Studies in the biochemistry of micro-organisms. 95. Rugulosin, a crystalline colouring matter of Penicillium rugulosum Thom

Abstract

Raper & Thom (1949) in their Manual of the Penicillia separate species in this genus into four major sections, Monoverticillata, Asymmetrica, Biverticillata-Symmetrica and Polyverticillata. They subdivide each of the sections into a number of series so that the Biverticillata-Symmetrica section, for example, includes six such series among which, for the purpose of this communication, the following are of interest: the P. luteum series including P. wortmanni Klocker; the P. funiculosum series including P. iBlandicum Sopp; and the P. rugulo8um series including P. rugulo8um Thom. In common with other series in the Biverticillata-Symmetrica, strains in the three series mentioned produce yellow to orange or reddish colours in the aerial vegetative mycelium with a colony reverse in similar colours or occasionally dark purple-red to almost black.A number of crystalline colouring matters have been isolated here from strains of P. i8landicum (Howard & Raistrick, 1949, 1950, 1954a, and we now report similar investigations on the colouring matters of P. rugulo8um and P. wortmsnni. This work was commenced early in 1939 by one of us (J.B.) and resulted in the isolation, from a highly pigmented strain of P. rugulo8um, strain H.Z., recently isolated from natural sources and cultivated in the laboratory on Czapek-Dox solution, of considerable quantities of a beautifully crystalline, bright yellow colouring matter which was named rugulosin, since it had not been described previously.The work was discontinued later in the year and was not taken up again until 9 years later (Raistrick, 1949;Dacre, 1950). By this time the yield of rugulosin obtainable from P. rugulo8um strain H.Z. was very much smaller than that obtained previously, but two other strains of the same species, i.e. strains S.M. 1 and S.M. 14, which had not been kept in laboratory culture for so long a time, gave very considerable yields of the colouring matter. In this connexion it is of interest to note that, according to Raper & Thom (1949), while newly isolated strains of P. rugulo8um usuallRy sporulate freely and have a bright orange-red reverse, the same strains after being held in laboratory culture for a long time sporulate much less heavily and have an almost white reverse. No rugulosin could be detected in three such strains.The yields of crude crystalline rugulosin obtained by ether extraction of the dried and defatted mycelium from the three strains of P. ruguloumm used in its preparation were considerable and amounted to 21 % ofthe dry weight ofthe mycelium of strain S.M. 1, 10-13 % from strain S.M. 14 and 7-8 % from strain H.Z. In addition, small amounts of crystalline rugulosin were isolated from strain P. 50 and from strain N.R.R.L. 1045 which is a direct descendant of Dr Charles Thom's original type strain.Rugulosin has also been isolated from cultures of P. wortmanni grown on Czapek-Dox solution. Hence, this species, which has bright yellow perithecia embedded in yellowish orange mycelium, links the perithecia-producing P. luteum series with strains ...

Red Pigment Formation by Interaction of Molds Part 2 Taxonomical Characteristics of Penicillium Strain L 9

“…Recently, needle crystals of skyrin were obtained from P. islandicum by HOWARD et al (17,18) and from P. wortmanni by BREEN et al (19) independently as a bianthraquinone derivative which is a polymer of anthraquinone compounds.…”

Structure of Wortmin, a new Metabolite from Penicillium wortmanni

“…Ein Teil der Resultate wurde bercits in Vortragsreferaten erwahnt [2]. a) Auszugsweise der Dissertation von H.-J.…”

Diversity and Ecological Significance of Fungal Endophyte Natural Products

“…Rugulosin (96) (Fig. 25) has been known for more than half a century as a bisanthraquinone [139] and it holds a wide range of biological activities, including DNA damage properties. In vitro, it was shown to reduce body weight and affect instar development in fumiferana fumerana [136b].…”