Academia.eduAcademia.edu
Supporting Information for the paper "Carneic acids A and B, Chemotaxonomically Significant Antimicrobial Agents from the Xylariaceous Ascomycete, Hypoxylon carneum" by Dang Ngoc Quang, Marc Stadler, Jacques Fournier and Yoshinori Asakawa Table S1. Comparison of biological activities of crude extracts from various Hypoxylon spp. (origin see in most cases cited references3-4 or otherwise in the legend), including H. carneum with those of those of standard antibiotics in the serial dilution assay against B. subtilis (BS, NB medium, 18h) and various fungi (YMG medium, 24h; YL. Y. lipolytica; MH. M. hiemalis; PG. P. griseofulvum; SC. S. chartarum; TH. T. harzianum) Concentrations tested: 100, 50, 25, 12.5, 6.25, 3.1, 1, and 0.1 µg ml-1). MIC = minimal inhibitory concentration. The extract of H. carneum is the only one that shows enhanced antifungal activities while being about equally active against B. subtilis. MIC [µg mL-1] Samples BS YL MH PG SC TA Hypoxylon carneum JF05048 (this study) 50 25 25 50 50 25 H. cercidicola JF-011293,7 50 >100 100 100 100 >100 100 100 >100 >100 >100 >100 50 >100 100 100 100 >100 H. howeanum STMA05214* 50 >100 100 100 100 >100 H. intermedium JF-031283 50 >100 100 100 100 >100 H. jecorinum * 50 >100 100 100 100 >100 H. juliani JF991123 50 >100 100 100 100 >100 100 >100 >100 100 100 >100 50 >100 100 100 100 >100 H. petriniae STMA04W02 3 50 >100 100 100 100 >100 H. pilgerianum4 50 >100 100 100 100 >100 50 >100 100 100 100 >100 100 100 >100 >100 >100 >100 100 >100 100 >100 >100 >100 50 >100 100 100 >100 >100 H. ulmophilum* 100 >100 100 >100 >100 >100 Penicillin G 3.12 >100 >100 >100 >100 >100 Actinomycin D >100 6.25 3.12 3.12 3.12 6.25 Crude Extracts/Species H. erythrostroma2,* H. fragiforme STMA03044 3 2, H. musceum2,* H. perforatum JF03126 3 H. rubiginosum JF-040173 H. rutilum JF-00291 3 H. ticinense JF-011813 H. subticinense JF-97075 3 3 ** The specimens used in this study that were not treated previously3,4 have the following collection data: H. erythrostroma: French Guiana, Paul Isnard, ca. 150 km S of St. Laurent du Moroni, Citron, 1617.3.1986, leg. Samuels, G.J. & Searwar, P. 4346, wood (New York Botanical Garden)2 - Contains rubiginosins and rutlins. H. howeanum: Germany, North Rhine Westphalia, Wuppertal, 18 July 2005, Betula sp., leg. M. S. (Fuhlrott Museum Wuppertal). - Contains mitorubrins. H. jecorinum: U.S.A., Louisiana, Langlois, A.B., corticated wood, as H. parasiticum, Ellis & Everh. (New York Botanical Garden)2. - Contains mitorubrins. H. musceum: Guyana, Cuyuni-Mazaruni Region, VII, Mazaruni Subregion, VII-2, vic. Chinoweing Village, 25.2.1987-3.3.1987, Samuels, G.J. et al. 4782, wood (New York Botanical Garden)2 - Contains mitorubrins. H. rickii: U.S.A., Louisiana, Langlois, A.B. 1992, wood, as Hypoxylon rubiginosum Pers. (New York Botanical Garden). - Contains mitorubrins. H. ulmophilum. Russia, Primorsky Territory, Khanka Lake Reserve, Ulmus japonica, 21 June 2003, leg. & det. L. Vasilyeva (Herbarium of Vladivostok, VLA). - Contains mitorubrins. Only selected, relatively fresh specimens were studied. Further species that showed similar HPLC