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Ikhlas A. Khan - One of the best experts on this subject based on the ideXlab platform.
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Quantitative determination of triterpenoids and formononetin in rhizomes of black cohosh (Actaea racemosa) and dietary supplements by using UPLC-UV/ELS detection and identification by UPLC-MS.
Planta medica, 2008Co-Authors: Bharathi Avula, Yan-hong Wang, Troy J. Smillie, Ikhlas A. KhanAbstract:A UPLC-UV/ELSD method has been developed for analysis of major triterpenoids and formononetin in Actaea RACEMOSA L. (family Ranunculaceae) samples. The best results were obtained with an Acquity UPLC BEH C18 (100 mmx2.1 mm, i. d., 1 microm) column system using gradient elution with a mobile phase consisting of water and acetonitrile:methanol (7:3) at a constant flow rate of 0.3 mL/min. Owing to their low UV absorption, the triterpene saponins were detected by evaporative light scattering. Within 5.5 minutes, three main triterpenoid glycosides [cimiracemoside A, 23- EPI-26-deoxyactein, and actein] and an isoflavonoid, formononetin, could be separated, with detection limits of 5, 5, 10, and 0.01 microg/mL, respectively. The method was successfully used to analyze different Actaea racemosa market products as well as to distinguish between two other Actaea species. There was a significant variability in the amounts of the selected triterpene glycosides for the products containing black cohosh and rhizomes of black cohosh. The isoflavone formononetin was not detected in the samples analyzed. LC-MS coupled with the electrospray ionization (ESI) interface method is described for the identification of formononetin and triterpenoid glycosides in plant samples and dietary supplements that claim to contain black cohosh and different species of Actaea.
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Chemical Fingerprinting of Actaea racemosa (Black Cohosh) and Its Comparison Study with Closely Related Actaea Species (A. pachypoda, A. podocarpa, A. rubra) by HPLC
Chromatographia, 2007Co-Authors: Bharathi Avula, Zulfiqar Ali, Ikhlas A. KhanAbstract:Black cohosh ( Actaea recemosa ) is a popular botanical used for women’s health. The rhizomes/roots used in black cohosh products are often collected from the wild; a correct identification is therefore crucial. An HPLC-ELSD method has been developed for the analysis of terpenoids in different Actaea species samples. The best results were obtained with a Phenomenex Discovery column using gradient mobile phase of water (0.1% acetic acid), acetonitrile (0.1% acetic acid) and reagent alcohol. Owing to their low UV absorption, the triterpene saponins were detected by evaporative light scattering. Elution was run at a flow rate of 1.0 mL min^−1. This paper discusses the use of the chemical fingerprinting technique as a means of identifying A . recemosa from three closely related species, A . pachypoda , A . podocarpa and A . rubra , respectively. This method suggests that the analytical method could be a useful method for quality control and identifying species.
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New cycloartane-type triterpene arabinosides from the roots of Actaea podocarpa and their biological study.
Planta medica, 2007Co-Authors: Zulfiqar Ali, Shabana I. Khan, Ikhlas A. KhanAbstract:Three new cycloartane-type triterpene arabinosides, podocarpasides H - J (1 - 3) were isolated from the roots of Actaea podocarpa (Ranunculaceae). Their structures were determined by spectroscopic and chemical methods. The isolates were tested for cytotoxic, estrogenic, antioxidant, and anticomplement activities. They were found inactive in the tested assays, except for podocarpaside I (2), which showed moderate anticomplement activity with an IC(50) value of 250 microM.
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9 10 seco 9 19 cyclolanostane arabinosides from the roots of Actaea podocarpa
Phytochemistry, 2007Co-Authors: Zulfiqar Ali, Shabana I. Khan, Frank R Fronczek, Ikhlas A. KhanAbstract:Abstract Seven 9,10-seco-9,19-cyclolanostane arabinosides, named podocarpasides A–G (1–7), were isolated from the roots of Actaea podocarpa DC., a species closely related to black cohosh (a well known dietary supplement). Their structures were determined with the help of spectroscopic data including extensive 2D NMR spectroscopy. The isolates were found inactive, when tested for cytotoxic, estrogenic, and antioxidant activities in cell based assays. They were also tested for anticomplement activity against the classical pathway of complement system and only podocarpaside C (3) inhibited modest complement activity with an IC50 value of 200 μM.
