扁茎黄芪植株中化学成分的分离鉴定及其抑菌活性
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摘要
为综合开发利用药用植物扁茎黄芪Astragalus complanatus,对其非药用部位的化学成分及抑菌活性进行了初步研究。采用硅胶柱层析和LH-20凝胶层析技术从扁茎黄芪植株中分离鉴定了7个化合物,并测定了各化合物对8种细菌的抑菌活性。根据波谱分析结果,7个化合物分别被鉴定为β-谷甾醇(1)、β-sitostenone (2)、lawsaritol A (3)、3β-羟基-5α,8α-桥二氧麦角甾-6,22-二烯(4)、3′,7-二羟基-2′,4′-二甲氧基异黄烷(5)、D-1-O-甲基肌醇(6)和沙苑子苷(7),所有化合物均为首次从扁茎黄芪植株中分离得到。抑菌活性测定结果表明:化合物5对蜡状芽孢杆菌Bacillus cereus、大肠杆菌Escherichia coli、金黄色葡萄球菌Staphylococcus aureus、枯草芽孢杆菌Bacillus subtilis、白菜软腐病菌Erwinia carotovora、猕猴桃溃疡病菌Pseudomonas syringaepv.actinidiae和烟草青枯病菌Ralstonia solanacearum均有不同程度的抑制作用,其中对猕猴桃溃疡病菌、烟草青枯病菌和白菜软腐病菌的最低抑制浓度(MIC)分别为37.5、18.8和75.0μg/mL。3′,7-二羟基-2′,4′-二甲氧基异黄烷(5)的农用抑菌活性为首次报道。
For the comprehensive utilization of medicinal plant Astragalus complanatus, the chemical constituents of its the non-meidcinal parts and their antibacterial activities were investigated preliminarily. Seven compounds were isolated by using silica gel and LH-20 gel chromatography, and their antibacterial activities against 8 species of bacteria were evaulated. After spectrometric analysis,the obtained compounds were identified as β-sitosterol(1), β-sitostenone(2), lawsaritol A(3), 8-epidioxy-5α,8α-ergosta-6,22 E-dien-3β-ol(4), 3′,7-dihydroxy-2′,4′-dimethoxyisoflavan(5), D-1-Omethyl inositol(6) and complanatuside(7). All of the above compounds were isolated from the aerial parts of A. complanatus for the first time. Compound 5 showed inhibition effect on Bacillus cereus,Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Erwinia carotovora, Pseudomonas syringae pv. actinidiae and Ralstonia solanacearum, and the MIC values of compound 5 against three species of plant pathogenic bacteria, including P. syringae, R. solanacearum and E. carotovora, were 37.5, 18.8 and 75 μg/mL, respectively. To our best knowledge, this is the first report about the inhibition effect of5 on plant pathogenic bacteria.
For the comprehensive utilization of medicinal plant Astragalus complanatus, the chemical constituents of its the non-meidcinal parts and their antibacterial activities were investigated preliminarily. Seven compounds were isolated by using silica gel and LH-20 gel chromatography, and their antibacterial activities against 8 species of bacteria were evaulated. After spectrometric analysis,the obtained compounds were identified as β-sitosterol(1), β-sitostenone(2), lawsaritol A(3), 8-epidioxy-5α,8α-ergosta-6,22 E-dien-3β-ol(4), 3′,7-dihydroxy-2′,4′-dimethoxyisoflavan(5), D-1-Omethyl inositol(6) and complanatuside(7). All of the above compounds were isolated from the aerial parts of A. complanatus for the first time. Compound 5 showed inhibition effect on Bacillus cereus,Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Erwinia carotovora, Pseudomonas syringae pv. actinidiae and Ralstonia solanacearum, and the MIC values of compound 5 against three species of plant pathogenic bacteria, including P. syringae, R. solanacearum and E. carotovora, were 37.5, 18.8 and 75 μg/mL, respectively. To our best knowledge, this is the first report about the inhibition effect of5 on plant pathogenic bacteria.
