Home > Archive>Volume 26, Issue 1, 2018 >85-91. DOI:10.11926/jtsb.3771
PDF HTML XML Export Cite reminder
Amide Alkaloids from the Seeds of Clausena lansium and Their Nematicidal Activities
Author:
  • Article
    • | |
  • Metrics
    • |
  • Reference [18]
    • |
  • Related [20]
    • | | |
  • Comments
    Abstract:

    In order to understand the nematicidal activities of amide alkaloids from the seeds of Clausena lansium, ten amide alkaloids were isolated by comprehensive chromatographic techniques. On the basis of spectral data, their structures were identified as:N-methyl-cinnamamide (1), clausenalansamide A (2), 3-dehydroxy-3-methoxyl-clausenalansamide A (3), clausenalansamide B (4), lansiumamide B (5), N-2-phenylethyl-cinnamamide (6), 2'-dehydroxy-2'-oxo-clausenalansamide B (7), lansamide-7 (8), homoclausenamide (9), 1,5-dihydro-5-hydroxy-1-methyl-3,5-diphenyl-2H-pyrrol-2-one (10). Among them, compounds 3, 7 and 10 were new natural products. Meanwhile, the nematicidal activity against Panagrellus redivivusl was tested for the first time. All of them showed the nematicidal activity, and compounds 2, 3, 5 and 8 presented stronger activities than dichlorofenthion, providing scientific evidence for the development of new pesticide.

