Isoprenylated flavonoids and clerodane diterpenoids from Dodonaea viscosa

Abstract

Phytochemical investigation of the aerial parts of Dodonaea viscosa led to the isolation of six new compounds including four isoprenylated flavonoids, dodovisones A-D (1-4), and two clerodane diterpenoids, dodovislactones A and B (5 and 6). Their structures were established by extensive spectroscopic analysis.

Isolation of Three New Diterpenes from <i>Dodonaea viscosa</i>

“…The EtOAcsoluble fraction was subjected to normal and reversed-phase silica gel column chromatography followed by repeated HPLC separation. This process gave three new compounds (1-3) as well four diterpenes [labd-13(E)-en-8,15-diol (4), 11,12) ent-15,16-epoxy-9αH-labda-13(16),14-diene-3β,8α-diol (5), 13) hautriwaic acid (6), 14,15) and 6-hydroxyhardwickjic acid (7), 16) ], four flavonoids [viscosine (8), 17) 5,7,4′-trihydroxy-3′-(4-hydroxy-3-methylbutyl)-5′-(3-methylbut-2-enyl)-3,6dimethoxyflavone (9), 10,18) alizarin (10), 18,19) and dodovisone C (11) 20) ], three coumarins [scopoletin (12), 21) isofraxidin (13), 22,23) and fraxetin (14) 24) ], one lignane [(+)-pinoresinol (15) 25) ] and five other compounds [protocatechuic acid (16), 26) (E)-cinnamic acid (17), 27) methyl hydrogen azelate (18), 28) β-hydroxylpropiovanillone (19), 29) and 4-hydroxyacetophenone (20) 30 ]. These known compounds were identified by comparing their observed spectroscopic data with previously reported data.…”

“…10) In the present study, as part of a continuous study of Okinawan plants, we describe the isolation of three new diterpenes (1-3) ( Fig. 1) and 17 known compounds (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) (Fig. 2) from the leaves of D. viscosa.…”

Polysubstituted Isoflavonoids from Spatholobus suberectus, Flemingia macrophylla, and Cudrania cochinchinensis

“…The particular downfield shifts (Δ ≈ +5 ppm) of aromatic methoxy carbons also implied the location of these groups. According to the empirical rule, the carbon signals of the methoxy groups with substituents in both ortho positions will appear at 60–62 ppm, while those sterically non-hindered at 55–57 ppm [ 15 ]. On the basis of the above analysis, the structure of 1 was established as 7,4′-dihydroxy-8,2′,3′-trimethoxyisoflavan.…”

Dodonaea viscosa Jacq: A Medicinal Plant with Cytotoxic Effect on Colon Cancer Cell Line (HT-29)

“…Prenylated flavonoids present in D. viscosa leaves have demonstrated anti-inflammatory effect due to several types of Dodoviscins isolated of the soluble fraction from the ethyl acetate extraction 16 . Otherwise, exist a relationship between the gut microbiota and colorectal cancer, when this microbiota is altered a chronic inflammation could be the starting point of the colorectal cancer progression 17,18 .…”