Chemical Constituents of the Lichen Stereocaulon Azoreum Antonio G

Total Page:16

File Type:pdf, Size:1020Kb

Chemical Constituents of the Lichen Stereocaulon Azoreum Antonio G Chemical Constituents of the Lichen Stereocaulon azoreum Antonio G. González, Elsa M. Rodrí guez Pérez, Consuelo E. Hernández Padrón*, and Jaime Bermejo Barrera Centro de Productos Naturales Orgänicos Antonio Gonzalez, I.P.N.A. Consejo Superior de Investigaciones Cientificas Carretera La Esperanza 2, La Laguna, 38206 Tenerife, Canary Islands, Spain * Departamento de Botanica, Facultad de Farmacia, Universidad de La Laguna, Tenerife, Canary Islands, Spain Z. Naturforsch. 47c, 503-507 (1992); received April 24, 1992 Stereocaulon azoreum, Lichens, Triterpenes, Sterols, Depsides Column chromatography of the acetone extract of the lichen Stereocaulon azoreum afforded several substances identified by chemical and spectral means; a-amyrin, lupeol, taraxerol, ursolic acid, ergosterol peroxide, brassicasterol, cerevisterol, stictic acid and an acetone-con- densation derivative, lobaric acid. Furthermore atranorin, methyl ß-orsellinate, atranol and, for the first time from the genus Stereocaulon, cryptostictic acid and the dibenzofuran, strepsi- lin were isolated. Introduction guing species was analyzed and afforded various types of substances. Four triterpenes, a-amyrin, Stereocaulon azoreum (Schaer.) Nyl. (Stereocau- laceae, Lecanorales) is a silver-grey lichen with fru- lupeol, taraxerol and ursolic acid, three sterols, er­ ticose thallus, very ramified, graceful pseudopode- gosterol peroxide (1), brassicasterol (2), and cere­ tia covered with squamulose or coralloidsquamu- visterol (3) and various lichen compounds were lose phyllocladia, no soralia, frequent subterminal obtained. apothecia, dark-brown-blackish flat-to-convex The major lichen substances were the depsi- disk. It is saxicolous and its preferred habitat in dones stictic acid (4) and lobaric acid (5) and the the Canaries is on the lava flow found on the depside atranorin, all three of which are of particu­ lar interest in the chemotaxonomic diagnosis of “green mountainside” at 800 to1 0 0 0 m altitude where it may be very abundant locally. It has been the species under study. An acetone-condensation reported as endemic to Madeira, the Azores and artifact of stictic acid, 4 a, two mono-arylic phe­ the Canary Islands (Lanzarote, Gran Canaria, nolic compounds, methyl ß-orsellinate (7) and Tenerife, Gomera, Hierro, and Palma). atranol (8 ) were also separated, as were the depsi- done cryptostictic acid (4 b) and the dibenzofuran The only chemical analysis of S. azoreum to date has been by thin-layer chromatography for che- strepsilin (9), found for the first time in a species of motaxonomic purposes. The most recent general Stereocaulon. study of Stereocaulon, by I. M. Lamb [1] charac­ terized S. azoreum chemotaxonomically as the Results and Discussion only member of the genus in which lobaric and Isolation and structural determination of the stictic acid are definitely known to co-exist and, terpenoids for the first time, indicated that atranorin, norstic- tic acid and, possibly, constictic and consalazinic A mixture of triterpenes was isolated from the acids were also present. From 1858 until recently, fractions 8 - 1 1 of the column chromatography S. azoreum was classified as Stereocaulon sphaero- and later separated by silver nitrate-impregnated TLC into a-amyrin, lupeol and taraxerol, all origi­ phoroides Tuck [2]. In an intensive study of the numerous and var­ nally isolated as lichen substances from Cladina ied Canary lichens, an Me2CO extract of this intri- macaronesica [3]. Fractions 17-19 yielded crystals with m.p. 146-147 °C, [a]D -60° and M + atm /z 398 for the molecular formula C 28H 460. The ’H N M R spec­ Verlag der Zeitschrift für Naturforschung, D-W-7400 Tübingen trum of this compound was very similar to that of 0939-5075/92/0700-0503 $ 01.30/0 