DOCSLIB.ORG

Chemistry Phytoalexins (Centres of Chirality)

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Chemistry Phytoalexins (Centres of Chirality) Acta Bot. Neerl. 29 (2/3), May 1980, p. 193-197. Brief communications Biological implications of the stereo- chemistry of isoflavonoid phytoalexins A. Fuchs and C.A.X.G.F. SichererI* Laboratoriumvoor Fytopathologie,Landbouwhogeschool,Binnenhaven 9,6709 PDWageningen** To properly evaluate the role of phytoalexins in plant disease resistance it is useful to know whether or not the pathogens involved are capable of metaboliz- ing and detoxifying these compounds. In studying this question, rather than the mechanism of sé the of in degradation per specificity fungi degrading phy- toalexins seems crucial. have the breakdown of For several years we been studying in vitro pterocar- panoid phytoalexins by various fungal pathogens (for recent literature, see with Fuchs & Hijwegen 1979; Fuchs et al. 1980a,b). The pterocarpan skeleton its numbering system is given infig. la; the most common sites of substitutionin the differentpterocarpans are the 2,3, and 4-positions in the A-ring, the 8,9, and 10-positions in the D-ring and the 6a-position. Due to the two asymmetric carbon atoms (centres of chirality) and the ef- fusionofthe B and C-ring, asevident fromNMR data (Pachler & Underwood of Fig. 1. a. Pterocarpan skeleton with preferred sites substitution (incircles); b. (-)-pterocarpan with 1 6aa, llaa-configuration(R = H: 6aR, laR; R = OH: 6aS, 1 laS); c. (+ )-pterocarpan with 6ap, 1 lap-configuration (R = H: 6aS, llaS; R = OH: 6aR, llaR). ‘Present address; Laboratorium voor Organische Chemie, Technische Hogeschool, Delft, The Netherlands. “Communicated at the Meeting ofthe section for Plant Pathology (Royal Botanical Society ofthe 1979. Netherlands) onNovember 22, 194 A. FUCHS AND C. A. X. G. F. SICHERER 1967), all pterocarpans occur in two enantiomeric forms (figs, lb, c). In general, absolute to designate configurations of pterocarpans the R, S nomenclature is used. With this nomenclatureit depends on the nature of the substituent at the C- whether is 6a position a certain absolute configuration indicated as 6aR, 11 aR or 6aS, llaS & Sicherer-Roetman With the (Sicherer 1980). a, p nomenclature, on the other hand, such a confusion is avoided, though the a, P nomenclatureis this not a priori unambigious. According to designation, irrespective of the of the C-6a in lb has the nature substituent at a pterocarpan as depicted fig. 6aa, 11 aa-configuration, with a negative valueof whereas the configuration as in 1c the 1 with value of given fig. represents 6a3, laP-configuration, a positive No (see tableI, which summarizes substituentsand absolute configuration at C- and C-l for of 6a la some common pterocarpans). Generally, each pterocarpan only one enantiomeris found in nature; however, in some instances two enanti- in omers co-occur one plant species (for instance, (+ )-inermin ( = maackiain) and ( + )-inermin (Perrin & Cruickshank 1969; Braz Filho et al. 1973). Literaturedata show that in some fungi differences in substitution pattern do interfere with the of not or hardly fungus’ ability to carry out a given type the degradation. For instance, alfalfa pathogen Stemphylium botryosum can its host & Millar convert phytoalexin medicarpin (Steiner 1974) as well as (-)- inermin (Higgins 1975) and phaseollin (Higgins et al. 1974) To their corres- ponding isoflavans by reductive opening of the dihydrofuran ring C (cf. fig. 2). Apparently, the substitution pattern at C-8 and 10 in the D-ring (cf. table I) does determinethe substrate of the involved in this not specificity enzyme(s) type of degradation. However, (+)- 6a-hydroxy-inermin, which has a substitution pattern in the A and differsfrom latter D-ring similarto thatof(-)-inermin, but the pterocarpanin its absolute configuration and in possessing a hydroxyl group at C-6a, is not Fig. 2. Conversion of the two enantiomers of inermin and 6a-hydroxy-inermin by Stemphylium botryosum (because