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9 19 cyclolanostane derivatives from the roots of Actaea pachypoda
Journal of Natural Products, 2007Co-Authors: Zulfiqar Ali, Shabana I. Khan, Daneel Ferreira, Rahul S Pawar, Ikhlas A. KhanAbstract:Phytochemical investigation of the chemical constituents of the roots of Actaea pachypoda afforded 12 9,19-cyclolanostane type triterpenoids, including the new 7,8-dihydroActaeaepoxide 3-O-beta-d-xylopyranoside (1), 12-deacetoxyActaeaepoxide 3-O-beta-d-xylopyranoside (2), and 12beta-acetoxycimigenol (3). Their structures were determined by spectroscopic and chemical methods.
Edward J Kennelly - One of the best experts on this subject based on the ideXlab platform.
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new monoterpene lactones from Actaea cimicifuga
Planta Medica, 2013Co-Authors: Yuehu Wang, Edward J Kennelly, Guihua Tang, Yeling Wang, Keyvan Dastmalchi, Chunlin LongAbstract:Three new monoterpene lactones, cimicifugolides A-C (1-3), along with a known one (4), were identified from the dried rhizome of Actaea cimicifuga L. that was used as traditional Chinese medicine for thousands of years with the Chinese common name of shengma. The structures of the new isolates were established using spectroscopic methods, including NMR, mass, UV, and IR spectra. The inhibition activity of compounds 1, 2, and 4 against pancreatic lipase was evaluated.
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phytochemical fingerprinting to thwart black cohosh adulteration a 15 Actaea species analysis
Phytochemical Analysis, 2011Co-Authors: Bei Jiang, Fredi Kronenberg, Timothy J Motley, Edward J KennellyAbstract:Introduction – The popular use of black cohosh products (Actaea racemosa L., syn. Cimicifuga racemosa L.) is growing as the demand for alternatives to estrogen therapy has increased. Critical to safe use is the assurance of unadulterated, high-quality products. Questions have been raised about the safety of black cohosh due to cases of liver toxicity in patients who reported taking it; subsequent evaluation found some products to be adulterated with other related herbal species. Correct plant species identification is a key first step for good manufacturing practices of safe black cohosh products. Objectives – To develop analytical methods which distinguish black cohosh from other species (American and Asian) of Actaea increasingly found as adulterants in commercially available black cohosh products. Material and methods – Fifteen species of Actaea were collected from North America and Asia, and the phytochemical fingerprints of these samples were established using HPLC-PDA and LC-MS techniques. Results – The HPLC and LC-MS fingerprints for polyphenols and triterpene glycosides revealed distinct patterns that make black cohosh clearly distinguishable from most other species of Actaea. Two marker compounds, cimifugin and cimiracemoside F, were found to be important to distinguish black cohosh from most Asian species of Actaea. Formononetin was not found from either Asian or American species of Actaea. Conclusions – Phytochemical fingerprinting is a practical, reliable method for authenticating black cohosh and distinguishing it from other species of Actaea increasingly found as adulterants in commercially available black cohosh products. This should facilitate the continued development of high-quality, unadulterated black cohosh products. Copyright © 2011 John Wiley & Sons, Ltd.
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Metabolic profiling of Actaea species extracts using high performance liquid chromatography coupled with electrospray ionization time-of-flight mass spectrometry
Journal of chromatography. A, 2011Co-Authors: Adam R. Kavalier, Bei Jiang, Edward J KennellyAbstract:Abstract Despite persistent questions about the safety of black cohosh ( Actaea racemosa L., syn. Cimicifuga racemosa L.), its products continue to be one of the most popular botanical supplements in the United States market. Black cohosh products have been associated with cases of liver toxicity, but subsequent evaluation found some products to be adulterated with other related plants from the same genus. US FDA regulations require that black cohosh products be unadulterated, and correct identification of different species of Actaea is a key first step for their good manufacturing practice. We have developed a phytochemical method to distinguish four different groups of Actaea , including: species other than A. racemosa , Asian species, A. racemosa , and North American species other than A. racemosa . Using HPLC–TOF-ESI-MS technique and principal component analysis, we identified 15 chemical markers (1–3, 5–6, 8–10, 12, 16–21). Three marker compounds were unambiguously identified using authentic standards, and 12 marker compounds were tentatively identified by comparison of fragmentation patterns with previously reported data. The presence of these marker compounds is critical for discrimination among the four groups of closely related plants. The use of metabolic profiling to distinguish black cohosh from related species of Actaea has broader implications in the identification of markers to help authenticate other important medicinal plants.
