Culpin, a novel hydroquinone antibiotic of fungal origin.

Abstract

Culpin, 1, is a novel antibiotic found during the course of screening for new antifungal agents. It is produced by a species of Preussia isolated from a soil sample collected in Culpeper, Virginia. In this note, wedescribe the taxonomyof the producing organism and the production, isolation, physicochemical properties and structure elucidation of this novel antibiotic. The producing organism is a saprophytic, coprophilous ascomycete that readily produces

Biosynthesis and function of polyacetylenes and allied natural products

“…Functional group diversity is scant, consisting of alkoxy and C 1 modifications to the aryl ring and, rarely, modification of the sesquiterpene unit. Representative compounds include eutypine (19A), eulatinol (19E), culpin (19H) from the ascomycete Preussia sp., and Stereum hirsutum metabolites 19G-K [243][244][245]. The grapevine-attacking ascomycete Eutypa lata, the causative pathogen for "dying-arm disease", produces a strain-dependant mixture of acetylenic phenols, chromenes and benzofurans [246,247].…”

Endophytic fungi found in association with Smallanthus sonchifolius (Asteraceae) as resourceful producers of cytotoxic bioactive natural products

“…Genus Papulaspora is a well-known competitive soil mold in the culture of mushrooms [28,29] and it has just been recently reported as an endophyte in a few species as Vitex negundo [24], Manilkara bidentata [30], Taxus chinensis [31], Amomum siamense [32] and Solanum tuberosum [25]. Preussia, however, is recognized either as a soil or a coprophilous genus [33,34] but has never been mentioned before as an endophyte.…”

Using Jasplakinolide to Turn on Pathways that Enable the Isolation of New Chaetoglobosins from Phomospis asparagi

“…The untreated cultures appeared to be rich in polyketides of masses below 400 amu. While an exhaustive dereplication was not undertaken, examples of these compounds were provisionally identified as 4,6-dihydroxymellein (t R = 21.0 min), 20 patulolide C (t R = 21.5 min), 21 convolvulopyrone (t R = 24.0 min), 22 culpin (t R = 24.5 min), 23 phompsiol (t R = 28.0 min), 24 To obtain milligram quantities of the new metabolites, scale-up cultures were grown (5 × 1 L) using methods and conditions outlined in the Experimental Section. The immediate goal was to characterize the new compounds and evaluate their biological properties.…”

“…The untreated cultures appeared to be rich in polyketides of masses below 400 amu. While an exhaustive dereplication was not undertaken, examples of these compounds were provisionally identified as 4,6-dihydroxymellein (t R ) 21.0 min), 20 patulolide C (t R ) 21.5 min), 21 convolvulopyrone (t R ) 24.0 min), 22 culpin (t R ) 24.5 min), 23 phompsiol (t R ) 28.0 min), 24 and 4-hydroxymellein (t R ) 34.0 min), 25 as seen in the chromatogram A of Figure 1. Spiking the vigorously growing culture with jasplakinolide caused a dramatic shift in the biosynthetic profile, as shown by chromatogram B of Figure 1.…”