7种黄檀属植物心材挥发油的成分分析及其抗菌活性
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摘要
为了研究7种黄檀属(Dalbergia L.)植物心材的挥发性成分及其抗菌活性,采用水蒸气蒸馏法提取黄檀属植物心材的挥发性成分,气相色谱-质谱联用技术(GC-MS)对其化学成分进行分析;采用滤纸片琼脂扩散法测定挥发性成分的抗菌活性。结果表明,两粤黄檀检出9种成分,占总含量的98.93%;斜叶黄檀检出6种成分,占总含量的91.80%;交趾黄檀检出13种成分,占总含量的86.23%;海南黄檀检出9种成分,占总含量的94.86%;降香黄檀检出8种成分,占总含量的97.38%;东京黄檀检出8种成分,占总含量的97.72%;白沙黄檀检出23种成分,占总含量的79.45%。两粤黄檀和斜叶黄檀相对百分含量最大的成分为榄香素,分别为83.38%和73.03%;交趾黄檀中相对百分含量最大的成分为美迪紫檀素,为27.72%;海南黄檀中相对百分含量最大的成分为亚油酸,为42.80%;降香黄檀和东京黄檀中相对百分含量最大的成分为(7R,10S)-2,6,10-三甲基-7,10-环氧-2,11-十二碳-6-醇及其同分异构体,二者之和分别为60.37%和53.23%;白沙黄檀中已鉴定出且相对百分含量较大的成分为榄香素,为7.81%。黄檀属植物心材挥发性成分主要有苯丙素类、倍半萜类、黄酮类、脂肪酸类和甾体等,黄檀属植物心材的挥发性成分均对金黄色葡萄球菌具有抑制作用,部分挥发油对不同的农业病原菌具有一定的抑制作用。本研究为黄檀属植物的资源保护和开发利用提供了科学依据。
The volatile constituents of the heartwood from seven different Dalbergia plants were extracted by the water distillation method, and further analyzed with GC-MS aiming to investigate the chemical constituents. The antibacterial activities of the volatile oils were assayed by the filter paper agar disc diffusion method. Nine components were detected from D. benthamii, accounting for 98.93% of the total content. Six components were detected from D. pinnata, accounting for 91.80% of the total content. Thirteen components were detected from D. cochinchinensis, accounting for86.23% of the total content. Nine components were detected from D. hainanensis, accounting for 94.86% of the total content. Eight components were detected from D. odorifera, accounting for 97.38% of the total content. Eight components were detected from D. tonkinensis, accounting for 97.72% of the total content. 23 components were detected from D. peishaensis, accounting for 79.45% of the total content. Elemicin was the highest component with relative percentage content in D. benthamii and D. pinnata, 83.38% and 73.03% respectively. The highest component of D. cochinchinensis was medicarpin with a value of 27.72%. The highest component of D. hainanensis was linoleic acid with a value42.80%. The highest component of D. odorifera and D. tonkinensis was(7 R,10 S)-2,6,10-trimethyl-7,10-epoxy-2,11-dodecadien-6-ol and its isomer, with values of 60.37% and 52.23% respectively. The component identified and with relatively high content of D. peishaensis was elemicin with a value of 7.81%. The phenylpropanoid compounds, sesquiterpenoids, flavonoids, fatty acids, and steroids etc. were the main components of the volatile constituents from the heartwood of Dalbergia plants. All volatile oils from the heartwood of Dalbergia plants exhibited an inhibitory effect on Staphylococcus aureus, and some also had certain inhibitory effects on different agricultural pathogens. This research could provide a scientific basis for the resource conservation and exploitation of Dalbergia plants.
