Structural elucidation, total synthesis, and cytotoxic activity of effphenol A

被引:12
|
作者
Liu, Hongxin [1 ]
Chen, Shanchong [1 ]
Zhang, Xiao [2 ]
Dong, Chunmao [2 ,3 ]
Chen, Yuchan [1 ]
Liu, Zhaoming [1 ]
Tan, Haibo [2 ,3 ]
Zhang, Weimin [1 ]
机构
[1] Guangdong Acad Sci, Guangdong Prov Key Lab Microbial Culture Collect, State Key Lab Appl Microbiol Southern China, Guangdong Open Lab Appl Microbiol,Guangdong Inst, Guangzhou 510070, Peoples R China
[2] Chinese Acad Sci, Key Lab Plant Resources Conservat & Sustainable U, Guangdong Prov Key Lab Appl Bot, Program Nat Prod Chem Biol,South China Bot Garden, Guangzhou 510650, Peoples R China
[3] Cent South Univ, Xiangya Sch Pharmaceut Sci, Changsha 410013, Peoples R China
基金
中国国家自然科学基金;
关键词
NATURAL-PRODUCTS; MEROTERPENOIDS; DERIVATIVES;
D O I
10.1039/d0ob01985b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly substituted phenol derivative, effphenol A (1), was isolated from the deep-sea-derived fungus Trichobotrys effuse FS524. Its complete structural assignment was established through a combination of spectroscopic analysis together with single-crystal X-ray diffraction experiments and further unequivocally confirmed by a biomimetic total synthesis. Structurally, effphenol A possesses a poly-substituted 6-5/6/6 tetracyclic ring system, which represents the first case of such a skeleton found in nature. Furthermore, the cytotoxic activity of effphenol A (1) toward four human cancer cell lines was assayed.
引用
收藏
页码:9035 / 9038
页数:4
相关论文
共 50 条
  • [1] Total synthesis and structural elucidation of (-)-delactonmycin
    Correa, IR
    Pilli, RA
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (26) : 3017 - 3020
  • [2] Adenophorone, An Unprecedented Sesquiterpene from Eupatorium adenophorum: Structural Elucidation, Bioinspired Total Synthesis and Neuroprotective Activity Evaluation
    Yin, Bo
    Li, Xiaohuan
    Li, Zi-Xiang
    Zhu, Xiao-Xin
    Zhang, Lan
    Zhou, Xian-Li
    Xu, Jin-Bu
    Chen, Feng-Zheng
    Tang, Pei
    Gao, Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (31)
  • [3] Total synthesis and structural elucidation of ent-micropyrone and (+)-ascosalipyrone
    Gregg, Claire
    Perkins, Michael V.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (32) : 6547 - 6553
  • [4] Total synthesis and structural elucidation of natural products:: (-)-delactonmycin, (+)-plumerinine, and (-)-parvistemoamide
    Pilli, RA
    Correa, IR
    Maldaner, AO
    Rosso, GB
    PURE AND APPLIED CHEMISTRY, 2005, 77 (07) : 1153 - 1160
  • [5] Asymmetric Total Synthesis and Structural Elucidation of Unusual Oxindole Alkaloid Leucolusine
    Pandey, Ganesh
    Khamrai, Jagadish
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (05) : 621 - 624
  • [6] Pellasoren: Structure Elucidation, Biosynthesis, and Total Synthesis of a Cytotoxic Secondary Metabolite from Sorangium cellulosum
    Jahns, Christine
    Hoffmann, Thomas
    Mueller, Stefan
    Gerth, Klaus
    Washausen, Peter
    Hoefle, Gerhard
    Reichenbach, Hans
    Kalesse, Markus
    Mueller, Rolf
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) : 5239 - 5243
  • [7] Total Synthesis of Two Possible Diastereomers of (+)-Sarcophytonolide C and Its Structural Elucidation
    Takamura, Hiroyoshi
    Iwamoto, Kohei
    Nakao, Eiji
    Kadota, Isao
    ORGANIC LETTERS, 2013, 15 (05) : 1108 - 1111
  • [8] Structure elucidation of nigricanoside A through enantioselective total synthesis
    Chen, Jie
    Koswatta, Panduka
    DeBergh, J. Robb
    Fu, Peng
    Pan, Ende
    MacMillan, John B.
    Ready, Joseph M.
    CHEMICAL SCIENCE, 2015, 6 (05) : 2932 - 2937
  • [9] Structural Elucidation and Biomimetic Synthesis of (±)-Cochlactone A with Anti-Inflammatory Activity
    Peng, Xing-Rong
    Lu, Shuang-Yang
    Shao, Li-Dong
    Zhou, Lin
    Qiu, Ming-Hua
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (10) : 5516 - 5522
  • [10] Synthesis, structural characterization, and cytotoxic activity of new spirocyclic octachlorocyclotetraphosphazenes
    Isiklan, Muhammet
    Sayin, Levent
    Sonkaya, Omer
    Hokelek, Tuncer
    Turk, Mustafa
    Oguztuzun, Serpil
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2016, 191 (09) : 1216 - 1222