短柱八角中二萜类成分及其抗炎活性
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摘要
目的研究短柱八角Illicium brevistylum A. C. Smith中二萜类成分及其抗炎活性。方法短柱八角80%乙醇提取物石油醚部位采用硅胶柱、反相ODS、Sephadex LH-20进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。用LPS诱导的293-Nf-κB-luc细胞模型对其进行抗炎活性检测。结果从中分离得到9个二萜类化合物,分别鉴定为异海松酸(1)、脱氢枞酸(2)、3,16α-二羟基-贝壳杉烷(3)、8,11,13,15-abietatetraen-19-oic acid (4)、methyl-16-nor-15-oxodehydroabietate (5)、12-羟基-脱氢枞酸(6)、3,4-开环海松烷-4,8 (9),15 (18)-三烯-3-酸甲酯(7)、15-羟基取代松香烷甲酯(8)、9β,13β-endoperoxide-abieta-8 (14)-en-18-oic acid (9)。化合物4～6、8均能降低LPS诱导的293-Nf-κB-luc细胞荧光强度。结论所有化合物均首次从该植物中分离得到,化合物3、7首次从该属植物中分离得到,化合物4～6、8均表现出较强的抗炎活性。
AIM To study the diterpenes from Illicium brevistylum A. C. Smith and their anti-inflammatory activities. METHODS The petroleum ether fraction of 80% ethanol fraction extract from I. brevistylum was isolated and purified by silica,reversed phase ODS and Sephadex LH-20,then the structures of obtained compounds were identified by physicochemical properties and spectral data. Their anti-inflammatory activities were evaluated by LPS-induced 293-Nf-κB-luc cell model. RESULTS Nine diterpenes were isolated and identified as isopimaric acid( 1),dehydroabietic acid( 2),3,16α-dihydroxy-kaurane( 3),8,11,13,15-abietatetraen-19-oic acid( 4),methyl-16-nor-15-oxodehydroabietate( 5),12-hydroxydehydroabietic acid( 6),3,4-secopimara-4,8( 9), 15( 18)-triene-3-acid-methylester( 7), methyl-15-hydroxydehydroabitetate( 8), 9β, 13β-endoperoxide-abieta-8( 14)-en-18-oic acid( 9). Compounds 4-6,8 significantly suppressed the fluorescence intensity in LPS induced 293-Nf-κB-luc cell model. CONCLUSION All the compounds are isolated from this plant for the first time,compounds 3 and 7 are first isolated from genus Illicium,and compounds 4-6,8 show good antiinflammatory activities.
AIM To study the diterpenes from Illicium brevistylum A. C. Smith and their anti-inflammatory activities. METHODS The petroleum ether fraction of 80% ethanol fraction extract from I. brevistylum was isolated and purified by silica,reversed phase ODS and Sephadex LH-20,then the structures of obtained compounds were identified by physicochemical properties and spectral data. Their anti-inflammatory activities were evaluated by LPS-induced 293-Nf-κB-luc cell model. RESULTS Nine diterpenes were isolated and identified as isopimaric acid( 1),dehydroabietic acid( 2),3,16α-dihydroxy-kaurane( 3),8,11,13,15-abietatetraen-19-oic acid( 4),methyl-16-nor-15-oxodehydroabietate( 5),12-hydroxydehydroabietic acid( 6),3,4-secopimara-4,8( 9), 15( 18)-triene-3-acid-methylester( 7), methyl-15-hydroxydehydroabitetate( 8), 9β, 13β-endoperoxide-abieta-8( 14)-en-18-oic acid( 9). Compounds 4-6,8 significantly suppressed the fluorescence intensity in LPS induced 293-Nf-κB-luc cell model. CONCLUSION All the compounds are isolated from this plant for the first time,compounds 3 and 7 are first isolated from genus Illicium,and compounds 4-6,8 show good antiinflammatory activities.
引文
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[12]黄荣韶,叶春秀,覃其昶,等.黄花三宝木中的二萜类化合物研究[J].中草药,2016,47(7):1079-1083.
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[14] Tanaka R,Ohtsu H,Matsunaga S. Abietane diterpene acids and other constituents from the leaves of Larix Kaempferi[J].Phytochemistry,1997,46(6):1051-1057.
[15] Kinouchi Y,Ohtsu H,Tokuda H,et al. Potential antitumorpromoting diterpenoids from the stem bark of Picea glehni[J].J Nat Prod,2000,63(6):817-820.
[16] Zhao Y X,Zhou L,Guo L,et al. A new diterpenoid and active stilbenes from Pinus armandii heartwood[J]. J Asian Nat Prod Res,2005,7(3):259-264.
[17] Xiang Y, Yang S P, Zhang Z J, et al. Terpenoids and Phenols from Taiwania flousiana[J]. Acta Bot Sin,2004,46(8):1002-1008.
[2]中国科学院《中国植物志》编辑委员会.中国植物志[M].北京:科学出版社,1996:199.
[3]董旭俊,罗仕德.匙叶八角中的酚性成分[J].中草药,2012,43(11):2111-2115.
[4]杨金,闵勇,易平,等.短柱八角的化学成分研究[J].红河学院学报,2011,9(4):13-14.
[5]来国防,董旭俊,杨剑坤,等.匙叶八角中一个新的倍半木脂素[J].云南植物研究,2010,32(3):281-284.
[6]叶全知,黄豆豆,陈伟,等.短柱八角化学成分及其抗炎活性的研究[J].中成药,2017,39(10):2081-2085.
[7]陈程.短柱八角干皮的化学成分研究及抗炎活性初探[D].上海:第二军医大学,2013.
[8]姚风艳,黄豆豆,黄光辉,等.短柱八角的化学成分研究[J].中草药,2014,45(11):1536-1539.
[9] Chen Y H,Dong Z Y,Huang D D,et al. Brevistylumsides A and B,diterpene glycosides from Illicium brevistylum[J]. Phytochem Lett,2015,14:27-30.
[10]杨保华,张卫东,顾正兵,等.长白落叶松树皮化学成分研究[J].中国中药杂志,2005,30(4):270-272.
[11]王亚丹,张贵杰,屈晶,等.大八角根中二萜类化学成分及其抗柯萨奇病毒活性[J].国际药学研究杂志,2013,40(6):772-777.
[12]黄荣韶,叶春秀,覃其昶,等.黄花三宝木中的二萜类化合物研究[J].中草药,2016,47(7):1079-1083.
[13]黄平,Karagianis G,Waterman P G.假地枫皮中的二萜酸类化合物研究[J].天然产物研究与开发,2005,17(3):309-312.
[14] Tanaka R,Ohtsu H,Matsunaga S. Abietane diterpene acids and other constituents from the leaves of Larix Kaempferi[J].Phytochemistry,1997,46(6):1051-1057.
[15] Kinouchi Y,Ohtsu H,Tokuda H,et al. Potential antitumorpromoting diterpenoids from the stem bark of Picea glehni[J].J Nat Prod,2000,63(6):817-820.
[16] Zhao Y X,Zhou L,Guo L,et al. A new diterpenoid and active stilbenes from Pinus armandii heartwood[J]. J Asian Nat Prod Res,2005,7(3):259-264.
[17] Xiang Y, Yang S P, Zhang Z J, et al. Terpenoids and Phenols from Taiwania flousiana[J]. Acta Bot Sin,2004,46(8):1002-1008.