引文
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[17]DITTRICH P, GIETL M, KANDLER O. D-1-O-methyl-mucoinositol in higher plants[J]. Phytochemistry, 1972, 11(1):245-250.
[18]毕志明,余庆涛,李萍,等.蒙古黄芪地上部分的黄酮类成分[J].中国天然药物, 2007, 5(4):263.BI ZM, YU QT, LI P, et al. Flavonoids from the aerial parts of Astragalus mongholicus[J]. Chin J Nat Med, 2007, 5(4):263.
[19]卢传礼,周光雄,王恒山,等.青天葵水溶性化学成分研究[J].时珍国医国药, 2010, 21(12):3087-3088.LU C L, ZHOU G X, WANG H S, et al. Water-soluble constituents from Nerviliae fordii[J]. Lishizhen Med Materia Medica Res, 2010,21(12):3087-3088.
[20]刘奇梅.沙苑子有效化学成分的提取分离及其药理活性的研究[D].广州:华南理工大学, 2013.LIU QM. Study on isolation and identification of active ingredient from Astragali complanati semen and its pharmacological activity[D].Guangzhou:South China University of Technology, 2013.
[21]李洪娟.沙苑子的化学成分研究[J].时珍国医国药, 2011, 22(3):545-546.LI H J. Chemical studies of seed of Astragalus complanatus[J].Lishizhen Med Materia Medica Res, 2011, 22(3):545-546.
[22]盛漪,华伟,谷文英.植物甾醇生理功能及其研究进展[J].西部粮油科技, 2003, 28(2):32-35.SHENG Y, HUA W, GU W Y. Research about the function of phytosterols[J]. China West Cereals Oils Technol, 2003, 28(2):32-35.
[2]田杏芳,赵平.扁茎黄芪[J].中国水土保持, 1989(4):29-30.TIAN X F, ZHAO P. Astragalus complantus[J]. Soil Water Conserv China, 1989(4):29-30.
[3]李昌勤.沙苑子化学成分及药理作用研究进展[J].时珍国医国药,2000, 11(11):1041-1042.LI CQ. Advances in research on chemical constituents and pharmacological effects of Astragali complanati semen[J]. Lishizhen Med Materia Medica Res, 2000, 11(11):1041-1042.
[4]刘春宇,顾振纶.沙苑子的化学成分和药理作用[J].中国野生植物资源, 2002, 21(2):1-3.LIU C Y, GU ZL. Chemical constituents and pharmacological effects of Astragali complanati semen[J]. Chin Wild Plant Resour, 2002,21(2):1-3.
[5]吴晓,刘银芳,刘春宇.沙苑子化学成分研究[J].安徽中医药大学学报, 2014, 33(3):91-94.WU X, LIU Y F, LIU C Y, et al. Study on chemical constituents of semen Astragali complanate[J]. J Anhui Univ Chin Med, 2014, 33(3):91-94.
[6]许梦莹,郭日新,张晓,等.沙苑子化学成分研究[J].中国中药杂志,2018, 43(7):1459-1466.XU M Y, GUO R X, ZHANG X, et al. Chemical constituents from seeds of Astragali complanati[J]. China J Chin Materia Medica, 2018,43(7):1459-1466.
[7]曾维才,谭敏,张佳琪,等.不同抑菌方法在食品防腐剂效果评价方面的比较[J].食品安全质量检测学报, 2010, 1(3):112-117.ZENG W C, TAN M, ZHANG J Q, et al. Effect of different inhibitory methods on the antimicrobial activity of preservative[J]. J Food Saf Qual, 2010, 1(3):112-117.
[8]祝瑞雪,曾维才,赵志峰,等.汉源花椒精油的化学成分分析及其抑菌作用[J].食品科学, 2011, 32(17):85-88.ZHU R X, ZENG W C, ZHAO Z F, et al. Chemical components and antibacterial activity of Hanyuan Zanthoxylum bungeanum seed oil[J].FoodSci, 2011, 32(17):85-88.
