马尾松松针挥发油化学成分及抗氧化活性研究
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摘要
采用水蒸气蒸馏法提取马尾松松针挥发油,利用气相色谱-质谱联用(GC-MS)对挥发油进行化学成分分析,并以DPPH自由基、ABTS自由基、超氧阴离子自由基的清除能力以及总还原力为评价指标,研究其抗氧化作用。结果表明,从马尾松松针挥发油中共分离鉴定出了34种化合物,其相对质量分数占挥发油总量的95.76%,主要化合物为石竹烯(15. 85%)、α-杜松醇(12. 12%)、大根香叶烯B(10. 81%)、β-古巴烯(7.94%)、1(10),4-杜松二烯(6.65%)、γ-依兰油烯(6.01%)、蛇麻烯(5.82%)和β-瑟林烯(3.63%)等。马尾松松针挥发油具有较强的抗氧化活性,DPPH自由基、ABTS自由基、超氧阴离子自由基的清除能力以及总还原力随挥发油质量浓度的增加而增强;DPPH自由基、ABTS自由基、超氧阴离子自由基的半数清除率IC_(50)值分别为5.16、5.47、4.34 mg/mL。通过本试验证实,马尾松松针挥发油作为天然抗氧化剂具有较大的开发潜质。
The volatile oil from masson pine needles has been extracted by steam distillation and the chemical component of the volatile oil has been analyzed by GC-MS. The antioxidant effect of the volatile oil was explored with DPPH free radicals, ABTS free radicals, super-oxide anion free radical(O_2~-) and total reducing power being the indicators. The results showed that the optimal extraction process is as follows: thirty-four compounds are identified by GC-MS technique, accounting for 95. 76% of total peak area. The major compounds in masson pine needles were caryophyllene(15.85%), a-terpineol(12.12%), Germacrene B(10. 81%), β-copaene(7.94%), Cadina-1(10), 4-dien(6. 65%), γ-Muurolene(6. 01%), Humulene(5. 82%), and β-Selinene(3. 63%)etc. The volatile oil exhibited strong antioxidant activity capacity and the DPPH fee radicals, ABTS free radicals, super-oxide anion free radical( O_2~-) scavenging abilities and total reducing power will grow as the increment of the concentrations of volatile oil. The half elimination IC_(50) o of DPPH, ABTS and super-oxide anion free radicals was50%, were 5. 16, 5. 47 and 4. 34 mg/mL, respectively. These results suggest that the essential oil from masson pine needles has potential to be used as a natural antioxidant agent in food processing.
The volatile oil from masson pine needles has been extracted by steam distillation and the chemical component of the volatile oil has been analyzed by GC-MS. The antioxidant effect of the volatile oil was explored with DPPH free radicals, ABTS free radicals, super-oxide anion free radical(O_2~-) and total reducing power being the indicators. The results showed that the optimal extraction process is as follows: thirty-four compounds are identified by GC-MS technique, accounting for 95. 76% of total peak area. The major compounds in masson pine needles were caryophyllene(15.85%), a-terpineol(12.12%), Germacrene B(10. 81%), β-copaene(7.94%), Cadina-1(10), 4-dien(6. 65%), γ-Muurolene(6. 01%), Humulene(5. 82%), and β-Selinene(3. 63%)etc. The volatile oil exhibited strong antioxidant activity capacity and the DPPH fee radicals, ABTS free radicals, super-oxide anion free radical( O_2~-) scavenging abilities and total reducing power will grow as the increment of the concentrations of volatile oil. The half elimination IC_(50) o of DPPH, ABTS and super-oxide anion free radicals was50%, were 5. 16, 5. 47 and 4. 34 mg/mL, respectively. These results suggest that the essential oil from masson pine needles has potential to be used as a natural antioxidant agent in food processing.
