Undescribed Amaryllidaceae Alkaloids from Zephyranthes citrina and Their Cytotoxicity

被引:0
作者
Kroustkova, Jana [1 ]
Kohelova, Eliska [1 ]
Muthna, Darina [2 ]
Kunes, Jiri [3 ]
Havelek, Radim [2 ]
Vrabec, Rudolf [1 ]
Malanik, Milan [4 ]
Suchankova, Daniela [1 ]
Chlebek, Jakub [1 ]
Jenco, Jaroslav [1 ]
Kosturko, Stefan [1 ]
Cahlikova, Lucie [1 ]
机构
[1] Charles Univ Prague, Dept Pharmacognosy & Pharmaceut Bot, Hradec Kralove 50003, Czech Republic
[2] Charles Univ Prague, Fac Med Hradec Kralove, Dept Med Biochem, Hradec Kralove 50003, Czech Republic
[3] Charles Univ Prague, Fac Pharm, Dept Bioorgan & Organ Chem, Hradec Kralove 50003, Czech Republic
[4] Masaryk Univ, Fac Pharm, Dept Nat Drugs, Brno 61200, Czech Republic
来源
JOURNAL OF NATURAL PRODUCTS | 2024年 / 87卷 / 09期
关键词
CHEMICAL-CONSTITUENTS; APOPTOSIS; CRINUM; HAEMANTHAMINE;
D O I
10.1021/acs.jnatprod.4c00825
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
This phytochemical study presents the isolation of eight alkaloids from Zephyranthes citrina Baker. The structures of the new alkaloids, zephycitrine (1) and 6-oxonarcissidine (2), were established by analysis of spectroscopic and spectrometric data. Processing the EtOH extract under acid-base conditions yielded the unreported isolation artifacts 3 and 4. This work also provides analytical data for alkaloids not properly described in the literature (5 and 6). The hippeastidine/zephyranine scaffolds in derivatives 3, 4, and 8-10 are also thoroughly discussed. Furthermore, a cytotoxicity screening of 25 Amaryllidaceae alkaloids isolated from Z. citrina was performed. Only the known alkaloids haemanthamine (12), haemanthidine (13), and lycorine (27) showed significant cell growth inhibition.
引用
收藏
页码:2317 / 2326
页数:10
相关论文
共 43 条
  • [1] CLASTOGENIC EFFECT OF HIPPEASTIDINE (HIPP) (1,2,3,4,4A,6 HEXAHYDRO-10,HYDROXY-3,8,9,TRIMETHOXY-5,10B, ETHANOPHENANTHRIDINE)
    ALARCON, M
    CEA, G
    WEIGERT, G
    [J]. BULLETIN OF ENVIRONMENTAL CONTAMINATION AND TOXICOLOGY, 1986, 37 (04) : 508 - 512
  • [2] [Anonymous], WORLD FLORA ONLINE H
  • [3] ALKALOIDE AUS CRINUM-, ZEPHYRANTHES-, LEUCOJUM- UND CLIVIA-ARTEN
    BOIT, HG
    DOPKE, W
    STENDER, W
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (10): : 2203 - 2206
  • [4] AMARYLLIDACEEN-ALKALOIDE .10. DIE ALKALOIDE EINIGER GARTENSORTEN VON NARCISSUS-PSEUDONARCISSUS UND N-INCOMPARABILIS
    BOIT, HG
    EHMKE, H
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1956, 89 (01): : 163 - 167
  • [5] Amaryllidaceae Alkaloids of Different Structural Types from Narcissus L. cv. Professor Einstein and Their Cytotoxic Activity
    Breiterova, Katerina
    Koutova, Darja
    Marikova, Jana
    Havelek, Radim
    Kunes, Jiri
    Majorosova, Martina
    Opletal, Lubomir
    Host'alkova, Anna
    Jenco, Jaroslav
    Rezacova, Martina
    Cahlikova, Lucie
    [J]. PLANTS-BASEL, 2020, 9 (02):
  • [6] Pancratium canariense as an Important Source of Amaryllidaceae Alkaloids
    Cedron, Juan C.
    Oberti, Juan C.
    Estevez-Braun, Ana
    Ravelo, Angel G.
    Del Arco-Aguilar, Marcelino
    Lopez, Matias
    [J]. JOURNAL OF NATURAL PRODUCTS, 2009, 72 (01): : 112 - 116
  • [7] Amaryllidaceae alkaloids from the bulbs of Crinum latifolium L. and their cholinesterase inhibitory activities
    Chaichompoo, Waraluck
    Rojsitthisak, Pornchai
    Pabuprapap, Wachirachai
    Siriwattanasathien, Yuttana
    Yotmanee, Pathumwadee
    Suksamrarn, Apichart
    [J]. PHYTOCHEMISTRY, 2024, 217
  • [8] Cytotoxic activities of Amaryllidaceae alkaloids against gastrointestinal cancer cells
    Doskocil, Ivo
    Hostalkova, Anna
    Safratova, Marcela
    Benesova, Nina
    Havlik, Jaroslav
    Havelek, Radim
    Kunes, Jiri
    Kralovec, Karel
    Chlebek, Jakub
    Cahlikova, Lucie
    [J]. PHYTOCHEMISTRY LETTERS, 2015, 13 : 394 - 398
  • [9] Biological Evaluation of Structurally Diverse Amaryllidaceae Alkaloids and their Synthetic Derivatives: Discovery of Novel Leads for Anticancer Drug Design
    Evidente, Antonio
    Kireev, Artem S.
    Jenkins, Aaron R.
    Romero, Anntherese E.
    Steelant, Wim F. A.
    Van Slambrouck, Severine
    Kornienko, Alexander
    [J]. PLANTA MEDICA, 2009, 75 (05) : 501 - 507
  • [10] ALKALOIDS OF THE AMARYLLIDACEAE .8. THE STRUCTURES OF NARCISSAMINE, PSEUDOLYCORINE AND METHYLPSEUDOLYCORINE
    FALES, HM
    GIUFFRIDA, LD
    WILDMAN, WC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (16) : 4145 - 4150