ergosterol peroxide (1 ) with signals for four sec- 504 A. G. Gonzalezet al. ■ Chemical Constituents of the Lichen Stereocaulon azoreum 3 R= H 3a R= Ac 4 R= CHO 4a R= C = C / \ H COMe 4b R= CH^OH Me Me T» Me H O<> - (' '>- COOMe HO CHO 0H Me Me oCHO OH 7 9 R= H 10 9a R= Ac A. G. Gonzalezet al. • Chemical Constituents of the Lichen Stereocaulon azoreum 505 ondary and three tertiary methyl groups, a signal traction. In 4 b, the same signal was replaced by for the geminal hydroxy proton as a multiplet at those at 8 4.80 and 4.90 (each 1 H, br s) for a 8 3.51, which underwent a paramagnetic shift of (-CH 2OH) radical. The physical and spectro­ approximately A 5 = 1 ppm by acetylation, a two- scopic data of 4, 4 a and 4 b proved to be identical proton multiplet for a double bond A22-23, and a to those of stictic acid (4), its acetone-condensa- broad doublet at 5 5.38 assigned to another vinyl tion product, 4 a, and cryptostictic acid (4 b), ear­ proton in the molecule. The above data exactly lier obtained from the lichen Lobaria pulmonaria match brassicasterol (2) [4]. [10]. Cryptostictic acid (4b), a substance biogeneti- A triterpene acid and a sterol with the physical cally related to 4, was isolated for the first time and spectroscopic data of ursolic acid [5] and er- from the genus Stereocaulon. Another depsidone gosterol peroxide (1 ) [6 ], respectively, were isolated from the fractions 25-28 crystallized as colourless from the fractions 20-30. needles, m.p. 196-197 °C. Its MS showed the M + Lastly, a sterol was obtained from the 51-58 at m /z 456 in accordance with the empirical formu­ fractions, and, when purified by chromatography la, C 2 5 H 280 8. Both the fragmentation pattern and on Sephadex LH-20 (hexane: chloroform: meth­ the proton signals in MS and ’H N M R coincided anol, 2 : 1 : 1 ), formed colourless needles, m.p. with those given in the literature for lobaric acid 250-253 °C (from CHCl3 :MeOH), M + at m /z (5) [8 , 9], 430, C 28H 460 3. Its 'H N M R spectrum greatly re­ A dibenzofuran with colourless needles, m.p. sembled that of ergosterol peroxide (1 ) with an ex­ 318-320 °C, was isolated from the fractions tra geminal proton at 5 3.57 (1H, d, .7=5.0 Hz) 31-38: its IR spectrum had absorption bands at coupled with a vinyl hydrogen at 8 5.29 ppm (1 H, 3463 and 3395 cm' 1 (hydroxy groups) and d, / = 5.0 Hz) sited at C-7. Treatment with Ac20 1736 cm “ 1 (carbonyl) and a typical aromatic band and Py afforded a diacetylated derivative, 3 a, with at 1626 c m '1. MS showed the M + at m /z 270 for signals for a tertiary hydroxyl in its IR spectrum. the empirical formula. C 15H 10O 5 and 'H N M R These data agree with those of cerevisterol (3), ear­ gave signals for an aromatic methyl at 8 2.89, two lier obtained as a lichen product from Ramalina meta aromatic protons at 8 6.94 and 7.12 (each hierrensis [7]. 1 H, br s), an aromatic proton at 8 7.34 (1 H, s), and a two-proton singlet at 8 6 . 0 1 typical of a (- 0 - C H 2 -Ar) benzylic methylene group. A di­ Isolation and structural determination of the lichen acetyl derivative, 9 a (see Experimental for its MS substances and 'H N M R spectra) was formed when the diben­ The only depside isolated was obtained from the zofuran was treated with Ac20-Py. All these data fractions 8 - 1 1 of the general column chroma­ match strepsilin (9) [11], isolated here for the first tography and its physical and spectral data agree time from the genus Stereocaulon. This is of espe­ with those reported for atranorin (6 ) [8 , 9], a corti­ cial interest as the substance usually isolated from cal substance present in most of the species of the this species is porphyrilic acid (10), a dibenzofuran genus Stereocaulon. produced by a different coupling of the two phenol A mixture of depsidones was obtained from the units [1 2 ]. fractions 39-58 and separated by chromatogra­ One mono-arylic compound was isolated from phy on Sephadex LH-20 (hexane: