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Studies on the Chemistry of the Lichen Genus Umbilicaria Hoffm. B Studies on the Chemistry of the Lichen Genus Umbilicaria Hoffm. B. Posner, G. B. Feige Botanisches Institut der Universität Gesamthochschule Essen, Fachbereich 9, Postfach 10 3764, D-W-4300 Essen 1, Bundesrepublik Deutschland S. Huneck Institut für Biochemie der Pflanzen, Weinberg, D-0-4050 Halle/Saale, Bundesrepublik Deutschland Z. Naturforsch. 47c, 1 -9 (1992); received July 22/October 24, 1991 Lichens, Umbilicaria, Aromatic Lichen Substances, Crustinic Acid, HPLC The aromatic compounds of more than 400 specimens of 33 species of the lichen genus Umbilicaria have been investigated by HPLC. Additionally to gyrophoric, hiascic, lecanoric, ovoic and umbilicaric acids, atranorin, norstictic and stictic acids, the new depside crustinic acid has been found. Structure elucidation of crustinic acid was made by means of HPLC cochromatography, NMR, UV and mass spectrometry. Now the secondary product patterns of Umbilicaria species are discussed and their significance for systematic purposes is shown. Introduction acid always occurs as a satellite compound of this The lichen genus Umbilicaria causes a series of tridepside. The concentration of lecanoric acid is taxonomic problems. Neither the investigations of much smaller than that of gyrophoric acid. The anatomy and morphology of the thallus [1-4] nor ratio can be given as 90:1. The combined occur­ of the thalloconidia [5, 6] give sufficient results rence of gyrophoric and lecanoric acids could indi­ serving as a basis to separate many species reliably. cate that lecanoric acid may be a hydrolysis prod­ The discussions on the separation of the species uct of gyrophoric acid as suggested by Leuckert U. nylanderiana and U. polyphylla are a good ex­ [13]. In case of the occurrence of this reaction orsellinic acid must be detected as a second prod­ ample to illustrate these difficulties [4, 7], However, secondary product chemistry of the uct of hydrolysis in the same molar proportion as lecanoric acid. However, orsellinic acid can never genus Umbilicaria has been overlooked up to now and thought not to be of any significance for the be proven by means of HPLC when the extracts solution of taxonomic problems [3, 4, 8-10] (Ta­ are analyzed immediately and the extractions are ble I). Former investigations [11, 12] of a few Um­ carried out at a temperature of +6°C. Orsellinic bilicaria species have shown that characteristic acid is detected only after 1 h of extraction. The product patterns can contribute to the clarification molar proportion of orsellinic and lecanoric acids of taxonomic problems. Therefore the secondary amounts to 1:4. The applied method shows that product patterns of 33 Umbilicaria species are pre­ the suggested hydrolysis of gyrophoric acid must sented in this paper and their contribution to the be rejected. Probably, lecanoric acid must be ac­ solution of taxonomic problems is discussed. cepted as a native lichen compound and as a link of a biosynthetic pathway. However, lecanoric Results and Discussion acid is not of any importance for chemosystematic purposes. Gyrophoric and lecanoric acids Crustinic acid The characteristic lichen substance of Umbili­ caria species is gyrophoric acid which could be Crustinic acid was classified as a depside by its demonstrated in 31 of 33 investigated species. The UV spectrum in methanol with maxima at ca. 260 biosynthetically closely related depside lecanoric and 306 nm. The mass spectrum (Ch. Leuckert) shows a molecular weight peak at m /z 484, which Reprint requests to Dr. B. Posner. made likely a hydroxy-gyrophoric acid. This is Verlag der Zeitschrift für Naturforschung, D-7400 Tübingen confirmed by the 'H NMR spectrum (250 MHz, 0939-5075/92/0100-0001 $01.30/0 acetone-t/6) of crustinic acid: three singulets at Dieses Werk wurde im Jahr 2013 vom Verlag Zeitschrift für Naturforschung This work has been digitalized and published in 2013 by Verlag Zeitschrift in Zusammenarbeit mit der Max-Planck-Gesellschaft zur Förderung der für Naturforschung in cooperation with the Max Planck Society for the Wissenschaften e.V. digitalisiert und unter folgender Lizenz veröffentlicht: Advancement of Science under a Creative Commons Attribution Creative Commons Namensnennung 4.0 Lizenz. 4.0 International License. 