New triterpenoids from the kernels of <i>Azadirachta indica</i>

doi:10.1007/s13659-013-0005-z

Natural Products and Bioprospecting

2013, Vol. 3

Issue (1) : 33-37 DOI: 10.1007/s13659-013-0005-z

Regular Article

New triterpenoids from the kernels of Azadirachta indica

Hong-Wei WANG^a,b, Jie-Qing LIU^a, Jin-Xiong CHEN^a,b, Yuan-Feng YANG^a,b, Yu-Xin YAN^a,b, Zhong-Rong LI^a, Ming-Hua QIU^a,b

a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b University of Chinese Academy of Sciences, Beijing 100049, China

Abstract
References
Related Articles
Metrics

Download: PDF(586 KB) HTML ()
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract Three new limonoids (1-3) and a new intact triterpenoid (4), along with three known constituents (5-7), were isolated from the dried kernels (after extracting azadirachtin) of Azadirachta indica. The structures of the new compounds 1-benzoyl-3-deacetyl-1-detigloyl salannin (1), 7-tigloyl-12-oxo vilasini (2), azadiralactone (3) and azadirahemiacetal (4) were elucidated by means of spectroscopic analysis. The cytotoxities of these isolated constituents were assayed.

Keywords Azadirachta indica triterpenoid limonoids

Fund:The project was financially supported by the Knowledge Innovation Program of the CAS (Grant No. KSCX2-YW-G-038, KSCX2-EW-R-15), Special Foundation for National Major Basic Research (No.SB2007FY400), as well as Foundation of State Key Laboratory of Phytochemistry and Plant Resources in West China (P2010-ZZ14). The authors were sincerely grateful to Mangshi Bright Neem Industry Developments Ltd. for providing research samples, and Professor Li Yan for cytotoxicity bioassay.

Issue Date: 11 February 2018

	Service

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

	Hong-Wei WANG
	Jie-Qing LIU
	Jin-Xiong CHEN
	Yuan-Feng YANG
	Yu-Xin YAN
	Zhong-Rong LI
	Ming-Hua QIU

Trendmd:

Cite this article:

Hong-Wei WANG,Jie-Qing LIU,Jin-Xiong CHEN, et al. New triterpenoids from the kernels of Azadirachta indica[J]. Natural Products and Bioprospecting, 2013, 3(1): 33-37.

URL:

http://npb.kib.ac.cn/EN/10.1007/s13659-013-0005-z OR http://npb.kib.ac.cn/EN/Y2013/V3/I1/33

