Coniferyl Ferulate Research Articles

Identification of Antioxidants in Essential Oil of Radix Angelicae Sinensis Using HPLC Coupled with DAD-MS and ABTS-Based Assay

Radix Angelicae sinensis (named danggui in Chinese), a commonly used traditional Chinese medicine, has multiple pharmacological activities. The essential oil of danggui is usually considered to be its main active fraction. However, to date, studies on the antioxidant potentials of danggui have focused on water-soluble compounds. In this paper, the antioxidant activity of the commercial essential oil of danggui was investigated by DPPH radical scavenging assay, ABTS radical scavenging assay, and beta-carotene bleaching test. Antioxidant constituents in the essential oil were identified using HPLC coupled with DAD-MS and ABTS-based assay. The results showed that the essential oil of danggui has concentration-dependent antioxidant activity, which can be attributed to its component (coniferyl ferulate). This is the first report on the antioxidant activity of essential oil from danggui; its antioxidant potential was lower than those of positive controls, ascorbic acid and BHA.

Screening and analysis of an antineoplastic compound in Rhizoma Chuanxiong by means of in vitro metabolism and HPLC-MS

A new screening and analysis method that combines in vitro metabolism with high-performance liquid chromatography-mass spectrometry (HPLC-MS) was developed for the screening and analysis of an antineoplastic compound, coniferyl ferulate, which is present in the rhizome of Rhizoma Chuanxiong. Infrared (IR), ultraviolet visible spectroscopy (UV-Vis), nuclear magnetic resonance (NMR) and element analysis were used to identify the molecular structure of coniferyl ferulate. The quantitative analysis of coniferyl ferulate in different extracts of Rhizoma Chuanxiong was carried out, and the metabolism of coniferyl ferulate was investigated by in vitro incubation with rat liver homogenate. The metabolite of coniferyl ferulate, ferulic acid ethyl ester, was identified by HPLC-MS, UV-Vis and IR. In addition, antineoplastic activities of coniferyl ferulate and ferulic acid ethyl ester were detected by the MTT assay. The observed inhibition rate of coniferyl ferulate on the activity of HeLa cells was over 80% at 5.4 ng microl(-1). However, its metabolite, ferulic acid ethyl ester, showed no antineoplastic activity in vitro.

Antibacterial activity of components from Lomatium californicum

The isolation, characterization and bioactivity testing of compounds from Lomatium californicum (Nutt.) are described. Ethyl acetate and hexane extracts of the roots of L. californicum were subjected to vacuum liquid chromatography (VLC), flash column chromatography (FCC) and separation by normal- and reverse-phase high-performance liquid chromatography (HPLC). Six compounds were isolated successfully and characterized by 1D and 2D nuclear magnetic resonance (NMR) experimentation. The bioactivity of the known compounds (+)-falcarindiol, coniferyl ferulate, ferulic acid and (Z)-ligustilide were confirmed against the Gram-positive bacteria Bacillus subtilis and Staphylococcus aureus. The known compounds senkyunolide I and trans-neocnidilide were also isolated but in too small a quantity for similar testing.

Time-Course Accumulation of Main Bioactive Components in the Rhizome ofLigusticum chuanxiong

Fresh rhizomes of Ligusticum chuanxiong, a commonly used traditional Chinese medicinal herb, were collected monthly from a cultivating base in China practicing good agriculture practice (GAP). These samples were analyzed by HPLC-UV for their main chemical ingredients. Senkyunolide A (6), coniferyl ferulate (7) and Z-ligustilide (8) were identified as the major ingredients. The accumulation of the main ingredients with time in the herb was elucidated. Both individual and total contents of all main components gradually increased from the beginning of October to the middle of next April. The weight of a single rhizome reached a plateau at the end of May, whilst the content of the major ingredients peaked in the middle of April. Based on these results, it is recommended that Rhizoma Chuanxiong be harvested between the middle of April and the end of May.

