Bioactive Diterpenes from Callicarpa longissima

Abstract

Investigation of the leaves and twigs of Callicarpa longissima resulted in the isolation of four new compounds (1-4), callilongisins A-D, and five known compounds, ursolic acid, 3-oxoanticopalic acid, (E)-6β-hydroxylabda-8(17),13-dien-15-oic acid, 5-hydroxy-3,6,7,4'-tetramethoxyflavone, and artemetin. Compounds 1-3 are 3,4-seco-abietane-type diterpenoids, and compound 4 is an analogue of a labdenoic-type diterpene. The structure of compound 1 was confirmed by X-ray crystallographic analysis. Cytotoxicity against a human prostate cancer cell line (PC3) and anti-inflammatory activities of the isolated compounds were evaluated.

Bioactive Diterpenoids from the Leaves of Callicarpa macrophylla

“…The relative configuration of 2 was deduced from the NOESY spectrum and Chem3D modeling. The NOESY correlations observed for H 3 Figure S13), the absolute configuration of 2 was assigned as 4R, 5R, 9R, 10R, 13R, and 14S, and the compound was named macrophypene B.…”

Peroxy natural products

“…263 Investigation of the leaves and twigs of Callicarpa longissima resulted in the isolation of a 3,4-seco-abietane peroxide named callilongisins A 446 with significant anti-inflammatory effect, whose structure was further confirmed by X-ray crystallographic analysis. 264 Three diterpenic acids 447-449 were isolated as their methyl ester derivatives from the leaves of Juniperus thurifera and Juniperus phoenicea. 265 Further members of the type included triptotins A 450 and B 451 from Tripterygium wilfordii, 266 6-oxo-12-peroxyabieta-8,11,13-triene 452 from Salvia multicaulis, 267 and glutinosin C 453 from Isodon glutinosa.…”

Randainins A–D, Based on Unique Diterpenoid Architectures, from Callicarpa randaiensis

“…The orientations of Me-17 and Me-20 in 1 was assumed to be α-orientated, as found in previous known diterpenoids. 15 Figure S28) also confirmed the 1β/5α trans-configuration of 4, in contrast with the negative Cotton effect in the ECD spectrum of 1α/5β trans-configurated ring system of 3. A comparison of the ECD spectra of 3 and 4 is shown in the Supporting Information.…”