2 B. Posner et al. ■ Chemistry of the Lichen Genus Umbilicaria Hoffm. Table I. Lichen substances of Umbilicaria species described in the literature so far. gyr = gyrophoric acid, umb = umbilicaric acid, ovo = ovoic acid, lec = lecanoric acid, atr = atranorin, nor = norstictic acid, Stic = stictic acid, us = unknown substances. U. haplocarpa, U.josiae, U. koidzumii, U. krempelhuberi, U. nepalensis, U. ruebeliana, U. tham- nodes, U. trabeculata, and U. yunnana have never been examined so far. Species gyr umb ovo lec atr nor stic us References angulata + + [20] arctica + + [20,21,30-33] caroliniana + + + [11,20,21,34] einereorufescens + + [3,20,21,24, 30,33,34] crustulosa a + [11,24,33,34] b + + c + + d + + eylindrica a no lichen substances [11, 17,20,21,24,33-35] b + de usta a + [16-21,33,34,37-42] b + + c + + esculent a + + [19] fre y i + [15] grisea + + [34] hirsuta a + + [16, 18,20, 24, 30,33,35,36,43] b + + hvperborea + + [1 6 - 18, 20, 24, 30, 33, 35, 36, 43] mammulata + [20,21,30] mühlenbergii + [20,21,30] nvlanderiana + + [24, 33, 34] polyphylla + + + [3, 16, 17, 20,21,24, 30,33,34, 36-38,44] polyrrhiza a + [16, 30,3 3 ,3 4 ,3 6 ,3 7 ] b + + + proboscidea a + + [11, 16, 1 9 -2 1 ,2 4 , 30, 3 4 ,3 6 -3 8 ,4 1 ,4 2 ,4 5 ] b + c + + + soralifera + [3] spodochroa + + + [11,33,34] torrefacta a + + + [11,20, 30,33,34, 46, 47] b + + c + + + + d + + + umbilicarioides no lichen substances [3] vellea + + [3, 1 9 -2 1 ,2 4 ,3 3 ,3 4 ] virginis a + [20,21,30,33] b + + 2.51 (3H ), 2.62 (3H ) and 2.71 ppm (3H ) corre­ depside is not identical with hiascic acid. For this spond to 3 methyl groups, two pairs of dublets at reason the hydroxy group must be in another posi­ 6.37 (2H , J = 2.4 Hz) and 6.90 ppm (2H, J = tion. The signals of the methyl groups appear in 2.2 Hz) correspond to two aromatic protons in the 13C NMR spectrum (62.76 MHz, acetone-^) meta-position and a singulet (1H) at 6.47 ppm of crustinic acid at 15.68, 23.11 and 24.31 ppm. corresponds to another aromatic proton. Of the 6 The chemical shift of the signal at 15.68 ppm indi­ theoretically possible hydroxy-gyrophoric acids cates a methyl group flanked by a hydroxy group. only the 5-isomer, hiascic acid, was isolated from Therefore the structures A and B can be proposed lichens. The comparison of crustinic acid with for crustinic acid (Fig. 1). A decision between A hiascic acid by means of HPLC indicates that this and B should be made a) after isolation of a bigger B. Posner et al. • Chemistry of the Lichen Genus Umbilicaria Hoffm. 3 Chemical races show a significantly distinguish­ able variable chemical composition with simple re­ placement of one or a few substances. However, in 4 Umbilicaria species (U. crustulosa, U. krempel- huberi, U. spodochroa and U. veiled) sequences of Fig. 1. Possible structures of crustinic acid. biosynthetically closely related secondary product A: R = OH, R' = H patterns have been detected. These sequences B: R = H, R' = OH could not be classified as chemical races because chemical intermediates were common. According to Elix [14] the sequences could be defined as amount of crustinic acid and hydrolysis of the chemosyndromic variations. Extreme forms of methylesters and identification of the hydrolysis chemosyndromic variation are discussed as products and b) after synthesis of both isomers. chemotypes here. The secondary product patterns of species Chemotaxonomy which have appeared as unique so far are summa­ rized below. Species showing chemical races Of chemosystematic importance for the genus Umbilicaria is the presence or absence of the dep- or chemotypes are summarized subsequently (Ta­ ble II). sides crustinic acid, hiascic acid, ovoic acid and umbilicaric acid which always occur together with gyrophoric acid. All depsides are accompanied by 1. Umbilicaria umbilicarioides (B. Stein) Krog and satellite compounds which could not be investigat­ Swinscow ed further due to lack of material. The presence or absence of the depsidones stictic According to Krog and Swinscow [3] no lichen acid and norstictic acid is also of systematic im­ products were found in U. umbilicarioides. Here portance. Accessory metabolites, e.g. connorstictic U. bolusiana Frey is reduced to a synonym of acid, a-methylethersalazinic acid, PCR-1 [11] and U. umbilicarioides. cryptostictic acid commonly occur with the main depsidones (Table II). In U. crustulosa and U. spodochroa the depside 2. U. hirsuta (Sw. ex Westr.) Ach and U. soralifera atranorin could be found. (Frey) Krog and Swinscow All investigated thalli contained the non-aro- matic substance ergosterol in rather equal Both species produce gyrophoric acid as the amounts as gyrophoric acid. The occurrence of main lichen substance (4-6.5% dw) which is al­ ways accompanied by lecanoric acid (0.5% dw). ergosterol has been proved additionally by means of mass spectrometry of Lasallia hispanica Additionally an unknown depside, RT 13, was de­ tected in small amounts (% dw < 0.1). Because of (C. Leuckert, pers. comm.). lack of material RT 13 could not be investigated further. The unknown depside occurs only when The secondary product patterns o f the gyrophoric acid is present in concentrations above species studied 6% dw. The secondary product patterns of 26 of 33 in­ In herbaria U. hirsuta is often confused with vestigated species of the genus Umbilicaria have U. grisea. However, beside morphological charac­ turned out to be unique so far. Chemical races are ters, e.g.
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