of the different numberingsystem ofpterocarpans and isoflavans the 6a-position of pterocarpans is comparablewith the 3-position of isoflavans). IMPLICATIONS OF STEREOCHEMISTRY OF PHYTOALEXINS 195 Table I. Substituents and absolute configurationat C-6a and C-11 a ofsome common pterocarpans. i.p. = isopentenyl Pterocarpan C-2 C-3 C-4 C-6a abs. C-8 C-9 C-10 conf. (-) medicarpin H OH H H ot H OCH3 H (-) pterocarpin H OCH H H •a O - CH - O H 3 2 H H - CH - O H (±)inermin(= H OH a or p O maackiain) 2 - - H ( ±) 6a-hydroxy-inermin H OH H OH a or p O CH O 2 H OCH H OH O - ch - 0 H (+) pisatin 3 P 2 ( + ) variabilin H OCH H OH P H H 3 OCHj (+) tuberosin H OH H OH P chromene (-O) H I H H (—) glyceollin (O-) chromene OH a H OH II H H OH (—) glyceollin chromene(-O) OH a H H H H (—) phaseollin OH a H (O-)chromene H H H H OH (—) phaseollidin OH a i.p. converted to its corresponding 3-hydroxy-inerminisoflavan (cf. fig. 2) by this On the other the certain fungus. hand, depending on fungus involved a pterocar- pan might be converted along very different pathways, as exemplified by pha- seollin, for which at least five types of conversion are known at this moment {cf. Van Etten& Pueppke 1976; Bailey et al. 1977). However, the available know- ledge, although limited, on the various pathways of fungal degradation of be does pterocarpans (for synopsis, see Hijwegen & Fuchs, to published) suggest thatsubstitution at C-6a as well as absolute configuration are amongthe of key determinantsfor degradation pterocarpans by a given fungal species. Another aspect to be taken into account in the evaluation of the role of phytoalexins is the sensitivity of fungi to these compounds. It should be realized that low or non-sensitivity can be eitheran intrinsic featureof the fungal species of of the involved or a consequence rapid breakdown phytoalexin concerned. the does in itself However, ability to degrade a phytoalexin not imply non- whereas f. and F. f. sensitivity ; Fusariumoxysporum sp. lycopersici oxysporum sp. sensitive in pisi are equally to pisatin a thin-layer chromatographic bioassay (Homans & Fuchs 1970) as well as in amycelial growth test (Fuchs & DeVries, to under normal be published), in vivo conditions the pea pathogen apparently cir- cumvents the toxic action of the phytoalexin through rapid degradation {cf. Fuchs et al. 1 980b). Unlike substrate specificity offungi with respect to phytoale- xin breakdown, sensitivity to phytoalexins does not seem to depend on the absolu- te configuration at C-6aand C-1 la. Although Perrin& Cruickshank (1969) and Van Etten (1976) disagree with each other aboutthe occurrence of a structure- activity relationship with regard to antifungal activity of pterocarpans, a given absolute configuration evidently is no prerequisite for fungitoxicity: (4-)-, (± )- and (-)-inermin inhibitedthe growth of Moniliniafructicola to the same extent. From the considerations given above it is evident that in such studies as currently performed by us on pterocarpanoid phytoalexin degradation hn exact is knowledge about absolute configurations indispensable. Substitution patterns 196 A. FUCHS AND C. A. X. G. F. SICHERER well conformationaldata the skeleton well be derived as as on pterocarpan may from NMR-analysis. However, up till now absolute configurations ofpterocar- pans have usually been established with reference to the absolute configuration of trifolirhizin (= (-)-inermin-(3-D-glucoside) as determinedby Ito et al. (1965) via degradation to (-)-paraconic acid. Because of the possibly significant role of the absolute configuration at C-6a and C-lla, it seems desirable to use less indirect methods, such as anomalous X-ray scattering, to establish the absolute of Use of directmethodsis stereochemistry pterocarpans. also more appropriate in theelucidation of biogenetic relationships among pterocarpans (Sicherer & Sicherer-Roetman, 1980) as well as in establishing the stereochemistry of iso- flavan analogues of pterocarpans (cf. Kurosawa et al., 1968, 1978). In this