benzofurans and butylidenephthalide

Angelica sinensis (Oliv.) hexane extract (AHE) has been reported as a proven and impressive repellent against laboratory-reared female Aedes aegypti mosquitoes. With the aim of promoting products of plant origin as a viable alternative to conventional synthetic substances, this study was designed to transform AHE-based repellents for exploitable commercial production by enhancing their efficacy and assessing their physical and biological stability as well as repellency against mosquitoes under laboratory and field conditions.. The chemical profile of AHE was analyzed by qualitative gas chromatography-mass spectrometry (GC-MS) technique. AHE was supplemented with vanillin, as a fixative, and then investigated for repellency and comparison to the standard synthetic repellent, DEET, under both laboratory and field conditions. Determination of physical and biological stability as a repellent was carried out after keeping AHE samples under varying temperatures and for different storage times.. GC-MS analysis revealed that AHE contained at least 21 phytochemical compounds, constituting 95.74 % of the total content, with the major constituent of 3-N-butylphthalide (66.67 %). Ethanolic formulations of AHE and DEET showed improvement of repellency in a dose-dependent manner when vanillin was added in laboratory assessment. While 5-25 % AHE alone provided median complete-protection times of 2.0-6.5 h against Ae. aegypti, these times were increased to 4.0-8.5 h with a combination of AHE and 5 % vanillin (AHEv). Protection times against Ae. aegypti were extended from 2.25 to 7.25 h to 4.25-8.25 h when 5-25 % DEET was combined with 5 % vanillin (DEETv). In determining stability, all stored AHE samples exhibited similar characteristics such as liquid phases with aromatic odor comparable to those of fresh preparations. Furthermore, repellent activity of stored AHE samples lasted for at least six months, with varied efficacy (4.5-10.0 h) against Ae. aegypti. Field trials revealed strong repellency from both 25 % AHEv and 25 % DEETv, with complete protection (100 %) against a wide range of local mosquito populations. A total of 5,718 adult female mosquitoes, with the most predominant being Culex quinquefasciatus (41.47 %), Armigeres subalbatus (41.13 %), and Culex vishnui (10.53 %), was collected during field applications. No local skin reaction or other allergic responses was observed during both laboratory and field study periods.. Angelica sinensis proved to have not only impressive repellency against both laboratory Ae. aegypti and a wide range of natural mosquito populations, but also relative stability in physical and biological performance.

Topics: Angelica sinensis; Animals; Benzofurans; Culicidae; Female; Humans; Insect Repellents; Linoleic Acid; Male; Molecular Structure; Phthalic Anhydrides; Plant Extracts; Thailand

To identify Chuanxiong Rhizoma,Angelicae Sinensis Radix and Ligustici Rhizoma et Radix by establishing the HPLC specific chromatograms of their volatile oil and to compare their specific peaks.. The HPLC method used methanol-water as mobile phase. Their specific peaks were analysed by HPLC-MS.. Under the selected spectrum condition, their HPLC specific chromatograms were established. Senkyunolide A, butylphalide, coniferylferulate, E-ligustilide, Z-ligustilide, neocnidilide and E-butylidenephthalide were identified as specific peaks in chromatograms based on their MS data.. This method is simple, accurate and available to identify Chuanxiong Rhizoma, Angelicae Sinensis Radix and Ligustici Rhizoma et Radix. It provides reference for quality control of their medicinal materials and Chinese Patent Medicine.

Topics: 4-Butyrolactone; Angelica sinensis; Benzofurans; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Ligusticum; Oils, Volatile; Phthalic Anhydrides; Plant Oils; Plant Roots; Rhizome

To study the constituents of essential oil from Shunaoxin dropping pills by GC-MS.. The essential oil from Shunaoxin dropping pills were extracted by absolute alcohol and analyzed by GC-MS.. 15 components from the essential oil of Shunaoxin dropping pills were identified.. The main components in the essential oil of Shunaoxin dropping pills are lactones such as Z-ligustilide, senkyunolide A,3-butylphthalide and 3-butylidenephthalide, other components are organic acids such as ethyl linoleate, 9,12-octadecadienoic acid and ethyl palmitate.