profiles, also revealing mitorubrin or other azaphilones3,4 were not available in sufficient quantities. Table S2. List of species of Xylariaceae, subfamily Hypoxyloideae, in whose MeOH extracts carneic acids (1-2) were not detected using HPLC profiling, including HPLC-MS, including so far ca. 2500 specimens and cultures. Only the names of currently accepted species and varieties are included, for current synonymy see the cited references. Further members of the subfamily Xylarioideae (Xylaria, Euepixylon, Kretzschmaria, Nemania, and Rosellinia spp. ) have been previously reported6 and are not listed here. All of those were also examined and found devoid of carneic acids, as well as any of the normal pigments of Hypoxyloideae. The taxonomy of Annulohypoxylon and Pyrenomyxa is given according to recent treatments7,19. Species Reference Annulohypoxylon annulatum (Schwein.) Y.M. Ju, J.D. Rogers & H.M. Hsieh, 16 A. archeri (Berk.) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. atroroseum (J.D. Rogers) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. bovei (Speggazini) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. bovei var. microspora (J.H. Mill.) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. cohaerens (Pers.) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. hians (Berk. & Cooke) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. ilanense (Y.M. Ju & J.D. Rogers) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. leptascum (Speg.) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. michelianum (Ces. & De Not.) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. minutellum (Syd. & P. Syd.) Y.M. Ju, J.D. Rogers & H.M. Hsieh 1 16 A. moriforme (Henn.) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. moriforme var. microdiscus (Y.M. Ju & J.D. Rogers) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. multiforme (Fr.) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. multiforme var. alaskense (Y.M. Ju & J.D. Rogers) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. nitens (Ces.) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. nothofagi (Y.M. Ju & J.D. Rogers) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. purpureonitens (Y.M. Ju & J.D. Rogers) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. stygium (Lév.) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. stygium var. annulatum (Rehm) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. thouarsianum (Lév.) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. truncatum (Schwein.) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 A. urceolatum (Rehm) Y.M. Ju, J.D. Rogers & H.M. Hsieh 16 Biscogniauxia mediterranea (De Not.) Kuntze 6 B. nummularia (Bull.) Kuntze 6 Daldinia albofibrosa M. Stadler, M. Baumgartner & Wollw. 