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Collect. Czech. Chem. Commun. 1978, 43, 2779-2799
https://doi.org/10.1135/cccc19782779

Use of structural changes for stereochemical assignments of natural α-exomethylene γ-lactones of the germacra-1(10),4-dienolide type on the basis of allylic and vicinal couplings of bridgehead protons. Hydrogenation of endocyclic double bonds

Zdeněk Samek and Juraj Harmatha

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  • Harmatha Juraj, Zídek Zdeněk, Kmoníčková Eva: Inhibitory Effect of Selected Guaianolide and Germacranolide Sesquiterpene Lactones on Nitric Oxide Production. Molecules 2024, 29, 3289. <https://doi.org/10.3390/molecules29143289>
  • Turdybekov K. M., Morozova O. A., Ivasenko S. A., Makhmutova A. S., Turdybekov D. M., Adekenov S. M.: Molecular Structure and Absolute Configuration of Tatridin A and B from Lepidolopha karatavica. Chem Nat Compd 2021, 57, 83. <https://doi.org/10.1007/s10600-021-03288-z>
  • Álvarez-Calero José María, Ruiz Enrique, López-Pérez José Luis, Jaraíz Martín, Rubio José E., Jorge Zacarías D., Suárez Margarita, Massanet Guillermo M.: 15-Hydroxygermacranolides as Sources of Structural Diversity: Synthesis of Sesquiterpene Lactones by Cyclization and Rearrangement Reactions. Experimental and DFT Study. J. Org. Chem. 2018, 83, 5480. <https://doi.org/10.1021/acs.joc.8b00407>
  • Adekenov S. M., Makubaeva A. I., Kokkozov D. N., Kanafin E. N., Korneev V. S., Gatilov Yu. V., Kishkentaeva A. S., Atazhanova G. A.: Chemical Composition of Artemisia aralensis. Chem Nat Compd 2016, 52, 417. <https://doi.org/10.1007/s10600-016-1662-z>
  • Harmatha Juraj, Vokáč Karel, Buděšínský Miloš, Zídek Zdeněk, Kmoníčková Eva: Immunobiological properties of sesquiterpene lactones obtained by chemically transformed structural modifications of trilobolide. Fitoterapia 2015, 107, 90. <https://doi.org/10.1016/j.fitote.2015.10.002>
  • Ríos V. Eunice, León Alejandra, Chávez María Isabel, Torres Yuridia, Ramírez-Apan María Teresa, Toscano Rubén A., Bravo-Monzón Ángel E., Espinosa-García Francisco J., Delgado Guillermo: Sesquiterpene lactones from Mikania micrantha and Mikania cordifolia and their cytotoxic and anti-inflammatory evaluation. Fitoterapia 2014, 94, 155. <https://doi.org/10.1016/j.fitote.2014.02.006>
  • Mukhamatkhanova R. F., Shamˈyanov I. D., Zakirov S. Kh., Tashkhodzhaev B., Levkovich M. G., Abdullaev N. D.: A new melampolide and other secondary metabolites from Artemisia baldshuanica. Chem Nat Compd 2011, 47, 726. <https://doi.org/10.1007/s10600-011-0044-9>
  • Barquera-Lozada José E., Quiroz-García Beatriz, Quijano Leovigildo, Cuevas Gabriel: Conformational Properties of the Germacradienolide 6-Epidesacetyllaurenobiolide by Theory and NMR Analyses. J. Org. Chem. 2010, 75, 2139. <https://doi.org/10.1021/jo902170w>
  • Adio Adewale M.: Germacrenes A–E and related compounds: thermal, photochemical and acid induced transannular cyclizations. Tetrahedron 2009, 65, 1533. <https://doi.org/10.1016/j.tet.2008.11.050>
  • Barquera-Lozada José Enrique, Cuevas Gabriel: Biogenesis of Sesquiterpene Lactones Pseudoguaianolides from Germacranolides: Theoretical Study on the Reaction Mechanism of Terminal Biogenesis of 8-Epiconfertin. J. Org. Chem. 2009, 74, 874. <https://doi.org/10.1021/jo802445n>