Topics: 4-Butyrolactone; Angelica; Apiaceae; Benzofurans; Drugs, Chinese Herbal; Gas Chromatography-Mass Spectrometry; Lactones; Oils, Volatile; Phthalic Anhydrides

In spite of numerous advances, the 5-year survival rate for head and neck squamous cell cancer has remained largely stagnant and few new anti-tumor drugs have been developed. PCH4, a derivative of n-butylidenephthalide, has been investigated for its anti-tumor effects on oral squamous cell carcinoma (OSCC). The aim of this study was to investigate the anti-tumor mechanism of a potential target gene, Nur77, in OSCC cells, which can be induced by PCH4 treatment. Data show that PCH4 promoted Nur77 translocation from the nucleus to the cytoplasm and induced cell apoptosis in OSCC cells. When Nur77 translocation was blocked, the degree of tumor apoptosis caused by PCH4 was significantly inhibited (p < 0.05). Within the MAPK pathway, PCH4 only induced JNK phosphorylation. Furthermore, treatment with a JNK inhibitor significantly reduced PCH4-induced apoptosis (p < 0.05) and decreased PCH4-induced Nur77 expression (p < 0.05). In a xenograft animal model, administration of PCH4 also showed anti-tumor effects. We have demonstrated that OSCC cells are sensitive to PCH4 and that Nur77 protein translocation from the nucleus to the cytoplasm might be associated with the induction of apoptosis by PCH4. These results indicate that PCH4 may serve as a potential anti-tumor drug for OSCC therapy.

Topics: Active Transport, Cell Nucleus; Animals; Antineoplastic Agents; Apoptosis; Benzofurans; Carcinoma, Squamous Cell; Cell Line, Tumor; Cell Proliferation; Cell Survival; Dose-Response Relationship, Drug; Ethylamines; Female; Humans; JNK Mitogen-Activated Protein Kinases; Mice; Mice, Inbred BALB C; Mice, Nude; Mouth Neoplasms; Nuclear Receptor Subfamily 4, Group A, Member 1; Phosphorylation; Phthalic Anhydrides; Protein Kinase Inhibitors; RNA, Messenger; Time Factors; Tumor Burden; Up-Regulation; Xenograft Model Antitumor Assays

In previous study, n-butylidenephthalide (BP), a natural compound from Angelica sinensis, has anti-glioblastoma multiform (GBM) cell effects. In this study, we modified BP structure to increase anti-GBM cell effects. The anti-GBM cell effects of one derivative of BP, (Z)-N-(2-(dimethylamino)ethyl)-2-(3-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)phenoxy)acetamide (PCH4) were tested in vitro and in vivo.. MTT assay and PI/Annexin V assay were performed to evaluate the anti-GBM effects of PCH4. The Nur77 expression and translocation were assayed by RT-PCR and Western blot. The Nur77 siRNA was used to downregulate the Nur77 expression. The JNK inhibitor (SP600125) was used to block the JNK pathway.. The anti-GBM effect of PCH4 is four times more than BP. The IC(50) of PCH4 on DBTRG-05MG cells was 50 µg/ml. Nur77 expression and translocation from the nucleus to the cytoplasm were important in PCH4-induced apoptosis. Furthermore, the downregulation of PCH4-induced Nur77 expression by Nur77 siRNA reduced PCH4-induced apoptosis. In addition, PCH4-induced apoptosis was associated with the JNK pathway. The JNK inhibitor, SP600125, inhibited Nur77 mRNA expression and reduced PCH4-induced apoptosis.. In conclusion, PCH4, a derivative of BP, induced Nur77-mediated apoptosis via the JNK pathway and this mechanism, which is different from that of BP, may explain the increase in the anti-tumor effects on GBM.

Topics: Angelica sinensis; Animals; Apoptosis; Benzofurans; Blotting, Western; Brain Neoplasms; Cell Proliferation; DNA-Binding Proteins; Ethylamines; Flow Cytometry; Glioblastoma; Humans; Luciferases; MAP Kinase Kinase 4; Mice; Mice, Nude; Nuclear Receptor Subfamily 4, Group A, Member 1; Nuclear Receptor Subfamily 4, Group A, Member 2; Phthalic Anhydrides; Protein Transport; Receptors, Steroid; Receptors, Thyroid Hormone; Reverse Transcriptase Polymerase Chain Reaction; RNA, Messenger; RNA, Small Interfering; Signal Transduction; Tumor Cells, Cultured; Xenograft Model Antitumor Assays