The volatile constituents of the heartwood from seven different Dalbergia plants were extracted by the water distillation method, and further analyzed with GC-MS aiming to investigate the chemical constituents. The antibacterial activities of the volatile oils were assayed by the filter paper agar disc diffusion method. Nine components were detected from D. benthamii, accounting for 98.93% of the total content. Six components were detected from D. pinnata, accounting for 91.80% of the total content. Thirteen components were detected from D. cochinchinensis, accounting for86.23% of the total content. Nine components were detected from D. hainanensis, accounting for 94.86% of the total content. Eight components were detected from D. odorifera, accounting for 97.38% of the total content. Eight components were detected from D. tonkinensis, accounting for 97.72% of the total content. 23 components were detected from D. peishaensis, accounting for 79.45% of the total content. Elemicin was the highest component with relative percentage content in D. benthamii and D. pinnata, 83.38% and 73.03% respectively. The highest component of D. cochinchinensis was medicarpin with a value of 27.72%. The highest component of D. hainanensis was linoleic acid with a value42.80%. The highest component of D. odorifera and D. tonkinensis was(7 R,10 S)-2,6,10-trimethyl-7,10-epoxy-2,11-dodecadien-6-ol and its isomer, with values of 60.37% and 52.23% respectively. The component identified and with relatively high content of D. peishaensis was elemicin with a value of 7.81%. The phenylpropanoid compounds, sesquiterpenoids, flavonoids, fatty acids, and steroids etc. were the main components of the volatile constituents from the heartwood of Dalbergia plants. All volatile oils from the heartwood of Dalbergia plants exhibited an inhibitory effect on Staphylococcus aureus, and some also had certain inhibitory effects on different agricultural pathogens. This research could provide a scientific basis for the resource conservation and exploitation of Dalbergia plants.
引文
[1]成俊卿,李秾,孙成志,等.中国热带及亚热带木材识别、材性和利用[M].北京:科学出版社,1980:258-262.
[2]Flora of China Editorial Board.Dalbergia[M].Beijing:Sciences Press,2010,10:121-130.
[3]国家药典编委会.中华人民共和国药典:一部[M].北京:中国医药科技出版社,2015:229-230.
[4]赵惠玲,韦建华.黄檀属植物化学成分和药理活性研究进展[J].中国民族民间医药,2018,27(5):40-47.
[5]Kahlert M,Albert R L,Anttila E L,et al.In vitro Assessment of antioxidant activity of Dalbergia latifolia barks extract against free radicals[J].European Geriatric Medicine,2014,5(7):188-194.
[6]Lee D S,Li B,Im N K,et al.4,2,5'-trihydroxy-4'-methoxychalcone from Dalbergia odorifera exhibits anti-inflammatory properties by inducing heme oxygenase-1 in murine macrophages[J].International Immunopharmacology,2013,16(1):114-121.
[7]Zhao X B,Mei W L,Gong M F,et al.Antibacterial activity of the flavonoids from Dalbergia odorifera on Ralstonia solanacearum[J].Molecules,2011,16(12):9775-9782.
[8]Koma O S,Sani I M.Betulinic acid from antimicrobial root wood extract of Dalbergia saxatilis Hook f.(Fabaceae)[J].European Journal of Medicinal Plants,2014,4(6):686-694.
[9]Wang H,Dong W H,Zuo W J,et al.Five new sesquiterpenoids from Dalbergia odorifera[J].Fitoterapia,2014,95:16-21.
[10]王昊,梅文莉,郭志凯,等.降香的化学成分研究[J].中国中药杂志,2014,39(9):1625-1629.
[11]Kiran V P,Neeraj S V,Vilas K M,et al.Effect of Dalbergia sissoo Roxb.on dexamethasone-induced insulin resistance in mice[J].Inventi Impact Ethnopharmacology,2012(1):13-15.
[12]王辉,梅文莉,赵夏博,等.降香檀的化学成分与药理活性研究进展[J].中国民族民间医药,2011,20(10):20-22.
[13]王秀丽,赵保胜.降香挥发油大鼠体内HPLC测定方法的建立[J].中国实验方剂学杂志,2010,16(1):51-52.
[14]赵夏博,梅文莉,龚明福,等.降香挥发油的化学成分及抗菌活性[J].广东农业科学,2012,3:95-96,99.
[15]郭丽冰,王蕾.降香中黄酮类化学成分研究[J].中草药,2008(8):1147-1149.
[16]王昊,梅文莉,杨德兰,等.降香中的酚性化合物[J].天然产物研究与开发,2014,26(6):856-859.
[17]Wang H,Dong W H,Zuo W J,et al.Three new phenolic compounds from Dalbergia odorifera[J].Journal of Asian Natural Products Research,2014,16(12),1109-1118.