    Reference
    [1] HUANG X S, LUO L J. Determination of the clausenaminade in the fruit and seed of Clausena lansium (Lour.) Skeels[J]. Sci Technol Food Ind, 2006, 27(6):172-173. doi:10.3969/j.issn.1002-0306.2006. 06.056. 黄雪松, 罗丽君. 黄皮果、黄皮核中黄皮酰胺的测定[J]. 食品工业科技, 2006, 27(6):172-173. doi:10.3969/j.issn.1002-0306.2006.06.056.
    [2] REN Q, LI F, LUO X Z, et al. Advances in coumarin compounds from Clausena[J]. Lishizhen Med Mat Med Res, 2009, 20(5):1283-1285. doi:10.3969/j.issn.1008-0805.2009.05.150. 任强, 李芳, 罗秀珍, 等. 黄皮属植物香豆素类成分研究进展[J]. 时珍国医国药, 2009, 20(5):1283-1285. doi:10.3969/j.issn.1008-0805.2009.05.150.
    [3] YANG M H, CHEN Y Y, HUANG L. Studies on the chemical constituents of (Clausena lansium) (Lour.) Skeels. Ⅱ:The isolation and structural elucidation of neoclausenamide and dehydrocycloclausenamide[J]. Acta Chim Sin, 1987, 5(3):267-272. doi:10.1002/cjoc.19870050312.
    [4] ZHANG J T, DUAN W Z, LIU S L, et al. Antidementia effects of (-)clausenamide[J]. Herald Med, 2001, 20(7):403-404. doi:10.3870/j.issn.1004-0781.2001.07.001. 张均田, 段文贞, 刘少林, 等. (-)黄皮酰胺的抗老年痴呆作用[J]. 医药导报, 2001, 20(7):403-404. doi:10.3870/j.issn.1004-0781.2001. 07.001.
    [5] ZUO M M, ZHOU J M, HU G H, et al. Synthesis and anti-tumor activities in vitro of cinnamic amide compounds[J]. Chem World, 2012, 53(4):239-242. doi:10.3969/j.issn.0367-6358.2012.04.014. 左明明, 周健民, 胡国辉, 等. 肉桂酰胺类化合物的合成及其体外抗肿瘤活性[J]. 化学世界, 2012, 53(4):239-242. doi:10.3969/j.issn. 0367-6358.2012.04.014.
    [6] LIU X M, MA F N, WAN S Q. Antifungal activity of the methanol extract of Clausena lansium[J]. Plant Prot, 2008, 34(2):64-66. doi:10. 3969/j.issn.0529-1542.2008.02.017. 刘序铭, 马伏宁, 万树青. 黄皮甲醇提取物的抑真菌作用[J]. 植物保护, 2008, 34(2):64-66. doi:10.3969/j.issn.0529-1542.2008.02.017.
    [7] MA Q Y, HUANG S Z, LI H F, et al. Studies on the biocontrol activity of compounds from Polygonum perfoliatum[J]. Hubei Agric Sci, 2013, 52(21):5245-5247. doi:10.3969/j.issn.0439-8114.2013.21.035. 马青云, 黄圣卓, 李红芳, 等. 杠板归中化学成分生防活性研究[J]. 湖北农业科学, 2013, 52(21):5245-5247. doi:10.3969/j.issn.0439-8114.2013.21.035.
    [8] SHEN W W, LI W, WANG G C, et al. Chemical constituents of Clausena lansium[J]. J Jinan Univ (Nat Sci), 2012, 33(5):506-509. doi:10.3969/j.issn.1000-9965.2012.05.015. 申文伟, 李雯, 王国才, 等. 黄皮核的化学成分[J]. 暨南大学学报(自然科学版), 2012, 33(5):506-509. doi:10.3969/j.issn.1000-9965. 2012.05.015.
    [9] MANEERAT W, THA-IN S, CHEENPRACHA S, et al. New amides from the seeds of Clausana lansium[J]. J Med Plant Res, 2011, 5(13):2812-2815.
    [10] YANG L, ZHENG Q Y, WANG D X, et al. Reversal of nucleophilicity of enamides in water:Control of cyclization pathways by reaction media for the orthogonal synthesis of dihydropyridinone and pyrolidinone Clausena alkaloids[J]. Org Lett, 2008, 10(12):2461-2464. doi:10.1021/ol800740h.
    [11] WANG G C, LI W, WANG Y, et al. A new amide and a new monoterpene from the seeds of Clausena lansium[J]. Nat Prod Res, 2013, 27(6):558-562. doi:10.1080/14786419.2012.678354.
    [12] BAYER A, MAIER M E. Synthesis of enamides from aldehydes and amides[J]. Tetrahedron, 2004, 60(31):6665-6677. doi:10.1016/j.tet. 2004.05.082.
    [13] BORGES-DEL-CASTILLO J, VAZQUEZ-BUENO P, SECUNDINOLUCAS M, et al. The N-2-phenylethylcinnamamide from Spilanthes ocymifolia[J]. Phytochemistry, 1984, 23(11):2671-2672. doi:10. 1016/S0031-9422(00)84123-0.
    [14] HIGUCHI, SHOHEI, ARAI, et al. Preparation and formulation of phenacylacetamides as drugs for the treatment of liver diseases:JP 03024009[P]. 1991-02-01.
    [15] SHEN D Y, NGUYEN T N, WU S J, et al. γ-and δ-Lactams from the leaves of Clausena lansium[J]. J Nat Prod, 2015, 78(11):2521-2530. doi:10.1021/acs.jnatprod.5b00148.
    [16] YANG M H, CHEN Y Y, HUANG L. Studies on the chemical constituents of Clausena Lansium (Lour.) Skeels Ⅲ:The structural elucidation of homo-and zeta-clausenamide(1)[J]. Chin Chem Lett, 1991, 2(4):291-292.
    [17] YANG L, LEI C H, WANG D X, et al. Highly efficient and expedient synthesis of 5-hydroxy-1H-pyrrol-2-(5H)-ones from FeCl3-catalyzed tandem intramolecular enaminic addition of tertiary enamides to ketones and 1,3-hydroxy rearrangement[J]. Org Lett, 2010, 12(17):3918-3921. doi:10.1021/ol101607z.
    [18] DENG H D. Study on the bioactive components from peels of Clausena lansium[D]. Haikou:Hainan University, 2014. 邓会栋. 黄皮果皮中的生物活性成分研究[D]. 海口:海南大学, 2014.
    Cited by
    Comments
    Comments
    分享到微博
    Submit
Get Citation

范玉娇,陈惠琴,梅文莉,许书慧,周丽曼,黄绵佳,戴好富.黄皮种子中酰胺类生物碱及其杀线虫活性研究[J].热带亚热带植物学报,2018,26(1):85~91

Copy
Share
Article Metrics
  • Abstract:1476
  • PDF: 1317
  • HTML: 369
  • Cited by: 0
History
  • Received:May 26,2017
  • Revised:July 18,2017
  • Online: January 30,2018
Article QR Code
You are the first4641376 Visitors
Governing Body：中国科学院
Organizer：中国科学院华南植物园 广东省植物学会
Address：Xingke Road 723,Tianhe District,Guangzhou,China
Phone：+86 (0)20-3725 2514
Journal of Tropical and Subtropical Botany ® 2025 All Rights Reserved