[1]	Tan, Q. G.; Luo, X. D. Chem. Rev. 2011, 111, 7437-7522.
[2]	Kikuchi, T.; Ishii, K.; Noto, T.; Takahashi, A.; Tabata, K.; Suzuki, T.; Akihisa, T. J. Nat. Prod. 2011, 74, 866-870.
[3]	Wu, S. H.; Chen, Y. W.; Shao, S. C.; Wang, L. D.; Li, Z. Y.; Yang, L. Y.; Li, S. L.; Huang, R. J. Nat. Prod. 2008, 71, 731-734.
[4]	van der Nat, J. M.; van der Sluis, W. G.; de Silva, K. T.; Labadie, R. P. J. Ethnopharmacol. 1991, 35, 1-24.
[5]	Nakahara, K.; Roy, M. K.; Ono, H.; Maeda, I.; Ohnishi Kameyama, M.; Yoshida, M.; Trakoontivakorn, G. J. Agric. Food Chem. 2003, 51, 6456-6460.
[6]	Wu, S. B.; Ji, Y. P.; Zhu, J. J.; Zhao, Y.; Xia, G.; Hu, Y. H.; Hu, J. F. Steroids 2009, 74, 761-765.
[7]	Siddiqui, S.; Mahmood, T.; Siddiqui, B. S.; Faizi, S. Planta Med. 1988, 54, 457-459.
[8]	He, L.; Yin, N.; Cheng, J. W.; Wu, X. Q.; Jiang, J. X.; Song, X. L. Fitoterapia 2009, 80, 399-403.
[9]	Siddiqui, B. S.; Rasheed, M.; Ghiasuddin; Faizi, S.; Naqvi, S. N. H.; Tariq, R. M. Tetrahedron 2000, 56, 3547-3551.
[10]	Siddiqui, B. S.; Rasheed, M.; Ghiasuddin; Faizi, S.; Naqvi, S. N. H.; Tariq, R. M. Phytochemistry 2000, 53, 371-376.
[11]	Nanduri, S.; Thunuguntla, S. S. R.; Nyavanandi, V. K.; Kasu, S.; Kumar, P. M.; Ram, P. S.; Rajagopal, S.; Kumar, R. A.; Deevi, D. S.; Rajagopalan, R.; Venkateswarlu. Bioorg. Med. Chem. Lett. 2003, 13, 4111-4115.
[12]	Chen, J. X.; Chen, J. C.; Sun, Y.; Yan, Y. X.; Kong, L. M.; Li, Y.; Qiu, M. H. Planta Med. 2011, 77, 1844-1847.
[13]	Akihisa, T.; Takahashi, A.; Kikuchi, T.; Takagi, M.; Watanabe, K.; Fukatsu, M.; Fujita, Y.; Banno, N.; Tokuda, H.; Yasukawa, K. J. Oleo Sci. 2011, 60, 53-59.
[14]	Chianese, G.; Yerbanga, S. R.; Lucantoni, L.; Habluetzel, A.; Basillico, N.; Taramelli, D.; Fattorusso, E.; Scafati, O. T. J. Nat. Prod. 2010, 73, 1448-1452.
[15]	Morgan, E. D. Bioorg. Med. Chem. 2009, 17, 4096-4105.
[16]	Garg, H. S.; Bhakuni, D. S. Phytochemistry 1984, 23, 2383-2385.
[17]	Garg, H. S.; Bhakuni, D. S. Phytochemistry 1985, 24, 866-867.
[18]	Zhang, Q.; Shi, Y.; Liu, X. T.; Liang, J. Y.; Ip, N. Y.; Min, Z. D. Planta Med. 2007, 73, 1298-1303.
[19]	Kumar, C. S. R.; Srinivas, M.; Yakkundi, S. Phytochemistry 1996, 43, 451-455.
[20]	Siddiqui, B. S.; Ghiasuddin, Faizi, S.; Siddiqui, S. Phytochemistry 1992, 31, 4275-4278.
[21]	Luo, X. D.; Wu, S. H.; Wu, D. G.; Ma, Y. B.; Qi, S. H. Tetrahedron 2002, 58, 6691-6695.
[22]	Hong, Z. L.; Xiong, J.; Wu, S. B.; Zhu, J. J.; Hong, J. L.; Zhao, Y.; Xia, G.; Hu, J. F. Phytochemistry 2013, 86, 159-167.
[23]	Fujioka, T.; Sakurai, A.; Mihashi, K.; Kashiwada, Y.; Chen, I. S.; Lee, K. H. Chem. Pharm. Bull. 1997, 45, 68-74.
[24]	Bokel, M.; Cramer, R.; Gutzeit, H.; Reeb, S.; Kraus, W. Tetrahedron 1990, 46, 775-782.
[25]	Mosmann, T. J. Immunol. Methods 1983, 65, 55-63.

