Progress on Danshensu derivatives

WANG Ting-fang; ZHENG Li-ping; ZHANG Ning; JIN Lei; WU Qiu-ye; ZHANG Chuan

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Volume 29 Issue 2

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2011 > 29(2): 83-88

WANG Ting-fang, ZHENG Li-ping, ZHANG Ning, JIN Lei, WU Qiu-ye, ZHANG Chuan. Progress on Danshensu derivatives[J]. Journal of Pharmaceutical Practice and Service, 2011, 29(2): 83-88.

Citation:

WANG Ting-fang, ZHENG Li-ping, ZHANG Ning, JIN Lei, WU Qiu-ye, ZHANG Chuan. Progress on Danshensu derivatives[J]. Journal of Pharmaceutical Practice and Service, 2011, 29(2): 83-88.

Progress on Danshensu derivatives

1.
School of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350108, China;New Drug Research Center, School of Pharmacy, Second Military Medical University, Shanghai 200433, China;Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China
2.
School of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350108, China;New Drug Research Center, School of Pharmacy, Second Military Medical University, Shanghai 200433, China
3.
New Drug Research Center, School of Pharmacy, Second Military Medical University, Shanghai 200433, China
4.
Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2010-08-25
Rev Recd Date: 2011-03-07

Abstract

Danshensu is the major water-soluble phenolic acids of Danshen. It possessed diverse pharmacological effects, especially the protective effects on cardiovascular diseases. Due to its significant pharmacological activities, synthesis of danshensu derivatives attracted much attention. A systematic review about Danshensu derivatives were carried out in this paper. It was hoped to provide some references to the resource exploitations of the danshensu derivatives.
- Danshensu,
- derivatives,
- biological activity