chloroform; the fractions 12-16 and another from the frac­ methanol, 2:1:1). A mixture of the similar com­ tions 16-19 of the general chromatography and pounds 4, 4 a and 4 b was obtained from the frac­ they were purified by chromatography on Sepha­ tions 18-24 and separated by preparative chroma­ dex LH-20 with 2:1:1 hexane: chloroform: meth­ tography on silica gel (Be: dioxan: HO Ac). The 'H anol as eluant. Their physical and spectral data N M R spectra of these three substances were alike were those of methyl ß-orsellinate (7) [13] and except that a signal for an aldehyde group at atranol (8 ) [14], respectively. These two sub­ 8 10.57 in 4 was replaced in 4a by those at 8 2.43 stances, together with atranorin (6 ) had previously (3H, s) and 7.05 and 7.94 (each 1 H, d ,/ = 16.7 Hz) been isolated from various species of Stereocaulon. for a radical (-CH = CH-COMe) as the result of a Caccamese et al. [14] have argued that 7 and8 are condensation reaction with acetone during the ex­ found in Stereocaulon vesuvianum as true natural 506 A. G. Gonzalezet al. ■ Chemical Constituents of the Lichen Stereocaulon azoreum products, dissenting from the earlier view that (2 g). The rest of the extract was passed through a atranorin degradation during the extraction proc­ column packed with 1 kg silica gel and eluted with ess probably accounted for these compounds [13]. mixtures of hexane-ethyl acetate of increasing Atranorin, which is probably involved in light har­ polarity. Fractions of 500 ml were collected and vesting and radiation protection, may fill another monitored by TLC, giving the following: the frac­ biological role in this context, being a depside with tions 1-7 (wax), the fractions 8-11 (a-amyrin + no intrinsic antibiotic activity, but able perhaps to lupeol + taraxerol (50 mg), 6 (500 mg)]; the frac­ serve as a storage compound which the plant uti­ tions 12-16 [7 (600 mg)]; the fractions 17-19 [8 lizes in order to defend itself against attack by (350 mg), 2 (30 mg)]; the fractions 20-30 [ursolic pathogen microorganisms, by slowly manufactur­ acid (500 mg), 1 (30 mg)]; the fractions 31-38 [9 ing the two bioactive compounds 7, a powerful (10 mg)]; the fractions 39-50 [4 (100 mg), 4 a fungicide, and 8 , a strong antimicrobial agent.
Recommended publications
  • A Re-Examination of John Shirley's Collection of Tasmanian Lichens
    l'u;,ns u11d Proceedings of'the Rom/ Socicrv n/7L1snw111a, Volume 122(2), /9RR 59 A RE-EXAMINATION OF JOHN SHIRLEY'S COLLECTION OF TASMANIAN LICHENS by Gintaras Kantvilas (with one table and one plate) KANTVILAS, G., 1988 (31 :x): A re-examination of John Shirley's collection of Tasmanian lichens. Pap. Proc. R. So, Tasn1. 122(2): 59-67. https://doi.org/10.26749/rstpp.122.2.59 ISSN 0080-4703. Department of Botany, University of Tasmania. G.P.O. Box 252(' Hohart. Tasmania, Australia 700 I. The Tasmanian lichen collection of John Shirley (1849-1922) (housed in the Queensland Herharium) is examined and re-determined. Two new comhinations, Rinodina 11sperat11 (Shirley) Kantvilas and P_1Tcn11/a ga!aoina (Shirley) Kantvilas, are proposed, and lectotypes are set up for Bacidia weymouthii (Shirley) Zahlbr. and Pyrenu/a ch/oroplaca Shirley from authentic material. Several lichen records are based on misidentifications and are deleted from the checklist of Tasmanian lichens. Key Words: Shirley, lichens, Tasmania. INTRODUCTION Shirley's a,sociation with Tasmania began in 1892 when he visited Hobart for a meeting of the John Francis Shirley was born in Dorchester, AAAS, held on 7-16 January. There he studied England, on 11 August 1849 and died in Brisbane. plants on nearby Mt Wellington and made the Australia, on 5 April 1922. He graduated with a acquaintance of William Anderson Weymouth, one Bachelor of Science degree from the University of of the leading amateur cryptogamic botanists in London where he qualified as a teacher. In 1878, he Tasmania at that time (Kantvilas 1983).