context, it is interesting to note that the absolute configuration of(-)-phaseollin Van HeuvelcI al. and DeMartinis al. as reported by den (1974) et (1977,1978) is contrary to current views, though not based on experimental evidence (Cof- DeMartinis et al., fen, pers. comm.; pers. comm.). As soon as theabsolute configuration of one pterocarpan has unequivocally that of others be determined been established, may by comparison, by means of circular dichroism (CD) or optical rotatory dispersion (ORD), rather than by estimation of one optical rotation value. For CD we simple [ot] D instance, using confirmed that the absolute configuration of pisatin from both Pisum sativum and Lathyrus odoratus is opposite to that of phaseollin (from bean), glycecollin (from soy bean) and medicarpin (from Jack bean). REFERENCES Bailey, J. A., R. S. Burden, A. Mynett & C. Brown (1977): Metabolism of phaseollinby Septoria nodorum and other non-pathogensof Phaseolus vulgaris. Phytochemistry 16:1541-1544. BrazFilho,R.,0. R. Gottlieb, S. L. Vieira Pinho,F. J. Queiroz Monte& A. I.daRocha (1973); Flavonoids from Amazonian Leguminosae. Phytochemistry 12; 1184 1186. DeMartinis, C., M. F. Mackay, D. R. Perrin & B. J. Poppleton(1977);The molecular structure of phaseollin. Tetrahedron Lett. 2981-2982. — & B. —, J. Poppleton (1978): The crystal and molecular structure of (-)-phaseollin.Tetrahedron 34; 1849-1852. Fuchs, A. &T. Hijweoen (1979): Specificity in degradationofisoflavonoid phytoalexins. ActaBot. Neerl. 28; 227-229. F.W. de Vries, C. A. Landheer & A. vanVeldhuizen —, (1980a): 3-Hydroxy-maackiainisoflavan, metabolic Fusarium f. a pisatin produced by oxysporum sp. pisi. Phytochemistry 19: 000-000. —,— & M. PlateroSanz (1980b):The mechanism of pisatin degradationby Fusarium oxysporum f. sp. pisi. Physiol. Plant Path. 16: 119-133. Heuvel, J. van den, H. D. van Etten, J. W. Serum, D. L. Coffen & T. H. Williams (1974): Identification of 1a-hydroxy phaseollone,aphaseollinmetabolite produced by Fusarium solani. Phytochemistry 13; 1129-1131. Higgins, V. J. (1975): Induced conversion of the phytoalexin maackiain to dihydromaackiainby the alfalfa pathogen Stemphylium botryosum. Physiol. Plant Path. 6; 5-18. A. Stoessl & M.
Load more

Recommended publications
  • The Science of Flavonoids the Science of Flavonoids
    The Science of Flavonoids The Science of Flavonoids Edited by Erich Grotewold The Ohio State University Columbus, Ohio, USA Erich Grotewold Department of Cellular and Molecular Biology The Ohio State University Columbus, Ohio 43210 USA [email protected] The background of the cover corresponds to the accumulation of flavonols in the plasmodesmata of Arabidopsis root cells, as visualized with DBPA (provided by Dr. Wendy Peer). The structure corresponds to a model of the Arabidopsis F3 'H enzyme (provided by Dr. Brenda Winkel). The chemical structure corresponds to dihydrokaempferol. Library of Congress Control Number: 2005934296 ISBN-10: 0-387-28821-X ISBN-13: 978-0387-28821-5 ᭧2006 Springer ScienceϩBusiness Media, Inc. All rights reserved. This work may not be translated or copied in whole or in part without the written permission of the publisher (Springer ScienceϩBusiness Media, Inc., 233 Spring Street, New York, NY 10013, USA), except for brief excerpts in connection with reviews or scholarly analysis. Use in connection with any form of information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed is forbidden. The use in this publication of trade names, trademarks, service marks and similar terms, even if they are not identified as such, is not to be taken as an expression of opinion as to whether or not they are subject to proprietary rights. Printed in the United States of America (BS/DH) 987654321 springeronline.com PREFACE There is no doubt that among the large number of natural products of plant origin, debatably called secondary metabolites because their importance to the eco- physiology of the organisms that accumulate them was not initially recognized, flavonoids play a central role.
