药学学报, 2021, 56(1): 283-288
引用本文:
石静亚, 李孟, 曾梦楠, 张靖柯, 刘娟娟, 朱登辉, 郑晓珂, 冯卫生. 怀菊花茎叶中一个新聚炔类化合物[J]. 药学学报, 2021, 56(1): 283-288.
SHI Jing-ya, LI Meng, ZENG Meng-nan, ZHANG Jing-ke, LIU Juan-juan, ZHU Deng-hui, ZHENG Xiao-ke, FENG Wei-sheng. A new polyacetylene from the stems and leaves of Chrysanthemum morifolium Ramat[J]. Acta Pharmaceutica Sinica, 2021, 56(1): 283-288.

怀菊花茎叶中一个新聚炔类化合物
石静亚1,2, 李孟1,2, 曾梦楠1,2, 张靖柯1,2, 刘娟娟1,2, 朱登辉1,2, 郑晓珂1,2, 冯卫生1,2
1. 河南中医药大学药学院, 河南 郑州 450046;
2. 河南省中药开发工程技术研究中心, 河南 郑州 450046
摘要:
采用多种色谱技术从怀菊花茎叶中分离得到8个聚炔类化合物。通过UV、IR、ESI-MS、HR-ESI-MS及NMR等波谱技术对其进行结构鉴定,分别为菊花新炔C(2E,4E,12Z-十四碳三烯-1-吡咯烷基-1-酮-8,10-二炔)(1)、tetradeca-2E,4E,12E-trien-8,10-diynoic acid pyrrolidide(2)、tetradeca-2E,4E-dien-8,10-diynoic acid pyrrolidide(3)、tetradeca-2E,4E,10Z-trien-8-ynoic acid pyrrolidide(4)、2E,4E,12E-tetradecatriene-8,10-diynoic acid isobutylamide(5)、2E,4E-undecyldiene-8,10-diynoic acid isobutylamide(6)、2E,4E,10E-N-isobutyl-2,4,10-tetradecatrien-8-ynoic acid amide(7)和十一-2E,4E-二烯-8,10-二炔酸苯乙胺(8)。其中化合物1为新化合物,化合物28为首次从植物菊花中分离得到。化合物58在一定浓度下对A549细胞具有显著的抑制活性,说明其具有潜在的抗癌活性。
关键词:    菊花      茎叶      化学成分      聚炔      细胞毒活性     
A new polyacetylene from the stems and leaves of Chrysanthemum morifolium Ramat
SHI Jing-ya1,2, LI Meng1,2, ZENG Meng-nan1,2, ZHANG Jing-ke1,2, LIU Juan-juan1,2, ZHU Deng-hui1,2, ZHENG Xiao-ke1,2, FENG Wei-sheng1,2
1. College of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, China;
2. The Engineering and Technology Center for Chinese Medicine Development of Henan Province, Zhengzhou 450046, China
Abstract:
Eight polyacetylenes were isolated from the extract of the stems and leaves of Chrysanthemum morifolium by various chromatographic methods. Their structures were determined as 2E,4E,12Z-tetradecatriene-1-pyrrolidine-1-oxo-8,10-diynoic (1), tetradeca-2E,4E,12E-trien-8,10-diynoic acid pyrrolidide (2), tetradeca-2E,4E-dien-8,10-diynoic acid pyrrolidide (3), tetradeca-2E,4E,10Z-trien-8-ynoic acid pyrrolidide (4), 2E,4E,12E-tetradecatriene-8,10-diynoic acid isobutylamide (5), 2E,4E-undecyldiene-8,10-diynoic acid isobutylamide (6), 2E,4E,10E-N-isobutyl-2,4,10-tetradecatrien-8-ynoic acid amide (7), and undeca-2E,4E-diene-8,10-diynoic acid phenylethylamide (8) by spectroscopic methods, including UV, IR, ESI-MS, HR-ESI-MS, 1D and 2D NMR spectra. Among them, compound 1 is a new polyacetylene, and compounds 2-8 were isolated from this plant for the first time. Compounds 5-8 inhibited the proliferation of A549 cell significantly at certain concentration, showing potent antitumor activity.
