天然小分子酚的肌肉松弛作用研究进展
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摘要
酚类化合物是一类小分子天然植物成分,广泛存在于自然界。酚类化合物因其结构上含有酚羟基而具有抗氧化、抗肿瘤、抑菌、抗炎等多种生物活性,对人类健康发挥着重要作用。此外,有文献报道酚类化合物具有显著肌肉松弛作用,但目前并没有相关的临床前研究总结。文章通过截止2016年6月SciFinder数据库对天然小分子酚的肌肉松弛作用研究进行检索,根据化学结构对其进行分类,总结其肌肉松弛作用及其作用机制的研究现状,并分析其化学结构与肌肉松弛作用之间的构效关系。
Phenolic compounds are a class of small-molecule natural plant constituents that are widely found in nature. Phenolic compounds, containing phenolic hydroxyl group, have antioxidant, anti-tumor, antibacterial, anti-inflammatory and other biological activities, which play an important role in human health. Recent literatures report that compounds, with phenolic hydroxyl group, have a significant muscle relaxation effect. However, there is no summary of relevant preclinical studies. In this paper, the SciFinder database was used to search for the muscle relaxation effects of small molecule natural phenols(SMNP) before June 2016. The SMNP were classified according to the chemical structures, and the current research status of their muscle relaxation effects, mechanisms, and the structure-activity relationships were summarized.
Phenolic compounds are a class of small-molecule natural plant constituents that are widely found in nature. Phenolic compounds, containing phenolic hydroxyl group, have antioxidant, anti-tumor, antibacterial, anti-inflammatory and other biological activities, which play an important role in human health. Recent literatures report that compounds, with phenolic hydroxyl group, have a significant muscle relaxation effect. However, there is no summary of relevant preclinical studies. In this paper, the SciFinder database was used to search for the muscle relaxation effects of small molecule natural phenols(SMNP) before June 2016. The SMNP were classified according to the chemical structures, and the current research status of their muscle relaxation effects, mechanisms, and the structure-activity relationships were summarized.
引文
[1]Huang W Y,Cai Y Z,Zhang Y.Natural phenolic compounds from medicinal herbs and dietary plants:potential use for cancer prevention.Nutr Cancer,2010,62(1):1-20
[2]李晓玲,张声生,杨成,等.仁术健脾理气方对功能性消化不良大鼠胃平滑肌收缩反应及GHSR蛋白表达的影响.中华中医药杂志,2015,30(4):1039-1042
[3]Xu Y,Leung S,Leung G,et al.Kaempferol enhances endotheliumdependent relaxation in the porcine coronary artery through activation of large-conductance Ca2+-activated K+channels.Br J Pharmacol,2015,172(12):3003-3014
[4]Di F,Zhai H,Li P,et al.Effects of dehydroeffusol on spasmogeninduced contractile responses of rat intestinal smooth muscles.Planta Med,2014,80(12):978-983
[5]Estrada S,Lopez-Guerrero J,Villalobos-Molina R,et al.Spasmolytic stilbenoids from Maxillaria densa.Fitoterapia,2004,75(7-8):690-695
[6]Estrada S,Rojas A,Mathison Y,et al.Nitric oxide/cGMP mediates the spasmolytic action of 3,4’-dihydroxy-5,5’-dimethoxybibenzyl from Scaphyglottis livida.Planta Med,1999,65(2):109-114
[7]Hernandez-Romero Y,Rojas J,Castillo R,et al.Spasmolytic effects,mode of action,and structure-activity relationships of stilbenoids from Nidema boothii.J Nat Prod,2004,67(2):160-167
[8]Hazekamp A,Verpoorte R,Panthong A.Isolation of a bronchodilator flavonoid from the Thai medicinal plant Clerodendrum petasites.J Ethnopharmacol,2001,78(1):45-49
[9]Hammol/Lad H,Abdalla S.Pharmacological effects of selected flavonoids on rat isolated ileum:structure-activity relationship.Gen Pharmacol,1997,28(5):767-771
[10]Ahn H,Lee J,Kim S J,et al.Pharmacological activities of flavonoids(V):Spasmolytic activities of flavones and flavonols on rat ileal smooth muscle contraction induced by electrical stimulation and anaphylactic reaction.Yakhak Hoechi,2007,51(2):150-156