  • Appendino Giovanni, Taglialatela-Scafati Orazio, Romano Adriana, Pollastro Federica, Avonto Cristina, Rubiolo Patrizia: Genepolide, a Sesterpene γ-Lactone with a Novel Carbon Skeleton from Mountain Wormwood (Artemisia umbelliformis). J. Nat. Prod. 2009, 72, 340. <https://doi.org/10.1021/np800468m>
  • Tashkhodzhaev B., Sham’yanov I. D., Izbosarov M. B., Antipin M. Yu.: Crystal and molecular structure of 13-diethanolamino-deacetyllaurenobiolide. Macrocycle conformation in linear germacrolides. Chem Nat Compd 2004, 40, 552. <https://doi.org/10.1007/s10600-005-0034-x>
  • Perry Katia S. P., Miguez Eduardo, de Amorim Mauro B., Boaventura Maria Amelia D., da Silva Antonio Jorge R.: Reassignment of NMR spectra and conformational study of the sesquiterpene lactone goyazensolide. Magnetic Reson in Chemistry 2001, 39, 219. <https://doi.org/10.1002/mrc.819>
  • Izbosarov M. B., Abduazimov B. Kh., Yusupova I. M., Tashkhodzhaev B., Vdovin A. D., Abdullaev N. D.: Germacranolide fromTanacetopsis mucronata. Chem Nat Compd 1998, 34, 456. <https://doi.org/10.1007/BF02329594>
  • Tashkhodzhaev B., Makhmudov M. K.: Conformational analysis of e,e-germacranes by the method of molecular mechanics. Chem Nat Compd 1997, 33, 289. <https://doi.org/10.1007/BF02234876>
  • Tashkhodzhaev B., Abduazimov B. Kh.: Stereochemistry of sesquiterpenes of the germacrane type. Chem Nat Compd 1997, 33, 382. <https://doi.org/10.1007/BF02282357>
  • Turdybekov K. M., Edil'baeva T. T.: Conformational analysis of sesquiterpene lactones of germacrane type. Russ Chem Bull 1997, 46, 254. <https://doi.org/10.1007/BF02494356>
  • Appendino Giovanni, Jakupovic Jasmin, Jakupovic Sven: Sesquiterpenoids from Pallenis spinosa. Phytochemistry 1997, 46, 1039. <https://doi.org/10.1016/S0031-9422(97)00386-5>
  • Edil'baeva T. T., Turdybekov K. M., Gafurov N. M., Adekenov S. M., Muldakhmetov Z. M.: Structure of the Z,Z-Germacranolide 1(10)Z,4Z-Hanphyllin. Chem Nat Compd 1996, 32, 39. <https://doi.org/10.1007/BF01373787>
  • Turdybekov K. M., Edil'baeva T. T.: Conformational analysis of sesquiterpene lactones of the germacrane type 1. 1(10)E,4E-Germacranolides. Russ Chem Bull 1996, 45, 2741. <https://doi.org/10.1007/BF01430633>
  • Turdybekov Koblandy M., Gafurov Nurlan M., Adekenov Sergazy M., Struchkov Yurii T.: Photochemical Transformation of Hanphilline and Crystal Structure of 1(10)Z,4Z-Hanphilline. Mendeleev Communications 1994, 4, 81. <https://doi.org/10.1070/MC1994v004n03ABEH000356>
  • Makhmudov M. K., Tashkhodzhaev B., Abduazimov B. Kh.: Spatial structure of the dimeric sesquiterpene germacrane lactone mikagoyanolide. Chem Nat Compd 1993, 29, 174. <https://doi.org/10.1007/BF00630109>
  • Cox Philip J.: X-ray and molecular mechanics studies on the sesquiterpene lactone eupatocunin-o-bromobenzoate ? An unusual case of disorder involving atropisomerism. Journal of Crystallographic and Spectroscopic Research 1993, 23, 203. <https://doi.org/10.1007/BF01190048>
  • Marco J.Alberto, Sanz-cervera Juan F., Carda Miguel, Lex Johann: Oxygenated germacranes from Santolina chamaecyparissus. Phytochemistry 1993, 34, 1549. <https://doi.org/10.1016/S0031-9422(00)90844-6>
  • Silva Gloria L., Gil Roberto R., Sosa Virginia E., Suárez Angela R.: Structural and conformation analysis of sesquiterpene lactones by proton nuclear magnetic resonance. Phytochemical Analysis 1992, 3, 258. <https://doi.org/10.1002/pca.2800030605>
