11139-99-4Relevant academic research and scientific papers
Total Synthesis of (+/-)-Lubimin and (+/-)-Oxylubimin. II. Transformation of (+/-)-15-Norsolavetivanes into (+/-)-Lubimin, (+/-)-Oxylubimin, and Related Compounds
Murai, Akio,Sato, Shingo,Masamune, Tadashi
, p. 2291 - 2294 (1984)
The transformation of (+/-)-15-norsolavetivone and related compounds, into (+/-)-lubimin and (+/-)-oxylubimin, which constitutes the total synthesis of these highly oxygenated spirovetivane phytoalexins, is described.
1H NMR Study of the Stereochemistry of Lubimin and Related Vetispirane Sesquiterpenoids
Ewing, David F.,Whitehead, Ian M.,Atkinson, Anne,Threlfall, David R.
, p. 343 - 348 (2007/10/02)
The stereochemistry at C-2 and C-10 in lubimin, 15-dihydrolubimin and 3-hydroxylubimin derivatives has been investigated by 1H NMR spectroscopy.Using parent compounds and acetyl derivatives (24 compounds) definitive spectroscopic assignments have been made.Nine oxidised derivatives (2- and 3-keto functionalisation) have also been investigated.The usefulness of diagnostic features in the spectra are illustrated and the conformational homogeneity of the series verified.
OXYSOLAVETIVONE. A NEW BIOSYNTHETIC PRECURSOR OF LUBIMIN IN POTATO
Murai, Akio,Yoshizawa, Yuko,Katsui, Nobukatsu,Sato, Shingo,Masamune, Tadashi
, p. 771 - 772 (2007/10/02)
The title compound, isolated newly as a metabolite from solavetivone, was converted into lubimin in potato.
The biosynthesis of lubimin from [1-14C]isopentenyl pyrophosphate by cell-free extracts of potato tuber tissue inoculated with an elicitor preparation from Phytophthora infestans
Coolbear, Timothy,Threlfall, David R.
, p. 1963 - 1971 (2007/10/02)
A cell-free enzyme system, which catalyses the incorporation of radiolabel from [ 1 2-14C]isopentenyl pyrophosphate into the sesquiterpenoid phytoalexin lubimin, has been prepared from tuber tissue of Solanum tuberosum inoculated with an elicitor preparation from Phytophthora infestans. Biosynthesis of lubimin is optimum at pH 7. 3 2-7.5 and is dependent upon Mg2+ and NADPH. Lubimin labelling by cell-free enzyme system prepared from tissue 48 hr after treatment with elicitor rises rapidly to a maximum over the first 30 min of incubation and does not decline for a further 150 min. The biosynthetic capacity for lubimin in cell free extracts can be observed as early as 3 hr after inoculation of tuber tissue, and rises to a maximum at about 48 hr after treatment, declining thereafter. Lubimin labelling is inhibited by iodoacetamide, the effect of which is reversed by 3,3-dimethylallylpyrophosphate. Preliminary observations on the cell-free system show that it will also catalyse the incorporation of [2-14C]mevalonic acid into lubimin in the presence ofan ATP-generating system.
Total Synthesis of (+/-)-Lubimin and (+/-)-Oxylubimin
Murai, Akio,Sato, Shingo,Masamune, Tadashi
, p. 513 - 514 (2007/10/02)
The total synthesis of the title compounds, examples of the spirovetivane type of phytoalexins in the genus Solanum, by transformation of (+/-)-15-norsolavetivone and its derivatives, is described.
Structure of Epilubimin, Epioxylubimin, and Isolubimin, Spirovetivane Stress Metabolites in Diseased Potato
Katsui, Nobukatsu,Yagihashi, Fujio,Murai, Akio,Masamune, Tadashi
, p. 2424 - 2427 (2007/10/02)
The isolation and structure elucidation of the title spirovetivane sesquiterpenes, stress metabolites produced in diseased potato tubers, are described.
