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Pterocarpans AND beta cells

Milou G M van de Schans, Jean-Paul Vincken, Pieter de Waard, Astrid R M Hamers, Toine F H Bovee, Harry Gruppen
Seven prenylated 6a-hydroxy-pterocapans and five prenylated 6a,11a-pterocarpenes with different kinds of prenylation were purified from an ethanolic extract of fungus-treated soybean sprouts. The activity of these compounds toward both human estrogen receptors (hERα and hERβ) was determined in a yeast bioassay and the activity toward hERα was additionally tested in an U2-OS based hERα CALUX bioassay. In the yeast bioassay, compounds with chain prenylation showed in general an agonistic mode of action toward hERα, whereas furan and pyran prenylation led to an antagonistic mode of action...
February 2016: Journal of Steroid Biochemistry and Molecular Biology
Biju Bhargavan, Divya Singh, Abnish K Gautam, Jay Sharan Mishra, Amit Kumar, Atul Goel, Manish Dixit, Rashmi Pandey, Lakshmi Manickavasagam, Shailendra D Dwivedi, Bandana Chakravarti, Girish K Jain, Ravishankar Ramachandran, Rakesh Maurya, Arun Trivedi, Naibedya Chattopadhyay, Sabyasachi Sanyal
Dietary isoflavones including genistein and daidzein have been shown to have favorable bone conserving effects during estrogen deficiency in experimental animals and humans. We have evaluated osteogenic effect of medicarpin (Med); a phytoalexin that is structurally related to isoflavones and is found in dietary legumes. Med stimulated osteoblast differentiation and mineralization at as low as 10⁻¹⁰ M. Studies with signal transduction inhibitors demonstrated involvement of a p38 mitogen activated protein kinase-ER-bone morphogenic protein-2 pathway in mediating Med action in osteoblasts...
January 2012: Journal of Nutritional Biochemistry
Florastina Payton-Stewart, Rahul S Khupse, Stephen M Boué, Steven Elliott, M Carla Zimmermann, Elena V Skripnikova, Hasina Ashe, Syreeta L Tilghman, Barbara S Beckman, Thomas E Cleveland, John A McLachlan, Deepak Bhatnagar, Thomas E Wiese, Paul Erhardt, Matthew E Burow
Glyceollins are pterocarpan phytoalexins elicited in high concentrations when soybeans are stressed. We have previously reported that the three glyceollin isomers (GLY I-III) exhibit antiestrogenic properties, which may have significant biological effects upon human exposure. Of the three isomers, we have recently shown that glyceollin I is the most potent antiestrogen. Natural (-)-glyceollin I recently was synthesized along with its racemate and unnatural (+) enantiomer. In this study, we compared the glyceollin I enantiomers' ER binding affinity, ability to inhibit estrogen responsive element transcriptional (ERE) activity and endogenous gene expression in MCF-7 cells...
December 2010: Steroids
Hyo Jung Kim, Hwa-Jin Suh, Jeong Hwan Kim, Sun Chul Kang, Sunmin Park, Choong Hwan Lee, Jong-Sang Kim
Glyceollins, which are synthesized from daidzein in soybeans cultured with fungi, have been shown to have antifungal effects and cancer preventive properties. Several studies have proposed that isoflavones and their metabolites act as a mixed agonist/antagonist for estrogen. Although glyceollins were reported to suppress some cancer cells via anti-estrogenic activity, it is not clear whether the compounds possess estrogenic potential. In contrast to the anti-estrogenic action reported thus far, we observed estrogenic effects of glyceollins using E-screen assay and pS2 expression, whereas glyceollins showed higher affinity for estrogen receptor (ER) beta than ERalpha...
April 2010: Journal of Medicinal Food
Sunmin Park, Il Sung Ahn, Jeong Hwan Kim, Mee Ryung Lee, Jong Sang Kim, Hyo Jung Kim
Glyceollins are a category of phytoalexins that are produced by soybeans under fungal stress, but their effects on glucose homeostasis remain unknown. We hypothesized that glyceollins play an important role in glucose homeostasis by regulating glucose utilization in adipocytes and improving beta-cell function and survival. Glyceollins improved insulin-stimulated glucose uptake in 3T3-L1 adipocytes without activating the peroxisome proliferator-activated receptor-gamma agonist. They decreased triacylglycerol accumulation in adipocytes...
