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Studies in the Biochemistry of Micro-Organisms, 84 Vol. 49 PERINEPHRIC AND INTERSCAPULAR FAT 563 mediate in type between those of the higher land It appears, therefore, that the fats of the tame animals and those of the reptiles and amphibia so rodents fed on.a suitable low-fat diet are generally far reported, in which the palmitic acid content is similar, but judged from the only detailed data somewhat reduced, being of the order of 10-20%, available there is reason to believe that the type of hexadecenoic acid being present in these fats to the fat elaborated by the tame rodents is not typical of extent of -1%.15 that of the wild varieties of the same species. Table 3 records the component acids ofthe rodents so far investigated. It is seen that the fats ofthe tame SUMMARY rabbit are on the whole similar to those of the other (tame) rodents. The palmitic acid content of the 1. The composition of the perinephric and inter- rabbit fats, however, is somewhat higher than that of scapular fats of an experimental rabbit has been the rat and guinea pig fats. The unsaturated C.8-acid investigated. content resembles that of the guinea pig rather than 2. The proportions ofthe component acids ofboth that ofthe rats, the guinea pig, however, elaborating fats were very similar, theperinephric fat being some- a considerable amount of polyethenoid C acids, what the more unsaturated. the amount being of the order of that present in the 3. Both fats were broadly similar to those ofother fats ofAmphibia and reptiles. The saturated acids of tame rodents, but differ appreciably from that the wild rabbit fat are likewise of the same order as recorded for a wild rabbit. those found in the fats ofthe tame rodents, but there We wish to thank Prof. T. P. Hilditch, F.R.S., for his is a marked difference in the proportions of the un- sustained interest in this investigation, and Prof. R. A. saturated acids present. Morton, F.R.S., for placing the rabbit at our disposal. REFERENCES Baldwin, A. R. & Longenecker, H. E. (1944). Arch. Biochem. Lewkowitsch, J. (1922). Chemical TechnologyandAnalysisof 5, 147. Oils, Fats and Waxes, vol. 2, pp. 680, 691. London: Hilditch, T. P. (1947). The Chemical Constitution of Natural Macmillan and Co. Fat8, 2nd ed. pp. 84, 298. London: Chapman and Hall. Longenecker, H. E. (1939). J. biol. Chem. 128, 645. Hilditch, T. P., Morton, R. A. & Riley, J. P. (1945). Analy8t, 70, 68. Studies in the Biochemistry of Micro-organisms, 84. THE COLOURING MATTERS OF PENICILLIUM NALGIOVENSIS LAXA. PART 1. NALGIOVENSIN AND NALGIOLAXIN. ISOLATION, DERIVATIVES AND PARTIAL STRUCTURES By H. RAISTRICK A J. ZIFFER Department of Biochemi8try, London School of Hygiene and Tropical Medicine, Univer8ity of London (Received 20 February 1951) Penicillium nalgioven88is Laxa was first described by included by Raper &'Thom (1949) in the P. canescens Laxa (1932), who isolated it during an examination series ofthe Asymnetrica-divaricata. Growth ofthe of the microflora of Ellischauer cheese, a form of species on cheese and in laboratory culture, particu- Camembert cheese peculiar to the Nalzovy region of larly on media containing proteins, is associated with Southern Bohemia-hence the specific name. The the production of considerable amounts of red pig- production of this type of cheese was started about ment. The species has not been reported from any 1880 in an. attempt to reproduce the flavour and other source than Ellischauer cheese. aroma of Camembert cheese. During the ripening It was noted in this laboratory that the mycelium process, the surface of the cheese is covered with of P. nalgiovensi8, grown on Raulin-Thom solution, white, velvet-like mycelium which gradually be- gave strong red colours when moist poftions of it comes greenish-grey in colour. Thesurfaceeventually were immersed in cold concentrated sulphuric acid becomes flecked with reddish patches from which or in aqueous sodium hydroxide, and pale to light cultures ofP. nalgioven8is can be isolated. According red colours when immersed in aqueous sodium to Laxa this mould is one of the principal species carbonate. On exhaustive extraction of the dried associated with the ripening process. The species is mycelium with light petroleum an orange solid 36.2 564. H. RAISTRICK AND J. ZIFFER & I95I separated in the boiling solvent. Purification of this by heating nalgiovensin dimethyl ether with methyl solid by crystallization from chloroform led to the iodide and dry silver oxide in dry benzene solution. isolation of a pure, hitherto undescribed, colouring It forms fine yellowish-green needles, m.p. 177-178°, matter for which the name nalgioven8in is proposed. which are insoluble in aqueous N-sodium hydroxide, Only a portion ofthe total colouring matters present but dissolve in cold concentrated sulphuric