山香圆叶中萜类成分及其生物活性研究

doi:10.6023/cjoc202507018

摘要/Abstract

从中药山香圆叶90%甲醇提取物中分离并鉴定得到22个萜类化合物,其中山香圆甲酸（1）和山香圆乙酸（2）分别为C-17降碳型松香烷型和半日花烷型二萜类新化合物。它们的结构是通过质谱、一维/二维核磁共振谱和圆二色谱（ECD）等波谱和光谱技术得以确定。化合物4、7、8、10-14、16-20和22均系首次从山香圆叶植物中分离得到。以细菌脂多糖（Lipopolysaccharide, LPS）刺激的小鼠单核巨噬细胞RAW264.7为模型,对所分离得到化合物的体外抗炎作用进行了评估,结果显示齐墩果烷型三萜类化合物坡模酸（pomolic acid, 19)和3β-顺式-对香豆酰氧基-2α,23-二羟基-齐墩果酸（3-cis-p-coumaroyloxy-2,23-dihydroxyolean-12-en-28-oicacid, 22）在LPS诱导RAW264.7细胞中表现出一氧化氮（Nitric Oxide, NO）生成的抑制作用（IC₅₀值分别为11.3和19.1 μM）。其中,化合物22的抗炎活性为首次报道。此外,乌苏烷型三萜类化合物2α,20β-二羟基-乌苏酸（isoyarumic acid,9）对人乳腺癌细胞MDA-MB-231表现出一定程度的细胞毒作用（IC₅₀值为17.6 μM）。

关键词: 山香圆叶, 二萜, 山香圆甲酸, 山香圆乙酸, 三萜类化合物, 抗炎活性, 细胞毒作用

A phytochemical investigation of the 90% MeOH extract of the leaves of Turpinia arguta led to the identification of 22 structurally diverse terpenoids, including two new ones: argutacid A (1, a 15-oxo-17-norabietane-type diterpenoid) and argutacid B (2, a labdane-type diterpenoid). Their structures were determined using spectroscopic techniques including mass spectrometry, one-dimensional/two-dimensional nuclear magnetic resonance (NMR) spectra, and electronic circular dichroism (ECD). Compounds 4, 7, 8, 10-14, 16-20, and 22 are reported from T. arguta for the first time. The isolated compounds were evaluated for their anti-inflammatory activity in lipopolysaccharide (LPS)-induced RAW 264.7 cells by suppressing nitric oxide (NO) production. Two oleanolic acid derivatives, pomolic acid (19) and 3β-cis-p-coumaroyloxy-2α,23-dihydroxyolean acid (22), were found to have anti-inflammatory activities with IC₅₀ values of 11.3 and 19.1 μM, respectively. Such an anti-inflammatory effect of 22 was reported for the first time. Furthermore, isoyarumic acid (9, a ursolic acid derivative) exhibited moderate cytotoxic effect against MDA-MB-231 cells, with an IC₅₀ value of 17.6 μM.

Key words: Turpinia arguta, Diterpenes, Argutacid A, Argutacid B, Triterpenoids, Anti-inflammatory activity, Cytotoxicity

引用此文

江哲璐, 赵泽宇, 池纯婧, 余江川, 颜鹂鸿, 胡金锋. 山香圆叶中萜类成分及其生物活性研究[J]. 有机化学, doi: 10.6023/cjoc202507018.

