Naphthalene Aglycones and Glycosides from the Australian Medicinal Plant,Dianella callicarpa

Abstract

The crude extract of the roots from the Australian medicinal plant Dianella callicarpa (Liliaceae) displayed significant antimicrobial and antiviral activities. This prompted a chemical investigation, resulting in the isolation of the new naphthalene glycoside, dianellose (10), together with dianellin (1), dianellidin (2), dianellinone (3), stellalderol (9) and 5-hydroxydianellin (11). The structures for compounds 1, 9 and 10 were secured by detailed spectroscopic analyses, while compounds 2, 3 and 11 were identified on the basis of comparisons to literature data. Whilst the chemistry of the genus Dianella has previously been investigated, we report the first isolation of stellalderol (9) from this genus, together with the chemical and biological evaluation of the callicarpa species. Biological evaluation of the isolated compounds established that 2 showed antiviral and mild antimicrobial properties and that compounds 1, 9 and 10 displayed moderate antitumour activities.

In vivo Antimalarial Activity of the Hydroalcoholic Extract of Kniphofia foliosa Hochst and Its Constituents

“…P < 0.05 were considered signi cant. to be in good agreement with 13 C NMR reports of similar glycosides [29,30]. Hence, the disaccharide moiety was con rmed to be rhamnose-glucose 1,6 linkage.…”

“…Lastly, the 13 C signals at 207.7 and 41.3 are the carbonyl carbon and its acetyl methyl. Therefore, based on the above evidence and in comparison with 1 H and 13 C NMR data of the same and related compounds [30,31], the structure of compound 1 was determined to be dianellin or 1-(1-hydroxy-3-methyl-8-(((2S,3R,4S,5S,6R)3,4,5-trihydroxy-6-((((2S,3S,4S,5S,6R)3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2yl)oxy)naphthalen-2-yl) ethanone. Table 1 summarizes the NMR data of compound 1.…”

“…Besides, two of them are elevated (δ 154.71 and δ 151.49) suggesting that they are oxygenated quaternary aromatic carbons. On the other hand, the two less elevated (δ 136.74 and δ 113.54) quaternary aromatic carbons are the bridgehead carbons of the fused aromatic system [30]. The remaining two quaternary aromatic carbon signals resonated at δ 124.73 (C-2) and δ 133.30 (C-3).…”

Cichorins D–F: Three New Compounds from Cichorium intybus and Their Biological Effects

“…Moreover, various naphthalene compounds (aglycones and glycosides) have been reported from plants that have similar substitution patterns, as in compound 2 . These compounds are dianellin [ 52 ], 5-hydroxydianellin [ 52 ], stellalderol [ 52 ], parvinaphthols A and B [ 53 ], penthosides A and B [ 54 ], Eucleanal [ 40 ], Eucleanal A and B [ 41 ]. Interestingly, anthraquinone 3 has an additional methyl group at C-7 in comparison to trimethoxylated emodin.…”

Isolation, Characterization, and Structure–Activity Relationship Analysis of Abietane Diterpenoids fromCallicarpa bodinierias Spleen Tyrosine Kinase Inhibitors

“…Callicarpa bodinieri is one of the species in the genus Callicarpa that has been used widely in traditional medicine, for the treatment of inflammation, rheumatism, analgesia, hematemesis, gastrointestinal bleeding, scrofula, and swollen sores . The diverse therapeutic applications of plants in the genus Callicarpa may be attributed to their bioactive constituents, including terpenoids, lignans, glycosides, − flavonoids, phenolic acids, − and their volatile oils. , The diterpenoids isolated from this genus have been reported to have anti-inflammatory activities in different disease models; − however, their target has not been identified.…”