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Pure Appl. Chem., 1967, Vol. 14, No. 1, pp. 89-114

The ginkgolides

K. Nakanishi

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  • Sabater-Jara A. B., Souliman-Youssef S., Novo-Uzal E., Almagro L., Belchí-Navarro S., Pedreño M. A.: Biotechnological approaches to enhance the biosynthesis of ginkgolides and bilobalide in Ginkgo biloba. Phytochem Rev 2013, 12, 191. <>
  • Napolitano José G., Lankin David C., Chen Shao-Nong, Pauli Guido F.: Complete 1H NMR spectral analysis of ten chemical markers of Ginkgo biloba. Magn. Reson. Chem. 2012, 50, 569. <>
  • Napolitano José G., Gödecke Tanja, Rodríguez-Brasco María F., Jaki Birgit U., Chen Shao-Nong, Lankin David C., Pauli Guido F.: The Tandem of Full Spin Analysis and qHNMR for the Quality Control of Botanicals Exemplified with Ginkgo biloba. Journal of Natural Product 2012, 75, 238. <>
  • Li Xin, Wang Bao-Min, Zhao Xue-Zhi, Gao Shuan-Hu, Tu Yong-Qiang, Li De-Run: Extensive Studies on the AlEt3/THF-promoted diastereoselective tandem rearrangement/reduction of α-Hydroxy (amino) heterocyclopropane: An efficient approach to 2-quaternary 1,3-diheteroatom units. Chin J Chem 2010, 22, 1177. <>
  • Kulkarni Mukund G., Shaikh Yunnus B., Borhade Ajit S., Dhondge Attrimuni P., Chavhan Sanjay W., Desai Mayur P., Birhade Deekshaputra R., Dhatrak Nagorao R., Gannimani Ramesh: The efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol and its isomers. Tet Asymm 2010, 21, 2394. <>
  • Shi Chun, Zhao Lina, Zhu Bilian, Li Qianxi, Yew David T., Yao Zhibin, Xu Jie: Protective effects of Ginkgo biloba extract (EGb761) and its constituents quercetin and ginkgolide B against β-amyloid peptide-induced toxicity in SH-SY5Y cells. Chemico Biological Interactions 2009, 181, 115. <>
  • Toyota Masahiro, Hibi Ayaka: Concise Assembly of the BCD Ring Part of Ginkgolide C via a Novel Cyclization Reaction. HETEROCYCLES 2009, 77, 173. <>
  • Asahi Kentaro, Nishino Hiroshi: Facile Endoperoxypropellane Synthesis by Manganese(III) Acetate-Mediated Aerobic Oxidation. Eur J Org Chem 2008, 2008, 2404. <>
  • Ding Shujing, Dudley Ed, Song Qingbao, Plummer Sue, Tang Jiandong, Newton Russell P., Brenton A. Gareth: Mass spectrometry analysis of terpene lactones inGinkgo biloba. Rapid Commun Mass Spectrom 2008, 22, 766. <>
  • Asahi Kentaro, Nishino Hiroshi: Manganese(III)-based dioxapropellane synthesis using tricarbonyl compounds. Tetrahedron 2008, 64, 1620. <>
  • Kishida Atsushi, Nagaoka Hiroto: Samarium(II) iodide-induced cascade reaction for tricyclic γ-lactone synthesis from acyclic keto diesters. Tetrahetron Lett 2008, 49, 6393. <>
  • Ghosh Arun K., Chapsal Bruno D., Weber Irene T., Mitsuya Hiroaki: Design of HIV Protease Inhibitors Targeting Protein Backbone: An Effective Strategy for Combating Drug Resistance. Acc. Chem. Res. 2008, 41, 78. <>
  • Busch Torsten, Kirschning Andreas: Recent advances in the total synthesis of pharmaceutically relevant diterpenes. Nat Prod Rep 2008, 25, 318. <>
  • Bisel Philippe, Al-Momani Loay, Müller Michael: The tert-butyl group in chemistry and biology. Org Biomol Chem 2008, 6, 2655. <>
  • Ghosh Arun K., Ramu Sridhar Perali, Kumaragurubaran Nagaswamy, Koh Yasuhiro, Weber Irene T., Mitsuya Hiroaki: Bis-Tetrahydrofuran: a Privileged Ligand for Darunavir and a New Generation of HIV Protease Inhibitors That Combat Drug Resistance. ChemMedChem 2006, 1, 939. <>
  • Dembitsky Valery M.: Natural neo acids and neo alkanes: Their analogs and derivatives. Lipid 2006, 41, 309. <>
  • van Beek Teris A.: Ginkgolides and bilobalide: Their physical, chromatographic and spectroscopic properties. biorg med chem 2005, 13, 5001. <>