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Analysis of polyphenolic compounds and radical scavenging activity of four American Actaea species
Phytochemical analysis : PCA, 2007Co-Authors: Paiboon Nuntanakorn, Bei Jiang, Hui Yang, Fredi Kronenberg, Miguel Cervantes-cervantes, Edward J KennellyAbstract:A reversed-phase high-performance liquid chromatography (RP-HPLC) method with diode array detection has been developed for analysis of the major polyphenols in the roots and rhizomes of black cohosh (Actaea racemosa), an important botanical dietary supplement for women's health, and three closely related American Actaea species, A. rubra, A. pachypoda and A. podocarpa. The method was validated with respect to sensitivity, linearity, precision, accuracy and recovery. The total content of eight major polyphenols in the dried root and rhizome of the four species was determined to be from 0.36 to 2.92% (w/w). The antioxidant activities of Actaea extracts and polyphenolic compounds isolated from A. racemosa were evaluated on 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radicals scavenging assay. The radical scavenging activity of the Actaea extracts correlates to their polyphenolic composition. This validated HPLC method can be used to distinguish A. racemosa from the other major American Actaea species based on this study. Copyright © 2007 John Wiley & Sons, Ltd.
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evaluation of the botanical authenticity and phytochemical profile of black cohosh products by high performance liquid chromatography with selected ion monitoring liquid chromatography mass spectrometry
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Bei Jiang, Paiboon Nuntanakorn, Fredi Kronenberg, Minghua Qiu, Edward J KennellyAbstract:Black cohosh (Actaea racemosa L., syn. Cimicifuga racemosa L.) has become increasingly popular as a dietary supplement in the United States for the treatment of symptoms related to menopause, but the botanical authenticity of most products containing black cohosh has not been evaluated, nor is manufacturing highly regulated in the United States. In this study, 11 black cohosh products were analyzed for triterpene glycosides, phenolic constituents, and formononetin by high-performance liquid chromatography-photodiode array detection and a new selected ion monitoring liquid chromatography-mass spectrometry method. Three of the 11 products were found to contain the marker compound cimifugin and not cimiracemoside C, thereby indicating that these plants contain Asian Actaea instead of black cohosh. One product contained both black cohosh and an Asian Actaea species. For the products containing only black cohosh, there was significant product-to-product variability in the amounts of the selected triterpene glycosides and phenolic constituents, and as expected, no formononetin was detected.
Zulfiqar Ali - One of the best experts on this subject based on the ideXlab platform.
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Chemical Fingerprinting of Actaea racemosa (Black Cohosh) and Its Comparison Study with Closely Related Actaea Species (A. pachypoda, A. podocarpa, A. rubra) by HPLC
Chromatographia, 2007Co-Authors: Bharathi Avula, Zulfiqar Ali, Ikhlas A. KhanAbstract:Black cohosh ( Actaea recemosa ) is a popular botanical used for women’s health. The rhizomes/roots used in black cohosh products are often collected from the wild; a correct identification is therefore crucial. An HPLC-ELSD method has been developed for the analysis of terpenoids in different Actaea species samples. The best results were obtained with a Phenomenex Discovery column using gradient mobile phase of water (0.1% acetic acid), acetonitrile (0.1% acetic acid) and reagent alcohol. Owing to their low UV absorption, the triterpene saponins were detected by evaporative light scattering. Elution was run at a flow rate of 1.0 mL min^−1. This paper discusses the use of the chemical fingerprinting technique as a means of identifying A . recemosa from three closely related species, A . pachypoda , A . podocarpa and A . rubra , respectively. This method suggests that the analytical method could be a useful method for quality control and identifying species.
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New cycloartane-type triterpene arabinosides from the roots of Actaea podocarpa and their biological study.
Planta medica, 2007Co-Authors: Zulfiqar Ali, Shabana I. Khan, Ikhlas A. KhanAbstract:Three new cycloartane-type triterpene arabinosides, podocarpasides H - J (1 - 3) were isolated from the roots of Actaea podocarpa (Ranunculaceae). Their structures were determined by spectroscopic and chemical methods. The isolates were tested for cytotoxic, estrogenic, antioxidant, and anticomplement activities. They were found inactive in the tested assays, except for podocarpaside I (2), which showed moderate anticomplement activity with an IC(50) value of 250 microM.
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9 10 seco 9 19 cyclolanostane arabinosides from the roots of Actaea podocarpa
Phytochemistry, 2007Co-Authors: Zulfiqar Ali, Shabana I. Khan, Frank R Fronczek, Ikhlas A. KhanAbstract:Abstract Seven 9,10-seco-9,19-cyclolanostane arabinosides, named podocarpasides A–G (1–7), were isolated from the roots of Actaea podocarpa DC., a species closely related to black cohosh (a well known dietary supplement). Their structures were determined with the help of spectroscopic data including extensive 2D NMR spectroscopy. The isolates were found inactive, when tested for cytotoxic, estrogenic, and antioxidant activities in cell based assays. They were also tested for anticomplement activity against the classical pathway of complement system and only podocarpaside C (3) inhibited modest complement activity with an IC50 value of 200 μM.