    [Show full text]
  • Thi Thu Tram NGUYEN
    ANNÉE 2014 THÈSE / UNIVERSITÉ DE RENNES 1 sous le sceau de l’Université Européenne de Bretagne pour le grade de DOCTEUR DE L’UNIVERSITÉ DE RENNES 1 Mention : Chimie Ecole doctorale Sciences De La Matière Thi Thu Tram NGUYEN Préparée dans l’unité de recherche UMR CNRS 6226 Equipe PNSCM (Produits Naturels Synthèses Chimie Médicinale) (Faculté de Pharmacie, Université de Rennes 1) Screening of Thèse soutenue à Rennes le 19 décembre 2014 mycosporine-like devant le jury composé de : compounds in the Marie-Dominique GALIBERT Professeur à l’Université de Rennes 1 / Examinateur Dermatocarpon genus. Holger THÜS Conservateur au Natural History Museum Londres / Phytochemical study Rapporteur Erwan AR GALL of the lichen Maître de conférences à l’Université de Bretagne Occidentale / Rapporteur Dermatocarpon luridum Kim Phi Phung NGUYEN Professeur à l’Université des sciences naturelles (With.) J.R. Laundon. d’Hô-Chi-Minh-Ville Vietnam / Examinateur Marylène CHOLLET-KRUGLER Maître de conférences à l’Université de Rennes1 / Co-directeur de thèse Joël BOUSTIE Professeur à l’Université de Rennes 1 / Directeur de thèse Remerciements En premier lieu, je tiens à remercier Monsieur le Dr Holger Thüs et Monsieur le Dr Erwan Ar Gall d’avoir accepté d’être les rapporteurs de mon manuscrit, ainsi que Madame la Professeure Marie-Dominique Galibert d’avoir accepté de participer à ce jury de thèse. J’exprime toute ma gratitude au Dr Marylène Chollet-Krugler pour avoir guidé mes pas dès les premiers jours et tout au long de ces trois années. Je la remercie particulièrement pour sa disponibilité et sa grande gentillesse, son écoute et sa patience.
    [Show full text]
  • Lichen Biota of the “Wrzosowiska Cedyńskie Im. Inż. Wiesława Czyżewskiego” Nature Reserve in the Cedynia Landscape Park (NW Poland)
    #0# Acta Biologica 24/2017 | www.wnus.edu.pl/ab | DOI: 10.18276/ab.2017.24-14 | strony 159–170 Lichen biota of the “Wrzosowiska Cedyńskie im. inż. Wiesława Czyżewskiego” nature reserve in the Cedynia Landscape Park (NW Poland) Anetta Wieczorek,1 Andrzej Łysko2 1 Department of Ecology, Institute for Research on Biodiversity, Faculty of Biology, University of Szczecin, Wąska 13, 71-412 Szczecin, Poland, *corresponding author: [email protected] 2 Department of Environmental Protection and Management, Western Pomeranian University of Technology, Szczecin, Poland, e-mail: [email protected] Keywords xerothermic lichens, rare lichens, protected species, threatened lichens, nature reserve, NW Poland Abstract Lichens of the “Wrzosowiska Cedyńskie im. inż. Wiesława Czyżewskiego” nature reserve were studied in 2005 and 2011. Within the examined area, 103 species of lichens were ob- served. These include 23 species that are new to this area, some of them calciphilous, e.g. Agonima gelatinosa and Collema crispum. Many of them are rare in the Polish lowlands, e.g. Cladonia stellaris, Rhizocarpon geographicum, R. polycarpum, Stereocaulon condensatum, and S. incrustatum. Biota porostów rezerwatu “Wrzosowiska Cedyńskie im. inż. Wiesława Czyżewskiego” w Cedyńskim Parku Krajobrazowym Słowa kluczowe porosty kserotermiczne, porosty rzadkie, gatunki chronione, porosty zagrożone, rezerwat przyrody, NW Polska Streszczenie Porosty rezerwatu “Wrzosowiska Cedyńskie im. Wiesława Czyżewskiego” badano w 2005 i 2011 roku. Na badanym obszarze zaobserwowano 103 gatunki porostów. Wśrod nich 23 tak- sony to gatunki nowe na tym obszarze, niektóre z nich to porosty kalcyfilne np.Agonima gelati- nosa i Collema crispum. Wiele z nich jest rzadkich na polskich nizinach, np. Cladonia stellaris, Rhizocarpon geographicum, R.
