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1

Tarbeeva, Darya V., Evgeny A. Pislyagin, Ekaterina S. Menchinskaya, et al. "Polyphenolic Compounds from Lespedeza bicolor Protect Neuronal Cells from Oxidative Stress." Antioxidants 11, no. 4 (2022): 709. http://dx.doi.org/10.3390/antiox11040709.

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Pterocarpans and related polyphenolics are known as promising neuroprotective agents. We used models of rotenone-, paraquat-, and 6-hydroxydopamine-induced neurotoxicity to study the neuroprotective activity of polyphenolic compounds from Lespedeza bicolor and their effects on mitochondrial membrane potential. We isolated 11 polyphenolic compounds: a novel coumestan lespebicoumestan A (10) and a novel stilbenoid 5’-isoprenylbicoloketon (11) as well as three previously known pterocarpans, two pterocarpens, one coumestan, one stilbenoid, and a dimeric flavonoid. Pterocarpans 3 and 6, stilbenoid
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2

Kim, Soyoung, Yu Jeong Jeong, Su Hyun Park, et al. "The Synergistic Effect of Co-Treatment of Methyl Jasmonate and Cyclodextrins on Pterocarpan Production in Sophora flavescens Cell Cultures." International Journal of Molecular Sciences 21, no. 11 (2020): 3944. http://dx.doi.org/10.3390/ijms21113944.

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Pterocarpans are derivatives of isoflavonoids, found in many species of the family Fabaceae. Sophora flavescens Aiton is a promising traditional Asian medicinal plant. Plant cell suspension cultures represent an excellent source for the production of valuable secondary metabolites. Herein, we found that methyl jasmonate (MJ) elicited the activation of pterocarpan biosynthetic genes in cell suspension cultures of S. flavescens and enhanced the accumulation of pterocarpans, producing mainly trifolirhizin, trifolirhizin malonate, and maackiain. MJ application stimulated the expression of structur
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3

Caamal-Fuentes, Edgar, Rosa Moo-Puc, Luis W. Torres-Tapia, and Sergio R. Peraza-Sanchez. "Pterocarpans from the Root Bark of Aeschynomene Fascicularis." Natural Product Communications 8, no. 10 (2013): 1934578X1300801. http://dx.doi.org/10.1177/1934578x1300801021.

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A new pterocarpan, aeschynocarpin (1), and the known pterocarpan 2-methoxymedicarpin (2) were isolated for the first time from Aeschynomene fascicularis (Fabaceae) and their structures elucidated by means of spectroscopic {UV/Vis, IR, and NMR (1H, 13C, COSY, HMQC, and HMBC)} and mass spectrometric (EI-MS and HRCIMS) techniques. Both compounds were tested in vitro for their cytotoxic and antiproliferative activities against a panel of cancer cell lines. This is the first report on the presence of pterocarpans in the genus Aeschynomene.
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4

Jaques, Ulrike, Helmut Keßmann, and Wolfgang Barz. "Accumulation of Phenolic Compounds and Phytoalexins in Sliced and Elicitor-Treated Cotyledons of Cicer arietinum L." Zeitschrift für Naturforschung C 42, no. 11-12 (1987): 1171–78. http://dx.doi.org/10.1515/znc-1987-11-1206.

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Upon slicing cotyledons of chickpea, Cicer arietinum L.. accumulate the pterocarpan phyto­alexins medicarpin and maackiain. Treatment of this tissue with an elicitor from the phytopathogcnic deuteromyccte Ascochyta rabiei (Pass.) Lab. greatly enhances accumulation of the pterocarpans and of other isoflavones and flavonoids. Isolation, chromatographic purification and structural elucidation by spectroscopic techniques of 16 phenolic compounds is described. Cotyledons induced for phytoalexin biosynthesis readily accumulate the isoflavones daidzein, formononetin, calycosin and pseudobaptigenin wh
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5

Okwute, Simon K., and Lester A. Mitscher. "Structure-Activity Relationship Among the Antibacterial Pterocarpans from African Erythrina Species: A Review." Tropical Journal of Phytochemistry and Pharmaceutical Sciences 3, no. 5 (2024): 303. https://doi.org/10.26538/tjpps/v3i5.2.