[11]Gorzalczany S,Moscatelli V,Acevedo C,et al.Spasmolytic activity of Artemisia copa aqueous extract and isolated compounds.Nat Prod Res,2013,27(11):1007-1011
[12]Meckes M,Calzada F,Paz D,et al.Inhibitory effect of xanthomicrol and 3 alpha-angeloyloxy-2 alpha-hydroxy-13,14Z-dehydrocativic acid from Brickellia paniculata on the contractility of guinea-pig ileum.Planta Med,2002,68(5):467-469
[13]Mustafa E,Abu Zarga M,Abdalla S.Effects of cirsiliol,a flavone isolated from Achillea fragrantissima,on rat isolated ileum.Gen Pharmacol,1992,23(3):555-560
[14]Van Den Broucke C.Chemical and pharmacological review of flavones in Thymus satureioides.Verh K Acad Geneeskd Belg,1983,45(4):381-402
[15]Abuniaaj L,Abuzarga M,Abdalla S.Isolation and inhibitory effects of eupatilin,a flavone isolated from Artemisia monosperma Del.,on rat isolated smooth muscle.Pharmaceut Biol,1996,34(2):134-140
[16]Leal L,Costa M,Pitombeira M,et al.Mechanisms underlying the relaxation induced by isokaempferide from Amburana cearensis in the guinea-pig isolated trachea.Life Sci,2006,79(1):98-104
[17]Hnatyszyn O,Moscatelli V,Rondina R,et al.Flavonoids from Achyrocline satureioides with relaxant effects on the smooth muscle of Guinea pig corpus cavernosum.Phytomedicine,2004,11(4):366-369
[18]Ko W,Kuo S,Sheu J,et al.Relaxant effects of quercetin methyl ether derivatives in isolated guinea pig trachea and their structureactivity relationships.Planta Med,1999,65(3):273-275
[19]Revuelta M,Hidalgo A,Cantabrana B.Involvement of cAMP and beta-adrenoceptors in the relaxing effect elicited by flavonoids on rat uterine smooth muscle.J Auton Pharmacol,1999,19(6):353-358
[20]Morales M,Tortoriello J,Meckes M,et al.Calcium-antagonist effect of quercetin and its relation with the spasmolytic properties of Psidium guajava L.Arch Med Res,1994,25(1):17-21
[21]Ram S,Dwivedi S,Pandey V,et al.Pharmacological actions of kaempferol 7-methyl ether isolated from Rhamnus triquerta.Fitoterapia,1989,60(3):273-274
[22]Achterrath-Tuckermann U,Kunde R,Flaskamp E,et al.Pharmacological investigations with compounds of chamomile.V.Investigations on the spasmolytic effect of compounds of chamomile and Kamillosan on the isolated guinea pig ileum.Planta Med,1980,39(1):38-50
[23]Amira S,Rotondo A,Mule F.Relaxant effects of flavonoids on the mouse isolated stomach:structure-activity relationships.Eur JPharmacol,2008,599(1-3):126-130
[24]Rojas A,Cruz S,Ponce-Monter H,et al.Smooth muscle relaxing compounds from Dodonaea viscosa.Planta Med,1996,62(2):154-159
[25]Abu-Niaaj L,Abu-Zarga M,Sabri S,et al.Isolation and biological effects of 7-O-methyleriodictyol,a flavanone isolated from Artemisia monosperma,on rat isolated smooth muscles.Planta Med,1993,59(1):42-45
[26]Amor E,Villasenor I,Ghayur M,et al.Spasmolytic flavonoids from Syzygium samarangense(Blume)Merr.&L.M.Perry.Z Naturforsch C,2005,60(1-2):67-71
[27]Ozaki M,Mori A,Yokoi I,et al.Antispasmodic containing(-)-epigall ocatechin,JP02264719A.1990
[28]Da Rocha M,Souza F,Dos Santos Estevam C,et al.Antispasmodic effect of 4’-methylepigallocatechin on guinea pig ileum.Fitoterapia,2012,83(7):1286-1290
[29]Ghayur M,Gilani A,Khan A,et al.Presence of calcium antagonist activity explains the use of Syzygium samarangense in diarrhoea.Phytother Res,2006,20(1):49-52
[30]Nagai H,He J,Tani T,et al.Antispasmodic activity of licochalcone A,a species-specific ingredient of Glycyrrhiza inflata roots.J Pharm Pharmacol,2007,59(10):1421-1426
[31]Matsuda Y,Kase H,Asano K,et al.Isoflavone derivatives,JP60199396A.1985
