A new optically active flavanone from the leaves of Rhododendron farrerae, tate

Abstract

A new optically active flavanone, for which the name farrerol is proposed, has been isolated from the leaves of Rhododendron furrerue. It has been shown to be 5 : 7 : 4'-trihydroxy-6 : 8-dimethylflavanone (4'-demethylmatteucinol) and so it has, in coxrunon with two of the other known optically active naturally occurring flavanones, methyl groups in the 6-and 8-positions.ARTHUR and HUI (J., 1954, 4683) reported that the leaves of the Rhododendrons of Hong Kong contain the triterpene acid, ursolic acid; they also showed (ihd., p. 2782) that the leaves of R . simsii contain in addition the flavanone, matteucinol. Examination of the leaves of the other Rhododeitdrons of Hong Kong in the manner adopted for R. simsii (Zoc cit.) reveals the presence of a new flavanone (hereafter called '' farrerol ") in R. farrerae, but flavonoid compounds were not obtained from R. championae, R. westlandii, or K.

Phytochemical Characterization ofRhododendron ferrugineumandIn VitroAssessment of an Aqueous Extract on Cell Toxicity

“…The flavonoid-containing fractions afforded compounds 1 to 12 (l " Fig. 1): compound 1, farrerol, which was newly recorded for R. ferrugineum, has been described for R. farrerae [20]. Also poriol 7-O-β-D-glucopyranoside (2) [21] was isolated and described for the first time in R. ferrugineum.…”

Antifungal Flavonoids from Hildegardia barteri

“…4 From the organic extract of the roots, we isolated a new isoflavan named hildegardiol (1), together with the known pterocarpan 2-hydroxymaackiain (2) 5 and the flavanone farrerol (3). 6 Our laboratory uses a preliminary analysis/dereplication scheme based on HPLC separation of a crude extract and evaluation by multiple detectors: ELSD, UV/vis, MS, and bioassay of fractions collected in microtiter plates. The UV and mass spectroscopic data of active fractions can be compared against various natural products databases to identify and eliminate quickly and efficiently known, frequently occurring compounds with minimal and/or nonspecific activity.…”

“…Compound 3 was identified by comparison with spectroscopic data reported in the literature (UV, MS, 1 H NMR, and [R] D ). 6,14 The isoflavans constitute one of the smaller groups of flavonoids. These are mainly substituted with hydroxyl and methoxyl groups, most commonly at positions 7, 2′, and 4′ and less often at 6, 8, and 3′.…”

Antimicrobial, antioxidant and butyrylcholinesterase inhibition activities of extracts and isolated compounds from Scadoxus pseudocaulus and semi-synthetic farrerol derivatives

“…The CHCl 3 and EtOAc soluble fractions from the MeOH crude extract of the whole plant of S. pseudocaulus were separately subjected to silica gel column chromatography to afforded six known compounds: sideroxylin (1) (Hillis and Koichiro, 1965), 5-hydroxylmethyl-2-furancarboxaldehyde (2) (Mikyung et al, 2004), C-6,O-7-dimethyldenaromadendrin (3) (Jari et al, 2005), 4-(hydroxymethyl)-5-hydroxy-2H-pyran-2-one (4) (Aiqun et al, 2008), 7-deoxy-transdihydronarciclasine or trans-dihydrolycoricidine (5) Pettit and Melody, 2005) and farrerol (6) (Arthur, 1955;Diaa et al, 1998) (Fig. 2.).…”

“…1.92 (3H, s, 8-CH 3 ) (Arthur, 1955;Diaa et al, 1998) (Arthur, 1955;Diaa et al, 1998) Compound 7 was obtained as white needles. The 1 H and 13 C NMR spectra (Tables 1 and 2) were so closed to those of 6 except the additional chemical shifts corresponding to two p-methylbenzoyl groups.…”