February 10, 2010: Journal of Agricultural and Food Chemistry
Fengming Xu, Hisashi Matsuda, Hiroki Hata, Kaoru Sugawara, Seikou Nakamura, Masayuki Yoshikawa
Three new flavonoid glycosides (cissosides I, II, and III) and a new benzofuran-type stilbene (cissusin) were isolated from the methanolic extract of the aerial parts of Cissus sicyoides cultivated in Brazil. Their structures were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of the isolated constituents on the release of beta-hexosaminidase as a marker of degranulation in rat basophilic leukemia (RBL-2H3) cells were examined. Cissusin, flavonols (kaempferol, quercetin), flavones (7,3',4'-trihydroxyflavone, lanceolatin B), pterocarpanes (homopterocarpin), chalcones (isoliquiritigenin, E-7-O-methylpongamol), and tryptanthrin markedly inhibited the release of beta-hexosaminidase...
October 2009: Chemical & Pharmaceutical Bulletin
Stephen M Boué, Syreeta L Tilghman, Steven Elliott, M Carla Zimmerman, K Y Williams, Florastina Payton-Stewart, Allen P Miraflor, Melanie H Howell, Betty Y Shih, Carol H Carter-Wientjes, Chris Segar, Barbara S Beckman, Thomas E Wiese, Thomas E Cleveland, John A McLachlan, Matthew E Burow
The primary induced isoflavones in soybean, the glyceollins, have been shown to be potent estrogen antagonists in vitro and in vivo. The discovery of the glyceollins' ability to inhibit cancer cell proliferation has led to the analysis of estrogenic activities of other induced isoflavones. In this study, we investigated a novel isoflavone, glycinol, a precursor to glyceollin that is produced in elicited soy. Sensitive and specific in vitro bioassays were used to determine that glycinol exhibits potent estrogenic activity...
May 2009: Endocrinology
Sergey A Fedoreyev, Victor P Bulgakov, Olga V Grishchenko, Marina V Veselova, Olga E Krivoschekova, Nadezda I Kulesh, Vladimir A Denisenko, Galina K Tchernoded, Yury N Zhuravlev
Isoflavonoids, an interesting and restricted group of secondary metabolites of legumes, exhibit estrogenic, antiangiogenic, and anticancer activities and are now popular as dietary supplements. Plant cell cultures that possess an increased ability to synthesize these metabolites were examined. During the investigation, cell cultures of the Far Eastern relict tree Maackia amurensis (Leguminosae) were established. A selection of seed-derived cell aggregates yielded the callus line designated A-18. This culture produces 20 isoflavonoids, namely, the isoflavones genistein, daidzein, formononetin, calycosin, derrone, and pseudobaptigenin and their glycosylated conjugates genistin, 6''-O-malonylgenistin, ononin, 6''-O-malonylononin, daidzin, 3'-methoxydaidzin, 4'-O-beta-D-glucopyranosyldaidzin, 4'-O-beta-D-glucopyranosylgenistin, and 7-O-beta-D-glucopyranosylcalycosin; the pterocarpans maackiain and medicarpin and their glycosylated conjugates 6'-O-malonyl-3-O-beta-D-glucopyranosylmaackiain and 6'-O-malonyl-3-O-beta-D-glucopyranosylmedicarpin; and the new pterocarpan glucoside 6'-O-malonyl-3-O-beta-D-glucopyranosyl-6,6a-dehydromaackiain...
August 27, 2008: Journal of Agricultural and Food Chemistry
K Dalkin, R Edwards, B Edington, R A Dixon
Alfalfa (Medicago sativa L.) cell suspension cultures accumulated high concentrations of the pterocarpan phytoalexin medicarpin, reaching a maximum within 24 hours after exposure to an elicitor preparation from cell walls of the phytopathogenic fungus Colletotrichum lindemuthianum. This was preceded by increases in the extractable activities of the isoflavonoid biosynthetic enzymes l-phenylalanine ammonia-lyase, cinnamic acid 4-hydroxylase, 4-coumarate coenzyme A-ligase, chalcone synthase, chalcone isomerase, and isoflavone O-methyltransferase...