[18]Wang H,Mei W L,Zeng Y B,et al.Phenolic compounds from Dalbergia odorifera[J].Phytochemistry Letters,2014,9:168-173.
[19]Goda Y,Kiuchi F,Shibuya M.Inhibitors of prostaglandin biosynthesis from Dalbergia odorifera[J].Chemical&Pharmaceutical Bulletin,1992,40(9):2452-2457.
[20]Chan S C,Chang Y S,Wang J P.Three new flavoanids and antiallergic,Anti-Inflammatory constituents form the heartwood of Dalbergia odorifera[J].Planta Medica,1998,64(2):153-158.
[21]Wang W,Weng X C,Cheng D L.Antioxidant activities of natural phenolic components from Dalbergia T.Chen[J].Food Chemistry,2000,71(1):45-49.
[22]Yu X L,Wang W,Yang M.Antioxidant activities of compounds isolated from Dalbergia odorifera T.Chen and their inhibition effects on the decrease of glutathione level of rat lens induced by UV irradiation[J].Food Chemistry,2007,104(2):715-720.
[23]余锟,尚孝堂,王大英.“药对”降香、红景天对心肌梗死后大鼠非梗死区胶原改建的影响[J].甘肃中医,2007,20(11):54-55.
[24]Yu S M,Kuo S C.Vasorelaxant effect of isoliquiritigenin,a novel soluble guany Late cyclase activator,in rat aorta[J].British Journal of Pharmacology,2012,114(8):1587-1594.
[25]Kim N.Butein sensitizes human leukemia cells to apoptosis induced by tumor necrosis factorrelated apoptosis inducing ligand(TRAIL)[J].Archives of Pharmacal Research,2008,31(9):1179.
[26]霍丽妮,刘华钢,廖艳芳,等.两粤黄檀体外抗氧化及α-葡萄糖苷酶抑制活性研究[J].江苏农业科学,2014,42(5):242-244.
[27]赵维波,张丹雁,徐展翅,等.斜叶黄檀香材挥发油成分及抗氧化活性研究[J].中药新药与临床药理,2017,28(5):659-662.
[28]Pornputtapitak W.Chemical constituents of the branches of Anomianthus dulcis and the branches of Dalbergia cochinchinensis Pierre[D].Bangkok:Silpakorn University,2008.
[29]刘荣华,温新潮,李于益,等.交趾黄檀化学成分研究[J].中药材,2015a,38(9):1868-1871.
[30]刘荣华,温新潮,张普照,等.交趾黄檀异黄酮类化学成分研究[J].中草药,2015,46(19):2851-2855.
[31]刘喜明,马景蕃,陈瑞英.交趾黄檀的化学特性研究[J].龙岩学院学报,2016,34(5):112-116.
[32]Nguyen M C,Ngu T N,Ninh T S,et al.Daltonkins A and B,two new carboxyethyl flavanones from the heartwood of Dalbergia tonkinensis[J].Bulletin Korean Chemical Society,2017,38(12):1511-1514.
[33]Ninh T S,Tsuyoshi Y,Yoshiyasu F.Chemotaxonomic aspects of the constituents of the plant Dalbergia tonkinensis[J].Biochemical Systematics and Ecology,2018,78:98-101.
[34]张培成,毋艳,于德泉.海南黄檀化学成分研究[J].中国中药杂志,2003,28(6):527-530.
[35]徐淑云,卞如濂,陈修.药理实验方法学[M].北京:人民卫生出版社,2003:651.
[36]刘洪玲.GC-MS法分析降香挥发油化学成分[J].中成药,2009,31(6):915-917.
[37]纪明慧,舒火明,陈光英,等.花梨木挥发油的提取及其包合物研究[J].中成药,2009,31(10):1526-1530.
[38]Rossi P G,Bao L,Anne L A,et al.(E)-Methylisoeugenol and elemicin:Antibacterial components of Daucus carota L.essential oil against Campylobacter jejuni[J].Journal of Agricultural and Food Chemistry,2007,55(18):7332-7336.
[39]Jayasinghe L,Kumarihamy B M M,Jayarathna K H R N,et al.Antifungal constituents of the stem bark of Bridelia retusa[J].Phytochemistry,2003,62(4):637-641.