引文
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[11]XIE Q, LIU Z H, LI Z Q. Chemical composition and antioxidant activity of essential oil of six Pinus Taxa Native to China[J]. Molecules, 2015, 20(5):9380-9392
[12]刘力恒,王立升,冯丹丹,等.马尾松和湿地松松针挥发性成分的提取及GC-MS比较分析[J].分析试验室,2008, 27(11):75-80LIU L H, WANG L S, FENG D D, et al. Extraction and comparison analysis of volatile constituents of leaves from pinus massoniana lamb needles and pinus elliottii engelm needles by GC-MS[J]. Chinese Journal of analysis laboratory, 2008, 27(11):75-80
[13]李军集,周丽珠,聂永雄,等.马尾松土贡种源松针挥发油化学成分GC/MS分析[J].西部林业科学,2014,43(3):27-30LI J J, ZHOU L Z, NIE Y X, et al. Analysis of chemical composition of pine needle oil from Pinus massoniana Tugong Provenance[J]. Journal of West China Forestry Science, 2014, 43(3):27-30
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[15]樊梓鸾,张艳东,张华,等.红松松针精油抗氧化和抑菌活性研究[J].北京林业大学学报,2017, 39(8):98-103FAN Z L, ZHANG Y D, ZHANG H, et al. Antioxidant and antibacterial activity of essential oil from Pinus koraiensis needles[J]. Journal of Beijing Forestry University, 2017,39(8):98-103
[16]刘荣,辛越,姚美玲,等.稠李属3种果实花色苷的抗氧化活性[J].食品与发酵工业,2012, 38(3):73-76LIU R, XIN Y, YAO M L. Study on antioxidant activity of anthocyanins extracted from three kinds of Padus Mill fruits[J]. Food and Fermentation Industries, 2012, 38(3):73-76
[17] ADSARES R, BELLARY A N, SOWBHAGYA H B, et al.Osmotic treatment for the impregnation of anthocyanin in candies from Indian gooseberry(Emblica officinalis)[J].Journal of Food Engineering, 2016, 175:24-32
[18]薛婷婷,臧华玉,李娟,等.桂花挥发油体外抗氧化活性研究[J].中国调味品,2014, 18-20XUE T T, ZANG H Y, LI J, et al. Antioxidant activity of volatile oil from Osmanthus fragransin vitro[J]. China Condiment, 2014, 18-20
[19]杨俊杰,王海燕,张耀洲.水杉种子中总黄酮含量及其清除自由基能力分析[J].湖北农业科学,2013, 52(2):423-424YANG J J, WANG H Y,ZHANG Y Z. Determination of total flavonoids in the seed of Metasequoia glyptostroboides and its anti-radical efficiency[J]. Hubei Agricultural Sciences, 2013, 52(2):423-424
[20]刘婷,厍文波,王婷,等.水蒸气蒸馏和超临界萃取薰衣草精油抗氧化作用研究[J].时珍国医国药,2009,20(12):3035-3037LIU T, SHE W B, WANG T, et al. Study on the antioxidative activity of lavender oil extracted by steam distillationand supercritical extraction[J]. Lishizhen Medicine and Materia Medica Research, 2009, 20(12):3035-3037
[21]丁海麦,李彩艳,孔凡青,等.内蒙古包头3种常食用葡萄抗氧化活性的研究[J].安徽农业科学,2010, 38(6):2945-2946DING H M, LI C Y, KONG F Q,et al. Radical scavenging activity of three kinds of grape in Baotou Inner Mongolia[J]. Journal of Anhui Agriculture Sciences, 2010, 38(6):2945-2946
[22]PASTOR J, GARCIA M, STEINBAUER S,et al. Combinations of ascaridole, carvacrol, and caryophyllene oxide against Leishmania[J]. Acta Tropic, 2015, 145:31-38
[23]PAN Z, WANG S K, CHENG X L, et al. Caryophyllene oxide exhibits anti-cancer effects in MG-63 human osteosarcoma cells via the inhibition of cell migration, generation of reactive oxygen species and induction of apoptosis[J].Bangladesh Journal of Pharmacology, 2016, 11(4):817-823
[24]YU B, ZHANG D, YAN X W, et al. Comparative evaluation of the chemical composition, antioxidant and antimicrobial activities of the volatile oils of Hawk tea from six botanical origins[J]. Chemistry&Biodiversity, 2016, 13(11):1573-1583
[25]PARVARDEH S, MOGHIMI M, ESLAMI P, et al. a-Terpineol attenuates morphine-induced physical dependence and tolerance in mice:role of nitric oxide[J]. Iranian Journal of Basic Medical Sciences, 2016, 19(2):201-208.
