Lomatia polymorpha (Hooker, 1936)

Deans, Bianca J., Tedone, Laura, Bissember, Alex C. & Smith, Jason A., 2018, Phytochemical profile of the rare, ancient clone Lomatia tasmanica and comparison to other endemic Tasmanian species L. tinctoria and L. polymorpha, Phytochemistry 153, pp. 74-78 : 75

2.2. Lomatia polymorpha

Maceration of L. polymorpha provided juglone (1) (0.32% w/w), and a mixture of three aliphatic n -alcohols (0.07% w/w), which were identified as tetracosanol (C 24 H 50 O), hexacosanol (C 26 H 54 O) and octacosanol (C 28 H 58 O) in addition to heptacosane and nonacosane. The respective GC-MS and retention data were consistent with the equivalent data in National Institute of Standards and Technology (NIST) reference libraries (see: Supporting Information). GC-MS analysis of the purified fraction also indicated the presence of 1-pentacosanol, 1-heptacosanol, and 1-nonacosanol in small quantities (see: Supporting Information). Notably, this represents the first isolation of n -alcohols from Lomatia leaves.

The PHWE extract provided dihydroquercetin 3- O -β- D-xyloside (4) (0.22% w/w), quercetin 3- O -β- D- glucose (5) (0.14% w/w), 1,4,8-trihydroxynaphthalene 1- O -β- D- glucose (6) (0.04% w/w), and 4- O -p - coumaroyl-D- glucose (7) as a mixture of diastereoisomers, (0.03% w/w) ( Fig. 2 ). The respective 1 H and 13 C NMR spectroscopic and MS data for compounds 4–6 were consistent with equivalent data previously reported in the literature (see: Supporting Information) ( Baderschneider and Winterhalter, 2001; Fernandez et al., 2005; Son, 1995). Flavonoids have previously been isolated from L. dentata ( Moir and Thompson, 1973) . The NMR spectroscopic data and MS data for ester 7 was consistent with the proposed structure (see: Supporting Information). However, only limited NMR spectroscopic data has been reported for this known compound ( Birkofer et al., 1969; Kuraishi et al., 1984).

Figures

Fig. 2. Dihydroquercetin 3-O-β-D-xyloside (4), quercetin 3-O-β-D-glucose (5), 1,4,8-trihydroxynaphthalene-1-O-β-D- glucose (6), and 4-O-p-coumaroyl-D-glucose (7).