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Nwe Haymar Lynn, Thein Zaw Linn, Cui Yanmei, Yuuki Shimozu, Shoko Taniguchi, Tsutomu Hatano
We used quantitative nuclear magnetic resonance analyses to measure the contents of major constituents of Acorus rhizome materials used as herbal drugs. The inhibitory effects of crude n-hexane extracts and their individual constituents on in vitro acetylcholine esterase activity were evaluated. The crude extracts had unexpectedly weak inhibitory effects (46-64% inhibition at 1.0 mg/mL), despite the high content (46-64%) of β-asarone, which independently had a potent effect (IC50 2.9 µM [0.61 µg/mL]). Further investigation revealed participation of eudesmin A, a lignan constituent, in the suppression of the inhibitory effect of β-asarone...
January 29, 2019: Bioscience, Biotechnology, and Biochemistry
Ki Hong Nam, Sang Ah Yi, Jaecheol Lee, Min Gyu Lee, Jee Hun Park, Hwamok Oh, Jieun Lee, Jong Woo Park, Jeung-Whan Han
Eudesmin has been reported to possess diverse therapeutic effects, including anti-tumor, anti-inflammatory, and anti-bacterial activities. However, its molecular action has not been implicated in metabolic disease. In this study, we show that treatment of mesenchymal stem cells (MSCs) with eudesmin disturbs adipogenesis via suppression of S6K1 signaling pathway. Eudesmin treatment inhibited activation and nuclear translocation of S6K1. Consequently, S6K1-mediated phosphorylation of H2B at serine 36 (H2BS36p) was reduced upon eudesmin treatment, further inducing the expression of Wnt6, Wnt10a, and Wnt10b, which disturbed adipogenic differentiation...
November 10, 2018: Biochemical and Biophysical Research Communications
Hyun Jong Kim, Yu Ran Nam, Joo Hyun Nam
Flos Magnoliae (FM, Chinese name: Xin-yi) is an oriental medicinal herb commonly used for symptomatic relief from allergic rhinitis, sinusitis, and headache, including in traditional Chinese and Korean medicine formulations. FM inhibits histamine release from mast cells and cytokine secretion from T cells. However, the mechanism of action of FM on the anoctamin-1 (ANO1) ion channel, which is responsible for nasal hypersecretion in allergic rhinitis, has not been elucidated. Therefore, in this study, we investigated the effect of a 30% ethanolic extract of FM (FMEtOH ) and its chemical constituents on ANO1 activity...
2018: American Journal of Chinese Medicine
Yi-Ran Wang, Yong-Hui Li, Tao Guo, Hai-Long Li, Yin-Feng Tan, Zhong Zhang, Xu-Guang Zhang, Shi-Ying Mai, Jun-Qing Zhang
The compounds of N-Methylanhydrotetrahydroberberrubine A, dictamnine and eudesmin were the primary bioactive components in the roots of Zanthoxylum armatum DC (Z. armatum). To clarify the pharmacokinetics and distribution of these three compounds, an ultra-fast liquid chromatography-tandem mass spectrometry (UFLC-MS/MS) was employed to determine the contents of these three compounds in rat plasma and seven tissues. The separation was achieved on a Kinetex XB-C18 100A column (2.1 × 50 mm, 2.6 μm, Phenomenex)...
June 15, 2018: Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences
Wei-Sheng Feng, Yu-Huan He, Xiao-Ke Zheng, Bei-Bei Dong, Yan-Li Zhang, Yan-Gang Cao, Yan-Yun Yang, Jing-Ke Zhang
The present study aims to investigate the lignans from the flower buds of Magnolia biondii. The isolation and purification of the compounds were performed by column chromatographies on Diaion HP-20, silica gel, and Sephadex LH-20, combined with semi-preparative HPLC. Their structures were elucidated on the basis of spectral data and physiochemical properties. Eighteen compounds were isolated and identified as magnolin (1), epimagnolin (2), eudesmin (3), kobusin (4), aschantin (5), lirioresinol B dimethyl ether (6), pinoresinol monomethy ether (7), (+)-de-O-methylmagnolin (8), isoeucommin A (9), syringaresinol 4-O-β-D-glucopyranoside (10), phillygenin (11), lariciresinol-4'-O-β-1-D-glucoside (12), conicaoside (13), (7'S, 8'R)-dihydrodehydrodiconiferylalcohol (14), 7R*, 8S*-dihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside (15), 7S, 8R-erythro-7, 9, 9'-trihydroxy-3, 3'-dimethoxy-8-O-4'-neolignan 4-O-β-D-glucopyranoside (16), 7S, 8R-erythro-4, 9, 9'-trihydroxy-3, 3'-dimethoxy-8-O-4'-neolignan-7-O-β-D-glucopyranoside (17), and (+)-isolariciresinol (18)...
