Anthraquinone, naphthalene, and naphthoquinone components of Asphodeline lutea

Abstract

The genus Asphodeline belongs to the family Asphodelaceae, subfamily Asphodeloideae. The 1,8-dihydroxyanthraquinones based on a chrysophanol unit are characteristic compounds of this subfamily. Anthraquinones, flavonoids, oxepines, and sesquiterpene lactones have been reported to occur in the genus Asphodeline [1][2][3][4].Asphodeline lutea is a perennial plant growing in the Mediterranian region. The only report found on this plant species reveals the presence of 1,8-dihydroxyanthraquinones, flavonoids, and a chlorogenic acid [5]. Data on the biological activity and the medicinal use of A. lutea are not available. However, the edible use of its roots, shoots, and flowers has been reported [6]. The ancient Greeks roasted the roots like potatoes and ate them with salt and oil or mashed them with figs. The raw fresh flowers are very decorative and a tasty addition to salad, while the young shoots are eaten cooked.The roots of A. lutea were collected in June 2005 near the town of Pernik, Bulgaria. The dried roots (0.70 kg) of A. lutea were extracted with methanol (3 times u 24 h u 2.7 L) at room temperature, then concentrated in vacuum to give a crude methanol extract (22.0 g). Solvent-solvent partition of this extract using petroleum ether, chloroform, and ethylacetate afforded the corresponding petroleum ether (4.3 g), chloroform (5.2 g), and ethylacetate (0.5 g) extracts and an aqueous residue (15.2 g).The petroleum ether extract was subjected to liquid vacuum chromatography (LVC) on silica gel using PE, PE-CHCl 3 (3:1o1:3), CHCl 3 , CHCl 3 -EtOAc (1:1), and EtOAc to give fractions F1-F6. Silica gel CC and repeated pTLC of F6 afforded compounds 1 (2 mg), 2 (6 mg), 3 (7 mg), 4 (3 mg), and 5 (1 mg).LVC of the chloroform extract with PE-CHCl 3 (20:1o1:1) and CHCl 3 gave fractions F1-F4. From F4 after silica gel CC and pTLC separation components 6 (4 mg), 7 (2 mg), 5 (5 mg), and 8 (6 mg) were isolated.The chemical structures of the isolated compounds were determined by a combination of spectral methods (UV, IR, 1D and 2D NMR, and MS) and comparison with literature data as chrysophanol (1) [7], 1,5,8-trihydroxy-3-methylanthraquinone (2) [8], 2-acetyl-1,8-dimethoxy-3-methylnaphthalene (3) [9, 10], 1-hydroxy-8-methoxy-3-methylanthraquinone (4) [11], asphodeline (5) [12], 2-acetyl-1-hydroxy-8-methoxy-3-methylnaphthalene (6) [9, 10], 2-acetyl-8-methoxy-3methylnaphthoquinone (7) [13], and 1,1c,8,8c,10-pentahydroxy-3,3c-dimethyl-10,7c-bianthracene-9,9c,10c-trione (8) [14]. Of them only chrysophanol (1) and asphodeline (5) have been reported to occur in A. lutea [5]. The anthraquinones 2 and 4 and the naphthalene compounds 3 and 6 are new for the genus Asphodeline. The naphthoquinone 7 is a known synthetic compound [13]. However, this is the first report on its natural occurrence and on the presence of naphthoquinones in Asphodeline species.A full assignment of all protons and carbons in the molecule of 3 was undertaken by detailed 1D and 2D NMR measurements because of the discrepancy between the assignments of C signals in ...

Investigation Of Antioxidant Potentials Of Solvent Extracts From Different Anatomical Parts Of <i>Asphodeline Anatolica</i> E. Tuzlaci: An Endemic Plant To Turkey

“…Likewise, A.globifera is used as a medicament for alleviating haemorrhoids symptoms, A. lutea and A. taurica are consumed in salads (Tuzlaci, 1985). Owing to their potential use in different purposes, several studies focused on secondary metabolites especially antraquinones, sesquiterpene and naphthalene components of Asphodeline species (Ulubelen et al, 1988;Ulubelen et al, 1989;Todorova et al, 2010). However, no scientific studies are reported on the antioxidant properties of different solvent extracts obtained from different parts of Asphodeline anatolica, which is endemic to Turkey..…”

Anthraquinone profile, antioxidant and enzyme inhibitory effect of root extracts of eightAsphodelinetaxa from Turkey: canAsphodelineroots be considered as a new source of natural compounds?

“…Again, several Asphodeline species (A. cilicica, A. damascena, A. globifera, A. lutea and A. taurica) are consumed as salad vegetables in different Turkey regions 22 . Recent studies show that Asphodeline leaves had good nutritional quality with high anthraquinones, essential amino acids and polyphenols levels [23][24][25][26] . However, to the best of our knowledge, the information on the anthraquinone profiles and biological effects of Asphodeline is scarce.…”

Hepatoprotective and antioxidant potential of Asphodeline lutea (L.) Rchb. roots extract in experimental models in vitro/in vivo

“…(Asphodelaceae) is a perennial plant native to Mediterranean area, mainly the Middle East-countries [1]. The edible use of its vegetative parts has been known for a long time [2]. The ancient Greeks roasted roots, several Asphodeline species are consumed in salads in Turkey and their leaves are characterized by a good nutritional quality [3].…”

“…Chrysophanol was the dominant anthraquinone derivative present in the majority of Asphodeline species [2,4]. Previous investigation of the A. lutea roots led to the isolation of two new anthraquinones for the genus Asphodeline: 1-hydroxy-8-methoxy-3-methylanthraquinone and 1,5,8-trihydroxy-3-methylanthraquinone (7), as well as the known chrysophanol (6), and bianthraquinones:…”