[40]Grice I D,Rogers K L,Griffiths L R.Isolation of bioactive compounds that relate to the anti-platelet activity of Cymbopogon ambiguous[J].Evidence-based Complementary and Alternative Medicine,2010,2011(11):1-8.
[41]Jail H,Wan W K,Ro L K,et al.Inhibition of proinflammatory cytokine generation in lung inflammation by the leaves of Perilla frutescens and its constituents[J].Biomolecules and Therapeutics,2014,22(1):62-67.
[42]周慧秋,于滨,乔婉红,等.甲基丁香酚药理作用研究[J].中医药学报,2000,(2):79-80.
[43]Masson E,Baumes R,Guerneve C L,et al.Identification of a precursor ofβ-methyl-γ-octalatone in the wood of sessile Oak(Quercus petraea(Matt.)Liebl)[J].Journal of Agricultural and Food Chemistry,2000,48(9):4306-4309.
[44]Bhargavan B,Singh D,Gautam A K,et al.Medicarpin,a legume phytoalexin,stimulates osteoblast differentiation and promotes peak bone mass achievement in rats:evidence for estrogen receptorβ-mediated osteogenic action of medicarpin[J].Journal Nutritional Biochemistry,2012,23:27-38.
[45]石荣火.刺果甘草化学成分及抗肿瘤活性研究[D].南京:南京中医药大学,2001.
[46]Rayanil K O,Bunchornmaspan P,Tuntiwachwuttikul P.Anew phenolic compound with anticancer activity from the wood of Millettia leucantha[J].Archives of Pharmacal Research,2011,34(6):881-886.
[47]Gatouillat G,Magid A A,Bertin E,et al.Cytotoxicity and apoptosis induced by Alfalfa(Medicago sativa)leaf extracts in sensitive and multidrug-resistant tumor cells[J].Nutrition and Cancer,2014,66(3):483-491.
[48]黎雄.资源植物朝鲜槐的化学成分、生物活性及其质量控制研究[D].沈阳:沈阳药科大学,2011.
[49]张春娥,张惠,刘楚怡,等.亚油酸的研究进展[J].粮油加工,2010(5):18-21.
[50]王威,曹翠平,陈颖,等.棕榈酸诱导胰岛素瘤细胞MIN6细胞凋亡[J].基础医学与临床,2010,30(4):401-405.
[51]张晶晶,孔凡青,李嘉欣,等.棕榈酸对胰岛MIN6细胞胰岛素成熟的影响[J].动物医学进展,2013,34(2):44-48.
[52]张丹,曹翠平,王威,等.棕榈酸诱导大鼠主动脉内皮细胞凋亡[J].中国现代医学杂志,2012,22(8):19-22.
[2]Flora of China Editorial Board.Dalbergia[M].Beijing:Sciences Press,2010,10:121-130.
[3]国家药典编委会.中华人民共和国药典:一部[M].北京:中国医药科技出版社,2015:229-230.
[4]赵惠玲,韦建华.黄檀属植物化学成分和药理活性研究进展[J].中国民族民间医药,2018,27(5):40-47.
[5]Kahlert M,Albert R L,Anttila E L,et al.In vitro Assessment of antioxidant activity of Dalbergia latifolia barks extract against free radicals[J].European Geriatric Medicine,2014,5(7):188-194.
[6]Lee D S,Li B,Im N K,et al.4,2,5'-trihydroxy-4'-methoxychalcone from Dalbergia odorifera exhibits anti-inflammatory properties by inducing heme oxygenase-1 in murine macrophages[J].International Immunopharmacology,2013,16(1):114-121.
[7]Zhao X B,Mei W L,Gong M F,et al.Antibacterial activity of the flavonoids from Dalbergia odorifera on Ralstonia solanacearum[J].Molecules,2011,16(12):9775-9782.
[8]Koma O S,Sani I M.Betulinic acid from antimicrobial root wood extract of Dalbergia saxatilis Hook f.(Fabaceae)[J].European Journal of Medicinal Plants,2014,4(6):686-694.