Zhe-Lu Jiang, Ze-Yu Zhao, Chun-Jing Chi, Jiang-Chuan Yu, Li-Hong, Yan, Jin-Feng Hu. Terpenoids from the Leaves of Turpinia arguta and Their Bioactivities[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202507018.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Newman D. J.; Cragg, G. M. J. Nat. Prod.2020, 83, 770.
中国药典(2020年版),一部. 北京: 中国医药科技出版社, 2020, pp. 31.
[2] Zhang G.-W.;Zhou, G,-P ; Yang, X.-J.; Xie, E.-L. Chin. J. Pharm. Anal.2009, 29, 912.
(章光文, 周国平, 杨香菊, 谢二磊. 药物分析杂志, 2009, 29, 912.)
[3] Xu, Z.-H. Clin. J. Chin. Med.2011, 3, 42.
(许哲洪. 中医临床研究, 2011, 3, 42.)
[4] Wu S.Master's Dissertation, Chengdu University of Traditional Chinese Medicine, Cheng-du, 2014 (in Chinese).
(吴珊. 硕士毕业论文. 成都中医药大学, 2014.)
[5] Luo X.-T.; Yu S.-P.; Xiong, Y.-X. Strait Pharm. J.2002, 14, 49.
(罗宪堂, 余世平, 熊友香. 海峡药学, 2002, 14, 49.)
[6] Hu J. M.; Cai J. H.; Hu X. R.; Wang L. J.; Cheng Q. Q.; Tao X. H. Horticulturae2024, 10, 587.
[7] Xiao C.-R.; Tu L.-F.; Zhang R.-Z.; Liu D.-P.; Luo, Y.-M. China J. Chin. Mater. Med.2019, 44, 1295.
(肖春荣, 涂林锋, 张睿增, 刘定平, 罗永明. 中国中药杂志, 2019, 44, 1295.)
[8] Ma S.-G.; Yuan S.-P.; Hou, Q; Li Y.; Chen X.; Yu, S.-S. China J. Chin. Mater. Med.2013, 38, 1747.
(马双刚, 袁绍鹏, 侯琦, 李勇, 陈霞, 庾石山.中国中药杂志, 2013, 38, 1747.)
[9] Ma S.-G.; Yuan S.-P.; Liu Y.-B.; Qu J.; Li Y.; Wang X.-J.; Wang R.-B.; Xu S.; Hou Q.; Yu S.-S. Fitoterapia2018, 124, 80.
[10] Zhang L.; Li J.; Yu S.-C.; Jin Y.; Lv X.-W.; Zou Y.-H.; Li Y. J. Ethnopharmacol.2008, 116, 167.
[11] Sun, J.-Y.; Liu, X.-R.; Wu, H.-Y.; Liu, K. Food and Drug 2012, 14, 253.
(孙敬勇, 刘秀荣, 武海艳, 刘珂.食品与药品, 2012, 14, 253.)
[12] Wu M.; Wu P.; Xie H. H.; Wu G. J.; Wei, X. Y. Planta Med.2011, 77, 284.
[13] Wu M.; Wu P.; Wei, X. Y. Chem. Nat. Compd.2014, 50, 772.
[14] Yan J.; Zhao L.-J.; Li Y.-M.; Zhang Z.-M.; Lin L.-M.; Xia B.-H. Chem. Biodivers.2022, 19, e202200459.
[15] Tanaka R.; Ohtsu H.; Matsunaga S. Phytochemistry1997, 46, 1051.
[16] García-Granados A.; Martínez A.; Molina A.; Onorato M. E.; Rico M.; de Buruaga A. S.; de Buruaga, J. M. S. Phytochemistry1985, 24, 1789.
[17] Tang T.; Li C.-H.; Li D.-S.; Jing S.-X.; Hua J.; Luo S.-H.; Liu Y.; Li S.-H.Phytochemistry 2020, 172, 112285.
[18] Hieda T.; Mikami Y.; Obi Y.; Kisaki, T. Agric. Biol. Chem.1982, 46, 2249.
[19] Mirzaei H. H.; Firuzi O.; Chandran J. N.; Schneider B.; Jassbi, A. R. Phytochem. Lett.2019, 29, 129.
[20] Kuo Y.-H.; Yu M. T. Phytochemistry1996, 42, 779.
[21] Wang C.-M.; Yeh K.-L.; Tsai S.-J.; Jhan Y.-L.; Chou C.-H.Molecules 2017, 22, 2119.
[22] Gossan D. P. A.; Magid A. A.; Yao-Kouassi P. A.; Josse J.; Gangloff S. C.; Morjani H.; Voutquenne-Nazabadioko L. Fitoterapia2016, 110, 89.
[23] Gutiérrez G.; Valencia L. M.; Giraldo-Dávila D.; Combariza M. Y.; Galeano E.; Balcazar N.; Panay A. J.; Jerez A. M.; Montoya G. Molecules2021, 26, 1064.
[24] Taniguchi S.; Imayoshi Y.; Kobayashi E.; Takamatsu Y.; Ito H.; Hatano T.; Sakagami H.; Tokuda H.; Nishino H.; Sugita D.; [25] Shimura, S.; Yoshida, T.Phytochemistry 2002, 59, 315.
[26] Okada Y.; Omae A.; Okuyama, T. Chem. Pharm. Bull.2003, 51, 452.
[27] Liang W.-J.; Ma Q.-Y.; Jiang H.-Z.; Zhou J.; Pang J.; Zhao, Y.-X. Chem. Nat. Compd.2012, 47, 935.
