Flavovirin — a new antifungal antibiotic produced by the pyrenomycete Melanconis flavovirens

Abstract

The pyrenomycete Melanconis flavovirens was found to produce a mixture of two antifungal antibiotics. The first has been already described; the antibiotic is identical with thermozymocidin (myriocin). The second antibiotic is a new compound, whose isolation and identification is presented in this paper. The chemical structure of this substance (C21H37NO5) was determined to be 2-amino-2-hydroxymethyl-3,4-trans-epoxy-14-oxo-eicos-trans-6-enoic acid. After the producer it was named flavovirin and it possesses strong activity against yeasts and a moderate effectivity against filamentous fungi.

Determination of the serine palmitoyl transferase inhibitor myriocin by electrospray and Q‐trap mass spectrometry

“…Sphingolipid metabolism is altered in several human diseases and its manipulation is an appealing therapeutic strategy (Hannun & Obeid, 2011). Myriocin [(2S,3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid] (Myr, or thermozymocidin or ISP-1; Figure 1) is a secondary metabolite initially isolated from some thermophilic ascomycetes (Kluepfel et al, 1972;Sailer et al, 1989) and recently found as a mycotoxin contaminant of grains (Shimshoni et al, 2013). Myriocin is one of the few substances known to inhibit de novo synthesis of sphingosine by inactivating serine palmitoyl transferase (SPT) with a complex mechanism that occurs in two steps, each of which has recently been elucidated.…”

Toward a Cancer Drug of Fungal Origin

“…Myriocin (Fig. ) is an antibiotic metabolite produced by Melanconis flavovirens , which was found to be identical to the previously isolated thermozycidin . It was later also isolated from Isaria sinclairii , and found to possess potent immunosuppressive activity, as well as from Mycelia sterilia .…”

“…2) is an antibiotic metabolite produced by Melanconis flavovirens, which was found to be identical to the previously isolated thermozycidin. 127 It was later also isolated from Isaria sinclairii, and found to possess potent immunosuppressive activity, 128 as well as from Mycelia sterilia. 129 Further, it was isolated from Myriococcum albomyces, 130 and as an antifungal metabolite from Cordyceps heteropoda, an entomopathogenic fungus isolated from an Australian cicada.…”