    [Show full text]
  • Dr. Duke's Phytochemical and Ethnobotanical Databases List of Chemicals for Fungicide
    Dr. Duke's Phytochemical and Ethnobotanical Databases List of Chemicals for Fungicide Chemical Dosage (+)-3-HYDROXY-9-METHOXYPTEROCARPAN IC26-78=100 uM (+)-VESTITONE -- (-)-3-HYDROXY-9-METHOXYPTEROCARPAN IC31-69=100 uM (-)-ACANTHOCARPAN ED50=<50-100 (-)-APIOCARPIN ED50=<50 (-)-CANESCACARPIN ED50=<50 (-)-CLANDESTACARPIN ED50=<50 (-)-CRISTACARPIN ED50=<50 (-)-DEMETHYLMEDICARPIN EC50=50-100 (-)-DOLICHIN-A ED50=>100 (-)-DOLICHIN-B ED50=>100 (-)-EPIGALLOCATECHIN-GALLATE -- (-)-GLYCEOCARPIN ED50=50-100 (-)-GLYCEOFURAN ED50=>100 (-)-GLYCEOLLIN-I ED50=<50 (-)-GLYCEOLLIN-II ED50=<50 (-)-GLYCEOLLIN-III ED50=<50 (-)-GLYCEOLLIN-IV ED50=<50 (-)-GLYCINOL ED50=50->100 (-)-ISOSATIVAN -- (-)-JASMONIC-ACID -- (-)-MEDICARPIN ED50=<50 (-)-VESTITOL -- (-)-VESTITONE -- (Z)-1,3-BIS(4-HYDROXYPHENYL)-1,4-PENTADIENE -- -METHOXYBRASSITIN -- 1,2-DIHYDROXY-4-GLUCOSYLNAPTHALENE -- Chemical Dosage 1,2-DIMETHOXY-3,8-DIHYDROXYXANTHONE > miconazole 1,7-DIHYDROXY-4-METHOXYXANTHONE <miconazole 1,8-CINEOLE -- 1-TULIPOSIDE-A -- 1-TULIPOSIDE-B -- 13',II8-BIAPIGENIN -- 15-GLUCOPYRANOSYL-GLAUCORUBOLONE -- 2'-HYDROXYDAIDZEIN ED50=>100 2'-HYDROXYGENISTEIN ED50=50->100 2,3-DEHYDROKIEVITONE -- 2,6-DIMETHOXY-P-BENZOQUINONE -- 2,7-DIMETHOXY-5-ISOPROPYL-3-METHYL-8,1-NAPTHALENE-CARBOLACTONE -- 2-HYDROXY-5-ISOPROPYL-7-METHOXY-3-METHYL-8,1-NAPTHALENE-CARBOLACTONE -- 2-METHOXYPHASEOLLINISOFLAVON IC80-89=100uM 26-DESGLUCOAVENACOSIDE-A -- 26-DESGLUCOAVENACOSIDE-B -- 3'-FORMYL-2',4',6'-TRIHYDROXY-5'-METHYLDIHYDROCHALCONE -- 3'-FORMYL-2',4',6'-TRIHYDROXYDIHYDROCHALCONE -- 3,4-DIMETHOXYTOLUENE
    [Show full text]
  • WO 2018/002916 Al O
    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2018/002916 Al 04 January 2018 (04.01.2018) W !P O PCT (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C08F2/32 (2006.01) C08J 9/00 (2006.01) kind of national protection available): AE, AG, AL, AM, C08G 18/08 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, (21) International Application Number: DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, PCT/IL20 17/050706 HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, (22) International Filing Date: KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, 26 June 2017 (26.06.2017) MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, (25) Filing Language: English SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, (26) Publication Language: English TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: (84) Designated States (unless otherwise indicated, for every 246468 26 June 2016 (26.06.2016) IL kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, (71) Applicant: TECHNION RESEARCH & DEVEL¬ UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, OPMENT FOUNDATION LIMITED [IL/IL]; Senate TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, House, Technion City, 3200004 Haifa (IL).
    [Show full text]
  • Genetic Regulation of the Elicitation of Glyceollin Biosynthesis in Soybean
    Graduate Theses, Dissertations, and Problem Reports 2019 GENETIC REGULATION OF THE ELICITATION OF GLYCEOLLIN BIOSYNTHESIS IN SOYBEAN Md. Asraful Jahan West Virginia University, [email protected] Follow this and additional works at: https://researchrepository.wvu.edu/etd Part of the Agricultural Science Commons, Genetics Commons, Molecular Genetics Commons, Plant Breeding and Genetics Commons, and the Plant Pathology Commons Recommended Citation Jahan, Md. Asraful, "GENETIC REGULATION OF THE ELICITATION OF GLYCEOLLIN BIOSYNTHESIS IN SOYBEAN" (2019). Graduate Theses, Dissertations, and Problem Reports. 3782. https://researchrepository.wvu.edu/etd/3782 This Dissertation is protected by copyright and/or related rights. It has been brought to you by the The Research Repository @ WVU with permission from the rights-holder(s). You are free to use this Dissertation in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you must obtain permission from the rights-holder(s) directly, unless additional rights are indicated by a Creative Commons license in the record and/ or on the work itself. This Dissertation has been accepted for inclusion in WVU Graduate Theses, Dissertations, and Problem Reports collection by an authorized administrator of The Research Repository @ WVU. For more information, please contact [email protected]. Genetic Regulation of the Elicitation of Glyceollin Biosynthesis in Soybean Md. Asraful Jahan Dissertation submitted to the Davis College of Agriculture, Natural Resources and Design at West Virginia University in partial fulfillment of requirements for the degree of Doctor of Philosophy in Genetics and Developmental Biology Nikola Kovinich, Ph.D., Committee Chair Daniel G.