  • Cisero Marco, Appendino Giovanni, Tagliapietra Silvia, Mario Nano Gian: A sesquiterpene alcohol from the fruits of Laurus nobilis. Phytochemistry 1992, 31, 2537. <https://doi.org/10.1016/0031-9422(92)83320-X>
  • Abduazimov B. Kh., Tashkhodzhaev B., Nasirov S., Sham'yanov I. D., Yagudaev M. R., Malikov V. M., Aminov S. N.: Structure of mucrolide. Chem Nat Compd 1991, 27, 15. <https://doi.org/10.1007/BF00629823>
  • Adekenov S. M., Gafurov N. M., Turdybekov K. M., Lindeman S. V., Struchkov Yu. T.: Chemical modification of the trans,trans-germacranolide stizolicin synthesis, molecular, and crystal structure of 6α-acetoxy-13-methoxy-1,10; 4,5-diepoxy-1,5,7α(H),8,11β(H)-E,E-germacr-8,12-olide. Chem Nat Compd 1991, 27, 690. <https://doi.org/10.1007/BF00629927>
  • Turdybekov K. M., Lindeman S. V., Timofeeva T. V., Struchkov Yu. T.: Conformations of the 10-membered ring and relative stabilities of conformers of (E,E)-?1(10),4-germacranolides. Chem Nat Compd 1991, 27, 288. <https://doi.org/10.1007/BF00630311>
  • Adekenov S. M., Turdybekov K. M., Kadirberlina G. M., Lindeman S. V., Struchkov Yu. T.: Molecular and crystal structure of jurineolide — A germacrane lactone from Jurinea multiflora. Chem Nat Compd 1991, 27, 426. <https://doi.org/10.1007/BF00636561>
  • Sanz Juan F., García-Sarrión Asunción, Marco J.Alberto: Germacrane derivatives from Santolina chamaecyparissus. Phytochemistry 1991, 30, 3339. <https://doi.org/10.1016/0031-9422(91)83205-Y>
  • Sigstad Emma E., Catalán César A.N., Gutiérrez Alicia B., Diaz Jesús G., Goedken Virgil L., Herz Werner: Guaianolides and germacranolides from Stevia grisebachiana. Phytochemistry 1991, 30, 1933. <https://doi.org/10.1016/0031-9422(91)85043-Y>
  • Makhmudov M. K., Tashkhodzhaev B., Zakirov S. Kh.: Molecular and crystal structure of the sesquiterpene lactone ketopelenolide A. Chem Nat Compd 1990, 26, 283. <https://doi.org/10.1007/BF00597849>
  • Makhmudov M. K., Tashkhodzhaev B., Saidkhodzhaev A. I., Ibragimov B. T.: X-ray structural investigation of sesquiterpene esters of plants of the genus Ferula. VI. Crystal and molecular structure of ugaferin. Chem Nat Compd 1990, 26, 157. <https://doi.org/10.1007/BF00607533>
  • Moiseeva G. P., Abduazimov B. Kh.: Stereochemical features of the structure of germacrane lactones and the applicability of Geissman's rule in this series. Chem Nat Compd 1990, 26, 630. <https://doi.org/10.1007/BF00630070>
  • Cowe Heather J., Cox Philip J., Alan Howie R.: Crystal and molecular structure of Zoapatanolide B, a sesquiterpene lactone. Journal of Crystallographic and Spectroscopic Research 1990, 20, 571. <https://doi.org/10.1007/BF01221899>
  • Makhmudov M. K., Tashkhodzhaev B., Yusunova I. M., Sham'yanov I. D., Yagudaev M. R., Malikov V. M.: Spatial structure of the germacrane lactones hanphyllin, salonitenolide, and sachosin. Chem Nat Compd 1989, 25, 657. <https://doi.org/10.1007/BF00598259>
  • Turdybekov K. M., Adekenov S. M., Timofeeva T. V., Lindeman S. V., Struchkov Yu. T.: Molecular and crystal structure of the germacranolides salonitenolide and hanphyllin. Chem Nat Compd 1989, 25, 662. <https://doi.org/10.1007/BF00598260>
  • Appendino Giovanni, Cravotto Giancarlo, Gariboldi Pierluigi, Claudi Francesco, Picci Vincenzo: A sesquiterpene alcohol from Pallenis spinosa. Phytochemistry 1989, 28, 849. <https://doi.org/10.1016/0031-9422(89)80127-X>
