Sphaerolone and dihydrosphaerolone, two bisnaphthyl-pigments from the fungus Sphaeropsidales sp. F-24'707.
Two new bisnaphthalene compounds, sphaerolone (1) and dihydrosphaerolone (2), together with 2-hydroxyjuglone (9), were isolated from the culture broth of a Sphaeropsidales sp. (strain F-24'707) after inhibition of the regular proceeding 1,8-dihydroxynaphthalene (DHN) biosynthesis with tricyclazole. The structures of 1 and 2 were established by detailed spectroscopic analysis and present novel bisnaphthalenes. The biosynthetic origin of 1 and 2 as dimerization products of 1,3,8-trihydroxynaphthalene, an intermediate of the DHN biosynthesis, is discussed.
Bode
H B
HB
Institut für Organische Chemie, Georg-August-Universität Göttingen, Germany.
Zeeck
A
A
D001572:Benzofurans / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D005658:Fungi / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D009281:Naphthalenes / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D009285:Naphthoquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D010860:Pigments, Biological / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism
D001572:Benzofurans; D009281:Naphthalenes; D009285:Naphthoquinones; D010860:Pigments, Biological; C420978:dihydrosphaerolone; C420977:sphaerolone; C420979:2-hydroxyjuglone