    [Show full text]
  • Chemical Constituents from the Antarctic Lichen, Stereocaulon
    Biochemical Systematics and Ecology 80 (2018) 73–75 Contents lists available at ScienceDirect Biochemical Systematics and Ecology journal homepage: www.elsevier.com/locate/biochemsyseco Chemical constituents from the Antarctic lichen, Stereocaulon caespitosum T ∗ Ui Joung Youna, , Jae Eun Soa,b, Ji Hee Kima, Se Jong Hana,b, Hyun Parkb,c, Il Chan Kima, Jung Han Yima a Division of Life Sciences, Korea Polar Research Institute, KIOST, Incheon, 21990, Republic of Korea b Department of Polar Sciences, University of Science and Technology, Incheon, 21990, South Korea c Unit of Polar Genomics, Korea Polar Research Institute, Incheon, 21990, South Korea ARTICLE INFO ABSTRACT Keywords: A phytochemical study of the methanol extract of the Antarctic lichen Stereocaulon caespitosum Redgr. led to the Stereocaulon caespitosum isolation of a tridepside (1), two depsides (2 and 3), a montagnetol derivative (4), and four mono-phenolic Antarctic lichen compounds (5–8). The structures of these compounds were confirmed by 1D- and 2D-nuclear magnetic re- Depside sonance (NMR) experiments, as well as by comparison with published values. This is the first phytochemical Montagnetol study of S. caespitosum. In particular, compounds 1, 3, 4, and 8 have been isolated for the first time from the genus Stereocaulon and the family Stereocaulaceae. The chemotaxonomic significance of the isolated compounds is discussed. 1. Subject and source 2. Previous work The genus Stereocaulon is widely distributed across the world, from In previous studies, about 75 compounds, including alkamides tropical regions to the Arctic and Antarctic areas, with about 130 spe- (Ingolfsdottir et al., 1997), benzofurans (Claudia et al., 2017), carbohy- cies in total.
    [Show full text]
  • Isolation and Characterization of Two Sterols from the Green Alga, Selenastrum Capricornutum
    Portland State University PDXScholar Dissertations and Theses Dissertations and Theses 1-1-1976 Isolation and characterization of two sterols from the green alga, Selenastrum capricornutum Raymond Mark Owings Portland State University Follow this and additional works at: https://pdxscholar.library.pdx.edu/open_access_etds Let us know how access to this document benefits ou.y Recommended Citation Owings, Raymond Mark, "Isolation and characterization of two sterols from the green alga, Selenastrum capricornutum" (1976). Dissertations and Theses. Paper 861. https://doi.org/10.15760/etd.861 This Dissertation is brought to you for free and open access. It has been accepted for inclusion in Dissertations and Theses by an authorized administrator of PDXScholar. Please contact us if we can make this document more accessible: [email protected]. ISOLATIO[\ At\D CHAHACTERIZATIOi\ OF 1\'JO STEROLS FRON Tr-lE GREEi\ ALGA. SELENASTRL::I CAPRICORl\UTt.:~l by RA YNOND HARK O~\ Ii\GS A thesis submitted in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY in Ef\VIRONHEl\TAL SCIEI\CE-CHEtv1[STRY Portland State University 1976 Ai': ABSTRA.CT OF THE THESIS OF Raymond tvlark O\vings for the Doctor of Philosophy in Environmental Science-Chemistry presented August 4, 1975. Title: Isolation and Characterization of Two Sterols From the Green Alga, Selanastrum capricornutum. APPROVED BY NEivlBERS OF THE THESIS COHNITTEE: Karl Dittmer, Chairman Norman C. Rose Edward N. Perdue Dennis \V. Barnum Richard R. Petersen 2 The green alga, Selenastrum capricornutum, was cul­ tured in artificial nutrient medium utilizing five-gallon carboys, each of which contained 16 1.
