Clerodane diterpenoids and prenylated flavonoids from Dodonaea viscosa

Abstract

Repeated column chromatography of the EtOAc-soluble fraction of the aerial parts of Dodonaea viscosa led to the isolation of two new modified clerodanes, methyl dodovisate A (1) and methyl dodovisate B (2), two new prenylated flavonoids, 5,7,4′-trihydroxy-3′,5′-di(3-methylbut-2-enyl)-3,6-dimethoxyflavone (10) and 5,7,4′-trihydroxy-3′-(4-hydroxy-3-methylbutyl)-5′-(3-methylbut-2-enyl)-3,6-dimethoxyflavone (11), together with eight known compounds, dodonic acid (3), hautriwaic acid (4), hautriwaic lactone (5), (+)-hardwickiic acid (6), 5α-hydroxy-1,2-dehydro-5,10-dihydroprintzianic acid methyl ester (7), strictic acid (8), dodonolide (9), and aliarin (12). The structures of the new compounds were elucidated by spectroscopic data analysis. Compounds 1–9 and 11 were evaluated on larvicidal activity against the fourth-instar larvae of Aedes albopictus and Culex pipens quinquefasciatus.

Keywords:

• Sapindaceae
• Dodonaea viscosa
• clerodane diterpenoids
• prenylated flavonoids

Acknowledgements

This work was funded by the grants of the Ministry of Education of China through its 111 and 985 projects (B08044 and MUC 985-3-3), the Ministry of Science and Technology of China (2008FY110400-2-2 and 2005DKA21006), and the Knowledge Innovation Program of the Chinese Academy of Sciences.