Diterpenes from the Fruits of Vitex rotundifolia

Abstract

Eight new labdane-type diterpenes (1-8) were isolated from the fruit of Vitex rotundifolia along with two known abietane-type diterpenoids (9, 10), and their structures were characterized on the basis of spectroscopic data and X-ray crystallographic analysis. Among them, the abietane-type diterpenoid ferruginol (9) exhibited a stronger antioxidative activity than the standard antioxidant, 3-tert-butyl-4-hydroxyanisole (BHA), using a ferric thiocyanate method.

Antioxidative, Antihyaluronidase and Antityrosinase Activities of Some Constituents from the Aerial Part of Piper elongatum VAHL.

“…in South America (Fournet et al, 1994). During the course of our screening for the antioxidative compounds from various herbs (Ono et al, 1995(Ono et al, , 1998(Ono et al, , 1999(Ono et al, , 2000(Ono et al, , 2001, the MeOH extract of the aerial part of P. elongatum VAHL. showed a stronger antioxidative activity than that of 3-tert-butyl-4-hydroxyanisole (BHA).…”

A new labdane diterpene fromVitex negundo

“…In the NOESY spectra of 1a, correlations were observed between H-8/H-20, H-19/H-20, H-3/H-18, H-5/H-3, H-14/H-17 and H-1/H-16, indicating a β-orientation for H-8, H-19, and H-20 and an α-orientation for H-3, H-5, H-17, and H-18. The β-configuration for the hydroxyl group at C-16 was confirmed from the low-field resonance of Ha-12 (δ H 2.53), which was deshielded by the hydroxyl group at C-16 (Kusumi et al, 1986;Ono et al, 1999). Compound 1a was therefore characterized as (rel 3S, 5S, 8R, 9R, 10S, 13S, 16S)-3-acetoxy-9, 13-epoxy-16-hydroxy-labda-15, 16-olide.…”

“…The major differences were the signals corresponding to an acetal proton (δ H 5.37, s in 1b; δ H 5.87, s in 1a) and two methylene protons adjacent to the carbonyl group (δ H 3.09, 2.42, d, J = 16.8 Hz in 1b; δ H 2.88, 2.71, d, J = 17.4 Hz in 1a). In addition, the configuration of the hydroxyl group at C-16 was determined to be α on the basis of NOESY spectra, which was further evidenced by the non-deshielded signal of H-12 (δ H 2.12, Ha; 1.99, Hb) compared to that of 1a (δ H 2.53, Ha; 1.83, Hb) (Ono et al, 1999 (Li et al, 2005). Compound 1 was tested for its antifungal activity against several pathogenic fungi isolates and showed good results (Table 2), especially for C. albicans (MIC 80 64 μg/mL), C. neoformans (MIC 80 16 μg/mL), and T. rubrum (MIC 80 32 μg/mL).…”

Effects of Vitex rotundifolia on radical scavenging and nitric oxide production

“…It is well known that V. rotundifolia. has essential oil such as a-pinene, camphene, terpineol, acetylester diterpene alchol, diterpene of labdane type, diterpene of abietane type (Masateru et al, 2000) and flavonoid such as casticin and artemetin (Ono et al, 1999). V. rotundifolia have been found possess anti-leukemic (Ko et al, 2000), anti-inflammatory (Zhu et al, 1998) and antiallergic properties (Shin et al, 2000).…”