Phenolic Glucosides from the Leaves of Vitex negundo var. cannabifolia.

Four new phenolic glucosides, cannabifolins G-J (1-4), together with four known ones (5-8), were isolated from the leaves of Vitex negundo var. cannabifolia. Their structures were established by comprehensive analysis of 1D and 2D NMR data and comparison of their spectroscopic and physical data with the literature values. Compound 7 exhibited weak inhibition of nitric oxide production stimulated by lipopolysaccharide in BV-2 microglial cells with IC50 value of 132.8 µM.

Definitely simultaneous determination of three lignans in rat using ultra-high performance liquid chromatography-tandem mass spectrometry.

Herbal medicines (HMs) have been widely demonstrated to be extremely complicated chemical pools, notably the occurrences of isomers that usually possess similar chromatographic and spectrometric behaviors, and the complexity will be further boosted in HMs-treated biological samples. Hence, there is a technical barrier regarding identity confirmation towards the acquisition of reliable quantitative information for those compounds-of-interest in biological matrices, although tandem mass spectrometry (MS/MS) is a favored tool because of the advantages in terms of specificity and selectivity, in particular being hyphenated with ultra-high performance liquid chromatography (UHPLC). More structural information should be involved in addition to retention times and precursor-to-product ion transitions, to consolidate the identities of the captured signals. Attempts were made here to strengthen quantitation confidences via matching MS2 spectra and relative response-collision energy curves (RRCECs) between each pair of suspect peak and the authentic signal, and UHPLC coupled to hybrid triple quadrupole-linear ion trap mass spectrometry (Qtrap-MS) that enabled simultaneous acquisition of qualitative and quantitative information acted as the analytical tool. Definitely simultaneous determination of a pair of regio-isomers namely 6­hydroxy­4­(4­hydroxy­3­methoxyphenyl)­3­hydroxymethyl­7­methoxy­3,4­dihydro­2­naphthaldehyde (VB-1) and vitedoin A (VB-2), together with another analogue namely detetrahydroconidendrin (VB-3), in rat plasma as well as tissues was conducted following oral administration of the extract of fruits of Vitex negundo var. cannabifolia. Diverse method validation assays in regard of selectivity, linearity, intra- and inter-day variations, matrix effect, and recovery were employed to demonstrate the newly developed method being able to fulfill the demands of rational quantitation. Overall, the current study offers a promising approach to accomplish confidence-enhanced quantitation in biological matrices.

Furofuran lignan glucosides from the leaves of Vitex negundo var. cannabifolia.

Two new furofuran lignan glucosides, cannabilignin (1) and isocannabilignin (2), together with four known compounds (3-6), were isolated from the leaves of Vitex negundo var. cannabifolia. The structures of the isolates were elucidated by analysis of spectroscopic data. Compound 3 exhibited weak inhibition of nitric oxide production in lipopolysaccharide-stimulated BV-2 microglial cells with IC50 value of 69.1 ± 5.8 µM.

Characterization of metabolites in rats after gavage of two lignans from fruits of Vitex negundo var. cannabifolia by UFLC-IT-TOF-MS / 中草药

Objective: To investigate in vivo metabolic profiles of two lignans, 6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-3- hydroxymethyl-7-methoxy-3,4-dihydro-2-naphthaldehyde (VB-1) and vitedoin A (VB-2) in the rats. Methods: A UFLC-IT- TOF-MS method was applied to characterize the prototypes and metabolites of VB-1 and VB-2 in rat feces, urine, bile, and plasma after oral administration. Results: Eleven metabolites of the two parent compounds were detected and two prototypes were identified unambiguously by comparing with references. Analysis of metabolites revealed that glucuronidation, sulfation, and hydroxylation were major biotransformation pathways of two lignans. Conclusion: In this study, under the analysis of metabolites of two lignans, its in vivo metabolic process is basically clarified. The results could be helpful for the further pharmacokinetics and pharmacological evaluations of VB-1 and VB-2.

[Chemical constituents from the fruits of Vitex negundo var. cannabifolia and their biological activities in vitro].

