Structure and Cytotoxicity of Arnamial and Related Fungal Sesquiterpene Aryl Esters

被引:47
|
作者
Misiek, Mathias [3 ]
Williams, Jessica [4 ]
Schmich, Kathrin [3 ]
Huettel, Wolfgang [3 ]
Merfort, Irmgard [3 ]
Salomon, Christine E. [4 ]
Aldrich, Courtney C. [4 ]
Hoffmeister, Dirk [1 ,2 ]
机构
[1] Univ Jena, Dept Pharmaceut Biol, D-07745 Jena, Germany
[2] Univ Jena, Hans Knoll Inst, D-07745 Jena, Germany
[3] Univ Freiburg, D-79104 Freiburg, Germany
[4] Univ Minnesota, Ctr Drug Design, Minneapolis, MN 55455 USA
来源
JOURNAL OF NATURAL PRODUCTS | 2009年 / 72卷 / 10期
关键词
SECONDARY MOLD METABOLITES; ARMILLARIA-MELLEA; ANTIBACTERIAL SESQUITERPENOIDS; GENE-CLUSTER; BIOSYNTHESIS; IROFULVEN; SYNTHASE; CANCER;
D O I
10.1021/np900314p
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
We report on the structure elucidation of arnamial, a new Delta(2,4)-protoilludane everninate ester from the fungus Armillaria mellea, and on the apoptotic activity of arnamial as well as the cytotoxic activity of structurally related compounds on selected human cancer cells. Arnamial showed cytotoxicity against Jurkat T cells, MCF-7 breast adenocarcinoma, CCRF-CEM lymphoblastic leukemia, and HCT-116 colorectal carcinoma cells at IC50 = 3.9, 15.4, 8.9, and 10.7 mu M, respectively, and the related aryl ester melledonal C showed cytotoxic activity against CCRF-CEM cells (IC50 = 14.75 mu M). [1,2-C-13(2)]Acetate feeding supports a polyketide origin of the orsellinic acid moiety of arnamial.
引用
收藏
页码:1888 / 1891
页数:4
相关论文
共 8 条
  • [1] SESQUITERPENE ARYL ESTERS FROM ARMILLARIA-MELLEA
    DONNELLY, DMX
    HUTCHINSON, RM
    COVENEY, D
    YONEMITSU, M
    PHYTOCHEMISTRY, 1990, 29 (08) : 2569 - 2572
  • [2] Biosynthesis of Fungal Drimane-Type Sesquiterpene Esters
    Huang, Ying
    Hoefgen, Sandra
    Valiante, Vito
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (44) : 23763 - 23770
  • [3] Bioactive Sesquiterpene Aryl Esters from the Culture Broth of Armillaria sp.
    Kobori, Hajime
    Sekiya, Atsushi
    Suzuki, Tomohiro
    Choi, Jae-Hoon
    Hirai, Hirofumi
    Kawagishi, Hirokazu
    JOURNAL OF NATURAL PRODUCTS, 2015, 78 (01): : 163 - 167
  • [4] Structure, cytotoxic activity and mechanism of protoilludane sesquiterpene aryl esters from the mycelium of Armillaria mellea
    Li, Zhijin
    Wang, Yunchao
    Jiang, Bin
    Li, Wenliang
    Zheng, Lihua
    Yang, Xiaoguang
    Bao, Yongli
    Sun, Luguo
    Huang, Yanxin
    Li, Yuxin
    JOURNAL OF ETHNOPHARMACOLOGY, 2016, 184 : 119 - 127
  • [5] Three New Sesquiterpene Aryl Esters from the Mycelium of Armillaria mellea
    Chen, Chien-Chih
    Kuo, Yueh-Hsiung
    Cheng, Jing-Jy
    Sung, Ping-Jyun
    Ni, Ching-Li
    Chen, Chin-Chu
    Shen, Chien-Chang
    MOLECULES, 2015, 20 (06) : 9994 - 10003
  • [6] Comparative Structure-Activity Analysis of the Antimicrobial Activity, Cytotoxicity, and Mechanism of Action of the Fungal Cyclohexadepsipeptides Enniatins and Beauvericin
    Olleik, Hamza
    Nicoletti, Cendrine
    Lafond, Mickael
    Courvoisier-Dezord, Elise
    Xue, Peiwen
    Hijazi, Akram
    Baydoun, Elias
    Perrier, Josette
    Maresca, Marc
    TOXINS, 2019, 11 (09)
  • [7] 2-Thienyl-4-furyl-6-aryl pyridine derivatives: Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study
    Thapa, Pritam
    Karki, Radha
    Thapa, Uttam
    Jahng, Yurngdong
    Jung, Mi-Ja
    Nam, Jung Min
    Na, Younghwa
    Kwon, Youngjoo
    Lee, Eung-Seok
    BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (01) : 377 - 386
  • [8] Structure-Activity Relationships Studies in a Series of N,N-Bis(alkanol)amine Aryl Esters as P-Glycoprotein (Pgp) Dependent Multidrug Resistance (MDR) Inhibitors
    Martelli, Cecilia
    Coronnello, Marcella
    Dei, Silvia
    Manetti, Dina
    Orlandi, Francesca
    Scapecchi, Serena
    Romanelli, Maria Novella
    Salerno, Milena
    Mini, Enrico
    Teodori, Elisabetta
    JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (04) : 1755 - 1762