[32]Borrelli F,Ascione V,Capasso R,et al.Spasmolytic effects of nonprenylated rotenoid constituents of Boerhaavia diffusa roots.J Nat Prod,2006,69(6):903-906
[33]Fusi F,Ferrara A,Koorbanally C,et al.Vascular myorelaxing activity of isolates from South African Hyacinthaceae partly mediated by activation of soluble guanylyl cyclase in rat aortic ring preparations.J Pharm Pharmacol,2008,60(4):489-497
[34]Dallmeier C,Carlini E.Pharmacology activity of eugenol derivatives.Cienc Cult,1980,32(Suppl):135-141
[35]Boegge S,Kesper S,Verspohl E,et al.Reduction of ACh-induced contraction of rat isolated ileum by coptisine,(+)-caffeoylmalic acid,Chelidonium majus,and Corydalis lutea extracts.Planta Med,1996,62(2):173-174
[36]Marcucci M,Ferreres F,Garcia-Viguera C,et al.Phenolic compounds from Brazilian propolis with pharmacological activities.J Ethnopharmacol,2001,74(2):105-112
[37]Aminov S,Vakhabov A.Pharmacology of some coumarins isolated from the plant Haplophyllum.Dokl Akad Nauk,1985(8):44-45
[38]Teng C,Yu S M,Chen C,et al.EDRF-release and Ca+(+)-channel blockade by magnolol,an antiplatelet agent isolated from Chinese herb Magnolia officinalis,in rat thoracic aorta.Life Sci,1990,47(13):1153-1161
[39]Campos M G,Oropeza M V,Villanueva T,et al.Xanthorrhizol induces endothelium-independent relaxation of rat thoracic aorta.Life Sci,2000,67(3):327-333
[40]Sarkar K,Tarafder P,Paul G.Bisphenol A inhibits duodenal movement ex vivo of rat through nitric oxide-mediated soluble guanylyl cyclase and alpha-adrenergic signaling pathways.J Appl Toxicol,2016,36(1):131-139
[41]Hayashi J,Sekine T,Deguchi S,et al.Phenolic compounds from Gastrodia rhizome and relaxant effects of related compounds on isolated smooth muscle preparation.Phytochem,2002,59(5):513-519
[42]Revuelta M,Cantabrana B,Hidalgo A.Transcriptional mechanisms involved in the relaxant effect of zeranol on isolated rat uterus.Gen Pharmacol,1997,28(4):561-565
[43]Mustafa M,Mohamad R,Din L,et al.Smooth muscle relaxant activities of compounds isolated from malaysian medicinal plants on rat aorta and guinea-pig ileum.Phytotherapy Res,1995,9(8):555-558
[44]Annahazi A,Roka R,Rosztoczy A,et al.Role of antispasmodics in the treatment of irritable bowel syndrome.World J Gastroenterol,2014,20(20):6031-6043
[45]Oztekin C,Gur S,Abdulkadir N,et al.Analysis of pomegranate juice components in rat corpora cavernosal relaxation.Int J Impot Res,2014,26(2):45-50
[46]Ponce-Monter H,Perez S,Zavala M,et al.Relaxant effect of xanthomicrol and 3alpha-angeloyloxy-2alpha-hydroxy-13,14zdehydrocativic acid from Brickellia paniculata on rat uterus.Biol Pharm Bull,2006,29(7):1501-1503
[47]Ogungbamila F,Samuelsson G.Smooth muscle relaxing flavonoids from Alchornea cordifolia.Acta Pharm Nord,1990,2(6):421-422
[48]王小红,张婵溪,李贵云,等.天然小分子酚的抗焦虑作用研究进展.中国中药杂志,2017,42(8):1557-1565
[2]李晓玲,张声生,杨成,等.仁术健脾理气方对功能性消化不良大鼠胃平滑肌收缩反应及GHSR蛋白表达的影响.中华中医药杂志,2015,30(4):1039-1042
[3]Xu Y,Leung S,Leung G,et al.Kaempferol enhances endotheliumdependent relaxation in the porcine coronary artery through activation of large-conductance Ca2+-activated K+channels.Br J Pharmacol,2015,172(12):3003-3014
[4]Di F,Zhai H,Li P,et al.Effects of dehydroeffusol on spasmogeninduced contractile responses of rat intestinal smooth muscles.Planta Med,2014,80(12):978-983
[5]Estrada S,Lopez-Guerrero J,Villalobos-Molina R,et al.Spasmolytic stilbenoids from Maxillaria densa.Fitoterapia,2004,75(7-8):690-695
[6]Estrada S,Rojas A,Mathison Y,et al.Nitric oxide/cGMP mediates the spasmolytic action of 3,4’-dihydroxy-5,5’-dimethoxybibenzyl from Scaphyglottis livida.Planta Med,1999,65(2):109-114
