Journal
JOURNAL OF NATURAL PRODUCTS
Volume 82, Issue 8, Pages 2268-2278Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.9b00462
Keywords
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Funding
- Guangdong Special Fund for Marine Economic Development [GDME-2018C004]
- National Natural Science Foundation of China [2187713, 41876153, 21472251]
- Key Project of Natural Science Foundation of Guangdong Province [2016A040403091]
- Special Promotion Program for Guangdong Provincial Ocean and Fishery Technology [A201701C06]
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Eleven new ophiobolin-type sesterterpenoids, asperophiobolins A-K (1-11), along with 12 known analogues (12-23) were isolated from the cultures of the mangrove endophytic fungus Aspergillus sp. ZJ-68. The structures of the new compounds were elucidated through spectroscopic analyses, and their absolute configurations were assigned by a combination of Mo-2(AcO)(4)-induced electronic circular dichroism spectra and quantum chemical calculations. Asperophiobolins A-D (1-4) represent the first examples possessing a five-membered lactam unit between C-5 and C-21 in ophiobolin derivatives. In the bioactivity assays, compounds 8-10 and 14-17 exhibited inhibitory effects on lipopolysaccharide-induced nitric oxide production in RAW 264.7 macrophage cells with IC50 values ranging from 9.6 to 25 mu M, and compound 8 was found to show comparable inhibition of Mycobacterium tuberculosis protein tyrosine phosphatase B with an IC50 value of 19 mu M.
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