References

[1]	江文德, 陈玉华, 王迎平,等. 丹参素及另两种水溶性丹参成分抗心肌缺血和对冠状动脉作用的研究[J]. 上海第一医学院学报, 1982, 9(1): 13.
[2]	董忠田, 江文德. 丹参素对猪离体冠状动脉的作用[J]. 药学学报,1982,17(3):226.
[3]	Wu L, Qiao H, Li Y, et al. Protective roles of puerarin and Danshensu on acute ischemic myocardial injury in rats[J]. Phytomedicine, 2007, 14(10): 652.
[4]	Lam FFY, Yeung JHK, Chan KM, et al. Relaxant effects of danshen aqueous extract and its constituent danshensu on rat coronary artery are mediated by inhibition of calcium channels[J]. Vascular Pharmacology, 2007, 46(4): 271.
[5]	Han JY, Horie Y, Fan JY, et al. Potential of 3,4-dihydroxy-phenyl lactic acid for ameliorating ischemia-reperfusion-induced microvascular disturbance in rat mesentery[J]. Am J Physiol Gastrointest Liver Physiol, 2009, 296(1):G36.
[6]	Zhou LM, Moses SSC, Zuo Z. Pharmacokinetics and bioavailability of danshensu in rats[J]. Drug Metab Rev, 2006, 38(1): 39.
[7]	潘坚扬, 赵筱萍, 邵青. 丹参素大鼠体内药代动力学及生物利用度研究[J]. 中国中药杂志, 2008, 33(2): 146.
[8]	江文德, 陈玉华, 王迎平, 等. 丹参素及另两种水溶性丹参成分抗心肌缺血和对冠状动脉作用的研究[J]. 上海第一医学院学报,1983, 9(1): 13.
[9]	董纪昌, 戴华娟, 薛芬, 等. 五种丹参素衍生物的合成[J]. 上海医科大学学报, 1987, 14(6): 447.
[10]	张智波, 董纪昌, 金昔陆, 等. 八种丹参素衍生物的合成[J]. 上海医科大学学报, 1996, 23(z):26.
[11]	Wong HNC, Xu ZL, Chang HM, et al. A modified synthesis of (±) -β-aryllactic acids[J]. Synthesis, 1992, 8(10): 793.
[12]	金昔陆, 陈滨凌, 吴卫江, 等. 8种丹参素衍生物对兔血小板聚集性的影响[J]. 上海医科大学学报, 2000, 27(3):181.
[13]	邓喜玲, 王新兵, 相颖, 等. β-(4-羟基苯基)乳酸的合成[J]. 石河子大学学报(自然科学版), 2005, 23 (1):22.
[14]	贾贵泉, 薛芬, 叶莹, 等. 若干邻二酚胺衍生物的合成[J]. 上海医科大学学报, 1991, 18(1): 67.
[15]	朱依谆, 王洋, 董村南. 一种丹参素衍生物及其制备方法和在药学上的应用[P]. 中国 CN 200810039162.0, 2009-12-23.
[16]	Zheng XH, Zhao XF, Zhao X, et al. Determination of the main bioactive metabolites of Radix Salvia miltiorrhizae in compound danshen dripping pills and the tissue distribution of danshensu in rabbit by SPE-HPLC-MSn[J]. J Sep Sci, 2007, 30(6), 851.
[17]	郑晓晖, 张延长, 王世祥, 等.β-(3,4 -二羟基苯基)-α-羟基丙酸异丙酯及其合成方法[P]. 中国CN200410026205.3, 2005-05-23.
[18]	张群正, 董岩, 南叶飞, 等. β-(3,4-二羟基苯基)-α-羟基丙酸异丙酯／冰片酯合成研究[J]. 有机化学, 2009, 29(9): 1466.。
[19]	Wang SP, Zang WJ, Kong SS, et al. Vasorelaxant effect of isopropyl 3-(3,4-dihydroxy phenyl)-2-hydroxypropanoate, a novel metabolite from Salvia miltiorrhiza,on isolated rat mesenteric artery[J]. Eur J Pharmacol, 2008, 579(1-3): 283.
[20]	郑晓晖,张群正,王世祥, 等.β-(3,4-二羟基苯基)-α-羟基丙酸冰片酯、其合成方法和用途[P]. 中国CN200610042787.3, 2006-05-15.
[21]	董村南, 王洋, 朱依谆. 丹参素衍生物的合成及生物活性筛选[J]. 药学学报,2007,42(增刊): 149.
[22]	Findrik, Z, Poljanac M, Vasi-Raèki D. Modelling and Optimization of the (R)-(+)-3,4-dihydroxyphenyllactic Acid Production Catalyzed with D-lactate Dehydrogenase from Lactobacillus leishmannii Using Genetic Algorithm[J]. Chem Biochem Eng Q, 2005, 19 (4), 351.
[23]	朱亮, 邵以德. 合成消旋丹参素及其衍生物对血小板聚集和CAIMP含量的影响[J]. 上海第一医学院学报, 1985, 12(6): 461.
[24]	周小鸣, 薛芬, 楼亚平, 等.用不对称环氧化合成光学活性β-苯基乳酸及其甲酯[J]. 上海医科大学学报,1988,15(2): 155.
[25]	周小鸣, 薛芬, 楼亚平, 等.R-和S-β-对氟苯基乳酸及其甲酯[J]. 上海医科大学学报,1989,16(2): 135.
[26]	Dong CN, Wang Y, Zhu YZ. Asymmetric synthesis and biological evaluation of Danshensu derivatives as anti-myocardial ischemia drug candidates[J]. Bioorg Med Chem, 2009, 17(9): 3499.
[27]	于建明, 薛芬, 戴华娟. 丹参素衍生物的合成[J]. 药学学报, 1991, 26(7):552.
[28]	李小玲, 单玉庆, 叶大炳,等. β-(3,4-二羟基苯基)-α-羟基-N-[(R)-3-苯基-1-乙氧酰基丙基]丙酰胺的合成[J]. 合成化学, 2008, 16(20): 239.
[29]	向卓, 景临林, 刘文中, 等. 乙酰丹参素单硝酸异山梨醇酯的合成及对心肌缺血/再灌注大鼠心脏的保护作用[J]. 第四军医大学学报, 2009, 30(14):1257.
[30]	Zhou LM, Chow MSS, Zuo Z. Effect of sodium caprate on the oral absorptions of danshensu[J]. Int J Pharm, 2009, 379 (1) :109.