March 2018: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
Jai-Sing Yang, Chao-Min Wang, Chiu-Hsian Su, Han-Chen Ho, Chiung-Hung Chang, Chang-Hung Chou, Yuan-Man Hsu
Eudesmin has been proven to possess anti-inflammatory effects. In the present study, the effects of eudesmin on Helicobacter pylori (H. pylori) -mediated autophagy, apoptosis, immune response and inflammation were determined in human gastric adenocarcinoma (AGS) cells in vitro and in C57BL/6 mice in vivo . Detection of the production of interleukin (IL)-8, IL-1β and immunoglobulin M (IgM) was performed using ELISA. Identification of the activation of apoptosis-associated caspase-3, -8 and -9 proteins, Bcl-2-associated X protein (Bax) and BH3 interacting domain death agonist (Bid) protein, was determined through western blot analysis...
March 2018: Experimental and Therapeutic Medicine
Naoki Mori
Lignans are a large class of naturally occurring secondary metabolites which are widely spread within the plant kingdom. Their diverse structures and variety of biological activities have fascinated organic chemists. For synthesizing optically active lignans, we have developed the novel asymmetric dimerization of cinnamic acid derivatives, and applied it to the enantioselective syntheses of furofuran lignans (yangambin, sesamin, eudesmin, caruilignan A) and diarylbutane lignans (sauriols A and B). This review summarizes the methodology of our asymmetric dimerization of cinnamic acid derivatives, and efficient total syntheses of furofuran and diarylbutane lignans reported by our and other groups...
January 2018: Bioscience, Biotechnology, and Biochemistry
Li-Li Jiang, Bai-Rong Sun, Chao Zheng, Gui-Lun Yang
CONTEXT: Limonoids possess broad range of biological activities, including antitumour, antimicrobial and antioxidant activities, etc. Eudesmin (EDN) is a type of limonoid which also possesses various activities. However, there is no report on the antitumour lung cancer (LC) activities of this compound. OBJECTIVE: The present study investigates the antitumour effects of EDN and its potential molecular mechanisms. MATERIALS AND METHODS: The in vitro antitumour effects of EDN on LC A549 cells were evaluated by using MTT assay...
December 2017: Pharmaceutical Biology
Ju-Hyun Kim, Soon-Sang Kwon, Hyeon-Uk Jeong, Hye Suk Lee
Magnolin, epimagnolin A, dimethyllirioresinol, eudesmin, and fargesin are pharmacologically active tetrahydrofurofuranoid lignans found in Flos Magnoliae. The inhibitory potentials of dimethyllirioresinol, epimagnolin A, eudesmin, fargesin, and magnolin on eight major human cytochrome P450 (CYP) enzyme activities in human liver microsomes were evaluated using liquid chromatography-tandem mass spectrometry to determine the inhibition mechanisms and inhibition potency. Fargesin inhibited CYP2C9-catalyzed diclofenac 4'-hydroxylation with a Ki value of 16...
May 1, 2017: International Journal of Molecular Sciences
Vinod Bhatt, Sushila Sharma, Neeraj Kumar, Upendra Sharma, Bikram Singh
The current study presents isolation and characterization of twelve compounds including catechin (1), isovitexin (2), hesperidin (3), psoralin (4), eudesmin (5), kobusin (6), fargesin (7), sesamin (8), asarinin (9), planispine-A (10), α-sanshool (11) and vitexin (12), from the leaves of Zanthoxylum armatum. Further, two rapid and simple ultra performance liquid chromatography-diode array detection (UPLC-DAD) methods were developed for the simultaneous quantitative determination of isolated compounds from Z...