[7]Hernandez-Romero Y,Rojas J,Castillo R,et al.Spasmolytic effects,mode of action,and structure-activity relationships of stilbenoids from Nidema boothii.J Nat Prod,2004,67(2):160-167
[8]Hazekamp A,Verpoorte R,Panthong A.Isolation of a bronchodilator flavonoid from the Thai medicinal plant Clerodendrum petasites.J Ethnopharmacol,2001,78(1):45-49
[9]Hammol/Lad H,Abdalla S.Pharmacological effects of selected flavonoids on rat isolated ileum:structure-activity relationship.Gen Pharmacol,1997,28(5):767-771
[10]Ahn H,Lee J,Kim S J,et al.Pharmacological activities of flavonoids(V):Spasmolytic activities of flavones and flavonols on rat ileal smooth muscle contraction induced by electrical stimulation and anaphylactic reaction.Yakhak Hoechi,2007,51(2):150-156
[11]Gorzalczany S,Moscatelli V,Acevedo C,et al.Spasmolytic activity of Artemisia copa aqueous extract and isolated compounds.Nat Prod Res,2013,27(11):1007-1011
[12]Meckes M,Calzada F,Paz D,et al.Inhibitory effect of xanthomicrol and 3 alpha-angeloyloxy-2 alpha-hydroxy-13,14Z-dehydrocativic acid from Brickellia paniculata on the contractility of guinea-pig ileum.Planta Med,2002,68(5):467-469
[13]Mustafa E,Abu Zarga M,Abdalla S.Effects of cirsiliol,a flavone isolated from Achillea fragrantissima,on rat isolated ileum.Gen Pharmacol,1992,23(3):555-560
[14]Van Den Broucke C.Chemical and pharmacological review of flavones in Thymus satureioides.Verh K Acad Geneeskd Belg,1983,45(4):381-402
[15]Abuniaaj L,Abuzarga M,Abdalla S.Isolation and inhibitory effects of eupatilin,a flavone isolated from Artemisia monosperma Del.,on rat isolated smooth muscle.Pharmaceut Biol,1996,34(2):134-140
[16]Leal L,Costa M,Pitombeira M,et al.Mechanisms underlying the relaxation induced by isokaempferide from Amburana cearensis in the guinea-pig isolated trachea.Life Sci,2006,79(1):98-104
[17]Hnatyszyn O,Moscatelli V,Rondina R,et al.Flavonoids from Achyrocline satureioides with relaxant effects on the smooth muscle of Guinea pig corpus cavernosum.Phytomedicine,2004,11(4):366-369
[18]Ko W,Kuo S,Sheu J,et al.Relaxant effects of quercetin methyl ether derivatives in isolated guinea pig trachea and their structureactivity relationships.Planta Med,1999,65(3):273-275
[19]Revuelta M,Hidalgo A,Cantabrana B.Involvement of cAMP and beta-adrenoceptors in the relaxing effect elicited by flavonoids on rat uterine smooth muscle.J Auton Pharmacol,1999,19(6):353-358
[20]Morales M,Tortoriello J,Meckes M,et al.Calcium-antagonist effect of quercetin and its relation with the spasmolytic properties of Psidium guajava L.Arch Med Res,1994,25(1):17-21
[21]Ram S,Dwivedi S,Pandey V,et al.Pharmacological actions of kaempferol 7-methyl ether isolated from Rhamnus triquerta.Fitoterapia,1989,60(3):273-274
[22]Achterrath-Tuckermann U,Kunde R,Flaskamp E,et al.Pharmacological investigations with compounds of chamomile.V.Investigations on the spasmolytic effect of compounds of chamomile and Kamillosan on the isolated guinea pig ileum.Planta Med,1980,39(1):38-50
[23]Amira S,Rotondo A,Mule F.Relaxant effects of flavonoids on the mouse isolated stomach:structure-activity relationships.Eur JPharmacol,2008,599(1-3):126-130
[24]Rojas A,Cruz S,Ponce-Monter H,et al.Smooth muscle relaxing compounds from Dodonaea viscosa.Planta Med,1996,62(2):154-159
[25]Abu-Niaaj L,Abu-Zarga M,Sabri S,et al.Isolation and biological effects of 7-O-methyleriodictyol,a flavanone isolated from Artemisia monosperma,on rat isolated smooth muscles.Planta Med,1993,59(1):42-45
