Chloctanspirones A and B, novel chlorinated polyketides with an unprecedented skeleton, from marine sediment derived fungus Penicillium terrestre

Dehai Li, Li Chen, Tianjiao Zhu, T. Kurtán, Attila Mándi, Zhimin Zhao, Jing Li, Qianqun Gu

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

Two novel chlorinated sorbicillinoids named chloctanspirones A (1) and B (2), possessing an unprecedented bicyclo[2.2.2]octane-2-spiro cyclohexane skeleton, together with their quasi-precursors terrestrols K (3) and L (4), two additional new chlorinated compounds, were isolated from a marine sediment derived fungus Penicillium terrestre. Their structures including absolute stereochemistries were elucidated by analysis of NMR, MS data, and TDDFT CD calculations. The cytotoxic effects of 1-4 were preliminarily evaluated in HL-60 and A-549 cells. Compound 1 was active against both HL-60 and A-549 cells with IC50s 9.2 and 39.7 μM, respectively, while 2 showed weaker activity only against HL-60 cells (IC50 37.8 μM).

Original languageEnglish
Pages (from-to)7913-7918
Number of pages6
JournalTetrahedron
Volume67
Issue number41
DOIs
Publication statusPublished - Oct 14 2011

Fingerprint

Geologic Sediments
Polyketides
Stereochemistry
Penicillium
Fungi
Skeleton
Sediments
Nuclear magnetic resonance
HL-60 Cells
Inhibitory Concentration 50
bicyclo(2.2.2)octane
Cyclohexane

Keywords

  • Marine derived fungus
  • Penicillium terrestre
  • Sorbicillinoids

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Chloctanspirones A and B, novel chlorinated polyketides with an unprecedented skeleton, from marine sediment derived fungus Penicillium terrestre. / Li, Dehai; Chen, Li; Zhu, Tianjiao; Kurtán, T.; Mándi, Attila; Zhao, Zhimin; Li, Jing; Gu, Qianqun.

In: Tetrahedron, Vol. 67, No. 41, 14.10.2011, p. 7913-7918.

Research output: Contribution to journalArticle

Li, Dehai ; Chen, Li ; Zhu, Tianjiao ; Kurtán, T. ; Mándi, Attila ; Zhao, Zhimin ; Li, Jing ; Gu, Qianqun. / Chloctanspirones A and B, novel chlorinated polyketides with an unprecedented skeleton, from marine sediment derived fungus Penicillium terrestre. In: Tetrahedron. 2011 ; Vol. 67, No. 41. pp. 7913-7918.
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