    [Show full text]
  • Evaluation of Certain Food Additives
    952 Food Additives WHO Technical Report Series WHO Technical Sixty-ninth report of the FOOD ADDITIVES Joint FAO/WHO Expert Committee on Food and Agriculture Organization of the United Nations S I N A P T A F I EVALUATION OF CERTAIN EVALUATION OF CERTAIN FOOD ADDITIVES WHO Technical Report Series 952 ISBN 978 92 4 120952 6 2,3-trimethylbutyramide (No. 1595) and N, , phytosterols, phytostanols and their esters, , calcium lignosulfonate (40–65), ethyl lauroyl arginate, paprika Pichia pastoris A. niger -unsaturated aldehydes, acids and related alcohols, acetals and esters; β , α expressed in niger Aspergillus L-monomenthyl glutarate (No. 1414). recommendations for intakes and Annexed to the report are tables summarizing the Committee’s toxicological evaluations of the food additives considered. aliphatic secondary alcohols, ketones and related esters; alkoxy-substituted allylbenzenes present in foods and essential oils and used as flavouring agents; esters of aliphatic acyclic primary alcohols with aliphatic linear saturated carboxylic acids; furan-substituted aliphatic hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and related esters, sulfides, disulfides and ethers; miscellaneous nitrogen-containing substances; monocyclic and bicyclic secondary alcohols, ketones and related esters; hydroxy- and alkoxy-substituted benzyl derivatives; and substances structurally related to menthol). Specifications for the following food additives were revised: canthaxanthin; carob bean gum and carob bean gum (clarified); chlorophyllin copper
    [Show full text]
  • A Multigene Phylogenetic Synthesis for the Class Lecanoromycetes (Ascomycota): 1307 Fungi Representing 1139 Infrageneric Taxa, 317 Genera and 66 Families
    A multigene phylogenetic synthesis for the class Lecanoromycetes (Ascomycota): 1307 fungi representing 1139 infrageneric taxa, 317 genera and 66 families Miadlikowska, J., Kauff, F., Högnabba, F., Oliver, J. C., Molnár, K., Fraker, E., ... & Stenroos, S. (2014). A multigene phylogenetic synthesis for the class Lecanoromycetes (Ascomycota): 1307 fungi representing 1139 infrageneric taxa, 317 genera and 66 families. Molecular Phylogenetics and Evolution, 79, 132-168. doi:10.1016/j.ympev.2014.04.003 10.1016/j.ympev.2014.04.003 Elsevier Version of Record http://cdss.library.oregonstate.edu/sa-termsofuse Molecular Phylogenetics and Evolution 79 (2014) 132–168 Contents lists available at ScienceDirect Molecular Phylogenetics and Evolution journal homepage: www.elsevier.com/locate/ympev A multigene phylogenetic synthesis for the class Lecanoromycetes (Ascomycota): 1307 fungi representing 1139 infrageneric taxa, 317 genera and 66 families ⇑ Jolanta Miadlikowska a, , Frank Kauff b,1, Filip Högnabba c, Jeffrey C. Oliver d,2, Katalin Molnár a,3, Emily Fraker a,4, Ester Gaya a,5, Josef Hafellner e, Valérie Hofstetter a,6, Cécile Gueidan a,7, Mónica A.G. Otálora a,8, Brendan Hodkinson a,9, Martin Kukwa f, Robert Lücking g, Curtis Björk h, Harrie J.M. Sipman i, Ana Rosa Burgaz j, Arne Thell k, Alfredo Passo l, Leena Myllys c, Trevor Goward h, Samantha Fernández-Brime m, Geir Hestmark n, James Lendemer o, H. Thorsten Lumbsch g, Michaela Schmull p, Conrad L. Schoch q, Emmanuël Sérusiaux r, David R. Maddison s, A. Elizabeth Arnold t, François Lutzoni a,10,
    [Show full text]
  • Redalyc.Biologically Active Metabolites of the Genus Ganoderma: Three Decades of Myco-Chemistry Research
    Revista Mexicana de Micología ISSN: 0187-3180 [email protected] Sociedad Mexicana de Micología México Trigos, Ángel; Suárez Medellín, Jorge Biologically active metabolites of the genus Ganoderma: Three decades of myco-chemistry research Revista Mexicana de Micología, vol. 34, diciembre, 2011, pp. 63-83 Sociedad Mexicana de Micología Xalapa, México Available in: http://www.redalyc.org/articulo.oa?id=88321339010 How to cite Complete issue Scientific Information System More information about this article Network of Scientific Journals from Latin America, the Caribbean, Spain and Portugal Journal's homepage in redalyc.org Non-profit academic project, developed under the open access initiative Biologically active metabolites of the genus Ganoderma: Three decades of myco-chemistry research Ángel Trigos 1,2 Jorge Suárez Medellín 1,3 1 Laboratorio de Alta Tecnología de Xalapa, Universidad Veracruzana. Calle Médicos, 5, Col. Unidad del Bosque. C.P. 91010, Xalapa, Veracruz, México. 2 Instituto de Ciencias Básicas, Universidad Veracruzana, Av. Dos Vistas s/n, Carretera Xalapa-Las Trancas, 91000 Xalapa, Veracruz, México. 3 Unidad de Investigación y Desarrollo en Alimentos, Instituto Tecnológico de Veracruz. Av. Miguel A. de Quevedo # 2779 Col. Formando Hogar, C. P. 91680 Veracruz, Veracruz, México 1 1 0 Metabolitos biológicamente activos del género Ganoderma: tres décadas de 2 , investigación mico-química 3 8 - 3 6 Resumen. Desde la antigüedad en la medicina tradicional de oriente, hasta los tiempos : 4 modernos, los hongos pertenecientes al género Ganoderma se han utilizado para el 3 A tratamiento y la prevención de diversas enfermedades como cáncer, hipertensión y Í G diabetes, entre muchas otras afecciones.
