Chloropestolide A, an antitumor metabolite with an unprecedented spiroketal skeleton from Pestalotiopsis fici.
Chloropestolide A (1), a highly functionalized spiroketal with an unprecedented skeleton derived from a chlorinated bicyclo-[2.2.2]-oct-2-en-5-one ring and a 2,6-dihydroxy-4-methylbenzoic acid unit, has been isolated from the scale-up fermentation extract of Pestalotiopsis fici. The structure of 1 was elucidated by NMR spectroscopy and X-ray crystallography. 1 could be derived from the same Diels-Alder precursors as 2 and showed significant inhibitory effects on growth of two human cancer cell lines, HeLa and HT29, with GI(50) values of 0.7 and 4.2 microM, respectively.
Liu
Ling
L
Key Laboratory of Systematic Mycology & Lichenology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, People's Republic of China.
Li
Yan
Y
Liu
Shuchun
S
Zheng
Zhihui
Z
Chen
Xulin
X
Zhang
Hua
H
Guo
Liangdong
L
Che
Yongsheng
Y
D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D005658:Fungi / Q000737:chemistry*; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D019073:HT29 Cells; D006367:HeLa Cells; D006801:Humans; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010944:Plants / Q000382:microbiology; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
D000970:Antineoplastic Agents; D005663:Furans; D013141:Spiro Compounds; C542302:chloropestolide A; C520774:spiroketal