[26]Amor E,Villasenor I,Ghayur M,et al.Spasmolytic flavonoids from Syzygium samarangense(Blume)Merr.&L.M.Perry.Z Naturforsch C,2005,60(1-2):67-71
[27]Ozaki M,Mori A,Yokoi I,et al.Antispasmodic containing(-)-epigall ocatechin,JP02264719A.1990
[28]Da Rocha M,Souza F,Dos Santos Estevam C,et al.Antispasmodic effect of 4’-methylepigallocatechin on guinea pig ileum.Fitoterapia,2012,83(7):1286-1290
[29]Ghayur M,Gilani A,Khan A,et al.Presence of calcium antagonist activity explains the use of Syzygium samarangense in diarrhoea.Phytother Res,2006,20(1):49-52
[30]Nagai H,He J,Tani T,et al.Antispasmodic activity of licochalcone A,a species-specific ingredient of Glycyrrhiza inflata roots.J Pharm Pharmacol,2007,59(10):1421-1426
[31]Matsuda Y,Kase H,Asano K,et al.Isoflavone derivatives,JP60199396A.1985
[32]Borrelli F,Ascione V,Capasso R,et al.Spasmolytic effects of nonprenylated rotenoid constituents of Boerhaavia diffusa roots.J Nat Prod,2006,69(6):903-906
[33]Fusi F,Ferrara A,Koorbanally C,et al.Vascular myorelaxing activity of isolates from South African Hyacinthaceae partly mediated by activation of soluble guanylyl cyclase in rat aortic ring preparations.J Pharm Pharmacol,2008,60(4):489-497
[34]Dallmeier C,Carlini E.Pharmacology activity of eugenol derivatives.Cienc Cult,1980,32(Suppl):135-141
[35]Boegge S,Kesper S,Verspohl E,et al.Reduction of ACh-induced contraction of rat isolated ileum by coptisine,(+)-caffeoylmalic acid,Chelidonium majus,and Corydalis lutea extracts.Planta Med,1996,62(2):173-174
[36]Marcucci M,Ferreres F,Garcia-Viguera C,et al.Phenolic compounds from Brazilian propolis with pharmacological activities.J Ethnopharmacol,2001,74(2):105-112
[37]Aminov S,Vakhabov A.Pharmacology of some coumarins isolated from the plant Haplophyllum.Dokl Akad Nauk,1985(8):44-45
[38]Teng C,Yu S M,Chen C,et al.EDRF-release and Ca+(+)-channel blockade by magnolol,an antiplatelet agent isolated from Chinese herb Magnolia officinalis,in rat thoracic aorta.Life Sci,1990,47(13):1153-1161
[39]Campos M G,Oropeza M V,Villanueva T,et al.Xanthorrhizol induces endothelium-independent relaxation of rat thoracic aorta.Life Sci,2000,67(3):327-333
[40]Sarkar K,Tarafder P,Paul G.Bisphenol A inhibits duodenal movement ex vivo of rat through nitric oxide-mediated soluble guanylyl cyclase and alpha-adrenergic signaling pathways.J Appl Toxicol,2016,36(1):131-139
[41]Hayashi J,Sekine T,Deguchi S,et al.Phenolic compounds from Gastrodia rhizome and relaxant effects of related compounds on isolated smooth muscle preparation.Phytochem,2002,59(5):513-519
[42]Revuelta M,Cantabrana B,Hidalgo A.Transcriptional mechanisms involved in the relaxant effect of zeranol on isolated rat uterus.Gen Pharmacol,1997,28(4):561-565
[43]Mustafa M,Mohamad R,Din L,et al.Smooth muscle relaxant activities of compounds isolated from malaysian medicinal plants on rat aorta and guinea-pig ileum.Phytotherapy Res,1995,9(8):555-558
[44]Annahazi A,Roka R,Rosztoczy A,et al.Role of antispasmodics in the treatment of irritable bowel syndrome.World J Gastroenterol,2014,20(20):6031-6043
[45]Oztekin C,Gur S,Abdulkadir N,et al.Analysis of pomegranate juice components in rat corpora cavernosal relaxation.Int J Impot Res,2014,26(2):45-50
[46]Ponce-Monter H,Perez S,Zavala M,et al.Relaxant effect of xanthomicrol and 3alpha-angeloyloxy-2alpha-hydroxy-13,14zdehydrocativic acid from Brickellia paniculata on rat uterus.Biol Pharm Bull,2006,29(7):1501-1503
[47]Ogungbamila F,Samuelsson G.Smooth muscle relaxing flavonoids from Alchornea cordifolia.Acta Pharm Nord,1990,2(6):421-422
[48]王小红,张婵溪,李贵云,等.天然小分子酚的抗焦虑作用研究进展.中国中药杂志,2017,42(8):1557-1565