February 1990: Plant Physiology
Nancy L Booth, Cassia R Overk, Ping Yao, Joanna E Burdette, Dejan Nikolic, Shao-Nong Chen, Judy L Bolton, Richard B van Breemen, Guido F Pauli, Norman R Farnsworth
OBJECTIVES: To document the chemical and biologic profile of a clinical phase II red clover (Trifolium pratense L.) extract by identifying and measuring the major and minor components visible in the high-performance liquid chromatography-ultraviolet (HPLC-UV) chromatogram and evaluating each compound for estrogenic and antioxidant activity. DESIGN: Individual compounds in the preformulated (i.e., no excipients present) extract were identified by either chemical isolation followed by structure elucidation or matching to retention time and molecular mass of chemical standards via liquid chromatography-mass spectrometry (LC-MS) analysis...
March 2006: Journal of Alternative and Complementary Medicine: Research on Paradigm, Practice, and Policy
Feng Xu, Yue Zhang, Shengyuan Xiao, Xiaowei Lu, Donghui Yang, Xiaoda Yang, Changling Li, Mingying Shang, Pengfei Tu, Shaoqing Cai
To profile absorption of Astragali Radix decoction and identify its orally absorbable constituents and their metabolites, four complementary in silico, in vitro, and in vivo methods, i.e., a computational chemistry prediction method, a Caco-2 cell monolayer model experiment, an improved rat everted gut sac experiment, and a healthy human volunteer experiment, were used. According to the in silico computation result, 26 compounds of Astragali Radix could be regarded as orally available compounds, including 12 flavonoids...
June 2006: Drug Metabolism and Disposition: the Biological Fate of Chemicals
Susumu Ohkawara, Yasunobu Okuma, Takashi Uehara, Takashi Yamagishi, Yasuyuki Nomura
The inhibitory effects of astrapterocarpan, formononetin, and calycosin isolated from Astragalus membraneceus on platelet-derived growth factor (PDGF)-BB-induced proliferative response in rat vascular smooth muscle cells (A10 cells) were investigated. Astrapterocarpan significantly inhibited PDGF-BB-induced cell proliferation and DNA synthesis in a concentration-dependent manner. This inhibition was not attributed to toxicity. In contrast, formononetin and calycosin had no effect. We next examined the effect of astrapterocarpan on PDGF-BB signal transduction...
November 21, 2005: European Journal of Pharmacology
Judith Fliegmann, Göde Schüler, Wilhelm Boland, Jürgen Ebel, Axel Mithöfer
Oxylipins of the jasmonate pathway and synthetic functional analogs have been analyzed for their elicitor-like activities in an assay based on the induced accumulation of glyceollins, the phytoalexins of soybean (Glycine max L.), in cell suspension cultures of this plant. Jasmonic acid (JA) and its methyl ester showed weak phytoalexin-inducing activity when compared to an early jasmonate biosynthetic precursor, 12-oxo-phytodienoic acid (OPDA), as well as to the bacterial phytotoxin coronatine and certain 6-substituted indanoyl-L-isoleucine methyl esters, which all were highly active...
March 2003: Biological Chemistry
A Mithöfer, J Fliegmann, A Daxberger, C Ebel, G Neuhaus-Url, A A Bhagwat, D L Keister, J Ebel
Soybean cell suspension cultures have been used to investigate the role of the elevation of the cytosolic Ca(2+) concentration in beta-glucan elicitors-induced defence responses, such as H(2)O(2) and phytoalexin production. The intracellular Ca(2+) concentration was monitored in transgenic cells expressing the Ca(2+)-sensing aequorin. Two lines of evidence showed that a transient increase of the cytosolic Ca(2+) concentration is not necessarily involved in the induction of H(2)O(2) generation: (i) a Bradyrhizobium japonicum cyclic beta-glucan induced the H(2)O(2) burst without increasing the cytosolic Ca(2+) concentration; (ii) two ion channel blockers (anthracene-9-carboxylate, A9C; 5-nitro-2-(3-phenylpropylamino)-benzoate, NPPB) could not prevent a Phytophthora soja beta-glucan elicitor-induced H(2)O(2) synthesis but did prevent a cytosolic Ca(2+) concentration increase...
