Prenylated Coumarins from Heracleum stenopterum, Peucedanum praeruptorum, Clausena lansium, and Murraya paniculata

doi:10.1007/s13659-016-0107-5

Natural Products and Bioprospecting

2016, Vol. 6

Issue (5) : 233-237 DOI: 10.1007/s13659-016-0107-5

Original article

Prenylated Coumarins from Heracleum stenopterum, Peucedanum praeruptorum, Clausena lansium, and Murraya paniculata

Xiang-Mei Li, Xian-Jun Jiang, Ku Yang, Li-Xia Wang, Shi-Zhen Wen, Fei Wang

BioBioPha Co., Ltd., Kunming 650201, People's Republic of China

Abstract
References
Related Articles
Metrics

Download: PDF(534 KB) HTML ()
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract Four hitherto unknown prenylated coumarins, namely 6"-O-β-D-apiofuranosylapterin (1), 4'-O-isobutyroylpeguangxienin (2), 6-(3-methyl-2-oxobutyroyl)-7-methoxycoumarin (3), and 6-hydroxycoumurrayin (4), were isolated from the ethanol extract of Heracleum stenopterum, Peucedanum praeruptorum, Clausena lansium, and Murraya paniculata, respectively. Their chemical structures were established on the basis of extensive spectroscopic analysis. Compound 2 exhibited in vitro cytotoxic activity against five human cancer cell lines (HL-60, A-549, SMMC-7721, MCF-7, and SW-480) with IC₅₀ values ranging from 15.9 to 23.2 μM.

Keywords Heracleum stenopterum Peucedanum praeruptorum Clausena lansium Murraya paniculata Prenylated coumarin Cytotoxicity

Fund:This work was financially supported by the "Large-scale Compound Library" project of National Development and Reform Commission of China

Issue Date: 08 February 2018

	Service

	E-mail this article
	E-mail Alert
	RSS
	Articles by authors

	Xiang-Mei Li
	Xian-Jun Jiang
	Ku Yang
	Li-Xia Wang
	Shi-Zhen Wen
	Fei Wang

Trendmd:

Cite this article:

Xiang-Mei Li,Xian-Jun Jiang,Ku Yang, et al. Prenylated Coumarins from Heracleum stenopterum, Peucedanum praeruptorum, Clausena lansium, and Murraya paniculata[J]. Natural Products and Bioprospecting, 2016, 6(5): 233-237.

URL:

http://npb.kib.ac.cn/EN/10.1007/s13659-016-0107-5 OR http://npb.kib.ac.cn/EN/Y2016/V6/I5/233

1. M. Berenbaum, Ecology 62, 1254-1266 (1981)
2. A.I. Gray, P.G. Waterman, Phytochemistry 17, 845-864 (1978)
3. Ł. Cieśla, A. Bogucka-Kocka, M. Hajnos, A. Petruczynik, M. Waksmundzka-Hajons, J. Chromatogr. A 1207, 160-168 (2008)
4. P. Sarkhail, J. Ethnopharmacol. 156, 235-270 (2014)
5. I. Kostova, Curr. Med. Chem. -Anti-Cancer Agents 5, 29-46 (2005)
6. F. Wang, X.L. Cheng, Y.J. Li, S. Shi, J.K. Liu, J. Nat. Prod. 72, 2005-2008 (2009)
7. F. Wang, M.F. Mao, G.Z. Wei, Y. Gao, F.C. Ren, J.K. Liu, Phytochemistry 95, 428-435 (2013)
8. K. Panthong, Y. Srisud, V. Rukachaisirikul, N. HutadilokTowatana, S.P. Voravuthikunchai, S. Tewtrakul, Phytochemistry 88, 79-84 (2013)
9. M. Hisamoto, H. Kikuzaki, H. Ohigashi, N. Nakatani, J. Agric. Food Chem. 51, 5255-5261 (2003)
10. W.L. Xiao, S.H. Li, Y.H. Shen, X.L. Li, H.D. Sun, Heterocycles 65, 1189-1196 (2005)
11. X.M. Niu, S.H. Li, L.X. Wu, L. Li, L.H. Gao, H.D. Sun, Planta Med. 70, 578-581 (2004)
12. Y.F. Zou, M. Lobera, B.B. Snider, J. Org. Chem. 70, 1761-1770 (2005)
13. F. Wang, X.L. Li, G.Z. Wei, F.C. Ren, J.K. Liu, Nat. Prod. Bioprospect. 3, 238-242 (2013)
14. H. Matsuda, T. Murakami, N. Nishida, T. Kageura, M. Yoshikawa, Chem. Pharm. Bull. 48, 1429-1435 (2000)
15. I.S. Chen, C.T. Chang, W.S. Sheen, C.M. Teng, I.L. Tsai, C.Y. Duh, F.N. Ko, Phytochemistry 41, 525-530 (1996)
16. H.N. Lv, S. Wang, K.W. Zeng, J. Li, X.Y. Guo, D. Ferreira, J.K. Zjawiony, P.F. Tu, Y. Jiang, J. Nat. Prod. 78, 279-285 (2015)

