Ophiobolin-Type Sesterterpenoids from the Mangrove Endophytic Fungus Aspergillus sp. ZJ-68.
Runlin CaiHongming JiangYaling MoHuixian GuoChunyuan LiYuhua LongZhenming ZangZhigang ShePublished in: Journal of natural products (2019)
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 Mo2(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 μM, and compound 8 was found to show comparable inhibition of Mycobacterium tuberculosis protein tyrosine phosphatase B with an IC50 value of 19 μM.
Keyphrases
- lipopolysaccharide induced
- mycobacterium tuberculosis
- nitric oxide
- inflammatory response
- molecular docking
- molecular dynamics
- density functional theory
- induced apoptosis
- cell cycle arrest
- high glucose
- adipose tissue
- high throughput
- structure activity relationship
- high resolution
- diabetic rats
- cell wall
- oxidative stress
- drug induced
- endoplasmic reticulum stress
- protein protein
- gram negative
- amino acid
- small molecule