  • Moiseeva G. P., Yusupova I. M., Abduazimov B. Kh., Sidyakin G. P.: Circular dichroism of some sesquiterpene lactones of the germacrane type. Chem Nat Compd 1986, 22, 163. <https://doi.org/10.1007/BF00574730>
  • Quijano Leovigildo, Calderón José S., Gómez-Garibay Federico, Bautista Simeon, Rios Tirso, Fronczek Frank R.: Montafrusin B, a germacrolide from Montanoa frutescens and the molecular structure of montafrusin A. Phytochemistry 1986, 25, 695. <https://doi.org/10.1016/0031-9422(86)88026-8>
  • De Pascual Teresa Joaquín, Morán Joaquín R., Hernández José M., Grande Manuel: 12-Hydroxytovarol and derivatives from Thapsia villosa var. minor. Phytochemistry 1986, 25, 1167. <https://doi.org/10.1016/S0031-9422(00)81573-3>
  • Stewart Edwin, Mabry Tom J.: Sesquiterpene lactones from Schkuhria anthemoidea var. wislizenii. Phytochemistry 1985, 24, 2731. <https://doi.org/10.1016/S0031-9422(00)80709-8>
  • Herz Werner, Kulanthaivel Palaniappan: Diterpenes and sesquiterpene lactones from Mikania congesta. Phytochemistry 1985, 24, 1761. <https://doi.org/10.1016/S0031-9422(00)82547-9>
  • de Pascual Teresa Joaquín, Morán Joaquín R., Hernández José M., Grande Manuel: Tovarol and other germacrane derivatives from Thapsia villosa. Phytochemistry 1985, 24, 1779. <https://doi.org/10.1016/S0031-9422(00)82550-9>
  • Seaman Fred C., Malcolm Arcelio J., H. Fischer Nikolaus: Germacra-12,6β-olides from Montanoa revealii and M. mollissima. Phytochemistry 1984, 23, 1063. <https://doi.org/10.1016/S0031-9422(00)82609-6>
  • Gershenzon J., Pfeil R.M., Liu Y.L., Mabry T.J., Turner B.L.: Sesquiterpene lactones from two newly-described species of Vernonia: V. jonesii and V. pooleae. Phytochemistry 1984, 23, 777. <https://doi.org/10.1016/S0031-9422(00)85024-4>
  • Appendino Giovanni, Gariboldi Pierluigi, Mario Nano Gian: Tanacetols A and B, non-volatile sesquiterpene alcohols, from Tanacetum vulgare. Phytochemistry 1983, 22, 509. <https://doi.org/10.1016/0031-9422(83)83035-0>
  • Malcolm Arcelio J., Carpenter Joel F., Fronczek Frank R., Fischer Nikolaus H.: Longicornins A to D, four cis-1(10),cis-4-germacradienolides from Melampodium longicorne. Phytochemistry 1983, 22, 2759. <https://doi.org/10.1016/S0031-9422(00)97691-X>
  • Appendino Giovanni, Gariboldi Pierluigi, Mario Nano Gian: Isomeric hydroperoxyeudesmanolides from Artemisia umbelliformis. Phytochemistry 1983, 22, 2767. <https://doi.org/10.1016/S0031-9422(00)97692-1>
  • Kasymov Sh. Z.: Advances in the chemistry of sesquiterpene lactones. Chem Nat Compd 1982, 18, 519. <https://doi.org/10.1007/BF00575031>
  • Romo de Vivar A., A.L. Pérez C., C. León N., Delgado G.: 11,13-Dehydroeriolin, schkuhrioidin and schkuhriolid, germacranolides from Schkuhria species. Phytochemistry 1980, 21, 2905. <https://doi.org/10.1016/0031-9422(80)85065-5>
  • Samek Z., Holub M., Bloszyk E., Drozdż B.: Über die Struktur von Schkuhriolid — einem neuen Lacton aus Schkuhria schkuhrioides (LINK et OTTO) THELLUNG. Zeitschrift fuer Chemie 1979, 19, 449. <https://doi.org/10.1002/zfch.19790191211>
  • Samek Zdeněk, Holub Miroslav, Rychlewska Urszula, Grabarczyk Halina, Dro· Bodhan: Germacra-1(10),4-diene-cis-6,12-olides: a novel stereochemical group of natural sesquiterpenic lactones from ursinia anthemoides (L.) poiret. Tetrahedron Letters 1979, 20, 2691. <https://doi.org/10.1016/S0040-4039(01)86388-7>