    [Show full text]
  • Enhanced Biosynthesis of the Natural Antimicrobial Glyceollins in Soybean Seedlings by Priming and Elicitation
    Enhanced biosynthesis of the natural antimicrobial glyceollins in soybean seedlings by priming and elicitation Kalli, S., Araya-Cloutier, C., Lin, Y., de Bruijn, W. J. C., Chapman, J., & Vincken, J. P. This is a "Post-Print" accepted manuscript, which has been Published in "Food Chemistry" This version is distributed under a non-commercial no derivatives Creative Commons (CC-BY-NC-ND) user license, which permits use, distribution, and reproduction in any medium, provided the original work is properly cited and not used for commercial purposes. Further, the restriction applies that if you remix, transform, or build upon the material, you may not distribute the modified material. Please cite this publication as follows: Kalli, S., Araya-Cloutier, C., Lin, Y., de Bruijn, W. J. C., Chapman, J., & Vincken, J. P. (2020). Enhanced biosynthesis of the natural antimicrobial glyceollins in soybean seedlings by priming and elicitation. Food Chemistry, 317, [126389]. https://doi.org/10.1016/j.foodchem.2020.126389 You can download the published version at: https://doi.org/10.1016/j.foodchem.2020.126389 Enhanced biosynthesis of the natural antimicrobial glyceollins in soybean seedlings by priming and elicitation Sylvia Kallia, Carla Araya-Cloutiera, Yiran Lina, Wouter J.C. de Bruijna, John Chapmanb, and Jean-Paul Vinckena,* a Laboratory of Food Chemistry, Wageningen University, P.O. Box 17, 6700 AA Wageningen, The Netherlands. b Unilever R&D Vlaardingen, Olivier van Noortlaan 120, 3133 AT, Vlaardingen, The Netherlands. * Correspondence to: [email protected] 1 Highlights • Priming prior to Rhizopus-elicitation enhances the production of glyceollins. • Priming with reactive oxygen species was superior to wounding in glyceollin production.
    [Show full text]
  • Potenciálisan Biológiailag Aktív Pterokarpán Származékok Előállítása
    Potenciálisan biológiailag aktív pterokarpán származékok előállítása Egyetemi doktori (PhD) értekezés Németh István Témavezető: Antus Sándor akadémikus Konzulens: Dr. Kurtán Tibor egyetemi docens DEBRECENI EGYETEM Természettudományi Doktori Tanács Kémiai Doktori Iskola Debrecen, 2012. Ezen értekezést a Debreceni Egyetem Természettudományi Doktori Tanács Kémiai Doktori Iskola Természetes eredetű heterociklusok és analógjaik szintézise és szerkezetvizsgálata (K/6) programja keretében készítettem a Debreceni Egyetem Természettudományi Doktori (PhD) fokozatának elnyerése céljából. Debrecen, 2012.11.21. .…………………… Németh István Tanúsítom, hogy Németh István doktorjelölt 2007-2012 között a fent megnevezett Doktori Iskola Természetes eredetű heterociklusok és analógjaik szintézise és szerkezetvizsgálata (K/6) programjának keretében irányításommal végezte munkáját. Az értekezésben foglalt eredményekhez a jelölt önálló alkotó tevékenységével meghatározóan hozzájárult. Az értekezés elfogadását javasolom. Debrecen, 2012.11.21. ……………………. Antus Sándor akadémikus témavezető Potenciálisan biológiailag aktív pterokarpán származékok előállítása Értekezés a doktori (PhD) fokozat megszerzése érdekében a kémia tudományágban Írta: Németh István okleveles vegyész Készült a Debreceni Egyetem Természettudományi és Technológiai Kar Kémiai Doktori Iskolája K/6 programja (Természetes eredetű heterociklusok és analógjaik szintézise és szerkezetvizsgálata) keretében Témavezető: Antus Sándor akadémikus A doktori szigorlati bizottság: elnök: Dr. Patonay Tamás ………………………
    [Show full text]
