We have previously reported a tetraketide origin for theobroxide and its related compound. In the present study, bioconversion of natural and deuterium-labeled precursors of this proposed biosynthetic pathway by Lasiodipoldia theobromae was investigated. Theobroxide was quantified after bioconversion from each proposed precursor. The transformation of the isotopically labeled precursor to products was tracked by 2H NMR measurement.
HiraiT. (1938) Disease of the banana in transport from Formosa (Japanese). Annual Meeting of the Phytopathological Society of Japan, 8, 145–166.
2.
AldridgeDCGaltS, GilesD, TurnerWB. (1971) Metabolites of Lasiodiplodia theobromae. Journal of Chemical Society, 9, 1623–1627.
3.
MeyerA, MierschO, ButtnerC, DatheW, SembdnerG. (1984) Occurrence of the plant growth regulator jasmonic acid in plants. Journal of Plant Growth Regulation, 3, 1–8.
4.
NishikawaH, KaishiNN. (1993) Metabolite from Aspergillus melleus. Nippon Nogeikagaku Kaishi, Journal of the Agricultural Chimerical Society of Japan, 9, 772–774.
5.
YabutaT, SumikiY, (1993) Metabolite from Aspergillus ochraceus. Nippon Nogeikagaku Kaishi, Journal of the Agricultural Chimerical Society of Japan, 9, 1264–1275.
6.
MoriK, GuptaAK (1985) Chiral synthesis of (R)-(-)-mellein and (3R, 4aS)-(+)-ramulosin. Tetrahedron, 41, 5295–5299.
7.
PengL, RyoT, KosakuT, KensukeN. (2006) Biosynthesis of theobroxide and its related compounds, metabolites of Lasiodiplodia theobromae. Phytochemistry, 68, 819–823.
8.
PengL, KosakuT, HideyukiM, YoshiharaT. (2005) Novel potato micro-tuber-inducing compound, (3R,6S)-6-Hydroxylasiodiplodin, from a strain of Lasiodiplodia theobromae. Bioscience, Biotechnology, and Biochemistry, 69, 1610–1612.
YoshiharaT, AmanumaM, TsutsumiT, OkumuraY, MatsuuraH, IchiharaA. (1996) Metabolism and transport of [2-14C]jasmonic acid in potato plant. Plant Cell Physiology, 37, 586–590.
11.
KashimaT, TakahashiK, MatsuuraH, NabetaK. (2009) Biosynthesis of resorcylic acid lactone lasiodiplodin in Lasiodiplodia theobromae. Bioscience, Biotechnology, and Biochemistry, 73, 1118–1122.
12.
TakeiR, TakahashiK, MatsuuraH, NabetaK. (2009) Biosynthesis of resorcylic acid lactone. (5S)-5-Hydroxylasiodiplodin in Lasiodiplodia theobromae. Bioscience, Biotechnology, and Biochemistry, 72, 2522–2524.
13.
BirchAJDonovanFW. (1953) Studies in relation to biosynthesis. Some possible routes to derivatives of orcinol and phloroglucinol. Australian Journal of Chemistry, 6, 360–368.
14.
BirchAJMassy-WestroppRAMoyeCJ. (1955) Studies in relation to biosynthesis. 2-Hydroxy-6-methylbenzoic acid in Penicillium griseofulvum Dierckx. Australian Journal of Chemistry, 8, 539–544.
15.
ElielELRivardDEBergstahlerAW. (1953) The synthesis of 6-formylsalicylic acid, esters of 6-bromomethylsalicylic acid, and related substances. Journal of Organic Chemistry, 18, 1979–1988.
16.
FrancescoM, SalvadoriP. (2005) An easy two-step reduction of salicylic acids and alcohols to 2-methylphenols. Synthesis, 15, 2479–2481.