acid to in the mycelium is extracted with light petroleum. yield a solution indistinguishable in colour from that Subsequent extraction with ether or, preferably, given by the dimethyl ether. It is dextrorotatory in with chloroform, yields further amounts of nalgio- chloroform solution. Methylation of nalgiovensin vensin and a second hitherto undescribed colouring with dimethyl sulphate and 10 % aqueous potassium matter for which the name nalgiolaxin is proposed. hydroxide resulted only in the formation of the Nalgiovensin constitutes about 1.0% of the dry dimethyl ether. weight of the mycelium of P. nalgiovenr8i8, and It appeared probable from the colour reactions of nalgiolaxin about 0-18 %. nalgiovensin and of its derivatives, and from its Nalgiovensin crystallizes from chloroform in long solubility in alkalis that this colouring matter is a orange needles, and from glacial acetic acid in polyhydroxyanthraquinone. This opinion was con- glistening orange plates, m.p. 199-200°, without finmed and the general structure ofnalgiovensin was decomposition. It has the molecular formula indicated by the fact that when a chloroform solution of it was chromatographed on a magnesium car- C181H606, i.e. C17HL305.OCH3, bonate column a single red band was formed. This contains one methyl group attached to carbon, one band became bluish-red and was considerably methoxyl group, and is dextrorotatory in chloroform diffused when the column was washed with absolute solution [cx]°1+48 1°; [cx]'O' +39.70 (c, 0.1786). methanol. Almost identical colours are given by Nalgiovensin does not dissolve in aqueous 0-5N- physcion, 4:5-dihydroxy-7-methoxy-2-methylan- sodium bicarbonate or in N-sodium carbonate, but thraquinone, structure (I) R = CH3, under the same dissolves readily in N-sodium hydroxide to give a conditions. deep-red solution with a slight bluish cast. It dis- The main features ofthe molecular constitution of solves in cold concentrated sulphuric acid to an nalgiovensin became clear as the result of oxidation intense red solution which appears somewhat orange experiments on nalgiovensin and its functional in shade by transmitted light. Its solution in glacial derivatives. Emodic acid trimethyl ether (4:5:7- acetic acid is yellow in colour and does not show trimethoxyanthraquinone-2-carboxylic acid) was fluorescence in daylight. obtained by the oxidation of nalgiovensin trimethyl The following functional derivatives of nalgio- ether with chromic acid in glacial acetic acid solution vensin were prepared. (a) Triacetylnalgioven8in, and also by the oxidation of nalgiovensin dimethyl C.4H22O9,i.e. Cj7H1002(OCH3) (OCOCH3)3, by heating ether with alkaline iodine in aqueous dioxan solu- with acetic anhydride and. anhydrous sodium tion, in which oxidation no iodoform could be de- acetate. It forms fine yellow needles, m.p. 147-148°, tected. On mild oxidation of nalgiovensin with and is laev6rotatory in chloroform solution. On chromic acid in glacial acetic acid solution at 600 alkaline hydrolysis of this acetate nalgiovensin is there was obtained a small yield of 4:5-dihydroxy- regenerated. (b) Nalgiovenain dimethyt ether, 7-methoxyanthraquinone-2-carboxylic acid (I), C20H20O6, i.e. C,7HR103(OCH3)3, by heating with R = COOH, together with a much larger yield of an dimethyl sulphate and anhydrous potassium car- at present unidentified oxidation product having the bonate in acetone solution. It forms yellow needles, molecular formula C18HL406. This substance which m.p. 187-188°, which are insoluble.in aqueous N- contains the same number of carbon and oxygen sodium hydroxide, indicating the absence of a atoms as, but has two hydrogen atoms less than, nuclear hydroxyl group, but dissolve in cold con- nalgiovensin is, unlike nalgiovensin, optically in- centrated sulphuric acid to give an intense red active. We believe it to have structure (I) in which Solution with a slight bluish cast. It is dextro- R = C3HR0 containing a CO group in place of CHOH. rotatory in chloroform solution. (c) Monoacetyl- On oxidation of triacetylnalgiovensin with nalgioven8n dimethyl ether, C22H2207, i.e. chromic acid in a mixture of glacial acetic acid and acetic anhydride there is formed 4:5-diacetoxy-7- C17HR0O2(OCH3)3(OCOCH3), methoxyanthraquinone-2-carboxylic acid (diacetyl- by ether with acetic emodic acid 7-methyl ether), i.e. the diacetate of heating nalgiovensin dimethyl = of this anhydride and anhydrous sodium acetate. It forms (I), R COOH, m.p. 214-215o. The structure thin yellow-green rods, m.p. 152.5-153°, which are oxidation product was proved by direct comparison dextrorotatory in chloroform solution. (d) Nalgio- of it with the oxidation product of diacetylphyscion ven8in trimethyl ether, i.e. which we prepared by a similar oxidation process. C21,H206, The two oxidation
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