[28] Haslinger E.; Michl, G. Liebigs Ann. Chem.1989, 1989, 677.
[29] Amin H. I. M.; Amin K. Y. M.; Armijos C.; Hussain F. H. S.; Jawhar Z. H.; Caprioglio D.; Mella M.; Vidari G. Molecules2024, 29, 1079.
[30] Chaturvedula V. S. P.; Norris A.; Miller J. S.; Ratovoson F.; Andriantsiferana R.; Rasamison V. E.; Kingston, D. G. I. J. Nat. Prod.2006, 69, 287.
[31] Lima R. D. C. L.; Kongstad K. T.; Kato L.; das Silva M. J.; Franzyk H.; Staerk D. Molecules2018, 23, 1755.
[32] Woo K. W.; Choi S. U.; Kim K. H.; Lee, K. R. J. Braz. Chem. Soc.2015, 26, 1450.
[33] Yamagishi T.; Zhang D.-C.; Chang J.-J.; McPhail D. R.; McPhail A. T.; Lees K.-H. Phytochemistry1988, 27, 3213.
[34] Banno N.; Akihisa T.; Tokuda H.; Yasukawa K.; Higashihara H.; Ukiya M.; Watanabe K.; Kimura Y.; Hasegawa J.-I.; Nishino, H. Biosci. Biotechnol. Biochem.2004, 68, 85.
[35] Cheng J.-J.; Zhang L.-J.; Cheng H.-L.; Chiou C.-T.; Lee I-J.; Kuo, Y.-H. J. Nat. Prod.2010, 73, 1655.
[36] Kakuno T.; Yoshikawa K.; Arihara S. Tetrahedron Lett.1991, 32, 3535.
[37] Gu J.-Q.; Park E. J.; Luyengi L.; Hawthorne M. E.; Mehta R. G.; Farnsworth N. R.; Pezzuto J. M.; Kinghorn A. D.Phytochemistry 2001, 58, 121.
[38] Tseng C.-H.; Cheng C.-M.; Tzeng C.-C.; Peng S.-I Yang C.-L.; Chen Y.-L. Bioorg. Med. Chem.2013, 21, 523.
[39] Chen F. L.; Liu D.-L.; Wang W.; Lv X.-M.; Li W. X.; Shao L.-D.; Wang, W.-J. Nat. Prod. Res.2020, 34, 2816.
[40] Zhang L.; Cheng Y.-X.; Liu A.-L.; Wang H.-D.; Wang Y.-L.; Du G.-H.Molecules 2010, 15, 8507.
[41] Han Y. Q.; Zhang L.; Li W.; Liu X. R.; Xiao J.; Chen G.; Li N.J. Nat. Med. 2019, 73, 456.
[42] Kim K. H.; Choi S. U.; Lee K. R.Bioorg. Med. Chem. Lett. 2010, 20, 1944.
[43] Park K. J.; Subedi L.; Kim S. Y.; Choi S. U.; Lee K. R.Bioorg. Chem. 2018, 77, 527.
[44] Elmaidomy A. H.; Mohammed R.; Owis A. I.; Hetta M. H.; AboulMagd, A. M.; Siddique, A. B.; Abdelmohsen, U. R.; Rateb, M. E.; El Sayed, K. A.; Hassan, H. M.RSC Adv. 2020, 10, 10584.
[45] Wan J.; Zang Y.; Xiao D.-A.; Li N.; Li J. M.; Jin Z.-X.; Chen D.-L.; Xiong J.; Li J.; Hu J.-F.RSC Adv. 2020, 10, 3343.
[46] Wan J.; Wang X.-J.; Guo N.; Wu X.-Y.; Xiong J.; Zang Y.; Jiang C.-X.; Han B.; Li J.; Hu J.-F.Molecules 2021, 26, 1911.
[47] Wu X.-Y.; Zhao Z.-Y.; Osman E. E. A.; Choo Y.-M.; Xiong J.; Hamann M. T.; Hu J.-F. Phytochem. Lett.2024, 64, 56.
[48] He Y.-H.; Li Q.-X.; Wu Y.-F.; Jiang C.-X.; Zhou Q.; Jin Z.-X.; Chen W.-X.; Mao Y.-C.; Hu J.-F.; Xiong, J. J. Org. Chem.2022, 87, 6927.
[49] He Y.-H.; Xiang H.; Li Q.-X.; Wu Y.-F.; Jin Z.-X.; Hu J.-F.; Mao Y.-C.; Xiong J. Phytochemistry2024, 218, 113956.
[50] Li H.; Tang Y.; Liang K.-Y.; Zang Y.; Osman E. E. A.; Jin Z.-X.; Li J.; Xiong J.; Li J. M.; Hu J.-F. Phytochemistry2022, 198, 113161.
[51] Ma G.-L.; Guo N.; Wang X.-L.; Li J. M.; Jin Z.-X.; Han Y. Q.; Dong S.-Z.; Xiong J.; Hu J.-F. Bioorg. Chem.2020, 105, 104445.
[52] Wang X.-J.; Xin J.-L.; Xiang H.; Zhao Z.-Y.; He Y.-H.; Wang H. B.; Mei G. Y.; Mao Y.-C.; Xiong J.; Hu J.-F.Chin. Chem. Lett. 2024, 35, 109682.
[53] Yang G. X.; Zhou P. J.; Li Y. J.; Ding J.; Hu J.-F. Tetrahedron Lett.2021, 85, 153463.