Chemical constituents from the fruits of Vitex negundo var. cannabifolia and their nitric oxide (NO) inhibitory and cytotoxic activities were investigated. The compounds were isolated and purified by various column chromatography, and their structures were identified by physiochemical properties and spectroscopic data. Thirteen lignans and six phenolic compounds were isolated from the CH2Cl2 extract of the fruits of V. negundo var. cannabifolia, respectively. Their structures were elucidated as 6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-3,4-dihydro-2-naphthaldehyde (1), vitedoin A (2), vitexdoin F (3), detetrahydroconidendrin (4), vitexdoin E (5), 4-oxosesamin (6), L-sesamin (7), (+)-beechenol (8), ligballinol (9), 2-(4-hydroxyphenyl)-6-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (10), (-)-pinoresinol (11), balanophonin (12), thero-guaiacylglycerol-ß-coniferyl aldehyde ether (13), trans-p-coumaryl aldehyde (14), coniferyl aldehyde (15), 5,7-dihydroxychromone (16), trans-3,5-dimethoxy-4-hydroxy-cinnamic aldehyde (17), frambinone (18), and alternariol 4-methyl ether (19). Compounds 8-10,14,18,19 were firstly isolated from Verbenaceae family, compound 13 was obtained from Vitex species, and 6,7,12,15-17 from V. negundo var. cannabifolia for the first time, respectively. The isolated compounds were evaluated for their anti-inflammatory and cytotoxic effects in vitro. Eight compounds (3,5,7,10,11,14,15,17) showed inhibition against NO production in LPS-stimulated RAW 267.4 cells (IC50 in the range of 7.8-81.1 µmol•L⁻¹) and four compounds (1-4) showed cytotoxicity on HepG-2 cells (IC50 in the range of 5.2-24.2 µmol•L⁻¹).

Chemical constituents from the fruits of Vitex negundo var. cannabifolia and their biological activities in vitro / 中国中药杂志

Chemical constituents from the fruits of Vitex negundo var. cannabifolia and their nitric oxide (NO) inhibitory and cytotoxic activities were investigated. The compounds were isolated and purified by various column chromatography, and their structures were identified by physiochemical properties and spectroscopic data. Thirteen lignans and six phenolic compounds were isolated from the CH2Cl2 extract of the fruits of V. negundo var. cannabifolia, respectively. Their structures were elucidated as 6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-3,4-dihydro-2-naphthaldehyde (1), vitedoin A (2), vitexdoin F (3), detetrahydroconidendrin (4), vitexdoin E (5), 4-oxosesamin (6), L-sesamin (7), (+)-beechenol (8), ligballinol (9), 2-(4-hydroxyphenyl)-6-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (10), (-)-pinoresinol (11), balanophonin (12), thero-guaiacylglycerol-β-coniferyl aldehyde ether (13), trans-p-coumaryl aldehyde (14), coniferyl aldehyde (15), 5,7-dihydroxychromone (16), trans-3,5-dimethoxy-4-hydroxy-cinnamic aldehyde (17), frambinone (18), and alternariol 4-methyl ether (19). Compounds 8-10,14,18,19 were firstly isolated from Verbenaceae family, compound 13 was obtained from Vitex species, and 6,7,12,15-17 from V. negundo var. cannabifolia for the first time, respectively. The isolated compounds were evaluated for their anti-inflammatory and cytotoxic effects in vitro. Eight compounds (3,5,7,10,11,14,15,17) showed inhibition against NO production in LPS-stimulated RAW 267.4 cells (IC₅₀ in the range of 7.8-81.1 μmol•L⁻¹) and four compounds (1-4) showed cytotoxicity on HepG-2 cells (IC₅₀ in the range of 5.2-24.2 μmol•L⁻¹).

Antioxidant lignans from the seeds of Vitex negundo var. cannabifolia.

A new phenyldihydronaphthalene-type lignan, vitexdoin F (1), along with 22 known lignan derivatives (2-23) was isolated from the seeds of Vitex negundo var. cannabifolia. Their structures were established by comprehensive 1D and 2D NMR spectroscopic analyses. The antioxidant activities of these lignans were evaluated through 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assays, and 16 of these isolates exhibited obvious radical-scavenging effect on the stable-free radical, DPPH.

Accumulation dynamics and distribution characters of vitexin in different parts of Vitex negundo var. cannabifolia / 中国药学杂志

OBJECTIVE: To study the accumulation dynamics and distribution law of vitexin during the whole year period in different parts of Vitex negundo var.cannabifolia (Sieb. et Zucc.). METHODS: Vitexin was obtained by ultrasonic extraction, and its content was determined by HPLC. Filodoor column (4.6 mm×150 mm, 5 μm) was used. Methanol-water (volume ratio of 4;6) was used as the mobile phase at a flow rate of 1 mL·min-1. The UV detective wavelength was set at 340 nm, injection volume was 5 μL, and the column temperature was set at 35°C. RESULTS: The content of vitexin was low in vitex negundo branches and flowers, and had obvious regularity in different growth periods of Vitex negundo leaves. The content of vitexin was the highest (1.380%-1.465%) in June and July. Along with the blooming and formation of negundo chastetree to their maturation, the content of vitexin in Vitex negundo leaves decreased. Its content was the lowest (0.720%-0.751%) in September and October. The content of vitexin in Vitex negundo seeds increased(0.435%-1.231%)with seed maturation. CONCLUSION: The content of vitexin in different parts of Vitex negundo presents a regular change in different periods. The detection of vitexin in different growth periods provides experimental basis for the selection of best collection phase and medical parts.