[1]	Xing Yu, Kai-Ting Duan, Zhen-Xiong Wang, He-Ping Chen, Xiao-Qing Gan, Rong Huang, Zheng-Hui Li, Tao Feng, Ji-Kai Liu. Anemhupehins A-C, Podocarpane Diterpenoids from Anemone hupehensis[J]. Natural Products and Bioprospecting, 2018, 8(1): 31-35.
[2]	Xin Wei, Afsar Khan, Da Song, Zhi Dai, Ya-Ping Liu, Hao-Fei Yu, Bei Wang, Pei-Feng Zhu, Cai-Feng Ding, Xu-Dong Zhao, Yi-Fen Wang, Xiao-Dong Luo. *Three New Pyridine Alkaloids from Vinca major* Cultivated in Pakistan**[J]. Natural Products and Bioprospecting, 2017, 7(4): 323-327.
[3]	Shai-Ping Hu, Wei-Wu Song, Si-Meng Zhao, Ning-Hua Tan. Clausenlanins A and B, Two Leucine-Rich Cyclic Nonapeptides from Clausena lansium[J]. Natural Products and Bioprospecting, 2017, 7(4): 307-313.
[4]	Xu-Jie Qin, Tong Shu, Qian Yu, Huan Yan, Wei Ni, Lin-Kun An, Pan-Pan Li, Yin-E Zhi, Afsar Khan, Hai-Yang Liu. Cytotoxic Acylphloroglucinol Derivatives from Callistemon salignus[J]. Natural Products and Bioprospecting, 2017, 7(4): 315-321.
[5]	Miao Liu, Zheng-Xi Hu, Yuan-Qing Luo, Min Zhou, Wei-Guang Wang, Xiao-Nian Li, Xue Du, Jian-Xin Pu, Han-Dong Sun. Two New Compounds from Schisandra propinqua var. propinqua[J]. Natural Products and Bioprospecting, 2017, 7(3): 257-262.
[6]	Li-Xia Wang, Hai-Rong Zheng, Fu-Cai Ren, Tian-Ge Chen, Xiang-Mei Li, Xian-Jun Jiang, Fei Wang. Polysubstituted Isoflavonoids from Spatholobus suberectus, Flemingia macrophylla, and Cudrania cochinchinensis[J]. Natural Products and Bioprospecting, 2017, 7(2): 201-206.
[7]	Satheesh Kumar Palanisamy, N. M. Rajendran, Angela Marino. Natural Products Diversity of Marine Ascidians (Tunicates; Ascidiacea) and Successful Drugs in Clinical Development[J]. Natural Products and Bioprospecting, 2017, 7(1): 1-111.
[8]	Mehtab Parveen, Faheem Ahmad, Ali Mohammed Malla, Shaista Azaz, Mahboob Alam, Omer A. Basudan, Manuela Ramos Silva, Pedro S. Pereira Silva. *Acetylcholinesterase and Cytotoxic Activity of Chemical Constituents of Clutia lanceolata* Leaves and its Molecular Docking Study**[J]. Natural Products and Bioprospecting, 2016, 6(6): 267-278.
[9]	Qian-Qian Meng, Xing-Rong Peng, Shuang-Yang Lu, Luo-Sheng Wan, Xia Wang, Jin-Run Dong, Rui Chu, Lin Zhou, Xiao-Nian Li, Ming-Hua Qiu. Lactam Triterpenoids from the Bark of Toona sinensis[J]. Natural Products and Bioprospecting, 2016, 6(5): 239-245.
[10]	Vincent E. Rasamison, Peggy J. Brodie, Emilio F. Merino, Maria B. Cassera, Michel A. Ratsimbason, Stephan Rakotonandrasana, Andriamalala Rakotondrafara, Elie Rafidinarivo, David G. I. Kingston, Harinantenaina L. Rakotondraibe. *Furoquinoline Alkaloids and Methoxyflavones from the Stem Bark of Melicope madagascariensis* (Baker) T. G. Hartley**[J]. Natural Products and Bioprospecting, 2016, 6(5): 261-265.
[11]	Ling Ni, Xiu-Hong Zhong, Jie Cai, Mei-Fen Bao, Bing-Jie Zhang, Jing Wu, Xiang-Hai Cai. Five New Alkaloids from Cephalotaxus lanceolata and C. fortunei var. alpina[J]. Natural Products and Bioprospecting, 2016, 6(3): 149-154.
[12]	Christian Bäcker, Malgorzata N. Drwal, Robert Preissner, Ulrike Lindequist. *Inhibition of DNA-Topoisomerase I by Acylated Triterpene Saponins from Pittosporum angustifolium* Lodd**[J]. Natural Products and Bioprospecting, 2016, 6(2): 141-147.
[13]	Fan Xia,Chun-Yan Wu,Xing-Wei Yang, Xian Li,Gang Xu. Diterpenoids from the Roots of Salvia yunnanensis[J]. Natural Products and Bioprospecting, 2015, 5(6): 307-312.
[14]	Tao Feng, Juan He, Hong-Lian Ai, Rong Huang, Zheng-Hui Li, Ji-Kai Liu. Three New Triterpenoids from European Mushroom Tricholoma terreum[J]. Natural Products and Bioprospecting, 2015, 5(4): 205-208.
[15]	Da-Song Yang, Shuang-Mei Wang, Wei-Bing Peng, Yong-Ping Yang, Ke-Chun Liu, Xiao-Li Li, Wei-Lie Xiao. *Minor Prenylated Flavonoids from the Twigs of Macaranga adenantha* and Their Cytotoxic Activity**[J]. Natural Products and Bioprospecting, 2015, 5(2): 105-109.

Viewed

Full text

Abstract

Cited

Shared

Discussed