  • Nakanishi Koji: Terpene trilactones from Gingko biloba: From ancient times to the 21st century. biorg med chem 2005, 13, 4987. <>
  • Goldring William P.D., Alexander Stephen P.H., Kendall David A., Pattenden Gerald: Novel phomactin analogues as PAF receptor ligands. Biorg Med Chem Lett 2005, 15, 3263. <>
  • Pihko Ainoliisa J., Koskinen Ari M.P.: Synthesis of propellane-containing natural products. Tetrahedron 2005, 61, 8769. <>
  • Tanaka Katsunori, Kester Kimberly D., Berova Nina, Nakanishi Koji: Preparation of ginkgolide and F-seco-ginkgolide lactols: the unique reactivity of α-hydroxy lactones toward NaBH4. Tetrahetron Lett 2005, 46, 531. <>
  • Blencowe Anton, Hayes Wayne: Development and application of diazirines in biological and synthetic macromolecular systems. Soft Matt 2005, 1, 178. <>
  • Tanaka Katsunori, Pimentel Marc, Berova Nina, Nakanishi Koji: Unique Reactivity of α-Alkoxy Ginkgolide Lactones to Nucleophilic Reagents: Preparation of New Lactol Derivatives. Bull Chem Soc Jpn 2005, 78, 1843. <>
  • Jaracz Stanislav, Malik Shahid, Nakanishi Koji: Isolation of ginkgolides A, B, C, J and bilobalide from G. biloba extracts. Phytochemisry 2004, 65, 2897. <>
  • Loungratana P., Tanaka H., Shoyama Y.: Production of Monoclonal Antibody Against Ginkgolic Acids in Ginkgo biloba Linn. Am. J. Chin. Med. 2004, 32, 33. <>
  • Xie L., Hettiarachchy N.S., Jane M.E., Johnson M.G.: Antimicrobial activity of Ginkgo biloba leaf extract on Listeria monocytogenes. J Fd Sci 2003, 68, 268. <>
  • Xu Mingcheng, Shi Zuoqing, Feng Lili, Liu Juxiang, Shi Rongfu, Xu Mancai, Lu Yanlin, He Binglin: Synthesis of gelatin–PVA adsorbent and its application in the separation of ginkgo flavonol glycosides and terpene lactones. React & Funct Polym 2001, 46, 273. <>
  • Nicolaou K. C., Vourloumis Dionisios, Winssinger Nicolas, Baran Phil S.: Der Stand der Totalsynthese zu Beginn des 21. Jahrhunderts. Angew Chem 2000, 112, 46. <<46::AID-ANGE46>3.0.CO;2-P>
  • Orhan Hilmi, Marol Serdar, Hepşen İbrahim F., Şahin Gönül: Effects of some probable antioxidants on selenite-induced cataract formation and oxidative stress-related parameters in rats. Toxicol 1999, 139, 219. <>
  • Hashizume Yoshinobu, Maki Shojiro, Ohashi Mamoru, Niwa Haruki: Regiocontrolled Construction of Functionalized Spiro[4.4]Nonanones Through Mercury(II) Salt-Assisted and Acid-Induced Spiroannulation Reactions. Synth Common 1999, 29, 1223. <>
  • Inoue Hiroki, Kamoda Shigehiro, Terada Tamami, Saburi Yoshimasa: Ginkgolide production in relation to organogenesis inGinkgo biloba . J Wood Sci 1998, 44, 375. <>
  • Shi Honglian, Niki Etsuo: Stoichiometric and kinetic studies on Ginkgo biloba extract and related antioxidants. Lipid 1998, 33, 365. <>
  • Berova Nina: Koji Nakanishi's enchanting journey in the world of chirality. Chirality 1997, 9, 395. <<395::AID-CHIR2>3.0.CO;2-5>
  • Laurain Dominique, Trémouillaux-Guiller Jocelyne, Chénieux Jean-Claude, van Beek Teris A.: Production of ginkgolide and bilobalide in transformed and gametophyte derived cell cultures of Ginkgo biloba. Phytochemisry 1997, 46, 127. <>
  • van Beek Teris A., Lankhorst Peter P.: Confirmation of the C-1 stereochemistry of ginkgolides by NMR. Tetrahedron 1996, 52, 4505. <>
  • Belougne E., Aguejouf O., Imbault P., Azougagh Oualane F., Doutremepuich F., Droy-Lefaix M.T., Doutremepuich C.: Experimental thrombosis model induced by laser beam. Application of aspirin and an extract of Ginkgo Biloba: EGb 761. Thromb Research 1996, 82, 453. <>