[2] YU L, ZHAO M, WANG J S, et al. Antioxidant, immunomodulatory and anti-breast cancer activities of phenolic extract from pine(Pinus massoniana Lamb)bark[J]. Innovative Food Science&Emerging Technologies, 2008, 9(1):122-128
[3]XU R B, YANG X, WANG J, et al. Chemical composition and antioxidant activities of three polysaccharide fractions from pine cones[J]. International Journal of Molecular Sciences, 2012, 13(11):14262-14277
[4]王好运,吴峰,吴昌明,等.马尾松不同叶型幼苗对干旱及复水的生长及生理响应[J].东北林业大学,2018, 46(1):1-6WANG H Y, WU F, WU C M, et al. Growth and physiological responses of seedlings with different leaf shapes to drought and re-watering in Pinus Massoniana[J]. Journal of Northeast Forestry University, 2018, 46(1):1-6
[5]张海涛,宫渊波,付万权,等.马尾松低效人工林不同改造模式下降雨及产流特征[J].浙江农林大学学报,2018, 35(1):29-34ZHANG H T, GONG Y B, FU W Q, et al. Rainfall and run off in low efficiency Pinus massoniana forests with different silvicultural prescriptions[J]. Journal of Zhejiang A&F University, 2018, 35(1):29-34
[6] DENG H, HONG T,WU C, et al. Application of endophytic fungi isolated from Pinus massoniana lamb. in resin tapping[J]. Bangladesh Journal of Botany, 2015, 44(5):753-758
[7] WANG S,WANG P, FAN C Q. Distribution of aluminum fractionation in the acidic rhizosphere soils of masson Pine(Pinus massoniana Lamb)[J]. Communications in Soil Science&Plant Analysis, 2015, 46(16):2033-2050
[8]LI X J, DONG G P, FANG J M, et al. Comparison of volatile organic compounds from uninfested and monochamus alternatus hope infested Pinus massoniana Lamb[J]. Entomological Research, 2017, 47(3):203-207
[9]XIAO Y C, YE L, ZHAO M X, et al. Two new sesquiterpene glycosides isolated from the fresh needles of Pinus massoniana Lamb[J]. Natural Product Research, 2017, 31(3):341-346
[10]QUAN W X, DING G. Root tip structure and volatile organic compound responses to drought stress in Masson pine(Pinus massoniana Lamb.)[J]. Acta Physiologiae Plantarum, 2017, 39(12):258-266
[11]XIE Q, LIU Z H, LI Z Q. Chemical composition and antioxidant activity of essential oil of six Pinus Taxa Native to China[J]. Molecules, 2015, 20(5):9380-9392
[12]刘力恒,王立升,冯丹丹,等.马尾松和湿地松松针挥发性成分的提取及GC-MS比较分析[J].分析试验室,2008, 27(11):75-80LIU L H, WANG L S, FENG D D, et al. Extraction and comparison analysis of volatile constituents of leaves from pinus massoniana lamb needles and pinus elliottii engelm needles by GC-MS[J]. Chinese Journal of analysis laboratory, 2008, 27(11):75-80
[13]李军集,周丽珠,聂永雄,等.马尾松土贡种源松针挥发油化学成分GC/MS分析[J].西部林业科学,2014,43(3):27-30LI J J, ZHOU L Z, NIE Y X, et al. Analysis of chemical composition of pine needle oil from Pinus massoniana Tugong Provenance[J]. Journal of West China Forestry Science, 2014, 43(3):27-30