[1]	Jin-Tang Cheng, Shi-Tao Chen, Cong Guo, Meng-Jiao Jiao, Wen-Jin Cui, Shu-Hui Wang, Zhe Deng, Chang Chen, Sha Chen, Jun Zhang, An Liu. *Triterpenoid Saponins from the Seeds of Aesculus chinensis* and Their Cytotoxicities**[J]. Natural Products and Bioprospecting, 2018, 8(1): 47-56.
[2]	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.
[3]	Guo-Lei Zhu, Di-Fan Zhu, Luo-Sheng Wan, Xing-Rong Peng, Ni-Man Bao, Zhi-Run Zhang, Lin Zhou, Ming-Hua Qiu. *Six New 9,19-Cycloartane Triterpenoids from Cimicifuga foetida* L**[J]. Natural Products and Bioprospecting, 2016, 6(4): 187-193.
[4]	Zhen-Zhu Zhao, He-Ping Chen, Ying Huang, Zheng-Hui Li, Ling Zhang, Tao Feng, Ji-Kai Liu. Lanostane Triterpenoids from Fruiting Bodies of Ganoderma leucocontextum[J]. Natural Products and Bioprospecting, 2016, 6(2): 103-109.
[5]	Qingxi Su, Peggy J. Brodie, Yixi Liu, James S. Miller, Naina M. Andrianjafy, Rabodo Antsiferana, Vincent E. Rasamison, David G. I. Kingston. *Antiproliferative Triterpenoid Saponins from Leptaulus citroides* Baill. from the Madagascar Rain Forest**[J]. Natural Products and Bioprospecting, 2016, 6(1): 31-39.
[6]	Qi Wang, Xue Qiao, Yi Qian, Zi-wei Li, Yew-min Tzeng, De-min Zhou, De-an Guo, Min Ye. *Intestinal Absorption of Ergostane and Lanostane Triterpenoids from Antrodia cinnamomea* Using Caco-2 Cell Monolayer Model**[J]. Natural Products and Bioprospecting, 2015, 5(5): 237-246.
[7]	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.
[8]	Di-Fan Zhu, Guo-Lei Zhu, Ling-Mei Kong, Ni-Man Bao, Lin Zhou, Yin Nian, Ming-Hua Qiu. *Cycloartane Glycosides from the Roots of Cimicifuga foetida* with Wnt Signaling Pathway Inhibitory Activity**[J]. Natural Products and Bioprospecting, 2015, 5(2): 61-67.
[9]	Lu Liu, Yun-Li Zhao, Gui-Guang Cheng, Ying-Ying Chen, Xu-Jie Qin, Chang-Wei Song, Xing-Wei Yang, Ya-Ping Liu, Xiao-Dong Luo. Limonoid and Steroidal Saponin from Azadirachta indica[J]. Natural Products and Bioprospecting, 2014, 4(6): 335-340.
[10]	Jian-Qiang Zhao, Yan-Ming Wang, Hong-Tao Zhu, Dong Wang, Sheng-Hong Li, Rong-Rong Cheng, Chong-Ren Yang, Yi-Fei Wang, Min Xu, Ying-Jun Zhang. Highly Oxygenated Limonoids and Lignans from Phyllanthus flexuosus[J]. Natural Products and Bioprospecting, 2014, 4(4): 233-242.
[11]	Wei-Ming Zhang, Jie-Qing Liu, Xing-Rong Peng, Luo-Sheng Wan, Zhi-Run Zhang, Zhong-Rong Li, Ming-Hua Qiu. Triterpenoids and Sterols from the Leaves and Twigs of Melia azedarach[J]. Natural Products and Bioprospecting, 2014, 4(3): 157-162.
[12]	Wei-Ming Zhang, Jie-Qing Liu, Yuan-Yuan Deng, Jian-Jun Xia, Zhi-Run Zhang, Zhong-Rong Li, Ming-Hua Qiu. Diterpenoids and Limonoids from the Leaves and Twigs of Swietenia mahagoni[J]. Natural Products and Bioprospecting, 2014, 4(1): 53-57.
[13]	Da-Song YANG, Wei-Bing PENG, Zi-Lei LI, Xue WANG, Jian-Guo WEI, Ke-Chun LIU, Yong-Ping YANG, Xiao-Li LI. *Chemical constituents from the aerial parts of Euphorbia sikkimensis* and their bioactivities**[J]. Natural Products and Bioprospecting, 2013, 3(3): 112-116.
[14]	Feng ZHANG, Xiu-Feng HE, Wen-Bin WU, Wan-Sheng CHEN, Jian-Min YUE. New apotirucallane-type triterpenoids from Chisocheton paniculatus[J]. Natural Products and Bioprospecting, 2012, 2(6): 235-239.
[15]	Xiao-Ying WANG, Gui-Hua TANG, Chun-Mao YUAN, Yu ZHANG, Li HOU, Qing ZHAO, Xiao-Jiang HAO, Hong-Ping HE. Two new tirucallane triterpenoids from Aphanamixis grandifolia[J]. Natural Products and Bioprospecting, 2012, 2(5): 222-226.

Viewed

Full text

Abstract

Cited

Shared

Discussed