Assay of free ferulic acid and total ferulic acid for quality assessment of Angelica sinensis

Activity of Chinese Danggui (DG), the processed root of Angelica sinensis (Oliv.) Diels, is linked to the ferulic acid content but the stability of ferulic acid during extraction for medicinal use is not known. The stabilities of ferulic acid and coniferyl ferulate were evaluated in the extracts of DG using a variety of extraction solvents. These included various combinations and proportions of methanol, water, formic acid, 1 M aqueous hydrochloric acid and 2% sodium hydrogen carbonate (NaHCO 3) in water. Coniferyl ferulate was found liable to hydrolyze into ferulic acid in neutral, strongly acidic and basic solvents, where heat and water could facilitate this hydrolysis. However, the hydrolysis was relatively resisted in weakly organic acid. Based on the stability evaluation, two new terms, namely: free ferulic acid and total ferulic acid, were suggested and defined. Free ferulic acid refers to the natural content of ferulic acid in herbs. Total ferulic acid means the sum of free ferulic acid plus the amount of related hydrolyzed components. Meanwhile, the high-performance liquid chromatographic (HPLC) method was developed to assay free ferulic acid and total ferulic acid in DG using methanol–formic acid (95:5) and methanol–2% NaHCO 3 in water (95:5) as extraction solvents, respectively. Ten DG samples were investigated on their contents of free and total ferulic acid. The results indicated that the amount variety of free ferulic acid was larger than that of their counterparts, and the ratio of total ferulic acid to free ferulic acid was 4.07 ± 2.73 (mean ± SD, n = 10). The chemical assay of DG using total ferulic acid content would be a better choice to assess the herbal quality and was recommended.

Development of high-performance liquid chromatographic fingerprints for distinguishing Chinese Angelica from related umbelliferae herbs

A high-performance liquid chromatographic (HPLC) fingerprint of Chinese Angelica (CA) was developed basing on the consistent chromatograms of 40 CA samples ( Angelica sinensis (Oliv.) Diels). The unique properties of this HPLC fingerprints were validated by analyzing 13 related herbs including 4 Japanese Angelicae Root samples (JA, A. acutiloba Kitagawa and A. acutiloba Kitagawa var. sugiyame Hikino), 6 Szechwan Lovage Rhizome samples (SL, Ligusticum chuanxiong Hort.) and 3 Cnidium Rhizome samples (CR, Cnidium officinale Makino). Both correlation coefficients of similarity in chromatograms and relative peak areas of characteristic compounds were calculated for quantitative expression of the HPLC fingerprints. The amount of senkyunolide A in CA was less than 30-fold of that in SL and CR samples, which was used as a chemical marker to distinguish them. JA was easily distinguished from CA, SL and CR based on either chromatographic patterns or the amount of coniferyl ferulate. No obvious difference between SL and CR chromatograms except the relative amount of some compounds, suggesting that SL and CR might have very close relationship in terms of chemotaxonomy. Ferulic acid and Z-ligustilide were unequivocally determined whilst senkyunolide I, senkyunolide H, coniferyl ferulate, senkyunolide A, butylphthalide, E-ligustilide, E-butylidenephthalide, Z-butylidenephthalide and levistolide A were tentatively identified in chromatograms based on their atmospheric pressure chemical ionization (APCI) MS data and the comparison of their UV spectra with those published in literatures.

Simultaneous analysis of seventeen chemical ingredients of Ligusticum chuanxiong by on-line high performance liquid chromatography-diode array detector-mass spectrometry.

An on-line high performance liquid chromatography (HPLC)-diode array detector (DAD)-mass spectrometry (MS) analytical method has been developed to simultaneously separate and identify seventeen main constituents of Chuanxiong ( Ligusticum chuanxiong Hort.), a traditional Chinese medicinal herb. In three Chuanxiong samples, nine compounds were unequivocally determined as vanillin (1), ferulic acid (2), senkyunolide I (4), senkyunolide H (5), senkyunolide A (6), coniferyl ferulate (7), Z-ligustilide (8), neocnidilide (9) and 3-butylidenephthalide (10) by comparing their t R, UV, and MS data with those obtained for the authentic compounds. Furthermore, additional eight compounds were tentatively identified as senkyunolide J (11), senkyunolide F (12), 3-butylphthalide (13), cnidilide (14), riligustilide (15) or Z,Z'-6,8',7,3'-diligustilide (16), tokinolide B (17), levistolide A (18) and senkyunolide P (19), based on their MS data and the comparison of their UV spectra with the published references. This is the first report to describe the development of an on-line HPLC-DAD-MS method to simultaneously analyse seventeen main constituents present in Chuanxiong and to construct the chemical profiles of various Chuanxiong samples.