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The genus Erythrina, a folkloric medicinal plant found in many tropical regions of the world, has yielded many flavonoids, including isoflavonoids of diverse structures. Some African Erythrina species have been investigated, and many have been found to contain isoflavonoids belonging to the sub-class pterocarpans which have displayed structural variations and interesting antibacterial activities. In this review, the structures and antibacterial activities of 14 pterocarpans reported in the literature from 8 African Erythrina species have been collated and subjected to structure-activity relati
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6

Höhl, Birgit, Martin Arnemann, Ludger Schwenen, et al. "Degradation of the Pterocarpan Phytoalexin (—)-Maackiain by Ascochyta rabiei." Zeitschrift für Naturforschung C 44, no. 9-10 (1989): 771–76. http://dx.doi.org/10.1515/znc-1989-9-1012.

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Ten strains of Ascochyta rabiei pathogenic to chickpea ( Cicer arietinum L.) were shown to be potent degraders of the chickpea pterocarpan phytoalexin ( - )-maackiain (1) ([6aR: 11 aR]-3- hydroxy-8,9-methylenedioxypterocarpan). In degradative studies with mycelial preparations and crude protein extracts seven catabolites could be isolated and structurally elucidated by spectroscopic techniques. The main routes of maackiain degradation are reduction to a 2´-hydroxyisoflavan (2) and oxidation to an 1 a-hydroxy-pterocarp-1,4-diene-3-one (3) with subsequent reductions of the early catabolites in r
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7

Tahara, Satoshi, and John L. Ingham. "Metabolism of the Prenylated Pterocarpan Edunol by Aspergillus flavus." Zeitschrift für Naturforschung C 42, no. 9-10 (1987): 1050–54. http://dx.doi.org/10.1515/znc-1987-9-1008.

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When incubated in liquid culture with Aspergillus flavus, the prenylated pterocarpan (-)-edunol [2-(3,3-dimethylallyl)-3-hydroxy-8,9-methylenedioxypterocarpan (1)] was converted into a dihydrofurano-pterocarpan (2), a dihydropyrano-pterocarpan (3). and a 2,3-dihydro- dihydroxyprenyl-substituted pterocarpan (4).
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8

Ingham, John L. "A Further Investigation of Phytoalexin Formation in the Genus Trifolium." Zeitschrift für Naturforschung C 45, no. 7-8 (1990): 829–34. http://dx.doi.org/10.1515/znc-1990-7-814.

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Abstract An earlier study of phytoalexin formation in the genus Trifolium has now been extended to include a further 61 species and subspecies. Using the drop-diffusate method, isoflavonoid phytoalexins were isolated from the fungus-inoculated leaflets of 55 accessions, whilst four others produced the stilbene derivative resveratrol. Phytoalexins could not be obtained from the leaflets of two species, T. billardieri and T. grandiflorum. The pterocarpan medicarpin was the most commonly encountered phytoalexin, occurring alone or in various combinations with the known Trifolium isofjavonoids maa
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9

Zhang, Zhi-Jun, Guo-Xian Li, Dan Liu, Xuan-Qin Chen, Hong-Mei Li, and Rong-Tao Li. "A Novel Pterocarpan Derivative From the Roots of Sophora flavescens." Natural Product Communications 15, no. 10 (2020): 1934578X2096467. http://dx.doi.org/10.1177/1934578x20964677.

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Flavescensin A (1), a novel rearrangement derivative of pterocarpan with an unusual spirotetrahydrofuran ring, along with 7 known pterocarpans were isolated from the roots of Sophora flavescens using several different chromatographic separations. The planar structure of 1 was elucidated by their nuclear magnetic resonance spectroscopic and high-resolution electrospray ionization mass spectrometry data, and the absolute configuration of 1 was determined on the basis of electronic circular dichroism data. Putative biosynthetic pathway toward 1 was proposed. In addition, all of the compounds were
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10

Máximo, Patrícia, Ana Lourenço, Sónia Savluchinske Feio, and Jose Carlos Roseiro. "Flavonoids from Ulex Species." Zeitschrift für Naturforschung C 55, no. 7-8 (2000): 506–10. http://dx.doi.org/10.1515/znc-2000-7-804.

