药学学报, 2020, 55(12): 2955-2959
引用本文:
梁旭, 杨新洲, 吴超群, 李余钊, 袁经权. 紫茎泽兰中一个新的杜松烷型倍半萜[J]. 药学学报, 2020, 55(12): 2955-2959.
LIANG Xu, YANG Xin-zhou, Wu Chao-qun, LI Yu-zhao, YUAN Jing-quan. A new cadinane-type sesquiterpenoid from Eupatorium adenophorum Spreng[J]. Acta Pharmaceutica Sinica, 2020, 55(12): 2955-2959.

紫茎泽兰中一个新的杜松烷型倍半萜
梁旭1, 杨新洲2, 吴超群2, 李余钊2, 袁经权1
1. 广西中医药大学, 广西 南宁 530200;
2. 中南民族大学药学院, 湖北 武汉 430074
摘要:
采用HP20大孔树脂、硅胶柱色谱、半制备高效液相色谱等对紫茎泽兰95%乙醇提取物的石油醚部位进行分离纯化,得到了4个杜松烷型倍半萜。根据其理化性质及波谱数据分别鉴定为泽兰酚(1)、(+)-(5R,7S,9R,10S)-2-oxocadinan-3,6(11)-dien-12,7-olide(2)、(1S,4R)-7-hydroxycalamenen-3-one(3)和(-)-(5R,6R,7S,9R,10S)-cadinan-3-ene-6,7-diol(4)。其中化合物1为新化合物,化合物3为首次从该属植物中分离得到。生物活性结果表明,化合物14均未表现明显的肿瘤细胞毒作用。
关键词:    紫茎泽兰      化学成分      杜松烷型倍半萜      外来入侵植物     
A new cadinane-type sesquiterpenoid from Eupatorium adenophorum Spreng
LIANG Xu1, YANG Xin-zhou2, Wu Chao-qun2, LI Yu-zhao2, YUAN Jing-quan1
1. Guangxi University of Chinese Medicine, Nanning 530200, China;
2. School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, China
Abstract:
Four cadinane-type sesquiterpenes were obtained from the petroleum ether of 95% ethanol extract of Eupatorium adenophorum Spreng by using an HP-20 macroporous resin column, silica gel, and semi-preparative HPLC. Their structures were determined by physical, chemical and spectroscopic methods and identified as eupatorinol (1), (+)-(5R,7S,9R,10S)-2-oxocadinan-3,6(11)-dien-12,7-olide (2), (1S,4R)-7-hydroxycalamenen-3-one(3) and (-)-(5R,6R,7S,9R,10S)-cadinan-3-ene-6,7-diol (4). Among them, compound 1 is a new cadinane-type sesquiterpene, and compound 3 was isolated from this genus for the first time. In bioassay, none of these compounds displayed obvious cytotoxicity.
Key words:    Eupatorium adenophorum Spreng    chemical constituent    cadinane-type sesquiterpenoid    alien invasive plant   
收稿日期: 2020-08-07
DOI: 10.16438/j.0513-4870.2020-1302
基金项目: 国家自然科学基金资助项目(81660656).
通讯作者: 袁经权,Tel:86-771-3946492,E-mail:yjqgx@163.com
Email: yjqgx@163.com
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参考文献:
[1] Qing S. The history and status of the study on croft on weed (Eupatorium adenophorum spreng.) a worst worldwide weed[J]. J Wuhan Bot Res (武汉植物学研究), 1998, 16:366-372.
[2] Yunnan Pharmaceutical Research Institute. List of Yunnan Medicinal Plants (云南药用植物名录)[M]. Kunming:Yunnan Pharmaceutical Research Institute, 1975:191.
[3] Li YM, Li ZY, Ye M. The chemical compositions and their bioactivities in the different parts of Eupatorium adenophorum Spreng.[J]. J Yunnan Agric Univ (云南农业大学学报), 2008, 1:42-43, 45-46, 72.
[4] Hu CJ, Wang CY, He ZR, et al. Study on antioxidant activity of extracts from Ageratina adenophora based on DPPH method[J]. Weed Sci (杂草科学), 2013, 31:9-12.
[5] Chen H, Yang J, Yuan JQ, et al. Study on the anti-hepatocarcinoma activity of Eupatorium adenophorum[J]. Chin Med Mat (中药材), 2018, 41:1211-1214.
[6] Guo LM, Lv JL, Zhang LB. Research progress on anti-inflammatory mechanism of natural sesquiterpenoids[J]. China J Chin Mater Med (中国中药杂志), 2018, 43:3989-3999.
[7] Wang FS, Wen Y, Long GF. Analysis on cadinane sesquiterpenoidnene composition in Vetiveria zizanioides[J]. J Anhui Agric Sci (安徽农业科学), 2009, 37:5636-5638.
[8] Shi YP. Monoterpene and Sesquiterpene Chemistry (单萜和倍半萜化学)[M]. Beijing:Chemical Industry Press, 2008.
[9] Li M, Wen JH, Ni FY, et al. Anti-inflammatory activity of two new sesquiterpenoids from Radix Angelicae Pubescentis[J]. Acta Pharm Sin (药学学报), 2019, 54:343-347.
[10] Chen H, Yuan JQ, Yang XZ, et al. α-Humulene inhibits hepatocellular carcinoma cell proliferation and induces apoptosis through the inhibition of Akt signaling[J]. Food Chem Toxicol, 2019, 134:110830.
[11] Xie YY, Li YX, Sun YM, et al. A new anti-hypoxia sesquiterpene from the rhizome of Petasites japonicas[J]. Acta Pharm Sin (药学学报), 2016, 51:1285-1289.
[12] Chen FY, Li HX, Chen J, et al. A pair of enantiomeric sesquiterpenoids with neuroprotective effects from Chloranthus henryi Hemsl.[J]. Acta Pharm Sin (药学学报), 2020, 55:1855-1858.
[13] Wang FP. Chemistry of Natural Product (现代天然产物化学)[M]. Beijing:Science Press, 2009.
[14] Luo B, Dong LM, Xu QL, et al. A new monoterpene and a new sesquiterpene from the roots of Ageratina adenophora[J]. Phytochem Lett, 2018, 24:67-70.
[15] Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 09, Revision D.01[M]. Wallingford CT:Gaussian Inc., 2010.
[16] Bruhn T, Schaumlöffel A, Hemberger Y, et al. SpecDics Version 1. 61 ed[M]. Würzburg:University of Würzburg, 2013.
[17] Bruhn T, Schaumlöffel A, Hemberger Y, et al. SpecDics:quantifying the comparison of calculated and experimental electronic circular dichroism spectra[J]. Chirality, 2013, 25:243-249.
[18] He L, Hou J, Gan M, et al. Cadinane sesquiterpenes from the leaves of Eupatorium adenophorum[J]. J Nat Prod, 2008, 71:1485-1488.
[19] Bowden BF, Coll JC, Engelhardt LM, et al. Studies of Australian soft corals XXXVI. The isolation and structure determination of 11 calamenene based sesquiterpenes from Lemnalia-Cervicornis (Coelenterata, Octocorallia, Alc-yonacea)[J]. Aust J Chem, 1986, 39:103-121.
[20] Yang J, Xu C, Chen H, et al. In vitro and in vivo antitumor effects of the diterpene-enriched extract from Taxodium ascendens through the mitochondrial-dependent apoptosis pathway[J]. Biomed Pharmacother, 2017, 96:1199-1208.