  • Glyceollin Is an Important Component of Soybean Plant Defense Against Phytophthora Sojae and Macrophomina Phaseolina
    Biochemistry and Cell Biology Glyceollin is an Important Component of Soybean Plant Defense Against Phytophthora sojae and Macrophomina phaseolina Anatoliy V. Lygin, Olga V. Zernova, Curtis B. Hill, Nadegda A. Kholina, Jack M. Widholm, Glen L. Hartman, and Vera V. Lozovaya First, second, third, fourth, fifth, and seventh authors: Department of Crop Sciences, University of Illinois, 1201 W. Gregory Drive, Urbana 61801; and sixth author: United States Department of Agriculture–Agricultural Research Service, University of Illinois, 1101 W. Peabody Drive, Urbana 61801. Accepted for publication 16 April 2013. ABSTRACT Lygin, A. V., Zernova, O. V., Hill, C. B., Kholina, N. A., Widholm, J. M., moter compared with the untransformed control during the 10-day obser- Hartman, G. L., and Lozovaya, V. V. 2013. Glyceollin is an important vation period, with the precursors of isoflavone synthesis being accumu- component of soybean plant defense against Phytophthora sojae and lated in the cotyledons of transgenic plants. These results indicated that Macrophomina phaseolina. Phytopathology 103:984-994. the lectin promoter could be active not only during seed development but also during seed germination. Downregulation of isoflavone synthesis only The response of soybean transgenic plants, with suppressed synthesis in the seed or in the whole soybean plant caused a strong inhibition of the of isoflavones, and nontransgenic plants to two common soybean patho- pathogen-inducible glyceollin in cotyledons after inoculation with P. s o j a e , gens, Macrophomina phaseolina and Phytophthora sojae, was studied. which resulted in increased susceptibility of the cotyledons of both trans- Transgenic soybean plants of one line used in this study were previously genic lines to this pathogen compared with inoculated cotyledons of un- generated via bombardment of embryogenic cultures with the phenyl- transformed plants.
    [Show full text]
  • The Synergistic Effect of Co-Treatment of Methyl Jasmonate
    International Journal of Molecular Sciences Article The Synergistic Effect of Co-Treatment of Methyl Jasmonate and Cyclodextrins on Pterocarpan Production in Sophora flavescens Cell Cultures 1,2, 1, 1 1 1 Soyoung Kim y, Yu Jeong Jeong y, Su Hyun Park , Sung-Chul Park , Saet Buyl Lee , Jiyoung Lee 1, Suk Weon Kim 1, Bo-Keun Ha 2, Hyun-Soon Kim 3, HyeRan Kim 3, Young Bae Ryu 4, Jae Cheol Jeong 1,* and Cha Young Kim 1,* 1 Biological Resource Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB), Jeongeup 56212, Korea; [email protected] (S.K.); [email protected] (Y.J.J.); [email protected] (S.H.P.); [email protected] (S.-C.P.); [email protected] (S.B.L.); [email protected] (J.L.); [email protected] (S.W.K.) 2 Department of Plant Biotechnology, College of Agriculture and Life Science, Chonnam National University, Gwangju 61186, Korea; [email protected] 3 Plant Systems Engineering Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB), Daejeon 34141, Korea; [email protected] (H.-S.K.); [email protected] (H.K.) 4 Functional Biomaterials Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB), Jeongeup 56212, Korea; [email protected] * Correspondence: [email protected] (J.C.J.); [email protected] (C.Y.K.); Tel.: +82-63-570-5001 (C.Y.K.); Fax: +82-63-570-5009 (C.Y.K.) These authors contributed equally to this work. y Received: 9 April 2020; Accepted: 29 May 2020; Published: 30 May 2020 Abstract: Pterocarpans are derivatives of isoflavonoids, found in many species of the family Fabaceae.
