Meroterpenoids with diverse ring systems from the sponge-associated fungus alternaria sp. JJY-32

Guojian Zhang, Guangwei Wu, Tianjiao Zhu, T. Kurtán, Attila Mándi, Jieying Jiao, Jing Li, Xin Qi, Qianqun Gu, Dehai Li

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Fifteen meroterpenoids (1-15) with diverse ring systems including an unprecedented oxaspiro[5.5]nonane-fused cyclohexenone (1), hydrogenated benzofurans (2-5), hydrogenated chromans (6, 7), hydrogenated cyclopenta[b]chromans (8-11), and four monocyclic structures (12-15) were isolated from the sponge-associated fungus Alternaria sp. JJY-32. The structures were elucidated by detailed spectroscopic analysis, including 2D NMR and electronic circular dichroism (ECD) calculations, and assisted by chemical derivatizations. On the basis of supplementation experiments with specific enzyme inhibitors and putative precursors, a shikimate-isoprenoid hybrid biosynthetic pathway is proposed. The NF-κB inhibitory activities of 1-15 were tested, and all of them, except 6 and 7 (IC50 > 100 μM), showed activities with IC50 values ranging from 39 to 85 μM in RAW264.7 cells.

Original languageEnglish
Pages (from-to)1946-1957
Number of pages12
JournalJournal of Natural Products
Volume76
Issue number10
DOIs
Publication statusPublished - Oct 25 2013

Fingerprint

Chromans
Alternaria
Porifera
Fungi
Inhibitory Concentration 50
Benzofurans
Spectroscopic analysis
Biosynthetic Pathways
Terpenes
Enzyme Inhibitors
Circular Dichroism
Nuclear magnetic resonance
Experiments

ASJC Scopus subject areas

  • Complementary and alternative medicine
  • Molecular Medicine
  • Organic Chemistry
  • Analytical Chemistry
  • Pharmaceutical Science
  • Pharmacology
  • Drug Discovery

Cite this

Meroterpenoids with diverse ring systems from the sponge-associated fungus alternaria sp. JJY-32. / Zhang, Guojian; Wu, Guangwei; Zhu, Tianjiao; Kurtán, T.; Mándi, Attila; Jiao, Jieying; Li, Jing; Qi, Xin; Gu, Qianqun; Li, Dehai.

In: Journal of Natural Products, Vol. 76, No. 10, 25.10.2013, p. 1946-1957.

Research output: Contribution to journalArticle

Zhang, G, Wu, G, Zhu, T, Kurtán, T, Mándi, A, Jiao, J, Li, J, Qi, X, Gu, Q & Li, D 2013, 'Meroterpenoids with diverse ring systems from the sponge-associated fungus alternaria sp. JJY-32', Journal of Natural Products, vol. 76, no. 10, pp. 1946-1957. https://doi.org/10.1021/np4005757
Zhang, Guojian ; Wu, Guangwei ; Zhu, Tianjiao ; Kurtán, T. ; Mándi, Attila ; Jiao, Jieying ; Li, Jing ; Qi, Xin ; Gu, Qianqun ; Li, Dehai. / Meroterpenoids with diverse ring systems from the sponge-associated fungus alternaria sp. JJY-32. In: Journal of Natural Products. 2013 ; Vol. 76, No. 10. pp. 1946-1957.
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