    [Show full text]
  • Literaturverzeichnis
    Literaturverzeichnis Abaimov, A.P., 2010: Geographical Distribution and Ackerly, D.D., 2009: Evolution, origin and age of Genetics of Siberian Larch Species. In Osawa, A., line ages in the Californian and Mediterranean flo- Zyryanova, O.A., Matsuura, Y., Kajimoto, T. & ras. Journal of Biogeography 36, 1221–1233. Wein, R.W. (eds.), Permafrost Ecosystems. Sibe- Acocks, J.P.H., 1988: Veld Types of South Africa. 3rd rian Larch Forests. Ecological Studies 209, 41–58. Edition. Botanical Research Institute, Pretoria, Abbadie, L., Gignoux, J., Le Roux, X. & Lepage, M. 146 pp. (eds.), 2006: Lamto. Structure, Functioning, and Adam, P., 1990: Saltmarsh Ecology. Cambridge Uni- Dynamics of a Savanna Ecosystem. Ecological Stu- versity Press. Cambridge, 461 pp. dies 179, 415 pp. Adam, P., 1994: Australian Rainforests. Oxford Bio- Abbott, R.J. & Brochmann, C., 2003: History and geography Series No. 6 (Oxford University Press), evolution of the arctic flora: in the footsteps of Eric 308 pp. Hultén. Molecular Ecology 12, 299–313. Adam, P., 1994: Saltmarsh and mangrove. In Groves, Abbott, R.J. & Comes, H.P., 2004: Evolution in the R.H. (ed.), Australian Vegetation. 2nd Edition. Arctic: a phylogeographic analysis of the circu- Cambridge University Press, Melbourne, pp. marctic plant Saxifraga oppositifolia (Purple Saxi- 395–435. frage). New Phytologist 161, 211–224. Adame, M.F., Neil, D., Wright, S.F. & Lovelock, C.E., Abbott, R.J., Chapman, H.M., Crawford, R.M.M. & 2010: Sedimentation within and among mangrove Forbes, D.G., 1995: Molecular diversity and deri- forests along a gradient of geomorphological set- vations of populations of Silene acaulis and Saxi- tings.
    [Show full text]
  • Antioxidant and Anti-Osteoporotic Activities of Aromatic Compounds and Sterols from Hericium Erinaceum
    molecules Article Antioxidant and Anti-Osteoporotic Activities of Aromatic Compounds and Sterols from Hericium erinaceum Wei Li 1, Sang Hyun Lee 2, Hae Dong Jang 2,*, Jin Yeul Ma 1,* and Young Ho Kim 3,* 1 Korean Medicine (KM) Application Center, Korea Institute of Oriental Medicine, Daegu 41062, Korea; [email protected] 2 Department of Food and Nutrition, Hannam University, Daejeon 34430, Korea; [email protected] 3 College of Pharmacy, Chungnam National University, Daejeon 34134, Korea * Correspondence: [email protected] (H.D.J.); [email protected] (J.Y.M.); [email protected] (Y.H.K.); Tel.: +82-42-629-8795 (H.D.J.); +82-53-940-3811 (J.Y.M.); +82-42-821-5933 (Y.H.K.) Academic Editor: Derek J. McPhee Received: 14 November 2016; Accepted: 2 January 2017; Published: 11 January 2017 Abstract: Hericium erinaceum, commonly called lion’s mane mushroom, is a traditional edible mushroom widely used in culinary applications and herbal medicines in East Asian countries. In this study, a new sterol, cerevisterol 6-cinnamate (6), was isolated from the fruiting bodies of H. erinaceum together with five aromatic compounds 1–5 and five sterols 7–11. The chemical structures of these compounds were elucidated using chemical and physical methods and comparison of HRESIMS, 1D-NMR (1H, 13C, and DEPT) and 2D-NMR (COSY, HMQC, HMBC, and NOESY) spectra with previously reported data. The antioxidant and anti-osteoporotic activities of extracts and the isolated compounds 1–11 were investigated. All compounds exhibited peroxyl radical-scavenging capacity but only compounds 1, 3, and 4 showed potent reducing capacity.