    [Show full text]
  • Isoflavonoid-Inducible Resistance to the Phytoalexin Glyceollin In
    JOURNAL OF BACTERIOLOGY, June 1991, p. 3432-3439 Vol. 173, No. 11 0021-9193/91/113432-08$02.00/0 Copyright X 1991, American Society for Microbiology Isoflavonoid-Inducible Resistance to the Phytoalexin Glyceollin in Soybean Rhizobia MARTIN PARNISKE,* BETTINA AHLBORN, AND DIETRICH WERNER Fachbereich Biologie der Philipps-Universitat, Karl-von-Frisch-Strasse, D-3550 MarburglLahn, Federal Republic of Germany Received 13 August 1990/Accepted 25 March 1991 The antibacterial effect of the soybean phytoalexin glyceollin was assayed using a liquid microculture technique. Log-phase cells of Bradyrhizobium japonicum and Sinorhizobium fredii were sensitive to glyceollin. As revealed by growth rates and survival tests, these species were able to tolerate glyceollin after adaptation. Incubation in low concentrations of the isoflavones genistein and daidzein induced resistance to potentially bactericidal concentrations of glyceollin. This inducible resistance is not due to degradation or detoxification of the phytoalexin. The inducible resistance could be detected in B. japonicum 110spc4 and 61A101, representing the two taxonomically divergent groups of this species, as well as in S. fredii HH103, suggesting that this trait is a feature of all soybean-nodulating rhizobia. Glyceollin resistance was also inducible in a nodDlD2YABC deletion mutant of B. japonicum 110spc4, suggesting that there exists another recognition site for flavonoids besides the nodD genes identified so far. Exudate preparations from roots infected with Phytophthora megasperma f. sp. glycinea exhibited a strong bactericidal effect toward glyceollin-sensitive cells of B. japonicum. This killing effect was not solely due to glyceollin since purified glyceollin at concentrations similar to those present in exudate preparations had a much lower toxicity.
    [Show full text]
  • Dr. Duke's Phytochemical and Ethnobotanical Databases List of Chemicals for Fungicide
    Dr. Duke's Phytochemical and Ethnobotanical Databases List of Chemicals for Fungicide Chemical Dosage (+)-3-HYDROXY-9-METHOXYPTEROCARPAN IC26-78=100 uM (+)-VESTITONE -- (-)-3-HYDROXY-9-METHOXYPTEROCARPAN IC31-69=100 uM (-)-ACANTHOCARPAN ED50=<50-100 (-)-APIOCARPIN ED50=<50 (-)-CANESCACARPIN ED50=<50 (-)-CLANDESTACARPIN ED50=<50 (-)-CRISTACARPIN ED50=<50 (-)-DEMETHYLMEDICARPIN EC50=50-100 (-)-DOLICHIN-A ED50=>100 (-)-DOLICHIN-B ED50=>100 (-)-EPIGALLOCATECHIN-GALLATE -- (-)-GLYCEOCARPIN ED50=50-100 (-)-GLYCEOFURAN ED50=>100 (-)-GLYCEOLLIN-I ED50=<50 (-)-GLYCEOLLIN-II ED50=<50 (-)-GLYCEOLLIN-III ED50=<50 (-)-GLYCEOLLIN-IV ED50=<50 (-)-GLYCINOL ED50=50->100 (-)-ISOSATIVAN -- (-)-JASMONIC-ACID -- (-)-MEDICARPIN ED50=<50 (-)-VESTITOL -- (-)-VESTITONE -- (Z)-1,3-BIS(4-HYDROXYPHENYL)-1,4-PENTADIENE -- -METHOXYBRASSITIN -- 1,2-DIHYDROXY-4-GLUCOSYLNAPTHALENE -- Chemical Dosage 1,2-DIMETHOXY-3,8-DIHYDROXYXANTHONE > miconazole 1,7-DIHYDROXY-4-METHOXYXANTHONE <miconazole 1,8-CINEOLE -- 1-TULIPOSIDE-A -- 1-TULIPOSIDE-B -- 13',II8-BIAPIGENIN -- 15-GLUCOPYRANOSYL-GLAUCORUBOLONE -- 2'-HYDROXYDAIDZEIN ED50=>100 2'-HYDROXYGENISTEIN ED50=50->100 2,3-DEHYDROKIEVITONE -- 2,6-DIMETHOXY-P-BENZOQUINONE -- 2,7-DIMETHOXY-5-ISOPROPYL-3-METHYL-8,1-NAPTHALENE-CARBOLACTONE -- 2-HYDROXY-5-ISOPROPYL-7-METHOXY-3-METHYL-8,1-NAPTHALENE-CARBOLACTONE -- 2-METHOXYPHASEOLLINISOFLAVON IC80-89=100uM 26-DESGLUCOAVENACOSIDE-A -- 26-DESGLUCOAVENACOSIDE-B -- 3'-FORMYL-2',4',6'-TRIHYDROXY-5'-METHYLDIHYDROCHALCONE -- 3'-FORMYL-2',4',6'-TRIHYDROXYDIHYDROCHALCONE -- 3,4-DIMETHOXYTOLUENE
    [Show full text]
  • Distinct Mechanisms of Biotic and Chemical Elicitors Enable Additive Elicitation of the Anticancer Phytoalexin Glyceollin I