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通讯作者: 陈斌, [email protected]

1.
沈阳化工大学材料科学与工程学院沈阳 110142

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Progress on Danshensu derivatives

1. School of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350108, China;New Drug Research Center, School of Pharmacy, Second Military Medical University, Shanghai 200433, China;Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

2. School of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350108, China;New Drug Research Center, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

3. New Drug Research Center, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

4. Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2010-08-25

Rev Recd Date: 2011-03-07

Key words:

Abstract: Danshensu is the major water-soluble phenolic acids of Danshen. It possessed diverse pharmacological effects, especially the protective effects on cardiovascular diseases. Due to its significant pharmacological activities, synthesis of danshensu derivatives attracted much attention. A systematic review about Danshensu derivatives were carried out in this paper. It was hoped to provide some references to the resource exploitations of the danshensu derivatives.

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Reference (30)

[1]	江文德, 陈玉华, 王迎平,等. 丹参素及另两种水溶性丹参成分抗心肌缺血和对冠状动脉作用的研究[J]. 上海第一医学院学报, 1982, 9(1): 13.
[2]	董忠田, 江文德. 丹参素对猪离体冠状动脉的作用[J]. 药学学报,1982,17(3):226.
[3]	Wu L, Qiao H, Li Y, et al. Protective roles of puerarin and Danshensu on acute ischemic myocardial injury in rats[J]. Phytomedicine, 2007, 14(10): 652.
[4]	Lam FFY, Yeung JHK, Chan KM, et al. Relaxant effects of danshen aqueous extract and its constituent danshensu on rat coronary artery are mediated by inhibition of calcium channels[J]. Vascular Pharmacology, 2007, 46(4): 271.
[5]	Han JY, Horie Y, Fan JY, et al. Potential of 3,4-dihydroxy-phenyl lactic acid for ameliorating ischemia-reperfusion-induced microvascular disturbance in rat mesentery[J]. Am J Physiol Gastrointest Liver Physiol, 2009, 296(1):G36.
[6]	Zhou LM, Moses SSC, Zuo Z. Pharmacokinetics and bioavailability of danshensu in rats[J]. Drug Metab Rev, 2006, 38(1): 39.
[7]	潘坚扬, 赵筱萍, 邵青. 丹参素大鼠体内药代动力学及生物利用度研究[J]. 中国中药杂志, 2008, 33(2): 146.
[8]	江文德, 陈玉华, 王迎平, 等. 丹参素及另两种水溶性丹参成分抗心肌缺血和对冠状动脉作用的研究[J]. 上海第一医学院学报,1983, 9(1): 13.
[9]	董纪昌, 戴华娟, 薛芬, 等. 五种丹参素衍生物的合成[J]. 上海医科大学学报, 1987, 14(6): 447.
[10]	张智波, 董纪昌, 金昔陆, 等. 八种丹参素衍生物的合成[J]. 上海医科大学学报, 1996, 23(z):26.