    [Show full text]
  • Water Column Distribution and Carbon Isotopic Signal of Cholesterol
    Water column distribution and carbon isotopic signal of cholesterol, brassicasterol and particulate organic carbon in the Atlantic sector of the Southern Ocean Anne-Julie Cavagna, Frank Dehairs, Steven Bouillon, V. Woule-Ebongué, Frédéric Planchon, Bruno Delille, Ioanna Bouloubassi To cite this version: Anne-Julie Cavagna, Frank Dehairs, Steven Bouillon, V. Woule-Ebongué, Frédéric Planchon, et al.. Water column distribution and carbon isotopic signal of cholesterol, brassicasterol and particulate organic carbon in the Atlantic sector of the Southern Ocean. Biogeosciences, European Geosciences Union, 2013, 10 (4), pp.2787-2801. 10.5194/bg-10-2787-2013. hal-00914348v2 HAL Id: hal-00914348 https://hal.archives-ouvertes.fr/hal-00914348v2 Submitted on 25 Apr 2020 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Distributed under a Creative Commons Attribution| 4.0 International License EGU Journal Logos (RGB) Open Access Open Access Open Access Advances in Annales Nonlinear Processes Geosciences Geophysicae in Geophysics Open Access Open Access Natural Hazards Natural Hazards and Earth System and Earth System Sciences Sciences Discussions Open Access Open Access Atmospheric Atmospheric Chemistry Chemistry and Physics and Physics Discussions Open Access Open Access Atmospheric Atmospheric Measurement Measurement Techniques Techniques Discussions Open Access Biogeosciences, 10, 2787–2801, 2013 Open Access www.biogeosciences.net/10/2787/2013/ Biogeosciences doi:10.5194/bg-10-2787-2013 Biogeosciences Discussions © Author(s) 2013.
    [Show full text]
  • Phytochemical Review of the Lichen Genus Stereocaulon (Fam
    Phytochem Rev https://doi.org/10.1007/s11101-018-9576-y Phytochemical review of the lichen genus Stereocaulon (Fam. Stereocaulaceae) and related pharmacological activities highlighted by a focus on nine species Friardi Ismed . Franc¸oise Lohe´zic-Le De´ve´hat . Annie Guiller . Nina Corlay . Amri Bakhtiar . Joel Boustie Received: 16 January 2018 / Accepted: 11 May 2018 Ó Springer Science+Business Media B.V., part of Springer Nature 2018 Abstract The Stereocaulon genus is one of the isolated compounds have been compiled. Biological fruticose lichen groups distributed worldwide from activities as cytotoxic, anti-inflammatory, antibacte- tropical zones to polar zones. However, the scientific rial, antifungal or antioxidant are reported. study of this tricky genus is still limited, making it a challenge to study the group further. Detailed mor- Keywords Biogenetic Á Bioactivities Á Folk phological studies are essential to discriminate closely medicines Á Lichens Á Secondary metabolites Á shaped species which is illustrated through personal Stereocaulon data focused on phyllocladia, apothecia and spores of nine species. Secondary metabolites isolated from Stereocaulon species are mostly some depsides, depsidones, diphenylethers and dibenzofurans which Introduction can have a taxonomic value. The use of Stereocaulon lichens as a traditional medicine in several regions of Among the symbiotic organism called lichen formed the world and pharmacological studies of extracts and between two major different partners that are fungi (mycobiont) and/or algae/cyanobacteria as photobiont without excluding the lichen-associated microbiome, Electronic supplementary material The online version of one of an interesting genus is Stereocaulon. The genus this article (https://doi.org/10.1007/s11101-018-9576-y) con- tains supplementary material, which is available to authorized Stereocaulon Hoffm.
    [Show full text]