January 5, 2017: Journal of Pharmaceutical and Biomedical Analysis
Kanok-On Rayanil, Wirunya Sutassanawichanna, Oranart Suntornwat, Pittaya Tuntiwachwuttikul
A new dihydrobenzofuran lignan, (2R,3S)-2-(3',4'-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydrobenzofuran-3-methyl acetate, named as mitredrusin (1), was isolated from the leaves of Mitrephora teysmannii (Annonaceae) together with 12 known compounds including a related dihydrobenzofuran lignan: (-)-3',4-di-O-methylcedrusin (2), four polyacetylenic acids: 13(E)-octadecene-9,11-diynoic acid (3), 13(E),17-octadecadiene-9,11-diynoic acid (4), octadeca-9,11,13-triynoic acid (5) and octadeca-17-en-9,11,13-triynoic acid (6), five lignans: (-)-eudesmin (7), (-)-epieudesmin (8), (-)-phillygenin (9), magnone A (10) and forsythialan B (11) and two megastigmans: (3S,5R,6S,7E,9R)-7-megastigmene-3,6,9-triol (12) and annoionol A (13)...
February 9, 2016: Natural Product Research
Yu Jiang, Bo Yu, Fang Fang, Huanhuan Cao, Tonghui Ma, Hong Yang
Plant lignans are diphenolic compounds widely present in vegetables, fruits, and grains. These compounds have been demonstrated to have protective effect against cancer, hypertension and diabetes. In the present study, we showed that two lignan compounds, kobusin and eudesmin, isolated from Magnoliae Flos, could modulate intestinal chloride transport mediated by cystic fibrosis transmembrane conductance regulator (CFTR) and calcium-activated chloride channels (CaCCs). The compounds activated CFTR channel function in both FRT cells and in HT-29 cells...
2015: Frontiers in Plant Science
Hao Liu, Zhi Song, Da-Guang Liao, Tian-Yi Zhang, Feng Liu, Kai Zhuang, Kui Luo, Liang Yang, Jing He, Jian-Ping Lei
This paper was designed to investigate anticonvulsant and sedative effects of eudesmin isolated from Acorus tatarinowii. The eudesmin (5, 10, and 20 mg/kg) was administered intraperitoneally (i.p.). The maximal electroshock test (MES) and pentylenetertrazole (PTZ)-induced seizures in male mice were used to evaluate anticonvulsant activities of eudesmin, and sedative effects of eudesmin were evaluated by pentobarbital sodium-induced sleeping time (PST) and locomotor activity in mice. Finally, the mechanisms of eudesmin were investigated by determining contents of glutamic acid (Glu) and gamma-aminobutyric acid (GABA) in epileptic mice, and expressions of glutamate decarboxylase 65 (GAD65), GABAA , Bcl-2, and caspase-3 in the brain of chronic epileptic rats...
July 2015: Phytotherapy Research: PTR
Yan-qun Liu, Sheng-hui Yang, Qiang Liu, Gang Pei, Wei-wei Pan, Min Liu, Cai-yun Peng
OBJECTIVE: To study the chemical constituents of Zanthoxyli Cortex. METHODS: The chemical constituents were isolated and purified by silica gel and HP-20, MCI gel, Sephadex LH -20 column chromatography, RP-18 and PTLC. Their structures were elucidated by the analysis of spectral data and chemical properties. RESULTS: Ten compounds were isolated from EtOAc extract and their structures were identified as: asarinin (I), fargesin (II), eudesmin (III), (1R, 2R, 5R, 6S)-2-(3,4-dimethoxyphenyl)-6-(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3...
November 2013: Zhong Yao Cai, Zhongyaocai, Journal of Chinese Medicinal Materials
Gang Ni, De-Quan Yu
Fifteen compounds were isolated from the rhizomes of Acorus tatarinowii by means of various chromatographic techniques such as silica gel, ODS, Sephadex LH-20 and preparative HPLC, and their structures were elucidated as tatanone A (1), calamusenone (2), acoronene (3), 2-acetyloxyacoronene (4), acorenone (5), alpha-asarone (6), beta-asarone (7), 1,2-dimethoxy-4-(1'Z-propenyl) benzene (8), methyleugenol (9), asarylaldehyde (10), acoramone (11), gamma-asarone (12), 5-hydroxymethyl-2-furaldehyde (13), galgravin (14) and eudesmin (15) on the basis of spectroscopic data analysis...
February 2013: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
Di Qiao, Li-She Gan, Jian-Xia Mo, Chang-Xin Zhou
OBJECTIVE: To study the chemical constituents contained in Acorus calamus. METHOD: The chemical constituents were separated and purified by various chromatographic methods including silica gel, ODS, HPLC and Sephadex LH-20, and their structures were identified on the basis of analysis on spectroscopic data. RESULT: Ten compounds were separated from A. calamus and identified as 1beta, 4beta, 7alpha-trihydroxyeudesmane (1), bullatantriol (2), teuclatriol (3), threo-1', 2'-dihydroxyasarone (4), erythro-1', 2'-dihydroxyasarone (5), (+)-de-4'-O-methyleudesmin (6), (+)-de-4'-0-methylmagnolin (7), (+)-eudesmin (8), (+)-magnolin (9) and beta-sitosterol (10), respectively...
