Modiolide and pyrone derivatives from the sea fan-derived fungus Curvularia sp. PSU-F22

Abstract

Investigation of secondary metabolites from the sea fan-derived fungus Curvularia sp. PSU-F22 resulted in isolation of three new metabolites, curvulapyrone (1), curvulalide (2) and curvulalic acid (3) together with six known compounds, modiolides A (4) and B (5), pyrenolide A (6), stagonolide E (7), mycoepoxydiene (8), and deacetylmycoepoxydiene (9). Their antimicrobial activity against Staphylococcus aureus ATCC 25923, methicillin-resistant S. aureus and Microsporum gypseum SH-MU-4 were examined.

One‐Flask Tethered Ring Closing Metathesis–Electrocyclic Ring Opening for the Highly Stereoselective Synthesis of Conjugated Z/E‐Dienes

“…Remarkably, while our work was in progress, Rukachaisirikul et al described the first isolation and structural elucidation of a novel natural product from the marine fungus Curvularia sp., to which the structure of (R)-9 and the name curvulalic acid were assigned. [70] The assignment of the R-configuration, originally based on comparison of the specific rotation with related natural products, could be corroborated by our total [70] for curvulalic acid}. It should, however, be noted that the 13 C NMR data reported for natural curvulalic acid and those observed by us for synthetic (R)-9 do not match very well.…”

Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

“…Cyanobacterium [8,9] Aspinolides A-C (1-3) Aspergillus chraceus (DSM-7428) Fungus [19] Sporostatin (M5032) (53) Sporormiella sp. M5032 Fungus [20] Herbarumins I-III (40)(41)(42) Phoma herbarum Fungus [21,22] Pyridomacrolidin (52) Beauveria bassiana Fungus [23,24] Microcarpalide (43) Unidentified Endophytic fungus [25] Multiplolides A, B (4, 5) Xylaria multiplex BCC 1111 Fungus [26] Xestodecalactones A-C (54-56) Penicillium cf. Montanense Marine-derived fungus [27] Fusanolides A, B (6, 7) Fusarium sp.…”

“…; Achaetomium cristalliferum Endophytic fungus [41] 3R,5R-Sonnerlactone (62) 3R,5S-Sonnerlactone (63) Unidentified Endophytic fungus [42] Curvulalide (34) Curvularia sp. PSUF22 Marine-derived fungus [43] to the characteristic macrolactone, they all share a methyl group at C-9, but differ in the number and nature of oxygen functionalities and the degree of unsaturation.…”

“…The first one covered synthetic studies on selected naturally occurring ten-membered lactones [5]. The second focused on synthetic approaches to three 10-membered lactones: mueggelone (39), microcarpalide (43), and Sch 642305 (57) [6]. The third review summarized the biological and synthetic studies of the metabolites belonging to the decarestrictine family [7].…”

A concise enantioselective synthesis of marine macrolide-stagonolide E via organocatalysis

“…PSU-F22. 2 This family of natural products displays a wide range of pharmacologically interesting properties such as antibacterial, antitumoral, and antifungal, and the inhibition of cholesterol biosynthesis. 3 The low availability of these macrolides coupled with their interesting biological profile continued to attract the attention of synthetic organic chemists worldwide.…”