A simple, rapid, accurate and selective 1H NMR spectroscopic method to detect and quantify euglobals in the leaves of Eucalyptus loxophleba ssp. lissophloia has been developed. The method allows for the estimation of total concentration of diformylphloroglucinol-monoterpene adducts, as well as the quantitation of sabinene- and α/β-phellandrene-adducts, separately. The method was validated for accuracy, precision and linearity using as reference standards 2-ethyl phenol and mixtures of jensenone, a monomeric formylated phloroglucinol, and 2-ethyl phenol.
KozukaM, SawadaT, MizutaE, KasaharaF, AmanoT, KomiyaT, GotoM. (1982) The granulation-inhibiting principles from Eucalyptus globulus Labill. III. The structures of euglobal -III, -IVb and -VII. Chemical and Pharmaceutical Bulletin, 30, 1964–1973.
2.
BharateSB, BhutaniKK, KhanSI, TekwaniBL, JacobMR, KhanIA, SinghIP. (2006) Biomimetic synthesis, antimicrobial, antileishmanial and antimalarial activities of euglobals and their analogues. Bioorganic and Medicinal Chemistry, 14, 1750–1761.
TakasakiM, KonoshimaT, KozukaM, HarunaM, ItoK, YoshidaS. (1994) Four euglobals from Eucalyptus blakelyi. Chemical and Pharmaceutical Bulletin, 42, 2177–2179.
5.
TakasakiM, KonoshimaT, EtohH, SinghIP, TokudaH, NishinoH. (2000) Cancer chemopreventive activity of euglobal G1 from leaves of Eucalyptus grandis. Cancer Letters, 155, 61–65.
ItoH, IwamoriH, KasajimaN, KanedaN, YoshidaT. (2004) Kunzeanones A, B and C: novel alkylated phloroglucinol metabolites from Kunzea ambigua. Tetrahedron, 60, 9971–9977.
8.
AmanoT, KomiyaT, HoriM, GotoM. (1981) Isolation and characterization of euglobals from Eucalyptus globulus Labill. by preparative reversed-phase liquid chromatography. Journal of Chromatography, 208, 347–355.
9.
TakasakiM, KonoshimaT, KozukaM, HarunaM, ItoK, CrowWD, PatonDM. (1994) Euglobal In-1, a new euglobal from Eucalyptus incrassata. Chemical and Pharmaceutical Bulletin, 42, 2113–2116.
10.
EschlerBM, PassDM, WillisR, FoleyWJ (2000) Distribution of foliar formylated phloroglucinol derivatives amongst Eucalyptus species. Biochemical Systematics and Ecology, 28, 813–824.
11.
del CampoG, BerregiI, CaracenaR, ZuriarrainJ. (2010) Quantitative determination of caffeine, formic acid, trigonelline and 5-(hydroxymethyl)furfural in soluble coffees by 1H NMR spectrometry. Talanta, 81, 367–371.
12.
CaligianiA, AcquottiD, PallaG, BocchiV. (2007) Identification and quantification of the main organic components of vinegars by high resolution 1H NMR spectroscopy. Analytica Chimica Acta, 585, 110–119.