Diterpenoids and flavonoids from the fruits of Vitex agnus‐castus and antioxidant activity of the fruit extracts and their constituents

Abstract

From the n-hexane fraction of the fruits of Vitex agnus-castus, two labdane-type diterpenes, vitetrifolin B and C, were isolated by means of multiple chromatographic separations, together with the previously identified rotundifuran, vitexilactone and the sesquiterpene spathulenol. From the EtOAc fraction, eupatorin was identified for the first time, besides the known casticin, penduletin, vitexin and orientin. The n-hexane, EtOAc and MeOH-H(2)O fractions of the MeOH extract of Agni-casti fructus were subjected to in vitro antioxidant assays. The EtOAc extract displayed a significant concentration-dependent effect when tested by 1,1-diphenyl-2-picrylhydrasyl (DPPH) free radical assay (IC(50) = 68 microg/mL) and against the autooxidation of a standard rat brain homogenate (IC(50) = 14 microg/mL). The MeOH-H(2)O fraction was less active with 3643 microg/mL (DPPH test) and IC(50) = 125 microg/mL (rat brain homogenate), while the n-hexane phase proved to be inactive. The main flavonoid constituents of the EtOAc extract, casticin, vitexin and orientin were assayed for antioxidant activity and found that only casticin possesses a marked lipid peroxidation inhibitory effect (IC(50) = 0.049 mm) compared with that of the positive control ascorbic acid (IC(50) = 0.703 mm).

Five New Diterpenoids, Viteagnusins A-E, from the Fruit of Vitex agnus-castus

“…Further, in the 13 C-NMR spectra of 1 obtained by measurements using CDCl 3 , C 5 D 5 N, and CD 3 OD as solvents, the peak height of 11 signals, which were assigned to C-2-C-7, C-9, C-11, C-12, C-19, and C-20, was found to be fairly low and a signal due to C-1 could not be detected (Table 2). A similar phenomenon, which was ascribable to short spin-spin relaxation times, was reported in the case of the 13 C-NMR signals for sclareol (9 C-NMR spectra of 2 were similar to those of 1, except for the absence of signals due to one olefinic proton and one olefinic methine carbon, and the presence of a signal due to one olefinic quaternary carbon. In a manner similar to that in the case of 1, these 1 H-and 13 C-NMR signals were examined in detail, and the planar structure of 2 was determined, as shown in Fig.…”

“…1) This fruit has been reported to contain essential oils, iridoids, flavonoids, and diterpenoids. [1][2][3][4][5][6][7][8][9] Further, linoleic acid isolated from this fruit was identified as an estrogenic compound. 10) In the course of our study on the constituents of Verbenaceae plants, [11][12][13][14] we have investigated the constituents of the fruit of V. agnus-castus.…”

Three New Diterpenoids from the Fruit of Vitex agnus-castus

“…1) This fruit has been reported to contain essential oils, iridoids, flavonoids, and diterpenoids. [1][2][3][4][5][6][7][8][9] Further, linoleic acid isolated from this fruit was identified as an estrogenic compound. 10) In a previous paper, 11) we reported the isolation and structural elucidation of seven diterpenoids from the hexane extract of V. agnuscastus.…”

Vitex agnus-castus dry extract BNO 1095 (Agnucaston®) inhibits uterine hyper-contractions and inflammation in experimental models for primary dysmenorrhea

“…Anti-inflammatory and anti-oxidative effects have been previously reported for VAC extracts and several single VAC constituents [25,52,53]. For example, Choudary et al demonstrated LO enzyme-inhibiting activity of casticin in vitro [54], and the flavonoid vitexin inhibited proinflammatory cytokine production and inflammationinduced pain [23] in an in vivo experimental inflammation model.…”

“…The mechanism of action of VAC herbal extracts in treating menstrual symptoms has not been completely elucidated, perhaps due to the large number of potentially active extract constituents, including iridoids, flavonoids, and diterpenes [22][23][24][25][26]. For example, a large body of evidence suggests that VAC extracts acts in the brain at dopamine D 2 receptors of the hypothalamus/ pituitary gland axis to inhibit the systemic release of prolactin from the pituitary gland resulting in the relief of PMS symptoms [27][28][29][30][31].…”