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Abstract Nine flavonoids have been isolated from Ulex jussiaei and U. minor (Leguminosae). From both species the isoflavonoids ulexin A and the new naturally occurring ulexin B have been identified, together with isoderrone, the pterocarpans (-)-maackiain and (-)-4-methoxymaackiain, and the chalcone isobavachromene. The pterocarpan (-)-2-methoxymaackiain was only present in the first species and the isoflavones isolupalbigenin and ulexone A have been identified in the second one. 13C NMR data of isobavachromene, isolupalbigenin and ulexone A are also included. The antifungal activity of the is
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11

Ingham, John L., and Satoshi Tahara. "Isoneorautenol and Other Pterocarpan Phytoalexins from Calopogonium mucunoides." Zeitschrift für Naturforschung C 40, no. 7-8 (1985): 482–89. http://dx.doi.org/10.1515/znc-1985-7-805.

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Abstract Following inoculation with the fungus Helm inthosporium carbonum , excised leaflets of the tropical papilionate legume Calopogonium mucunoides have been found to produce isoneorautenol, a new dimethylpyrano-substituted isoflavonoid (pterocarpan) phytoalexin. This compound accumulates together with dem ethylm edicarpin, neodunol, tuberosin, sophorap-terocarpan A, and a sixth highly antifungal isoflavonoid (calopocarpin) characterised as 3,9-dihydroxy-2-(3,3-dimethylallyl)pterocarpan. Chromatographic and spectroscopic examination of ‘hom oedudiol’ (a pterocarpan from N eorautanenia edul
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12

Benhabrou, Hakim, Fatma Bitam, Luigia Cristino, et al. "Prenyl Pterocarpans from Algerian Bituminaria bituminosa and Their Effects on Neuroblastoma." Molecules 29, no. 15 (2024): 3678. http://dx.doi.org/10.3390/molecules29153678.

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The pterocarpan fraction from aerial parts of Bituminaria bituminosa was investigated for both chemical characterization and biological evaluation. Chemical studies were in accordance with the literature data on Bituminaria genus resulting in the identification of typical 4,8-prenyl pterocarpans. Three new members, bituminarins A–C (1–3), were isolated along with main bitucarpin A (4), erybraedin C (5) and erybraedin D (6) already reported from this plant. Further, biological studies evidenced antiproliferative properties of the most abundant pterocarpans 4 and 5 on neuroblastoma SH-SY5Y cell
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13

., Wan-Yaacob Ahamd, Ikram M. Said ., Siau-Yuen Soon ., Hiromitsu Takayama ., Mirako Kitajima ., and Norio Aimi . "A Pterocarpan from Erythrina variegata." Journal of Biological Sciences 2, no. 8 (2002): 542–44. http://dx.doi.org/10.3923/jbs.2002.542.544.

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14

Lichtenfels, Ricardo A., Antonio L. Coelho, and Paulo R. R. Costa. "Total synthesis of pterocarpan: (±)-neorautenane." J. Chem. Soc., Perkin Trans. 1, no. 7 (1995): 949–51. http://dx.doi.org/10.1039/p19950000949.

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15

Tanaka, Hitoshi, Toshihiro Tanaka, and Hideo Etoh. "A pterocarpan from Erythrina orientalis." Phytochemistry 45, no. 1 (1997): 205–7. http://dx.doi.org/10.1016/s0031-9422(96)00841-2.

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16

Máximo, Patrícia, and Ana Lourenço. "A pterocarpan from Ulex parviflorus." Phytochemistry 48, no. 2 (1998): 359–62. http://dx.doi.org/10.1016/s0031-9422(97)01090-x.

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17

Tanaka, Hitoshi, Toshihiro Tanaka, and Hideo Etoh. "A pterocarpan from Erythrina orientalis." Phytochemistry 42, no. 5 (1996): 1473–75. http://dx.doi.org/10.1016/0031-9422(96)00138-0.

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18

Mackenbrock, Ulrike, and Wolfgang Barz. "Elicitor-Induced Formation of Pterocarpan Phytoalexins in Chickpea (Cicer arietinum L.) Cell Suspension Cultures from Constitutive Isoflavone Conjugates upon Inhibition of Phenylalanine Ammonia Lyase." Zeitschrift für Naturforschung C 46, no. 1-2 (1991): 43–50. http://dx.doi.org/10.1515/znc-1991-1-208.