6 D. bakeri Lloyd 17,20 D. bambusicola Y.M. Ju, J.D. Rogers & F. San Martín 6 D. caldariorum Henn. 6 D. childiae J.D. Rogers & Y.M. Ju 6 D. clavata Henn. (1902) 6 D. concentrica (Bolton) Ces. & De Not. 6 D. cudonia (Berk. & M.A. Curtis) Lloyd 6 D. cuprea Starbäck 6 D. decipiens Wollw. & M. Stadler 6 D. dennisii Wollw., J.A. Simpson & M. Stadler 17 D. dennisii var. microspora Wollw. & M. Stadler 17 D. eschscholzii (Ehrenb.) Rehm 6 D. fissa Lloyd 6 D. graminis Dargan & K.S. Thind 6 D. grandis Child 6,17 D. lloydii Y.M. Ju, J.D. Rogers & F. San Martín 6 D. loculata (Lév.) Sacc. 6 D. loculatoides Wollw. & M. Stadler 17 Species D. macaronesica M. Stadler, Wollw. & J.M. Castro D. martinii M. Stadler, Venturella & Wollw. D. novaezelandiae Wollw. & M. Stadler D. palmensis M. Stadler, Wollw. & Tichy D. petriniae Y.M. Ju, J.D. Rogers & F. San Martín D. pyrenaica M. Stadler & Wollw. D. raimundi M. Stadler, Venturella & Wollw. D. steglichii M. Stadler, M. Baumgartner & Wollw. D. vanderguchtiae M. Stadler, Wollw. & Briegert Reference 20 20 17 20 6 6 20 6 20 Entonaema cinnabarinum (Cooke & Massee) Lloyd E. dengii J.D. Rogers E. globosum R. Heim E. liquescens A. Möller E. moluccanum J.D. Rogers E. pallidum G.W. Martin 5 5 5 5 5 5 Hypoxylon aucklandiae Y.-M. Ju & J. D. Rogers H. cercidicola (Berk. & M.A. Curtis ex Peck) Y.M. Ju & J.D. Rogers H. crocopeplum Berk. & M. A. Curtis H. commutatum Nitschke H. duranii J. D. Rogers H. hypomiltum Mont. H. hypomiltum Mont. var. lavandulocinereum Y.-M. Ju & J.D. Rogers H. fendleri Berk. ex Cooke H. ferrugineum Otth H. fuscopurpureum (Schw.: Fr.) M. A. Curtis H. fuscum (Pers.) Fr. H. howeanum Peck H. intermedium (Schwein.: Fr.) Y.-M. Ju & J. D. Rogers H. julianii L. Petrini H. laschii Nitschke H. lenormandii Berk. & M. A. Curtis H. monticulosum Mont. H. investiens (Schwein.) M. A. Curtis H. liviae Granmo H. macrocarpum Pouzar H. notatum Berk. & M. A. Curtis H. pilgerianum Henn. H. polyporoideum Berk. ex Cooke H. rubiginosum (Pers. : Fr.) Fr H. rutilum Tul. & C. Tul. H. subcorticeum Y.-M. Ju & J. D. Rogers H. subgilvum Berk. & Broome H. subticinense Y.-M. Ju & J.D. Rogers H. ticinense L. Petrini H. perforatum (Schwein.: Fr.) Fr. H. salicicola Granmo H. submonticulosum Y.-M. Ju & J. D. Rogers H. tortisporum Y.-M. Ju & J. D. Rogers H. trugodes Berk. & Broome H. vogesiacum (Pers.) Sacc. 4 3 4 3 4 4 4 4 3 18 18 3 3 3 3 4 4 4 3 18 4 4 4 3 3 4 4 3 3 3 3 3 4 4 3 Phylacia bomba (Mont.) Pat. Ph. globosa Lév. Ph. poculiformis (Mont.) Mont. Ph. sagraeana Mont. 5 5 5 5 Species Ph. surinamensis (Berk.) Dennis Ph. turbinata (Berk.) Dennis Pyrenomyxa invocans Morgan Py. morganii M. Stadler, Læssoe & Vassiljeva Py. picea M. Stadler, Læssoe & Vassiljeva Thamnomyces camerunensis Henn. T. chamissonis Ehrenb. T. chordalis Fr. T. dendroidea Cooke & Massee T. fuciformis Berk. T. rostratus Mont. Reference 5 5 19 19 19 5 5 5 5 5 5 Further References (list continued from the manuscript) on polythetic taxonomy of Xylariaceae, including HPLC profiling (16) (17) (18) (19) (20). Quang, D. N.; Hashimoto, T.; Nomura, Y.; Wollweber, H.; Hellwig, V.; Fournier, J.; Stadler, M.; Asakawa, Y. Phytochemistry 2005, 65, 797-809. Stadler, M.; Læssøe, T.; Simpson, J.A.; Wollweber, H. Mycol. Res. 2004, 108, 1025-1041. Mühlbauer, A.; Triebel, D.; Persoh, D.; Wollweber, H.; Seip, S.; Stadler, M. Mycol. Progr. 2002, 1, 235-248. Stadler, M.; Læssøe, T.; Vasilyeva, L. Mycologia 2005, 97, 1129-1139. Stadler, M.; Wollweber, H.; Jäger, W.; Briegert, M.; Venturella, G.; Castro, J.M.; Tichy, H.-V. Mycol. Res. 2004, 108, 257-273.