Key words:    Chrysanthemum morifolium    stem and leave    chemical constituent    polyacetylenes    cytotoxicity   
收稿日期: 2020-08-24
DOI: 10.16438/j.0513-4870.2020-1376
基金项目: 河南省重大科技专项(171100310500);国家重点研发计划-中医药现代化研究(2019YFC1708802);河南省高层次人才特殊支持计划“中原千人计划”-中原领军人才(ZYQR2018100).
通讯作者: 冯卫生,Tel:86-371-60190296,E-mail:fwsh@hactcm.edu.cn
Email: fwsh@hactcm.edu.cn
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参考文献:
[1] Chinese Pharmacopoeia Commission. Pharmacopoeia of the People's Republic of China (中华人民共和国药典一部)[S]. Beijing:China Medical Science Press, 2015:310.
[2] Zeng MN, Li M, Chen YJ, et al. A new bisepoxylignan dendranlignan A isolated from Chrysanthemum flower inhibits the production of inflammatory mediators via the TLR4 pathway in LPS-induced H9c2 cardiomyocytes[J]. Arch Biochem Biophys, 2020, 690:108506.
[3] Chen WJ, Zeng MN, Li M, et al. Four new sesquiterpenoids from Dendranthema morifolium (Ramat.) kitam flowers[J]. Phytochem Lett, 2018, 23:52-56.
[4] Feng WS, Chen WJ, Li M, et al. Glycosides from the flowers of Chrysanthemum morifolium[J]. J Chin Med Mater (中药材), 2018, 41:338-341.
[5] Feng WS, Chen WJ, Zheng XK, et al. Flavonoids from the flowers of Chrysanthemum morifolium Ramat[J]. Chin Pharm J (中国药学杂志), 2017, 52:1497-1502.
[6] Xu RH, Fan H, Zhang L, et al. Caffeoyl quinic acids in Chrysanthemum morifolium improve LPS-induced HUVEC vascular endothelial cell injury by regulating ERK/MAPK signaling pathway[J]. Acta Pharm Sin (药学学报), 2019, 54:1207-1213.
[7] Feng WS, Fan H, Xu RH, et al. The mechanism of the improvement of vascular endothelial cell injury induced by eriodictyol-7-O-β-D-glucoside[J]. J Chin Med Mater (中药材), 2018, 41:1176-1180
[8] Duan JA. Resources Chemistry of Chinese Medicinal Materials:Theoretical Basis and Resource Recycling Utilization (中药资源化学——理论基础与资源循环利用)[M]. Beijing:Science Press, 2015:22-27, 40-41.
[9] Harald G, Christa Z, Ferdinand B. Pyrrolidine and piperidine amides from Achillea[J]. Phytochemistry, 1984, 23:1503-1505.
[10] Pollo L, Frederico MJ, Bortoluzzi AJ, et al. A new polyacetylene glucoside from Vernonia scorpioides and its potential antihyperglycemic effect[J] Chem Biol Interact, 2018, 279:95-101.
[11] Jin L, Zhou W, Li R, et al. A new polyacetylene and other constituents with anti-inflammatory activity from Artemisia halodendron[J]. Nat Prod Res, 2020. DOI:10.1080/14786419.2019.1610962.
[12] Guo J, Wang A, Yang K, et al. Isolation, characterization and antimicrobial activities of polyacetylene glycosides from Coreopsis tinctoria Nutt.[J]. Phytochemistry, 2017, 136:65-69.
[13] Hofer O, Greger H, Robien W, et al. 13C NMR and 1H NMR lanthanide induced shifts of naturally occurring alkamides with cyclic amide moieties-amides from Achillea falcata[J]. Tetrahedron, 1986, 42:2707-2716.
[14] Greger H, Hofer O. Polyenoic acid piperideides and other alkamides from Achillea millefolium[J]. Phytochemistry, 1989, 28:2363-2368.
[15] Jakupovic J, Schuster A, Bohlmann F, et al. New lignans and isobutyl lamides from Heliopsis buphthalmoides[J]. Planta Med, 1986, 52:18-20.
[16] Dong J, Yuan J, Wang JL, et al. Study on screening antitumor active fractions and chemical components in active fractions from root of Anaycclus pyrethrum[J]. China J Chin Mater Med (中国中药杂志), 2017, 42:3932-3937.
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