Structure-Activity Relationship of 39 Analogs of Laetispicine with Antidepressant Properties

doi:10.1142/S0192415X13500924

	Structure-Activity Relationship of 39 Analogs of Laetispicine with Antidepressant Properties
	Xie, Hui 3; Liu, Juan 4; Yu, Min 4; Wang, Yong 3; Yao, Chunyan 3; Yao, Shuyi 1; Jin, Di 4; Hu, Dingyu 1; Wang, Yanlin 2; Shen, Jingkang 1
刊名	AMERICAN JOURNAL OF CHINESE MEDICINE
	2013
卷号	41 期号:6 页码:1377-1392
关键词	Antidepressant Laetispicine Analogues Structure-Activity Relationship
ISSN号	0192-415X
DOI	10.1142/S0192415X13500924
文献子类	Article
英文摘要	The natural product Laetispicine (N-isobutyl-(3,4-methylendioxyphenyl)-2E, 4E, 9E-undecatrienoamide), was isolated from the Piper laetispicum C. DC and screened, for its antidepressant activity and antinociceptive effects. Structure-functional activities of five natural products indicated that biological activity is dependent on double bonds present within the benzene ring and a conjugated double bond located at positions 2-3 and 4-5 in the molecular structure. To further understand the structural-activity relationship of Laetispicine as a new potent and safe antidepressant, the structural-activity relationship of 39 analogs of Laetispicine were synthetized and tested in forced swimming tests in mice whilst also in protective effects against glutamate or H2O2 induced apoptosis in PC12 cells. The results show that the compound 30 - N-isobutyl-11-(4-chlorophenyl) undeca-2E, 4E, 9E-trienamide exhibited the same activity as the parental compound Laetispicine, and furthermore, the effective dose of this compound is lower than Laetispicine. Therefore, the compound 30 might be a potentially useful therapy in the treatment of depression. For structure, the conjugated double bonds located at 2-3, 4-5 and isolated double bonds from benzene ring are necessary for the antidepressant activities no matter the different length of carbon chain; the isobutyl connected with acylamino also are necessary; and the benzodioxole moiety is replaceable, the halogen atom in phenyl ring at the para-position could enhance this kind of activity.
资助项目	Ministry of Science and Technology of the People's Republic of China[2009ZX09103-075] ; Science Committee of Shanghai, China[08DZ1971203] ; Fudan University, China[00000000]
WOS关键词	PC12 CELLS ; MAJOR DEPRESSION ; IN-VITRO ; EXTRACT ; RATS ; PROLIFERATION ; ANTIOXIDANT ; GLUTAMATE ; CORTICOSTERONE ; INVOLVEMENT
WOS研究方向	Integrative & Complementary Medicine ; General & Internal Medicine
语种	英语
出版者	WORLD SCIENTIFIC PUBL CO PTE LTD
WOS记录号	WOS:000327354400012
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/277775]
专题	药物化学研究室中科院受体结构与功能重点实验室新药研究国家重点实验室
通讯作者	Pan, Shengli
作者单位	1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China; 2.Yumen Oilfield Hosp, Yumen 735019, Gansu, Peoples R China 3.Fudan Univ, Sch Pharm, Shanghai 201203, Peoples R China; 4.Jiamusi Univ, Coll Pharm, Dept Pharmacognosy, Jiamusi 154007, Peoples R China;
推荐引用方式 GB/T 7714	Xie, Hui,Liu, Juan,Yu, Min,et al. Structure-Activity Relationship of 39 Analogs of Laetispicine with Antidepressant Properties[J]. AMERICAN JOURNAL OF CHINESE MEDICINE,2013,41(6):1377-1392.
APA	Xie, Hui.,Liu, Juan.,Yu, Min.,Wang, Yong.,Yao, Chunyan.,...&Pan, Shengli.(2013).Structure-Activity Relationship of 39 Analogs of Laetispicine with Antidepressant Properties.AMERICAN JOURNAL OF CHINESE MEDICINE,41(6),1377-1392.
MLA	Xie, Hui,et al."Structure-Activity Relationship of 39 Analogs of Laetispicine with Antidepressant Properties".AMERICAN JOURNAL OF CHINESE MEDICINE 41.6(2013):1377-1392.