[14]叶强,李生茂,敖慧,等.不同产地绿壳砂仁挥发油组分比较[J].中成药,2014, 36(5):1033-1037YE Q, LI S M, AO H, et al. Comparison of the compositions in volatile oil from Amomum villosum Lour. var. xanthioides T. L. Wu et senjen from different habitats[J]. Chinese Traditional Patent Medicine, 2014, 36(5):1033-1037
[15]樊梓鸾,张艳东,张华,等.红松松针精油抗氧化和抑菌活性研究[J].北京林业大学学报,2017, 39(8):98-103FAN Z L, ZHANG Y D, ZHANG H, et al. Antioxidant and antibacterial activity of essential oil from Pinus koraiensis needles[J]. Journal of Beijing Forestry University, 2017,39(8):98-103
[16]刘荣,辛越,姚美玲,等.稠李属3种果实花色苷的抗氧化活性[J].食品与发酵工业,2012, 38(3):73-76LIU R, XIN Y, YAO M L. Study on antioxidant activity of anthocyanins extracted from three kinds of Padus Mill fruits[J]. Food and Fermentation Industries, 2012, 38(3):73-76
[17] ADSARES R, BELLARY A N, SOWBHAGYA H B, et al.Osmotic treatment for the impregnation of anthocyanin in candies from Indian gooseberry(Emblica officinalis)[J].Journal of Food Engineering, 2016, 175:24-32
[18]薛婷婷,臧华玉,李娟,等.桂花挥发油体外抗氧化活性研究[J].中国调味品,2014, 18-20XUE T T, ZANG H Y, LI J, et al. Antioxidant activity of volatile oil from Osmanthus fragransin vitro[J]. China Condiment, 2014, 18-20
[19]杨俊杰,王海燕,张耀洲.水杉种子中总黄酮含量及其清除自由基能力分析[J].湖北农业科学,2013, 52(2):423-424YANG J J, WANG H Y,ZHANG Y Z. Determination of total flavonoids in the seed of Metasequoia glyptostroboides and its anti-radical efficiency[J]. Hubei Agricultural Sciences, 2013, 52(2):423-424
[20]刘婷,厍文波,王婷,等.水蒸气蒸馏和超临界萃取薰衣草精油抗氧化作用研究[J].时珍国医国药,2009,20(12):3035-3037LIU T, SHE W B, WANG T, et al. Study on the antioxidative activity of lavender oil extracted by steam distillationand supercritical extraction[J]. Lishizhen Medicine and Materia Medica Research, 2009, 20(12):3035-3037
[21]丁海麦,李彩艳,孔凡青,等.内蒙古包头3种常食用葡萄抗氧化活性的研究[J].安徽农业科学,2010, 38(6):2945-2946DING H M, LI C Y, KONG F Q,et al. Radical scavenging activity of three kinds of grape in Baotou Inner Mongolia[J]. Journal of Anhui Agriculture Sciences, 2010, 38(6):2945-2946
[22]PASTOR J, GARCIA M, STEINBAUER S,et al. Combinations of ascaridole, carvacrol, and caryophyllene oxide against Leishmania[J]. Acta Tropic, 2015, 145:31-38
[23]PAN Z, WANG S K, CHENG X L, et al. Caryophyllene oxide exhibits anti-cancer effects in MG-63 human osteosarcoma cells via the inhibition of cell migration, generation of reactive oxygen species and induction of apoptosis[J].Bangladesh Journal of Pharmacology, 2016, 11(4):817-823
[24]YU B, ZHANG D, YAN X W, et al. Comparative evaluation of the chemical composition, antioxidant and antimicrobial activities of the volatile oils of Hawk tea from six botanical origins[J]. Chemistry&Biodiversity, 2016, 13(11):1573-1583
[25]PARVARDEH S, MOGHIMI M, ESLAMI P, et al. a-Terpineol attenuates morphine-induced physical dependence and tolerance in mice:role of nitric oxide[J]. Iranian Journal of Basic Medical Sciences, 2016, 19(2):201-208.