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After inhibition of phenylalanine ammonia lyase by L- α-aminooxy-β-phenylpropionic acid, the constitutively formed formononetin 7-O-glucoside-6″-O-malonate is metabolized with the isoflavone aglycone being used as an intermediate in the elicitor-induced formation of pterocarpan phytoalexins in chickpea cell suspension cultures. In elicited cultures not treated with the inhibitor phytoalexins are synthesized de novo from phenylalanine. Therefore, in chickpea cells the constitutive isoflavone conjugate metabolism and the elicitor-induced pterocarpan formation show metabolic linkage under specifi
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19

Höhl, Birgit, and Wolfgang Barz. "Partial Characterization of an Enzyme from the Fungus Ascochyta rabiei for the Reductive Cleavage of Pterocarpan Phytoalexins to 2′-Hydroxyisoflavans." Zeitschrift für Naturforschung C 42, no. 7-8 (1987): 897–901. http://dx.doi.org/10.1515/znc-1987-7-828.

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Crude protein extracts from the chickpea (Cicer arietinum L.) pathogenic fungus Ascochyta rabiei catalyze the NADPH dependent conversion of the pterocarpan phytoalexins medicarpin and maackiain to 1) 2′-hydroxyisoflavans, 2) 1 a-hydroxypterocarp-1,4-diene-3-one, and 3) 10,2′-dihydroxyisoflav-8-ene-7-one derivatives. A pterocarpan : NADPH oxidoreductase which cleaves the benzylphenyl ether bond of the phytoalexins was purified some 100-fold and partially characterized with regard to its kinetic properties. The oxidoreductase was shown to be specific for NADPH and 3-hydroxypterocarpans. The enzy
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20

Dyshlovoy, Sergey A., Darya Tarbeeva, Sergey Fedoreyev, et al. "Polyphenolic Compounds from Lespedeza Bicolor Root Bark Inhibit Progression of Human Prostate Cancer Cells via Induction of Apoptosis and Cell Cycle Arrest." Biomolecules 10, no. 3 (2020): 451. http://dx.doi.org/10.3390/biom10030451.

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From a root bark of Lespedeza bicolor Turch we isolated two new (7 and 8) and six previously known compounds (1–6) belonging to the group of prenylated polyphenols. Their structures were elucidated using mass spectrometry, nuclear magnetic resonance and circular dichroism spectroscopy. These natural compounds selectively inhibited human drug-resistant prostate cancer in vitro. Prenylated pterocarpans 1–3 prevented the cell cycle progression of human cancer cells in S-phase. This was accompanied by a reduced expression of mRNA corresponding to several human cyclin-dependent kinases (CDKs). In c
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21

Ruangrungsi, Nijsiri, Pranorm Khaomek, Ekarin Saifah, et al. "A New Pterocarpan from Erythrina fusca." HETEROCYCLES 63, no. 4 (2004): 879. http://dx.doi.org/10.3987/com-03-9994.

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22

Babu, U. V., S. P. S. Bhandari, and H. S. Garg. "Barbacarpan, a pterocarpan from Crotalaria barbata." Phytochemistry 48, no. 8 (1998): 1457–59. http://dx.doi.org/10.1016/s0031-9422(97)00876-5.

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23

Manjary, Frédéric, Alain Petitjean, Jean-Yves Conan, et al. "A prenylated pterocarpan from Mundulea striata." Phytochemistry 33, no. 2 (1993): 515–17. http://dx.doi.org/10.1016/0031-9422(93)85554-5.

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24

Yamamoto, Hirobumi, Masahiko Ichimura, Noriko Ishikawa, Toshiyuki Tanaka, Munekazu Iinuma, and Mizuo Mizuno. "Localization of Prenylated Flavonoids in Sophora flavescens var. angustifolia Plants." Zeitschrift für Naturforschung C 47, no. 7-8 (1992): 535–39. http://dx.doi.org/10.1515/znc-1992-7-808.