    molecules Article Distinct Mechanisms of Biotic and Chemical Elicitors Enable Additive Elicitation of the Anticancer Phytoalexin Glyceollin I Kelli Farrell 1,†, Md Asraful Jahan 2,† and Nik Kovinich 2,* 1 Department of Biology, West Virginia University, Morgantown, WV 26506, USA; [email protected] 2 Division of Plant and Soil Sciences, West Virginia University, Morgantown, WV 26506, USA; [email protected] * Correspondence: [email protected]; Tel.: +1-304-293-9240 † These Authors contributed equally to this article. Received: 16 June 2017; Accepted: 25 July 2017; Published: 27 July 2017 Abstract: Phytoalexins are metabolites biosynthesized in plants in response to pathogen, environmental, and chemical stresses that often have potent bioactivities, rendering them promising for use as therapeutics or scaffolds for pharmaceutical development. Glyceollin I is an isoflavonoid phytoalexin from soybean that exhibits potent anticancer activities and is not economical to synthesize. Here, we tested a range of source tissues from soybean, in addition to chemical and biotic elicitors, to understand how to enhance the bioproduction of glyceollin I. Combining the inorganic chemical silver nitrate (AgNO3) with the wall glucan elicitor (WGE) from the soybean pathogen Phytophthora sojae had an additive effect on the elicitation of soybean seeds, resulting in a yield of up to 745.1 µg gt−1 glyceollin I. The additive elicitation suggested that the biotic and chemical elicitors acted largely by separate mechanisms. WGE caused a major accumulation of phytoalexin gene transcripts, whereas 00 AgNO3 inhibited and enhanced the degradation of glyceollin I and 6 -O-malonyldaidzin, respectively. Keywords: bioproduction; phytoalexin; isoflavonoid; glyceollin; soybean [Glycine max (L.) Merr.] 1.
    [Show full text]
  • Phytoserms in Licorice
    University of Mississippi eGrove Electronic Theses and Dissertations Graduate School 1-1-2019 Cheminformatic Approach for Deconvolution of Active Compounds in a Complex Mixture - phytoserms in Licorice Manal Mohammad Alhusban Follow this and additional works at: https://egrove.olemiss.edu/etd Part of the Pharmacy and Pharmaceutical Sciences Commons Recommended Citation Alhusban, Manal Mohammad, "Cheminformatic Approach for Deconvolution of Active Compounds in a Complex Mixture - phytoserms in Licorice" (2019). Electronic Theses and Dissertations. 1954. https://egrove.olemiss.edu/etd/1954 This Dissertation is brought to you for free and open access by the Graduate School at eGrove. It has been accepted for inclusion in Electronic Theses and Dissertations by an authorized administrator of eGrove. For more information, please contact [email protected]. CHEMINFORMATIC APPROACH FOR DECONVOLUTION OF ACTIVE COMPOUNDS IN A COMPLEX MIXTURE - PHYTOSERMS IN LICORICE A Dissertation Presented in partial fulfillment of requirements for the degree of Doctor of Philosophy in Pharmaceutical Sciences, Emphasis in Pharmacognosy The University of Mississippi Manal M. Alhusban August 2019 Copyright © 2019 by Manal M. Alhusban All rights reserved ABSTRACT The genus Glycyrrhiza, encompasses several species exhibiting complex structural diversity of secondary metabolites and hence biological activities. The intricate nature of botanical remedies, such as licorice, rendered them obsolete for scientific research or medical industry. Understanding and finding the mechanisms of efficacy or safety for a plant-based therapy is very challenging, yet it remains crucial and warranted. The licorice plant is known to have Selective Estrogen Receptor Modulatory effects (SERMs), with a spectrum of estrogenic and anti-estrogenic activities attributed to women’s health.
    [Show full text]