Chemical constituents of the ascomycete Daldinia concentrica.
Four compounds, daldinone A (1), daldinone B (2), daldiniapyrone (4-methoxy-5-carbomethoxy-6-pentyl-2H-pyran-2-one, 3), and daldinialanone (22R-hydroxylanosta-7,9(11),24-trien-3-one, 4), were isolated from an ethyl acetate extract of fruit bodies of Daldinia concentrica collected in Europe. In addition, 11 known compounds, 4:5:4':5'-tetrahydroxy-1:1'-binaphthyl (5), 3,4,5-trihydroxy-1-tetralone (6), (+)-orthosporin (7), curuilignan D (8), (22E)-cholesta-4,6,8(14),22-tetraen-3-one (9), 3beta,22-dihydroxylanosta-7,9(11),24-triene (10), concentricol (11), concentricol B (12), concentricol C (13), concentricol D (14), and phenochalasin B (15), were obtained. The structures of the new compounds were elucidated by 2D NMR, MS, IR, and UV spectra and by X-ray crystallographic analysis. The absolute configurations of 1 and 4 were determined by CD spectroscopy and the modified Mosher's method, respectively. The chemotaxonomic relevance of the compounds obtained in this investigation is discussed.
Quang
Dang Ngoc
DN
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
Hashimoto
Toshihiro
T
Tanaka
Masami
M
Baumgartner
Manuela
M
Stadler
Marc
M
Asakawa
Yoshinori
Y
D001203:Ascomycota / Q000737:chemistry*; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D031661:Fraxinus / Q000737:chemistry; D005858:Germany; D008968:Molecular Conformation; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry / Q000302:isolation & purification*; D011753:Pyrones / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry / Q000302:isolation & purification*
D011084:Polycyclic Aromatic Hydrocarbons; D011753:Pyrones; D013256:Steroids