[9]Wang H,Dong W H,Zuo W J,et al.Five new sesquiterpenoids from Dalbergia odorifera[J].Fitoterapia,2014,95:16-21.
[10]王昊,梅文莉,郭志凯,等.降香的化学成分研究[J].中国中药杂志,2014,39(9):1625-1629.
[11]Kiran V P,Neeraj S V,Vilas K M,et al.Effect of Dalbergia sissoo Roxb.on dexamethasone-induced insulin resistance in mice[J].Inventi Impact Ethnopharmacology,2012(1):13-15.
[12]王辉,梅文莉,赵夏博,等.降香檀的化学成分与药理活性研究进展[J].中国民族民间医药,2011,20(10):20-22.
[13]王秀丽,赵保胜.降香挥发油大鼠体内HPLC测定方法的建立[J].中国实验方剂学杂志,2010,16(1):51-52.
[14]赵夏博,梅文莉,龚明福,等.降香挥发油的化学成分及抗菌活性[J].广东农业科学,2012,3:95-96,99.
[15]郭丽冰,王蕾.降香中黄酮类化学成分研究[J].中草药,2008(8):1147-1149.
[16]王昊,梅文莉,杨德兰,等.降香中的酚性化合物[J].天然产物研究与开发,2014,26(6):856-859.
[17]Wang H,Dong W H,Zuo W J,et al.Three new phenolic compounds from Dalbergia odorifera[J].Journal of Asian Natural Products Research,2014,16(12),1109-1118.
[18]Wang H,Mei W L,Zeng Y B,et al.Phenolic compounds from Dalbergia odorifera[J].Phytochemistry Letters,2014,9:168-173.
[19]Goda Y,Kiuchi F,Shibuya M.Inhibitors of prostaglandin biosynthesis from Dalbergia odorifera[J].Chemical&Pharmaceutical Bulletin,1992,40(9):2452-2457.
[20]Chan S C,Chang Y S,Wang J P.Three new flavoanids and antiallergic,Anti-Inflammatory constituents form the heartwood of Dalbergia odorifera[J].Planta Medica,1998,64(2):153-158.
[21]Wang W,Weng X C,Cheng D L.Antioxidant activities of natural phenolic components from Dalbergia T.Chen[J].Food Chemistry,2000,71(1):45-49.
[22]Yu X L,Wang W,Yang M.Antioxidant activities of compounds isolated from Dalbergia odorifera T.Chen and their inhibition effects on the decrease of glutathione level of rat lens induced by UV irradiation[J].Food Chemistry,2007,104(2):715-720.
[23]余锟,尚孝堂,王大英.“药对”降香、红景天对心肌梗死后大鼠非梗死区胶原改建的影响[J].甘肃中医,2007,20(11):54-55.
[24]Yu S M,Kuo S C.Vasorelaxant effect of isoliquiritigenin,a novel soluble guany Late cyclase activator,in rat aorta[J].British Journal of Pharmacology,2012,114(8):1587-1594.
[25]Kim N.Butein sensitizes human leukemia cells to apoptosis induced by tumor necrosis factorrelated apoptosis inducing ligand(TRAIL)[J].Archives of Pharmacal Research,2008,31(9):1179.
[26]霍丽妮,刘华钢,廖艳芳,等.两粤黄檀体外抗氧化及α-葡萄糖苷酶抑制活性研究[J].江苏农业科学,2014,42(5):242-244.
[27]赵维波,张丹雁,徐展翅,等.斜叶黄檀香材挥发油成分及抗氧化活性研究[J].中药新药与临床药理,2017,28(5):659-662.
[28]Pornputtapitak W.Chemical constituents of the branches of Anomianthus dulcis and the branches of Dalbergia cochinchinensis Pierre[D].Bangkok:Silpakorn University,2008.
[29]刘荣华,温新潮,李于益,等.交趾黄檀化学成分研究[J].中药材,2015a,38(9):1868-1871.
[30]刘荣华,温新潮,张普照,等.交趾黄檀异黄酮类化学成分研究[J].中草药,2015,46(19):2851-2855.
[31]刘喜明,马景蕃,陈瑞英.交趾黄檀的化学特性研究[J].龙岩学院学报,2016,34(5):112-116.