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A histochemical analysis was carried out on the distribution of flavonoid derivatives in Sophora flavescens var. angustifolia plant. Prenylated flavonoids such as kushenol I, kurarinone, sophoraflavanone G and des-O-methylanhydroicaritin were mainly localized in the periderm (cork layers, and cork layer-like tissues scattered in parenchymatous tissues of the root system). Pterocarpan derivatives, maackiain, maackiain-3-O-glucoside (trifolirhizin) and its 6′-O-malonyl ester, were distributed in the cortex, cambium and pith as an ester form. In the aerial parts of the plant, neither pterocarpan
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25

Kiss, Loránd, László Szilágyi, and Sándor Antus. "A Simple Conversion of 2'-Benzyloxyflavanone to Pterocarpan." Zeitschrift für Naturforschung B 57, no. 10 (2002): 1165–68. http://dx.doi.org/10.1515/znb-2002-1014.

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26

Osswald, Wolfgang F., Sigrid Zieboll, and E. F. Elstner. "Comparison of pH Changes and Elicitor Induced Production of Glyceollin Isomers in Soybean Cotyledons." Zeitschrift für Naturforschung C 40, no. 7-8 (1985): 477–81. http://dx.doi.org/10.1515/znc-1985-7-804.

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Abstract During the incubation of soybean cotyledons with Pmg-elicitor for 22 hours the pH of the diffusion droplets increases from 7.2 to 8.3. This pH-shift is a precondition for the formation of the typical red colour of the diffusion droplet. After inhibiting the pH-shift by the use of 100 mм phosphate or Tris buffer instead of 10 mм buffer as solvent for the elicitor, the red colour is no longer formed with the exeption of 100 mM Ammediol buffer. However, the normal pattern of pterocarpan induction can be measured in the absence of the red colour in the diffusion droplet. Tris and Ammediol
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27

Lu, Kai‐Zhou, Zi‐Ming Feng, Xiang Yuan, et al. "Five Novel Pterocarpan Derivatives from Sophora flavescens." Chinese Journal of Chemistry 39, no. 10 (2021): 2763–68. http://dx.doi.org/10.1002/cjoc.202100357.

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28

Herath, H. M. T. B., R. S. Dassanayake, A. M. A. Priyadarshani, Susila De Silva, G. P. Wannigama, and Joanne Jamie. "Isoflavonoids and a pterocarpan from Gliricidia sepium." Phytochemistry 47, no. 1 (1998): 117–19. http://dx.doi.org/10.1016/s0031-9422(97)00517-7.

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29

Spencer, Gayland F., Barry E. Jones, Ronald D. Plattner, David E. Barnekow, Linda S. Brinen, and Jon Clardy. "A pterocarpan and two isoflavans from alfalfa." Phytochemistry 30, no. 12 (1991): 4147–49. http://dx.doi.org/10.1016/0031-9422(91)83483-2.

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30

Subarnas, Anas, Yoshiteru Oshima, and Hiroshi Hikino. "Isoflavans and a pterocarpan from Astragalus mongholicus." Phytochemistry 30, no. 8 (1991): 2777–80. http://dx.doi.org/10.1016/0031-9422(91)85143-n.

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31

Kobayashi, Akio, Kohki Akiyama, and Kazuyoshi Kawazu. "A pterocarpan, (+)-2-hydroxypisatin from Pisum sativum." Phytochemistry 32, no. 1 (1992): 77–78. http://dx.doi.org/10.1016/0031-9422(92)80110-z.

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32

LICHTENFELS, R. A., A. L. COELHO, and P. R. R. COSTA. "ChemInform Abstract: Total Synthesis of Pterocarpan: (.+-.)-Neorautenane." ChemInform 26, no. 33 (2010): no. http://dx.doi.org/10.1002/chin.199533246.

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33

MAXIMO, P., and A. LOURENCO. "ChemInform Abstract: A Pterocarpan from Ulex parviflorus." ChemInform 29, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.199839267.

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34

T�th, E., Z. Dinya, and S. Antus. "Mass spectrometric studies of the pterocarpan skeleton." Rapid Communications in Mass Spectrometry 14, no. 24 (2000): 2367–72. http://dx.doi.org/10.1002/1097-0231(20001230)14:24<2367::aid-rcm174>3.0.co;2-c.

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35

ARVIND, KUMAR JAIN. "A New Pterocarpan Glycoside from Trifolium pratense." Journal of Indian Chemical Society Vol. 65, Jan 1988 (1988): 69. https://doi.org/10.5281/zenodo.6122710.

