New potato micro-tuber-inducing cyclohexene compounds related to theobroxide from Lasiodiplodia theobromae.
Two new cyclohexene compounds related to theobroxide (3) were isolated from the mycelia of Lasiodiplodia theobromae OCS71. The structures of these compounds were determined to be (4S,5S)-4,5-dihydroxy-2-methyl-cyclohex-2-enone (1) and (3aS,4R,5S,7aR)-4,5-dihydroxy-7-methyl-3a,4,5,7a-tetrahydrobenzo[1,3]dioxol-2-one (2) by means of spectroscopic analyses and chemical correlation to 3. Compound 2 was shown to take up the carbonate ion to form a carbonic acid ester non-enzymatically. The compounds also showed potato micro-tuber-inducing activities at a concentration of 10(-3) M, using a culture of single-node segments of potato stems in vitro.
Takei
Ryo
R
Division of Applied Bioscience, Research Faculty of Agriculture, Hokkaido University, Sapporo, Japan.
Takahashi
Kosaku
K
Matsuura
Hideyuki
H
Nabeta
Kensuke
K
D003510:Cyclohexanes / Q000737:chemistry*; D053138:Cyclohexenes / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D011198:Solanum tuberosum / Q000737:chemistry*
D003510:Cyclohexanes; D053138:Cyclohexenes; D004852:Epoxy Compounds; C496818:theobroxide; C052568:cyclohexene