[9]侯文久,杨凤影,王维新.中草药对刺参腐皮综合症病原菌的抑菌试验[J].中国农学通报, 2013, 29(5):76-80.HOU W J, YANG F Y, WANG W X. In vitro bacteriostatic effect of Chinese herbs against causative pathogens of skin ulcer syndrome in sea cucumber Apostichopus japonicus[J]. Chin Agric Sci Bull, 2013,29(5):76-80.
[10]陈秀枢,屠涛.微量肉汤稀释法测定MIC的评价[J].中华医学检验杂志, 1994, 17(2):95-98.CHEN X S, TU T. A microdilution broth method for the minimum inhibitory concentration[J]. Chin J Med Lab Sci, 1994, 17(2):95-98.
[11]海力茜,张庆英,赵玉英,等.多序岩黄芪化学成分研究[J].中国中药杂志, 2004, 29(5):432-434.HAI L Q, ZHANGQ Y, ZHAO Y Y, et al. Studies on chemical constituents fromroot of Hedysarumpolybotrys[J]. China J Chin Materia Medica, 2004, 29(5):432-434.
[12]田敏卿,鲍光明,季乃云,等.红树林植物海漆中的三萜和甾体化合物[J].中国中药杂志, 2008, 33(4):405-408.TIAN M Q, BAO G M, JIN Y, et al. Triterpenoids and steroids from Excoecaria agallocha[J]. China J Chin Materia Medica, 2008, 33(4):405-408.
[13]GUPTAS, AL IM, ALAM M S, et al. Isolation and characterization of a dihydroxysterol from Lawsonia inermis[J]. Nat Prod Lett, 1994,4(3):195-201.
[14]HYBELBAUEROVáS, SEJBALJ, DRA?íNSKYM, et al. Chemical constituents of Stereum subtomentosumand two other birchassociated basidiomycetes:an interspecies comparative study[J].Chem Biodivers, 2008, 5(5):743-750.
[15]姜北,赵勤实,彭丽艳,等.雪茶化学成分研究[J].云南植物研究,2002, 24(4):525-530.JIANG B, ZHAO Q S, PENG L Y, et al. Constituents from Thamnolia vermicularis[J]. Acta Botanica Yunnanica, 2002, 24(4):525-530.
[16]HE Z Q, FINDLAY J A. Constituents of Astragalus membranaceus[J]. J Nat Prod, 1991, 54(3):810-815.
[17]DITTRICH P, GIETL M, KANDLER O. D-1-O-methyl-mucoinositol in higher plants[J]. Phytochemistry, 1972, 11(1):245-250.
[18]毕志明,余庆涛,李萍,等.蒙古黄芪地上部分的黄酮类成分[J].中国天然药物, 2007, 5(4):263.BI ZM, YU QT, LI P, et al. Flavonoids from the aerial parts of Astragalus mongholicus[J]. Chin J Nat Med, 2007, 5(4):263.
[19]卢传礼,周光雄,王恒山,等.青天葵水溶性化学成分研究[J].时珍国医国药, 2010, 21(12):3087-3088.LU C L, ZHOU G X, WANG H S, et al. Water-soluble constituents from Nerviliae fordii[J]. Lishizhen Med Materia Medica Res, 2010,21(12):3087-3088.
[20]刘奇梅.沙苑子有效化学成分的提取分离及其药理活性的研究[D].广州:华南理工大学, 2013.LIU QM. Study on isolation and identification of active ingredient from Astragali complanati semen and its pharmacological activity[D].Guangzhou:South China University of Technology, 2013.
[21]李洪娟.沙苑子的化学成分研究[J].时珍国医国药, 2011, 22(3):545-546.LI H J. Chemical studies of seed of Astragalus complanatus[J].Lishizhen Med Materia Medica Res, 2011, 22(3):545-546.
[22]盛漪,华伟,谷文英.植物甾醇生理功能及其研究进展[J].西部粮油科技, 2003, 28(2):32-35.SHENG Y, HUA W, GU W Y. Research about the function of phytosterols[J]. China West Cereals Oils Technol, 2003, 28(2):32-35.