
23. Muraoka O, Morikawa T, Miyake S, Akaki J, Ninomiya K, Yoshikawa M (2010) Quantitative determination of potent α-glucosidase inhibitors, salacinol and kotalanol, in / Salasia species using liquid chromatography-mass spectrometry. J Pharm Biomed Anal 52:770-73 CrossRef
24. Muraoka O, Morikawa T, Miyake S, Akaki J, Ninomiya K, Pongpiriyadacha Y, Yoshikawa M (2011) Quantitative analysis of neosalacinol and neokotalanol, another two potent α-glucosidase inhibitors from / Salacia species, by LC-MS with ion pair chromatography. J Nat Med 65:142-48 CrossRef
25. Matsuda H, Morikawa T, Toguchida I, Yoshikawa M (2002) Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity. Chem Pharm Bull 50:788-95 CrossRef
26. Yoshikawa M, Morikawa T, Murakami T, Toguchida I, Harima S, Matsuda H (1999) Medicinal flowers. I. aldose reductase inhibitors and three new eudesmane-type sesquiterpenes, kikkanols A, B, and C, from the flowers of / Chrysanthemum indicum L. Chem Pharm Bull 47:340-45 CrossRef
27. Matsuda H, Morikawa T, Toguchida I, Harima S, Yoshikawa M (2002) Medicinal flowers. VI. Absolute stereostructures of two new flavanone glycosides and a phenylbutanoid glycoside from the flowers of / Chrysanthemum indicum L.: their inhibitory activities for rat lens aldose reductase. Chem Pharm Bull 50:972-75 CrossRef
28. Yoshikawa M, Murakami T, Ishiwada T, Morikawa T, Kagawa M, Higashi Y, Matsuda H (2002) New flavonol oligoglycosides and polyacylated sucroses with inhibitory effects on aldose reductase and platelet aggregation from the flowers of / Prunus mume. J Nat Prod 65:1151-155 CrossRef
29. Matsuda H, Morikawa T, Yoshikawa M (2002) Antidiabetogenic constituents from several natural medicines. Pure Appl Chem 74:1301-308 CrossRef
30. Xie H, Wang T, Matsuda H, Morikawa T, Yoshikawa M, Tani T (2005) Bioactive constituents from Chinese natural medicines. XV. Inhibitory effect on aldose reductase and structures of saussureosides A and B from / Saussurea medusa. Chem Pharm Bull 53:1416-422 CrossRef
31. Morikawa T, Xie H, Wang T, Matsuda H, Yoshikawa M (2008) Bioactive constituents from Chinese natural medicines. XXXII. Aminopeptidase N and aldose reductase inhibitors from / Sinocrassula indica: structures of sinocrassosides B4, B5, C1, and D1–D3. Chem Pharm Bull 56:1438-444 CrossRef
32. Morikawa T, Chaipech S, Matsuda H, Hamao M, Umeda Y, Sato H, Tamura H, Kon’i H, Ninomiya K, Yoshikawa M, Pongpiriyadacha Y, Hayakawa T, Muraoka O (2012) Antidiabetogenic oligostilbenoids and 3-ethyl-4-phenyl-3,4-dihydroisocoumarins from the bark of / Shorea roxburghii. Bioorg Med Chem 20:832-40 CrossRef
33. Morikawa T, Kishi A, Pongiriyadacha Y, Matusda H, Yoshikawa M (2003) Structures of new friedelane-type triterpenes and eudesmane-type sesquiterpene and aldose reductase inhibitors from / Salacia chinensis. J Nat Prod 66:1191-196 CrossRef - 作者单位：Toshio Morikawa (1) (2)
Kiyofumi Ninomiya (1) (2)
Mio Imamura (1)
Junji Akaki (1)
Shota Fujikura (1)
Yingni Pan (1) (3)
Dan Yuan (3)
Masayuki Yoshikawa (1)
Xiaoguang Jia (4)
Zheng Li (5)
Osamu Muraoka (1) (2)
1. Pharmaceutical Research and Technology Institute, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka, 577-8502, Japan
2. Antiaging Centre, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka, 577-8502, Japan
3. School of Traditional Chinese Medicines, Shenyang Pharmaceutical University, 103 Wenhua Rd., Shenyang, 110016, People’s Republic of China
4. Xinjiang Institute of Chinese Materia Medica and Ethnodrug, 9 Xinmin Rd., ürümqi, 830002, Xinjiang, People’s Republic of China
5. Eishin Trading Co., Ltd., 2-13-4 Doshin, Kita-ku, Osaka, 530-0035, Japan - ISSN：1861-0293
文摘
Acylated phenylethanoid glycosides, echinacoside (1) and acteoside (2), principal constituents in stems of Cistanche tubulosa (Orobanchaceae), inhibited the increase in postprandial blood glucose levels in starch-loaded mice at doses of 250-00?mg/kg p.o. These compounds (1 and 2) also significantly improved glucose tolerance in starch-loaded mice after 2?weeks of continuous administration at doses of 125 and/or 250?mg/kg/day p.o. without producing significant changes in body weight or food intake. In addition, several constituents from C. tubulosa, including 1 (IC50?=?3.1?μM), 2 (1.2?μM), isoacteoside (3, 4.6?μM), 2-acetylacteoside (4, 0.071?μM), tubulosides A (5, 8.8?μM) and B (9, 4.0?μM), syringalide A 3-O-α-l-rhamnopyranoside (10, 1.1?μM), campneoside I (13, 0.53?μM), and kankanoside J1 (14, 9.3?μM), demonstrated potent rat lens aldose reductase inhibitory activity. In particular, the potency of compound 4 was similar to that of epalrestat (0.072?μM), a clinical aldose reductase inhibitor.