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9 19 cyclolanostane derivatives from the roots of Actaea pachypoda
Journal of Natural Products, 2007Co-Authors: Zulfiqar Ali, Shabana I. Khan, Daneel Ferreira, Rahul S Pawar, Ikhlas A. KhanAbstract:Phytochemical investigation of the chemical constituents of the roots of Actaea pachypoda afforded 12 9,19-cyclolanostane type triterpenoids, including the new 7,8-dihydroActaeaepoxide 3-O-beta-d-xylopyranoside (1), 12-deacetoxyActaeaepoxide 3-O-beta-d-xylopyranoside (2), and 12beta-acetoxycimigenol (3). Their structures were determined by spectroscopic and chemical methods.
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podocarpaside a triterpenoid possessing a new backbone from Actaea podocarpa
Organic Letters, 2006Co-Authors: Zulfiqar Ali, Shabana I. Khan, Daneel Ferreira, Ikhlas A. KhanAbstract:Podocarpaside (1), a novel arabinoside possessing a unique triterpene skeleton was isolated from Actaea podocarpa, a closely related species to black cohosh (dietary supplement used for menopausal disorders). Podocarpaside belongs to a new class of triterpenoids, for which the name “ranunculane” is proposed. Compound 1 possesses anticomplement activity.
Bei Jiang - One of the best experts on this subject based on the ideXlab platform.
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phytochemical fingerprinting to thwart black cohosh adulteration a 15 Actaea species analysis
Phytochemical Analysis, 2011Co-Authors: Bei Jiang, Fredi Kronenberg, Timothy J Motley, Edward J KennellyAbstract:Introduction – The popular use of black cohosh products (Actaea racemosa L., syn. Cimicifuga racemosa L.) is growing as the demand for alternatives to estrogen therapy has increased. Critical to safe use is the assurance of unadulterated, high-quality products. Questions have been raised about the safety of black cohosh due to cases of liver toxicity in patients who reported taking it; subsequent evaluation found some products to be adulterated with other related herbal species. Correct plant species identification is a key first step for good manufacturing practices of safe black cohosh products. Objectives – To develop analytical methods which distinguish black cohosh from other species (American and Asian) of Actaea increasingly found as adulterants in commercially available black cohosh products. Material and methods – Fifteen species of Actaea were collected from North America and Asia, and the phytochemical fingerprints of these samples were established using HPLC-PDA and LC-MS techniques. Results – The HPLC and LC-MS fingerprints for polyphenols and triterpene glycosides revealed distinct patterns that make black cohosh clearly distinguishable from most other species of Actaea. Two marker compounds, cimifugin and cimiracemoside F, were found to be important to distinguish black cohosh from most Asian species of Actaea. Formononetin was not found from either Asian or American species of Actaea. Conclusions – Phytochemical fingerprinting is a practical, reliable method for authenticating black cohosh and distinguishing it from other species of Actaea increasingly found as adulterants in commercially available black cohosh products. This should facilitate the continued development of high-quality, unadulterated black cohosh products. Copyright © 2011 John Wiley & Sons, Ltd.
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Metabolic profiling of Actaea species extracts using high performance liquid chromatography coupled with electrospray ionization time-of-flight mass spectrometry
Journal of chromatography. A, 2011Co-Authors: Adam R. Kavalier, Bei Jiang, Edward J KennellyAbstract:Abstract Despite persistent questions about the safety of black cohosh ( Actaea racemosa L., syn. Cimicifuga racemosa L.), its products continue to be one of the most popular botanical supplements in the United States market. Black cohosh products have been associated with cases of liver toxicity, but subsequent evaluation found some products to be adulterated with other related plants from the same genus. US FDA regulations require that black cohosh products be unadulterated, and correct identification of different species of Actaea is a key first step for their good manufacturing practice. We have developed a phytochemical method to distinguish four different groups of Actaea , including: species other than A. racemosa , Asian species, A. racemosa , and North American species other than A. racemosa . Using HPLC–TOF-ESI-MS technique and principal component analysis, we identified 15 chemical markers (1–3, 5–6, 8–10, 12, 16–21). Three marker compounds were unambiguously identified using authentic standards, and 12 marker compounds were tentatively identified by comparison of fragmentation patterns with previously reported data. The presence of these marker compounds is critical for discrimination among the four groups of closely related plants. The use of metabolic profiling to distinguish black cohosh from related species of Actaea has broader implications in the identification of markers to help authenticate other important medicinal plants.