November 2012: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
Feng Zhao, Sujuan Wang, Xiuli Wu, Yang Yu, Zhenggang Yue, Bo Liu, Sheng Lin, Chenggen Zhu, Yongchun Yang, Jiangong Shi
Twenty-one non-anthraquinones constituents were isolated for the first time from an ethanol extract of the roots of Knoxia valerianoides by using a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and reversed-phase HPLC. Their structures were identified by their physical-chemical properties and spectroscopic analysis including NMR and MS. The compounds include ten triterpenoids: ursolic acid (1), oleanolic acid (2), 2-oxo pomolic acid (3), pomolic acid (4), maslinic acid (5), rotungenic acid (6), tormentic accid (7), rotundic acid 3,23-acetonide (8), arjungenin (9), and 2alpha, 3beta, 19alpha, 23-tetrahydroxy-urs-12-en-28-oic acid (10), four sitosterones: (24R)-24-ethylcholesta-4,22-dien-3-one (11), 3-oxo-4-en-sitosterone (12), 7-oxostigmasterol (13), and 7-oxo-beta-sitosterol (14), two lignans: eudesmin (15) and ciwujiatone (16), one coumarin: cnidilin (17), and four simple aromatic analogues: 5-hydroxymethylenefural (18), 3-hydroxy-4-methoxybenzoic acid (19), benzoic acid (20), and 2-hydroxy-5-methxoycinnamaldehydes (21)...
July 2012: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
Thi Nga Vo, Phi Linh Nguyen, Lam Truong Tuong, Lawrence Michael Pratt, Phung Nguyen Vo, Kim Phi Phung Nguyen, Ngoc Suong Nguyen
Two new lignans, pseuderesinol (1), pseuderanoside (2) and a new triterpene, pseuderanic acid (3) were isolated from the dried root of Pseuderanthemum carruthersii (SEEM.) GUILL. var. atropurpureum (BULL.) FOSB. (Acanthaceae), together with ten known compounds, including five lignans, (+)-eudesmin (4), (+)-magnolin (5), (+)-syringaresinol (6), (+)-episyringaresinol (7), (+)-1-hydroxysyringaresinol (8) and five triterpenes, squalene (9), oleanolic acid (10), lupeol (11), betulin (12), betulinic acid (13). Their chemical structures were elucidated by 1D- and 2D-NMR, computational quantum chemistry, as well as high resolution-electrospray ionization (HR-ESI)-MS spectroscopic analysis...
2012: Chemical & Pharmaceutical Bulletin
Niko S Radulović, Marko Z Mladenović, Nevenka D Ethorđević
The fruit essential oils of two populations of Astrantia major L. (Apiaceae, subfamily Saniculoideae) were analyzed in detail by GC and GC/MS analyses. Seventy-six constituents identified accounted for 92.7-94.0% of the oils. The two oils differed significantly: the wild-growing population from Serbia contained zingiberene (47.9%), β-bisabolene (9.7%), and β-sesquiphellandrene (7.9%), while the one from Poland (botanical gardens) was sesquiterpene-poor with the major contributors oleic acid (38.6%), nonacosane (15...
July 2012: Chemistry & Biodiversity
Risoleta Ortet, Soizic Prado, Erik L Regalado, Frederick A Valeriote, Joseph Media, Judith Mendiola, Olivier P Thomas
The chemical composition of the aerial parts of the Cape Verdean endemic shrub Artemisia gorgonum Webb (Asteraceae) was careful investigated, which led to the isolation and identification of six known furfuran lignans: eudesmin (1), magnolin (2), epimagnolin A (3), aschantin (4), kobusin (5), sesamin (6) and a flavone: artemetin (7). Compounds 1-7 were evaluated in vitro for their cytotoxicity in a screening panel consisting of various mammalian tumor cell lines, for their antimalarial activity against chloroquine-resistant Plasmodium falciparum (FcB1 strain) and for their cytotoxicity against murine normal cells (CFU-GM)...
November 18, 2011: Journal of Ethnopharmacology
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