[11]	Wong HNC, Xu ZL, Chang HM, et al. A modified synthesis of (±) -β-aryllactic acids[J]. Synthesis, 1992, 8(10): 793.
[12]	金昔陆, 陈滨凌, 吴卫江, 等. 8种丹参素衍生物对兔血小板聚集性的影响[J]. 上海医科大学学报, 2000, 27(3):181.
[13]	邓喜玲, 王新兵, 相颖, 等. β-(4-羟基苯基)乳酸的合成[J]. 石河子大学学报(自然科学版), 2005, 23 (1):22.
[14]	贾贵泉, 薛芬, 叶莹, 等. 若干邻二酚胺衍生物的合成[J]. 上海医科大学学报, 1991, 18(1): 67.
[15]	朱依谆, 王洋, 董村南. 一种丹参素衍生物及其制备方法和在药学上的应用[P]. 中国 CN 200810039162.0, 2009-12-23.
[16]	Zheng XH, Zhao XF, Zhao X, et al. Determination of the main bioactive metabolites of Radix Salvia miltiorrhizae in compound danshen dripping pills and the tissue distribution of danshensu in rabbit by SPE-HPLC-MSn[J]. J Sep Sci, 2007, 30(6), 851.
[17]	郑晓晖, 张延长, 王世祥, 等.β-(3,4 -二羟基苯基)-α-羟基丙酸异丙酯及其合成方法[P]. 中国CN200410026205.3, 2005-05-23.
[18]	张群正, 董岩, 南叶飞, 等. β-(3,4-二羟基苯基)-α-羟基丙酸异丙酯／冰片酯合成研究[J]. 有机化学, 2009, 29(9): 1466.。
[19]	Wang SP, Zang WJ, Kong SS, et al. Vasorelaxant effect of isopropyl 3-(3,4-dihydroxy phenyl)-2-hydroxypropanoate, a novel metabolite from Salvia miltiorrhiza,on isolated rat mesenteric artery[J]. Eur J Pharmacol, 2008, 579(1-3): 283.
[20]	郑晓晖,张群正,王世祥, 等.β-(3,4-二羟基苯基)-α-羟基丙酸冰片酯、其合成方法和用途[P]. 中国CN200610042787.3, 2006-05-15.
[21]	董村南, 王洋, 朱依谆. 丹参素衍生物的合成及生物活性筛选[J]. 药学学报,2007,42(增刊): 149.
[22]	Findrik, Z, Poljanac M, Vasi-Raèki D. Modelling and Optimization of the (R)-(+)-3,4-dihydroxyphenyllactic Acid Production Catalyzed with D-lactate Dehydrogenase from Lactobacillus leishmannii Using Genetic Algorithm[J]. Chem Biochem Eng Q, 2005, 19 (4), 351.
[23]	朱亮, 邵以德. 合成消旋丹参素及其衍生物对血小板聚集和CAIMP含量的影响[J]. 上海第一医学院学报, 1985, 12(6): 461.
[24]	周小鸣, 薛芬, 楼亚平, 等.用不对称环氧化合成光学活性β-苯基乳酸及其甲酯[J]. 上海医科大学学报,1988,15(2): 155.
[25]	周小鸣, 薛芬, 楼亚平, 等.R-和S-β-对氟苯基乳酸及其甲酯[J]. 上海医科大学学报,1989,16(2): 135.
[26]	Dong CN, Wang Y, Zhu YZ. Asymmetric synthesis and biological evaluation of Danshensu derivatives as anti-myocardial ischemia drug candidates[J]. Bioorg Med Chem, 2009, 17(9): 3499.
[27]	于建明, 薛芬, 戴华娟. 丹参素衍生物的合成[J]. 药学学报, 1991, 26(7):552.
[28]	李小玲, 单玉庆, 叶大炳,等. β-(3,4-二羟基苯基)-α-羟基-N-[(R)-3-苯基-1-乙氧酰基丙基]丙酰胺的合成[J]. 合成化学, 2008, 16(20): 239.
[29]	向卓, 景临林, 刘文中, 等. 乙酰丹参素单硝酸异山梨醇酯的合成及对心肌缺血/再灌注大鼠心脏的保护作用[J]. 第四军医大学学报, 2009, 30(14):1257.
[30]	Zhou LM, Chow MSS, Zuo Z. Effect of sodium caprate on the oral absorptions of danshensu[J]. Int J Pharm, 2009, 379 (1) :109.

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Progress on Danshensu derivatives

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通讯作者: 陈斌, [email protected]

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