Metabolites of the marine fungus Humicola fuscoatra KMM 4629

Abstract

A new sesquiterpene of the caryophyllene series, fuscoatrol А (1), and known compounds, 11 epiterpestacin (2) and β nitropropionic acid (3), were isolated from the marine fungus Humicola fuscoatra (Traaen) KMM 4629 associated with the Kuril colonial ascidium. The structure of 1 was established on the basis of X ray diffraction data and 2D NMR spectroscopy. The antimicrobial and cytotoxic activities of compounds 1-3 were studied.

The importance of asking “how and why?” in natural product structure elucidation

“…2). 8 On the basis of the downeld chemical shi of C(8) in cytosporolide A (1a) (87.5 ppm), compared to the analogous hydroxylated C(8) position of 6-hydroxypunctaporonin B (2) (74.2 ppm), Che and coworkers proposed that the cytosporolides contained an unusual 9-membered peroxylactone ring (Fig. 2).…”

Cytosporinols A-C, new caryophyllene sesquiterpenoids from Cytospora sp.

“…20 Therefore, 3 was assigned 1R, 2R, 5S, 6S, 8R, 9S, 10R, 11R, and 12S absolute configuration. Cytosporinols A-C (1-3) are closely related to the known taedolidol, 3 6-epitaedolidol, 3 and punctaporonin C (4), 7-9 all possessing the rare oxatetracyclo[6.3.2.0 1,4 .0 5,13 ]tridecane skeleton, but differ by having different substituents at C-6 (1), C-10 (1-3), and C-11 (3), as well as a tetrasubstituted olefin (1) and a terminal olefin (2). In addition, 1-3 are structurally similar to a synthetic byproduct 5 created in the acid-mediated cyclization of the nonatural enantiomer pestalotiopins, 23,24 but differ in having different configurations for all stereogenic centers and substituents at C-6 and C-11, respectively.…”

“…isolated from Taxus brevifolia; 1,2 pestalotiopsolide A, teadolidol, and 6-epiteadolidol, highly oxidized caryophyllenes from a Pestalotiopsis sp. endophytic to the bark of Pinus taeda; 3 the 6-hydroxpunctaporonins, antibacterial metabolites from a fungicolous Pestalotiopsis disseminata; 4 fuscoatrol A, a cytotoxic agent from a marine-derived Humicola fuscoatra KMM 4629; 5 the punctaporonins (also named as punctatins), antifungal agents from a coprophilous Poronia punctata; [6][7][8][9][10][11] walleminol and walleminone, two cis-fused iso-caryophyllenes from the toxigenic fungus Wallemia sebi; 12 and Sch 725432, 601253, 601254, and 725434, antifungal agents from Chrysosporium pilosum. 13 During an ongoing search for new bioactive natural products from fungi of unique habitats, we initiated chemical studies of the fungi either inhabiting the fruiting body and larvae of Cordyceps sinensis 14 or its surface soil.…”

Punctaporonins H–M: Caryophyllene-Type Sesquiterpenoids from the Sponge-Associated Fungus Hansfordia sinuosae

“…The majority of caryophyllene-related analogues have been isolated from terrestrial plants [2,3,4] and the plant-associated fungal species [5,6,7,8,9,10,11,12]. Marine-derived caryophyllane-type compounds were found from the soft coral Sinularia nanolobata [13,14] and the gorgonian coral Subergorgia suberosa [15], while fuscoatrol A is the only caryophyllene sesquiterpene isolated from the marine fungus Humicola fuscoatra [16]. Some caryophyllene derivatives exhibited immunosuppressive [9], cytotoxic [15], and antibiotic activities [17,18].…”