  • Jeon Mee Hee, Sung Sang Hyun, Jeon Soonwha, Huh Hoon, Kim Jinwoong, Kim Young Choong: Cultures ofGinkgo biloba, effect of nutritional and hormonal factors on the growth of cultured cells derived fromGinkgo biloba . Arch Pharm Res 1993, 16, 244. <>
  • ARCHER C.B.: Platelet activating factor-a mediator of inflammation in the skin-medical implications. Clin Exp Dermatol 1993, 18, 489. <>
  • Hölzl Josef: Inhaltsstoffe von Ginkgo biloba. Pharm Unserer Zeit 1992, 21, 215. <>
  • Flesch Valérie, Jacques Monique, Cosson L., Teng B.P., Petiard V., Balz J.P.: Relative importance of growth and light level on terpene content of Ginkgo biloba. Phytochemisry 1992, 31, 1941. <>
  • Nakanishi Koji: Past and present studies with ponasterones, the first insect molting hormones from plants. Steroid 1992, 57, 649. <>
  • Corey E.J., Rao K.Srinivas, Ghosh Arun K.: Intramolecular and intermolecular hydroxyl reactivity differences in ginkgolides A, B and C and their chemical applications. Tetrahetron Lett 1992, 33, 6955. <>
  • Braquet Pierre, Esanu André, Buisine Eric, Hosford David, Broquet Colette, Koltai Matyas: Recent progress in ginkgolide research. Med Res Rev 1991, 11, 295. <>
  • Chauret Nathalie, Carrier Julie, Mancini Michael, Neufeld Ronald, Weber Martin, Archambault Jean: Gas chromatographic-mass spectrometric analysis of ginkgolides produced by Ginkgo biloba cell culture. J Chromatogr A 1991, 588, 281. <>
  • Braquet Pierre, Hosford David: Ethnopharmacology and the development of natural PAF antagonists as therapeutic agents. Journal of Ethanopharmacology 1991, 32, 135. <>
  • Fu-shun Yan, Evans K.A., Stevens L.H., Beek T.A., Schoonhoven L.M.: Deterrents extracted from the leaves of Ginkgo biloba: effects on feeding and contact chemoreceptors. Entomologia Experimental et Applicata 1990, 54, 57. <>
  • Pincemail J., Dupuis M., Nasr C., Hans P., Haag-Berrurier M., Anton R., Deby C.: Superoxide anion scavenging effect and superoxide dismutase activity ofGinkgo biloba extract. CMLS Cell Mol Life Sci 1989, 45, 708. <>
  • Harrison Timothy, Myers Peter L., Pattenden Gerald: Radical cyclisations onto 2(5)-furanone and maleate electrophores. An approach to the spiro- and linear-fused γ-lactone ring systems found in the ginkgolides. Tetrahedron 1989, 45, 5247. <>
  • Trost Barry M., Acemoglu Murat: A cycloaddition strategy directed toward the spiro ring system of the ginkgolides. Tetrahetron Lett 1989, 30, 1495. <>
  • Hosford David, Mencia-Huerta Jean-Michel, Page Clive, Braquet Pierre: Natural antagonists of platelet-activating factor. Phytother Res 1988, 2, 1. <>
  • Harrison Timothy, Pattenden Gerald, L. Myers Peter: Radical cyclisations onto 2(5)-furanone and maleate electrophores leading to spiro- and linear-fused γ-lactone ring systems. Tetrahetron Lett 1988, 29, 3869. <>
  • Schreiber Stuart L., Desmaele Didier, Porco John A.: On the use of unsymmetrically substituted furans in the furan-carbonyl photocycloaddition reaction: Synthesis of a kadsurenone-ginkgolide hybrid. Tetrahetron Lett 1988, 29, 6689. <>
  • Nasr Chamel, Haag-Berrurier Micheline, Lobstein-Guth Annelise, Anton Robert: Kaempferol coumaroyl glucorhamnoside from Ginkgo biloba. Phytochemisry 1986, 25, 770. <>
  • Corey E.J., Desai Manoj C.: Simple synthesis of (±)-β-trans-bergamotene. Tetrahetron Lett 1985, 26, 3535. <>
  • Weinges Klaus, Bähr Wolfgang: Naturstoffe aus Arzneipflanzen, XVI. NMR- und massenspektrometrischer Vergleich des Bilobalids C15H18O8 mit den Ginkgoliden C20H24O9–11. Justus Liebigs Ann Chem 1972, 759, 158. <>
  • Weinges Klaus, Bähr Wolfgang, Rao Makineni Panduranga: Naturstoffsynthesen, I. Synthese des Hexahydro-5H-dicyclopenta[b.c]furan-5a(6H)-ols. Justus Liebigs Ann Chem 1971, 753, 100. <>