[32]Nguyen M C,Ngu T N,Ninh T S,et al.Daltonkins A and B,two new carboxyethyl flavanones from the heartwood of Dalbergia tonkinensis[J].Bulletin Korean Chemical Society,2017,38(12):1511-1514.
[33]Ninh T S,Tsuyoshi Y,Yoshiyasu F.Chemotaxonomic aspects of the constituents of the plant Dalbergia tonkinensis[J].Biochemical Systematics and Ecology,2018,78:98-101.
[34]张培成,毋艳,于德泉.海南黄檀化学成分研究[J].中国中药杂志,2003,28(6):527-530.
[35]徐淑云,卞如濂,陈修.药理实验方法学[M].北京:人民卫生出版社,2003:651.
[36]刘洪玲.GC-MS法分析降香挥发油化学成分[J].中成药,2009,31(6):915-917.
[37]纪明慧,舒火明,陈光英,等.花梨木挥发油的提取及其包合物研究[J].中成药,2009,31(10):1526-1530.
[38]Rossi P G,Bao L,Anne L A,et al.(E)-Methylisoeugenol and elemicin:Antibacterial components of Daucus carota L.essential oil against Campylobacter jejuni[J].Journal of Agricultural and Food Chemistry,2007,55(18):7332-7336.
[39]Jayasinghe L,Kumarihamy B M M,Jayarathna K H R N,et al.Antifungal constituents of the stem bark of Bridelia retusa[J].Phytochemistry,2003,62(4):637-641.
[40]Grice I D,Rogers K L,Griffiths L R.Isolation of bioactive compounds that relate to the anti-platelet activity of Cymbopogon ambiguous[J].Evidence-based Complementary and Alternative Medicine,2010,2011(11):1-8.
[41]Jail H,Wan W K,Ro L K,et al.Inhibition of proinflammatory cytokine generation in lung inflammation by the leaves of Perilla frutescens and its constituents[J].Biomolecules and Therapeutics,2014,22(1):62-67.
[42]周慧秋,于滨,乔婉红,等.甲基丁香酚药理作用研究[J].中医药学报,2000,(2):79-80.
[43]Masson E,Baumes R,Guerneve C L,et al.Identification of a precursor ofβ-methyl-γ-octalatone in the wood of sessile Oak(Quercus petraea(Matt.)Liebl)[J].Journal of Agricultural and Food Chemistry,2000,48(9):4306-4309.
[44]Bhargavan B,Singh D,Gautam A K,et al.Medicarpin,a legume phytoalexin,stimulates osteoblast differentiation and promotes peak bone mass achievement in rats:evidence for estrogen receptorβ-mediated osteogenic action of medicarpin[J].Journal Nutritional Biochemistry,2012,23:27-38.
[45]石荣火.刺果甘草化学成分及抗肿瘤活性研究[D].南京:南京中医药大学,2001.
[46]Rayanil K O,Bunchornmaspan P,Tuntiwachwuttikul P.Anew phenolic compound with anticancer activity from the wood of Millettia leucantha[J].Archives of Pharmacal Research,2011,34(6):881-886.
[47]Gatouillat G,Magid A A,Bertin E,et al.Cytotoxicity and apoptosis induced by Alfalfa(Medicago sativa)leaf extracts in sensitive and multidrug-resistant tumor cells[J].Nutrition and Cancer,2014,66(3):483-491.
[48]黎雄.资源植物朝鲜槐的化学成分、生物活性及其质量控制研究[D].沈阳:沈阳药科大学,2011.
[49]张春娥,张惠,刘楚怡,等.亚油酸的研究进展[J].粮油加工,2010(5):18-21.
[50]王威,曹翠平,陈颖,等.棕榈酸诱导胰岛素瘤细胞MIN6细胞凋亡[J].基础医学与临床,2010,30(4):401-405.
[51]张晶晶,孔凡青,李嘉欣,等.棕榈酸对胰岛MIN6细胞胰岛素成熟的影响[J].动物医学进展,2013,34(2):44-48.
[52]张丹,曹翠平,王威,等.棕榈酸诱导大鼠主动脉内皮细胞凋亡[J].中国现代医学杂志,2012,22(8):19-22.
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