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Chemistry Department, Dr. H. S. Gour Vishwavidyalay,&nbsp;Sagar-470 009 <em>Manuscript received 16 April 1987, revised 23 September 1987, accepted 2 December 1987</em>&nbsp; TRIFOLIUM pratense (N.O. Leguminosae) is native from Kashmir to Garhwal, and is reported to be used as expectorant and also as an important ingradient for the treatment of ulcers. The present communication reports the isolation of maackiain 3-<em>O-&beta;</em>-D-galactopyranoside from its roots.
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36

Bleβ, W., and W. Barz. "Isolation of pterocarpan synthase, the terminal enzyme of pterocarpan phytoalexin biosynthesis in cell suspension culures of Cicer arietinum." FEBS Letters 239, no. 1 (1988): 159. http://dx.doi.org/10.1016/0014-5793(88)80567-2.

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37

Bleß, Wolfgang, and Wolfgang Barz. "Isolation of pterocarpan synthase, the terminal enzyme of pterocarpan phytoalexin biosynthesis in cell suspension cultures of Cicer arietinum." FEBS Letters 235, no. 1-2 (1988): 47–50. http://dx.doi.org/10.1016/0014-5793(88)81231-6.

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38

Gunia, Werner, Walter Hinderer, Uta Wittkampf, and Wolfgang Barz. "Elicitor Induction of Cytochrome P-450 Monooxygenases in Cell Suspension Cultures of Chickpea (Cicer arietinum L.) and Their Involvement in Pterocarpan Phytoalexin Biosynthesis." Zeitschrift für Naturforschung C 46, no. 1-2 (1991): 58–66. http://dx.doi.org/10.1515/znc-1991-1-210.

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Abstract A yeast glucan elicitor causes the accumulation of the pterocarpan phytoalexins medicarpin and maackiain in chickpea (Cicer arietinum) cell suspension cultures established from seeds. A cell culture line from a chickpea cultivar resistant against its main fungal pathogen Ascochyta rabiei accumulates large amounts (944 nm ol/g fr. wt.) whereas a cell culture line from a susceptible cultivar accumulates only low amounts (38 nm ol/g fr. wt.) of the phytoalexins. This is consistent with differential accumulation of pterocarpan phytoalexins in intact plants [1], The first reactions in the
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39

Niu, De-Yun, Yin-Ke Li, Xian-Xue Wu, Yun-Dong Shi, Qiu-Fen Hu, and Xue-Mei Gao. "Pterocarpan Derivatives from Clinopodium urticifolium and Their Cytotoxicity." Asian Journal of Chemistry 25, no. 17 (2013): 9672–74. http://dx.doi.org/10.14233/ajchem.2013.15127.

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40

Leonti, Marco, Laura Casu, Jürg Gertsch, et al. "A pterocarpan from the seeds of Bituminaria morisiana." Journal of Natural Medicines 64, no. 3 (2010): 354–57. http://dx.doi.org/10.1007/s11418-010-0408-7.

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41

Chattopadhyay, Shital K., Indranil Kundu, and Ratnava Maitra. "The coumarin–pterocarpan conjugate – a natural product inspired hybrid molecular probe for DNA recognition." Org. Biomol. Chem. 12, no. 40 (2014): 8087–93. http://dx.doi.org/10.1039/c4ob01360c.

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Thermally induced cascade sigmatropic rearrangement of a butynyloxycoumarin derivative has led to a quick access to the coumarin–pterocarpan hybrid molecule. Biophysical studies together with molecular modeling show that this nature-inspired hybrid molecule is capable of binding to the minor groove of DNA as a non-conventional entity.
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42

Meng, Qingyan, Syed G. A. Moinuddin, Sung-Jin Kim, et al. "Pterocarpan synthase (PTS) structures suggest a common quinone methide–stabilizing function in dirigent proteins and proteins with dirigent-like domains." Journal of Biological Chemistry 295, no. 33 (2020): 11584–601. http://dx.doi.org/10.1074/jbc.ra120.012444.