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Analysis of polyphenolic compounds and radical scavenging activity of four American Actaea species
Phytochemical analysis : PCA, 2007Co-Authors: Paiboon Nuntanakorn, Bei Jiang, Hui Yang, Fredi Kronenberg, Miguel Cervantes-cervantes, Edward J KennellyAbstract:A reversed-phase high-performance liquid chromatography (RP-HPLC) method with diode array detection has been developed for analysis of the major polyphenols in the roots and rhizomes of black cohosh (Actaea racemosa), an important botanical dietary supplement for women's health, and three closely related American Actaea species, A. rubra, A. pachypoda and A. podocarpa. The method was validated with respect to sensitivity, linearity, precision, accuracy and recovery. The total content of eight major polyphenols in the dried root and rhizome of the four species was determined to be from 0.36 to 2.92% (w/w). The antioxidant activities of Actaea extracts and polyphenolic compounds isolated from A. racemosa were evaluated on 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radicals scavenging assay. The radical scavenging activity of the Actaea extracts correlates to their polyphenolic composition. This validated HPLC method can be used to distinguish A. racemosa from the other major American Actaea species based on this study. Copyright © 2007 John Wiley & Sons, Ltd.
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evaluation of the botanical authenticity and phytochemical profile of black cohosh products by high performance liquid chromatography with selected ion monitoring liquid chromatography mass spectrometry
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Bei Jiang, Paiboon Nuntanakorn, Fredi Kronenberg, Minghua Qiu, Edward J KennellyAbstract:Black cohosh (Actaea racemosa L., syn. Cimicifuga racemosa L.) has become increasingly popular as a dietary supplement in the United States for the treatment of symptoms related to menopause, but the botanical authenticity of most products containing black cohosh has not been evaluated, nor is manufacturing highly regulated in the United States. In this study, 11 black cohosh products were analyzed for triterpene glycosides, phenolic constituents, and formononetin by high-performance liquid chromatography-photodiode array detection and a new selected ion monitoring liquid chromatography-mass spectrometry method. Three of the 11 products were found to contain the marker compound cimifugin and not cimiracemoside C, thereby indicating that these plants contain Asian Actaea instead of black cohosh. One product contained both black cohosh and an Asian Actaea species. For the products containing only black cohosh, there was significant product-to-product variability in the amounts of the selected triterpene glycosides and phenolic constituents, and as expected, no formononetin was detected.
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polyphenolic constituents of Actaea racemosa
Journal of Natural Products, 2006Co-Authors: Paiboon Nuntanakorn, Bei Jiang, Hui Yang, Fredi Kronenberg, Linda Saxe Einbond, I B Weinstein, Edward J KennellyAbstract:A new lignan, Actaealactone (1), and a new phenylpropanoid ester derivative, cimicifugic acid G (2), together with 15 known polyphenols, protocatechuic acid, protocatechualdehyde, p-coumaric acid, ...
Dongming Zhang - One of the best experts on this subject based on the ideXlab platform.
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cytotoxic 9 19 cycloartane triterpenoids from the roots of Actaea dahurica
Fitoterapia, 2019Co-Authors: Xuyan Wang, Jiwu Huang, Nan Wang, Cangjie Shen, Dongming ZhangAbstract:Abstract Eight undescribed 9,19-cycloartane type triterpenoid glycosides (cimdalglnoside A-H) and ten known analogues were obtained from the phytochemical research on the roots of Actaea dahurica (syn. Cimicifuga dahurica ). All compounds were characterised by spectroscopic experiments, and chemical method. All the compounds isolated were assayed for cytotoxicity to five human cancer cell lines. Cimdalglnoside G showed promising cytotoxicities against Hela, and MCF-7 cell lines with IC 50 values at 7.7 and 12.2 μM.
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cytotoxic 9 19 cycloartane type triterpenoid glycosides from the roots of Actaea dahurica
Phytochemistry, 2019Co-Authors: Xuyan Wang, Nan Wang, Cangjie Shen, Fangyou Chen, Dongming ZhangAbstract:Abstract Ten undescribed 9,19-cycloartane type triterpenoid glycosides (cimdahxynoside A-J) and five known analogues were obtained from the phytochemical research on the roots of Actaea dahurica (syn. Cimicifuga dahurica). All compounds were characterised by spectroscopic experiments, chemical method and X-ray Single-crystal diffraction analysis. Cimdahxynoside A represented the first X-ray crystallography of 9,19-cycloartane type triterpenoid diglycoside. The cytotoxicity of all compounds were tested against five human cancer cell lines. Cimdahxynoside F showed significant cytotoxicity, with IC50 values between 6.6 and 9.9 μM.
