Furanaspermeroterpenes A (1) and B (2), with a unique 6/6/6/5/5 pentacyclic skeleton, and five new congeners aspermeroterpenes D-H (3-7) were co-isolated from the marine-derived fungus Aspergillus terreus GZU-31-1. Among them, compounds 1 and 2 with rare five-membered D/E coupling rings were the first example of DMOA-derived meroterpenoids. Moreover, compound 3 was the first reported 6/6/6/6/5 pentacyclic meroterpenoid featuring an unusual cis-fused A/B ring. In the bioassays, all of the isolates were evaluated on the inhibitory activities against lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells, and compounds 3-7 exhibited significant anti-inflammatory activity with IC values ranging from 6.74 to 29.59 μM than positive control (Indomethacin, IC 30.98 μM).
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.bioorg.2021.105111 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Bialorastins A-F, highly oxygenated and polycyclic andrastin-type meroterpenoids with proangiogenic activity from the deep-sea cold-seep-derived fungus Penicillium bialowiezense CS-283.
Bioorg Chem
February 2024
CAS and Shandong Province Key Laboratory of Experimental Marine Biology, Center for Ocean Mega-Science, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China; Laboratory of Marine Biology and Biotechnology, Qingdao National Laboratory for Marine Science and Technology, Wenhai Road 1, Qingdao 266237, China. Electronic address:
Six new highly oxygenated and polycyclic andrastin-type meroterpenoids, namely, bialorastins A-F (1-6), were discovered from the culture of Penicillium bialowiezense CS-283, a fungus isolated from the deep-sea cold seep squat lobster Shinkaia crosnieri. The planar structures and absolute configurations of these compounds were determined by detailed analysis of spectroscopic data, single crystal X-ray diffraction, and TDDFT-ECD calculations. Structurally, bialorastin A (1) represents a rare 17-nor-andrastin that possesses an unusual 2-oxaspiro[4.
View Article and Find Full Text PDFSpectasterols, Aromatic Ergosterols with 6/6/6/5/5, 6/6/6/6, and 6/6/6/5 Ring Systems from .
J Nat Prod
June 2023
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Spectasterols A-E (-), aromatic ergosterols with unique ring systems, were isolated from . Compounds and possess a 6/6/6/5/5 ring system with an additional cyclopentene, while and have an uncommon 6/6/6/6 ring system generated by the D-ring expansion via 1,2-alkyl shifts. Compound exhibited cytotoxic activity (IC 6.
View Article and Find Full Text PDFHemiacetalmeroterpenoids A-C and Astellolide Q with Antimicrobial Activity from the Marine-Derived Fungus sp. N-5.
Mar Drugs
August 2022
School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China.
Four new compounds including three andrastin-type meroterpenoids hemiacetalmeroterpenoids A-C (-), and a drimane sesquiterpenoid astellolide Q (), together with eleven known compounds (-) were isolated from the cultures of the marine-derived fungus sp. N-5, while compound was first isolated from a natural source. The structures of the new compounds were determined by analysis of detailed spectroscopic data, and the absolute configurations were further decided by a comparison of the experimental and calculated ECD spectra.
View Article and Find Full Text PDFFuranaspermeroterpenes A and B, two unusual meroterpenoids with a unique 6/6/6/5/5 pentacyclic skeleton from the Marine-derived fungus Aspergillus terreus GZU-31-1.
Bioorg Chem
September 2021
School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou 510006, China; Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158, China. Electronic address:
Furanaspermeroterpenes A (1) and B (2), with a unique 6/6/6/5/5 pentacyclic skeleton, and five new congeners aspermeroterpenes D-H (3-7) were co-isolated from the marine-derived fungus Aspergillus terreus GZU-31-1. Among them, compounds 1 and 2 with rare five-membered D/E coupling rings were the first example of DMOA-derived meroterpenoids. Moreover, compound 3 was the first reported 6/6/6/6/5 pentacyclic meroterpenoid featuring an unusual cis-fused A/B ring.
View Article and Find Full Text PDFHyperprins A and B, Two Complex Meroterpenoids from .
Org Lett
April 2020
School of Pharmacy, State Key Laboratory of Medical Neurobiology, Fudan University, Shanghai 201203, People's Republic of China.
Hyperprins A () and B (), two polyprenylated acylphloroglucinol related meroterpenoids with undescribed carbon skeletons, were isolated from . Compound possesses a new 6/6/6/6/5/5 hexacyclic system with an unprecedented tetracyclo[10.3.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!