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The biochemical activities of dirigent proteins (DPs) give rise to distinct complex classes of plant phenolics. DPs apparently began to emerge during the aquatic-to-land transition, with phylogenetic analyses revealing the presence of numerous DP subfamilies in the plant kingdom. The vast majority (&gt;95%) of DPs in these large multigene families still await discovery of their biochemical functions. Here, we elucidated the 3D structures of two pterocarpan-forming proteins with dirigent-like domains. Both proteins stereospecifically convert distinct diastereomeric chiral isoflavonoid precursor
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43

Al-Oriquat, Galib, and Mohammad Afzal. "Proton Magnetic Resonance Spectra of Pterocarpan and Related Phytoalexins." HETEROCYCLES 24, no. 10 (1986): 2911. http://dx.doi.org/10.3987/r-1986-10-2911.

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44

Lwande, W., M. D. Bentley, C. Macfoy, F. N. Lugemwa, A. Hassanali, and E. Nyandat. "A new pterocarpan from the roots of Tephrosia hildebrandtii." Phytochemistry 26, no. 8 (1987): 2425–26. http://dx.doi.org/10.1016/s0031-9422(00)84742-1.

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45

Mizuno, Mizuo, Toshiyuki Tanaka, Masami Katsuragawa, Harumi Saito, and Munekazu Iinuma. "A New Pterocarpan from the Heartwood of Cladrastis platycarpa." Journal of Natural Products 53, no. 2 (1990): 498–99. http://dx.doi.org/10.1021/np50068a037.

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46

Kraft, B., L. Schwenen, D. St�ckl, and W. Barz. "Degradation of the pterocarpan phytoalexin medicarpin by Ascochyta rabiei." Archives of Microbiology 147, no. 2 (1987): 201–6. http://dx.doi.org/10.1007/bf00415285.

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47

HERATH, H. M. T. B., R. S. DASSANAYAKE, A. M. A. PRIYADARSHANI, S. DE SILVA, G. P. WANNIGAMA, and J. JAMIE. "ChemInform Abstract: Isoflavonoids and a Pterocarpan from Gliricidia sepium." ChemInform 29, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.199813226.

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48

Wang, Hong-Yan, Teng Li, Rui Ji, et al. "Metabolites of Medicarpin and Their Distributions in Rats." Molecules 24, no. 10 (2019): 1966. http://dx.doi.org/10.3390/molecules24101966.

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Abstract:
Medicarpin is a bioactive pterocarpan that has been attracting increasing attention in recent years. However, its metabolic fate in vivo is still unknown. To clarify its metabolism and the distribution of its metabolites in rats after oral administration, the HPLC-ESI-IT-TOF-MSn technique was used. A total of 165 new metabolites (13 phase I and 152 phase II metabolites) were tentatively identified, and 104, 29, 38, 41, 74, 28, 24, 15, 42, 8, 10, 3, and 17 metabolites were identified in urine, feces, plasma, the colon, intestine, stomach, liver, spleen, kidney, lung, heart, brain, and thymus, r
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49

Engler, Thomas A., Kenneth O. LaTessa, Rajesh Iyengar, Wenying Chai, and Konstantinos Agrios. "Stereoselective syntheses of substituted pterocarpans with anti-HIV activity, and 5-aza-/5-thia-pterocarpan and 2-aryl-2,3-dihydrobenzofuran analogues." Bioorganic & Medicinal Chemistry 4, no. 10 (1996): 1755–69. http://dx.doi.org/10.1016/0968-0896(96)00192-7.

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50

Daniel, Susanne, Walter Hinderer, and Wolfgang Barz. "Elicitor-induced Changes of Enzyme Activities Related to Isoflavone and Pterocarpan Accumulation in Chickpea (Cicer arietinum L.) Cell Suspension Cultures." Zeitschrift für Naturforschung C 43, no. 7-8 (1988): 536–44. http://dx.doi.org/10.1515/znc-1988-7-810.

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The extractable activities of thirteen enzymes of primary and secondary metabolism have been measured in chickpea (Cicer arietinum L.) cell suspension cultures after treatment with an elicitor from the fungus Ascochyta rabiei (Pass.) Lab. The cell culture, derived from the A. rabiei resistant cultivar ILC 3279, constitutively accumulated the isoflavones biochanin A and formononetin together with their 7-O-glucosides and the 7-O-glucoside-6″-malonates. After elicitor application the cells rapidly form the pterocarpan phytoalexins medicarpin and maackiain. Among the enzymes of primary metabolism
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