To analyze the chemical components in Danggui (the roots of Angelica sinensis (Oliv.) Diel).. HPLC-MS/MS was used to identify the main components in Danggui. Furthermore, the MS fragmentation regularity of the phthalides was proposed. The mobile phase of HPLC consisted of 0.5% acetic acid in water and 0.5% acetic acid in acetonitrile, analytical column was Hypersil ODS2 (250 mm x 4.6 mm, 5 microm), flow rate 1.0 mL x min(-1), injected volume 2 microL. The ionization source was ESI in positive ion mode.. Ferulic acid, nine known phthalides and one unknown phthalide derivative were tentatively identified in chromatograms based on their MS data and the comparison of their UV spectra with those published in the literatures.. The structural information of phthalides was obtained via HPLC-MS/MS, which provides an accurate and fast method to identify the phthalides and provides more scientific information for quality control of Danggui.

Topics: 4-Butyrolactone; Angelica sinensis; Benzofurans; Chromatography, High Pressure Liquid; Coumaric Acids; Molecular Structure; Phthalic Anhydrides; Plant Roots; Plants, Medicinal; Reproducibility of Results; Spectrometry, Mass, Electrospray Ionization

A valid chromatographic fingerprint method using liquid chromatography-diode array detection-atmospheric pressure chemical ionization mass spectrometry in negative mode (LC-DAD-APCI-MS) is proposed for studying the absorption and metabolites of a traditional Chinese medicine (TCM) Angelica sinensis (danggui) in rabbit plasma, after the rabbit is administered with danggui oral solution (DOS). More than thirty-two common components were detected in both DOS and rabbit plasma, which shows that the components in the DOS were absorbed into the body of the rabbit. Of these, senkyunolide I, senkyunolide H, Z-6,7-epoxyligustilide, 3-butylidene-7-hydroxyphthalide, Z-ligustilide, Z-butylidenephthalide, Diels-Alder dimers of ligustilide, linolenic acid, linoleic acid and falcarindiol were tentatively identified from their MS, UV spectra and retention behavior by comparing the results with the published literature. At least ten components were found in rabbit plasma but not in DOS, indicating that these components must be metabolites of some of the components in the original extract. The results prove that the proposed method can be used to rapidly analyze multiple constituents in TCMs, and to screen for bioactive compounds by comparing and contrasting the chromatographic fingerprints of DOS and plasma samples.

Topics: 4-Butyrolactone; Absorption; Administration, Oral; Aldehydes; alpha-Linolenic Acid; Angelica sinensis; Animals; Benzofurans; Diynes; Drugs, Chinese Herbal; Fatty Alcohols; Linoleic Acid; Mass Spectrometry; Phthalic Anhydrides; Plant Extracts; Rabbits

Inhibitory effects of cnidium rhizome-derived phthalides on competence and progression phases of fetal bovine serum (10%)-induced proliferation were compared in primary cultures of mouse aorta smooth muscle cells (SMC). Their potencies for the competence inhibition were in the order of senkyunolide L ((Z)-6-hydroxy-7-chloro-6,7-dihydroligustilide) > senkyunolide H ((Z)-6,7-dihydroxy-6,7-dihydroligustilide) > senkyunolide J ((3S)-(E)-6,7-dihydroxy-3,6,7,8-tetrahydroligustilide) > senkyunolide I ((E)-6,7-dihydroxy-6,7-dihydroligustilide) > ligustilide = senkyunolide A ((3S)-3,8-dihydroligustilide) > butylidenephthalide. The order of their potencies for the progression inhibition was parallel with that for the competence inhibition. Senkyunolide L is considered to have been formed during the extraction of cnidium. These results demonstrate that the (Z)-6,7-dihydroxy isomer of the dihydroligustilide derivatives is essential for the anti-competent effect on proliferation of the SMC in primary culture. Senkyunolide H in cnidium rhizome may be a prototype for a new anti-atherosclerotic drug.

Topics: 4-Butyrolactone; Analysis of Variance; Animals; Aorta, Thoracic; Benzofurans; Cell Division; Cells, Cultured; Drugs, Chinese Herbal; Male; Mice; Muscle, Smooth, Vascular; Phthalic Anhydrides; Structure-Activity Relationship