Alkaloids isolated from Haemanthus humilis Jacq., an indigenous South African Amaryllidaceae: Anticancer activity of coccinine and montanine

被引:28
作者
Masi, M. [1 ]
Van Slambrouck, S. [2 ]
Gunawardana, S. [2 ]
van Rensburg, M. J. [3 ]
James, P. C. [2 ]
Mochel, J. G. [2 ]
Heliso, P. S. [2 ]
Albalawi, A. S. [2 ]
Cimmino, A. [1 ]
van Otterlo, W. A. L. [3 ]
Kornienko, A. [4 ]
Green, I. R. [3 ]
Evidente, A. [1 ]
机构
[1] Complesso Univ Monte S Angelo, Univ Naples Federico II, Dept Chem Sci, Via Cintia 4, I-80126 Naples, Italy
[2] South Dakota State Univ, Dept Chem & Biochem, Brookings, SD 57007 USA
[3] Univ Stellenbosch, Dept Chem & Polymer Sci, Private Bag X1, ZA-7602 Stellenbosch, South Africa
[4] Texas State Univ, Dept Chem & Biochem, San Marcos, TX 78666 USA
基金
新加坡国家研究基金会; 美国国家科学基金会;
关键词
Alkaloids; Anticancer activity; Coccinine and montanine; Haemanthus humilis; South African Amaryllidaceae; BIOSYNTHETIC INTERMEDIATE; ABSOLUTE-CONFIGURATION; BIOLOGICAL EVALUATION; LYCORINE; NARCICLASINE; DERIVATIVES; INCARTINE; ISOCARBOSTYRILS; EXTRACTS; ANALOGS;
D O I
10.1016/j.sajb.2019.01.036
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Haemanthus humilis Jacq., an indigenous South African Amaryllidaceae, was studied for the first time for its alkaloid content. From the acid extract of its bulbs, albomaculine, incartine, coccinine and montanine, belonging to the lycorine-, homolycorine- and isoquinoline-type alkaloids respectively, were isolated. Coccinine was the main metabolite (1.49 g/kg) and to the best of our knowledge H. humilis is to date the best natural source of this alkaloid. It is noteworthy that this Amaryllidaceae does not synthesize lycorine, the main and most common alkaloid produced by this plant genus. All the isolated alkaloids were bio-assayed for their anticancer activity against a panel of six human cancer cell lines, with coccinine evaluated for the first time. The results showed that coccinine and montanine have significant activity at low micromolar concentrations. (C) 2019 Published by Elsevier B.V. on behalf of SAAB.
引用
收藏
页码:277 / 281
页数:5
相关论文
共 61 条
  • [1] 5-HT and the immune system
    Ahern, Gerard P.
    [J]. CURRENT OPINION IN PHARMACOLOGY, 2011, 11 (01) : 29 - 33
  • [2] Bioinspired Total Synthesis of Montanine-Type Amaryllidaceae Alkaloids
    Bao, Xu
    Cao, Ye-Xing
    Chu, Wen-Dao
    Qu, Hu
    Du, Ji-Yuan
    Zhao, Xian-He
    Ma, Xiao-Yan
    Wang, Cheng-Tao
    Fan, Chun-An
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (52) : 14167 - 14172
  • [3] Phylogenetic selection of target species in Amaryllidaceae tribe Haemantheae for acetylcholinesterase inhibition and affinity to the serotonin reuptake transport protein
    Bay-Smidt, M. G. K.
    Jager, A. K.
    Krydsfeldt, K.
    Meerow, A. W.
    Stafford, G. I.
    Van Staden, J.
    Ronsted, N.
    [J]. SOUTH AFRICAN JOURNAL OF BOTANY, 2011, 77 (01) : 175 - 183
  • [4] Revised NMR data for incartine:: an alkaloid from Galanthus elwesii
    Berkov, Strahil
    Reyes-Chilpa, Ricardo
    Codina, Caries
    Viladomat, Francesc
    Bastida, Jaume
    [J]. MOLECULES, 2007, 12 (07) : 1430 - 1435
  • [5] Identification of Alkaloids from Hippeastrum aulicum (Ker Gawl.) Herb. (Amaryllidaceae) Using CGC-MS and Ambient Ionization Mass Spectrometry (PS-MS and LS-MS)
    Bessa, Carliani D. P. B.
    de Andrade, Jean P.
    de Oliveira, Renata S.
    Domingos, Eloilson
    Santos, Heloa
    Romao, Wanderson
    Bastida, Jaume
    Borges, Warley S.
    [J]. JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2017, 28 (05) : 819 - 830
  • [6] ALKALOIDS OF THE AMARYLLIDACEAE .7. ALKALOIDS CONTAINING THE HEMIACETAL OR LACTONE GROUP
    BRIGGS, CK
    HIGHET, PF
    HIGHET, RJ
    WILDMAN, WC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (12) : 2899 - 2904
  • [7] Cabezas F, 2003, CHEM PHARM BULL, V51, P315
  • [8] Control of cyclooxygenase-2 expression and tumorigenesis by endogenous 5-methoxytryptophan
    Cheng, Huei-Hsuan
    Kuo, Cheng-Chin
    Yan, Jiann-Long
    Chen, Hua-Ling
    Lin, Wei-Chung
    Wang, Kai-Hsuan
    Tsai, Kelvin K. -C.
    Guven, Hayrettin
    Flaberg, Emilie
    Szekely, Laszlo
    Klein, George
    Wu, Kenneth K.
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2012, 109 (33) : 13231 - 13236
  • [9] The number of known plants species in the world and its annual increase
    Christenhusz, Maarten J. M.
    Byng, James W.
    [J]. PHYTOTAXA, 2016, 261 (03) : 201 - 217
  • [10] Amaryllidaceae alkaloids: Absolute configuration and biological activity
    Cimmino, Alessio
    Masi, Marco
    Evidente, Marco
    Superchi, Stefano
    Evidente, Antonio
    [J]. CHIRALITY, 2017, 29 (09) : 486 - 499