Comparative study of roots ofAngelica sinensis and related umbelliferous drugs by thin layer chromatography, high-performance liquid chromatography, and liquid chromatography - mass spectrometry

Thin layer and high performance liquid chromatographic methods for a rapid and clear differentiation of morphologically similar umbelliferous drugs, namely Angelica sinensis (Oliv.) Diels, A. pubescens Maxim. f. biserrata Shan et Yuan, A. dahurica (Fisch. ex Hoffm.) Benth et Hook, Ligusticum porteri Coulter & Rose, L. chuanxiong Hort. and Levisticum officinale Koch have been developed. A. pubescens, characterized by osthol and various angelol type coumarins, and A. dahurica, containing mainly linear furanocoumarins, are very easy to distinguish from A. sinensis, which contains Z-ligustilide as a major compound. On the other hand, very similar phthalides and phthalide dimers, as well as falcarindiol and coniferyl ferulate have been found in A. sinensis, Ligusticum chuanxiong, L. porteri and Levisticum officinale, with mainly quantitative differences. A. sinensis and L. officinale differed only in the quantity of the polyacetylene falcarindiol, which was confirmed by liquid chromatography-mass spectrometry. Coniferyl ferulate is described for the first time as a constituent of A. sinensis, Ligusticum porteri and Levisticum officinale. Copyright © 1998 John Wiley & Sons, Ltd.

Comparative study of roots of Angelica sinensis and related umbelliferous drugs by thin layer chromatography, high‐performance liquid chromatography, and liquid chromatography – mass spectrometry

Thin layer and high performance liquid chromatographic methods for a rapid and clear differentiation of morphologically similar umbelliferous drugs, namely Angelica sinensis (Oliv.) Diels, A. pubescens Maxim. f. biserrata Shan et Yuan, A. dahurica (Fisch. ex Hoffm.) Benth et Hook, Ligusticum porteri Coulter & Rose, L. chuanxiong Hort. and Levisticum officinale Koch have been developed. A. pubescens, characterized by osthol and various angelol type coumarins, and A. dahurica, containing mainly linear furanocoumarins, are very easy to distinguish from A. sinensis, which contains Z-ligustilide as a major compound. On the other hand, very similar phthalides and phthalide dimers, as well as falcarindiol and coniferyl ferulate have been found in A. sinensis, Ligusticum chuanxiong, L. porteri and Levisticum officinale, with mainly quantitative differences. A. sinensis and L. officinale differed only in the quantity of the polyacetylene falcarindiol, which was confirmed by liquid chromatography-mass spectrometry. Coniferyl ferulate is described for the first time as a constituent of A. sinensis, Ligusticum porteri and Levisticum officinale. Copyright © 1998 John Wiley & Sons, Ltd.

Liquid chromatographic–electrospray mass spectrometric study of the phthalides of Angelica sinensis and chemical changes of Z-ligustilide

High-performance liquid chromatography–electrospray ionization–mass spectrometry has been applied to analyze the chemical constituents of Danggui (the rhizome of Angelica sinensis) and to study chemical changes of Z-ligustilide. Twelve phthalides were unambiguously identified as senkyunolide I ( 3), senkyunolide H ( 4), sedanenolide ( 8), butylphthalide ( 9), E-ligustilide ( 13), Z-ligustilide ( 14), Z-butylidenephthalide ( 15), Z, Z′-6.8′,7.3′-diligustilide ( 16), angelicide ( 17), levistolide A ( 18), Z-ligustilide dimer E-232 ( 19) and Z, Z′-3.3′,8.8′-diligustilide ( 20) in Danggui extract. The existence of 12 other phthalides ( 2, 5– 7, 11, 12, 22– 27), ferulic acid ( 1) and coniferyl ferulate ( 10) in Danggui extract has also been demonstrated. Phthalides 3, 4, 16– 18 and 20 were determined to be the products from chemical change of Z-ligustilide. This is the first report of the existence of 16 compounds ( 2– 8, 10– 12, 20, 22– 25 and 27) in Danggui extract.

An acetylenic epoxide and a ferulate from Coreopsis longula

The aerial parts of Coreopsis longula gave, in addition to known compounds, a new acetylenic epoxide, hepta-deca-1,9 E,15 E-trien-11,13-diyn-7,8-epoxide, while the roots afforded a new ferulate, coniferyl ferulate.

Components of Cnidium officinale Makino: occurrence of pregnenolone, coniferyl ferulate, and hydroxyphthalides.

The rhizome of Cnidium officinale Makino was found to contain pregnenolone (1) and coniferyl ferulate (2), and also nine hydroxyphthalide derivatives (4-12) which were optically inactive except 12. Most of them were supposed to be derived secondarily from the major volatile alkylphthalides.