TY - JOUR

T1 - Cohaerins A and B, azaphilones from the fungus Hypoxylon cohaerens, and comparison of HPLC-based metabolite profiles in Hypoxylon sect. Annulata

AU - Quang, Dangngoc

AU - Hashimoto, Toshihiro

AU - Nomura, Yoko

AU - Wollweber, Hartmund

AU - Hellwig, Veronika

AU - Fournier, Jacques

AU - Stadler, Marc

AU - Asakawa, Yoshinori

N1 - Funding Information: It is our pleasure to gratefully acknowledge financial support of JSPS (Japan Society for the Promotion of Science) for granting a postdoctoral fellowship to D.N. Quang. Thanks are also due to Masami Tanaka and Yasuko Okamoto (TBU, Japan) for recording NMR and mass spectra, respectively, and to Stephan Seip (BHC) for recording HPLC-MS. We thank Dink Müller and Arne Rix (BHC) for expert technical assistance. Our special thanks go to Drs. Jack D. Rogers (Washington State University, Pullman, USA) and Yu-Ming Ju (Institute of Botany, Academia Sinica, Taipei, Taiwan), who did not only provide the framework for this study, due to their morphological studies of Hypoxylon, but also selected and supplied several crucial specimens. Finally, the kind co-operation of several individuals and institutions who kindly provided further reference specimens is gratefully acknowledged: Curators of the herbaria B (Berlin, Germany), BPI (Beltville, Md, USA), GLM (Görlitz, Germany), K (Kew, UK), L (Leiden, Netherlands), M (Munich, Germany), PDD (Auckland, New Zealand), S (Stockholm, Sweden), STU (Stuttgart, Germany), our colleagues Françoise Candoussau, Matthias Eckel, Jean-François Magni, Hans-Volker Tichy and Derek Pers̆oh, and numerous other mycologists who had provided us with specimens of other groups of Xylariaceae in the past.

PY - 2005/4/1

Y1 - 2005/4/1

N2 - Azaphilones, named cohaerins A and B were isolated from stromata of the xylariaceous ascomycete Hypoxylon cohaerens. Their absolute structures were determined by spectroscopic methods (2D NMR, MS, IR, UV CD), and subsequently confirmed by acetylation. Stromatal metabolite profiles of several taxa of Hypoxylon sect. Annulata were also generated using analytical HPLC with diode array and MS detection. The cohaerins were neither found in other Hypoxylon spp., nor in other Xylariaceae. However, they were present even in holotype material of H. cohaerens, collected over 200 years ago. The binaphthalene BNT was also omnipresent in sect Annulata, and its derivatives, the benzo[j]fluoranthenes daldinone A and truncatone, as well as presumably related compounds. These fungi were found devoid of other types of azaphilone pigments of the Xylariaceae, such as mitorubrins and daldinins, the latter of which are widespread in certain groups of Hypoxylon sect. Hypoxylon. Hence, chemotaxonomic data largely support the current generic concept. The original source of truncatone was identified as Hypoxylon annulatum.

AB - Azaphilones, named cohaerins A and B were isolated from stromata of the xylariaceous ascomycete Hypoxylon cohaerens. Their absolute structures were determined by spectroscopic methods (2D NMR, MS, IR, UV CD), and subsequently confirmed by acetylation. Stromatal metabolite profiles of several taxa of Hypoxylon sect. Annulata were also generated using analytical HPLC with diode array and MS detection. The cohaerins were neither found in other Hypoxylon spp., nor in other Xylariaceae. However, they were present even in holotype material of H. cohaerens, collected over 200 years ago. The binaphthalene BNT was also omnipresent in sect Annulata, and its derivatives, the benzo[j]fluoranthenes daldinone A and truncatone, as well as presumably related compounds. These fungi were found devoid of other types of azaphilone pigments of the Xylariaceae, such as mitorubrins and daldinins, the latter of which are widespread in certain groups of Hypoxylon sect. Hypoxylon. Hence, chemotaxonomic data largely support the current generic concept. The original source of truncatone was identified as Hypoxylon annulatum.

KW - Chemistry

KW - Chomosystematics

KW - Fungi

KW - Structure elucidation

KW - HPLC profiling

UR - http://www.scopus.com/inward/record.url?scp=15744386370&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/16c9aaa9-7599-340d-bd8a-54d702b3d35a/

U2 - 10.1016/j.phytochem.2005.02.006

DO - 10.1016/j.phytochem.2005.02.006

M3 - Journal articles

VL - 66

SP - 797

EP - 809

JO - Phytochemistry

JF - Phytochemistry

SN - 0031-9422

IS - 7

ER -