Meroterpenoid and Diphenyl Ether Derivatives from Penicillium sp. MA-37, a Fungus Isolated from Marine Mangrove Rhizospheric Soil

Abstract

Penicillium sp. MA-37, which was obtained from the rhizospheric soil of the mangrove plant Bruguiera gymnorrhiza, exhibited different chemical profiles in static and shaken fermentation modes. Three new meroterpenoid derivatives, 4,25-dehydrominiolutelide B (1), 4,25-dehydro-22-deoxyminiolutelide B (2), and isominiolutelide A (3), together with three known ones were characterized from its static fermentation, while three new diphenyl ether derivatives, namely, Δ(1('),3('))-1'-dehydroxypenicillide (4), 7-O-acetylsecopenicillide C (5), and hydroxytenellic acid B (6), along with five related metabolites were isolated from the shaken culture. The structures of these compounds were elucidated on the basis of spectroscopic analysis, and the structure of compound 2 was confirmed by X-ray crystallographic analysis. The absolute configurations of 1-3 and 6 were determined by ECD and modified Mosher's method, respectively. All isolated compounds were evaluated for brine shrimp lethality and antibacterial activity.

Diphenyl ethers from Aspergillus sp. and their anti-Aβ42 aggregation activities

“…[10,11], Leathesia nana [12], Phyllanthus atropurpureus [13], Symphyocladia latiuscula [14], and so on. Diphenyl ethers exhibit a wide range of interesting biological activities, such as antimicrobial [1,3,6,8,10], cytotoxic [2,6,9], radical-scavenging [11], enzyme inhibitory [5], actin inhibitory [15], anti-HSV-1 [2], and phytocidal activities [16,17]. In early chemical investigation, we reported the isolation of two diphenyl ethers, 2-isopentenyldiorcinol (9) and diorcinol (10), from a strain of endolichenic fungus Aspergillus sp.…”

“…In subsequent bioactive screening, diorcinol (10) showed significant Aβ 42 aggregation inhibitory activity with IC 50 value of 20.1 μM, while 2-isopentenyldiorcinol (9) was inactive. It is firstly discovered that diorcinol (10) with the character of diphenyl ether structure has anti-Aβ 42 aggregation activity. However, not all of diphenyl ethers displayed anti-Aβ 42 aggregation activity.…”

Synthesis and bioactivity evaluation of novel benzamide derivatives containing a diphenyl ether moiety

“…1), have played an important role in the field of agrochemicals, 6,7) can inhibit the growth of pathogenic fungi and can cause their eventual death by interfering with the respiration of the pathogen. 8,9) In our previous research, many substituted diphenyl ether derivatives were synthesized and found to have good antimicrobial activities, 10,11) and many natural diphenyl ether derivatives also elicited pharmacologically powerful activities, [12][13][14] such as antifungal, antibiotic, antimitotic and immunosuppressive activities. [15][16][17] Hence, whether the amide derivatives containing a diphenyl ether moiety will have good bioactivities is of interest.…”

First Total Syntheses and Antimicrobial Evaluation of Penicimonoterpene, a Marine-Derived Monoterpenoid, and Its Various Derivatives

“…Recently, marine-derived fungi have triggered our interest, due to their ability to produce structurally interesting bioactive secondary metabolites [5,6,7,8,9]. …”