November 16, 2001: FEBS Letters
M E Burow, S M Boue, B M Collins-Burow, L I Melnik, B N Duong, C H Carter-Wientjes, S Li, T E Wiese, T E Cleveland, J A McLachlan
The flavonoid family of phytochemicals, particularly those derived from soy, has received attention regarding their estrogenic activity as well as their effects on human health and disease. In addition to these flavonoids other phytochemicals, including phytostilbene, enterolactone, and lignans, possess endocrine activity. The types and amounts of these compounds in soy and other plants are controlled by both constitutive expression and stress-induced biosynthesis. The health benefits of soy-based foods may, therefore, be dependent upon the amounts of the various hormonally active phytochemicals within these foods...
April 2001: Journal of Clinical Endocrinology and Metabolism
S Kirmizigül, N Gören, S W Yang, G A Cordell, C Bozok-Johansson
The roots of Ononis spinosa subsp. leiosperma (Leguminosae) afforded a new glycoside, spinonin (1), possessing a novel skeleton, in addition to the known isoflavonoid glycoside, ononin [7beta-(glucosyloxy)formononetin] (2) and the known pterocarpan, 7-demethoxy-7-D-(glucosyloxy)homopterocarpin (3). The structure of the new isolate was elucidated by spectral methods including 1H and 13C NMR, COSY, APT, HETCOR, HMBC, NOESY, CD, FABMS, HRMS, EIMS, CIMS, and some chemical reactions. Spinonin was inactive against a number of human cancer cell lines and HIV-1 reverse transcriptase...
April 1997: Journal of Natural Products
M G Hahn, J J Cheong, R Alba, F Côté
We are studying the cellular signalling pathway leading to pterocarpan phytoalexin biosynthesis in soybean that is induced by a branched hepta-beta-glucoside originally isolated from the mycelial walls of the phytopathogenic oomycete, Phytophthora megasperma f. sp. glycinea. Our research has focused on the first step in this signal pathway, namely the specific recognition of the hepta-beta-glucoside elicitor by plasma-membrane-localized binding protein(s) in soybean cells. Binding of a radio-iodinated derivative of the elicitor-active hepta-beta-glucoside by membrane elicitor-binding proteins is specific, reversible, saturable and of high affinity (Kd = 0...
1994: Biochemical Society Symposium
M Walker-Simmons, L Hadwiger, C A Ryan
The Proteinase Inhibitor Inducing Factor, PIIF, a pectic polysaccharide that induces synthesis and accumulation of proteinase inhibitor proteins in tomato and potato leaves, is an effective elicitor of the phytoalexin pisatin in pea pod tissues. The levels of pisatin induced by PIIF, and the time course of elicitation, are similar to those induced by chitosans, beta-1,4 glucosamine polymers, which are potent elicitors of pisatin in pea pods. Similarly, the chitosans, found in both insect and fungal cell walls, are the most potent inducers yet found of proteinase inhibitor accumulation in excised tomato cotyledons...
January 14, 1983: Biochemical and Biophysical Research Communications
N L Paiva, R Edwards, Y J Sun, G Hrazdina, R A Dixon
The major phytoalexin in alfalfa is the isoflavonoid (-)-medicarpin (or 6aR, 11aR)-medicarpin. Isoflavone reductase (IFR), the penultimate enzyme in medicarpin biosynthesis, is responsible for introducing one of two chiral centers in (-)-medicarpin. We have isolated a 1.18 kb alfalfa cDNA (pIFRalf1) which, when expressed in Escherichia coli, converts 2'-hydroxyformononetin stereospecifically to (3R)-vestitone, as would be predicted for IFR from alfalfa. The calculated molecular weight of the polypeptide (35,400) derived from the 954 bp open reading frame compares favorably to estimated Mrs determined for IFR proteins purified from other legumes...
October 1991: Plant Molecular Biology
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