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Pure Appl. Chem., 2000, Vol. 72, No. 8, pp. 1493-1523


Nomenclature of Lignans and Neolignans (IUPAC Recommendations 2000)

G. P. Moss

Department of Chemistry, Queen Mary and Westfield College, Mile End Road, London, E1 4NS, UK

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  • Hasebe Ayaka, Nishiwaki Hisashi, Akiyama Koichi, Sugahara Takuya, Kishida Taro, Yamauchi Satoshi: Quantitative Structure–Activity Relationship Analysis of Antifungal (+)-Dihydroguaiaretic Acid Using 7-Phenyl Derivatives. J. Agric. Food Chem. 2013, 61, 8548. <>
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  • Arias Leire, Vara Yosu, Cossío Fernando P.: Regioselective Preparation of Benzo[b]furans from Phenols and α-Bromoketones. J Org Chern 2012, 77, 266. <>
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  • Tsai Yu-Chi, Lai Wan-Chun, Du Ying-Chi, Wu Shou-Fang, El-Shazly Mohamed, Lee Chia-Lin, Yen Ming-Hong, Hou Ming-Feng, Wu Yang-Chang, Chang Fang-Rong: Lignan and Flavonoid Phytoestrogens from the Seeds of Cuscuta chinensis. J. Nat. Prod. 2012, 120525113124004. <>
  • Pereira A.C., Magalhães L.G., Gonçalves U.O., Luz P.P., Moraes A.C.G., Rodrigues V., da Matta Guedes P.M., da Silva Filho A.A., Cunha W.R., Bastos J.K., Nanayakkara N.P.D., e Silva M.L.A.: Schistosomicidal and trypanocidal structure–activity relationships for (±)-licarin A and its (−)- and (+)-enantiomers. Phytochemistry 2011, 72, 1424. <>
  • Merchan Arenas Diego R., Rojas Ruíz Fernando A., Kouznetsov Vladimir V.: Highly diastereoselective synthesis of new heterolignan-like 6,7-methylendioxy-tetrahydroquinolines using the clove bud essential oil as raw material. Tetrahetron Lett 2011, 52, 1388. <>
  • Nishiwaki Hisashi, Kumamoto Mitsuko, Shuto Yoshihiro, Yamauchi Satoshi: Stereoselective Syntheses of All Stereoisomers of Lariciresinol and Their Plant Growth Inhibitory Activities. J AGRIC FD CHEM 2011, 59, 13089. <>
  • Pinto Orlando, Sardinha João, Vaz Pedro D., Piedade Fátima, Calhorda Maria J., Abramovitch Rudolph, Nazareth Nair, Pinto Madalena, Nascimento Maria S. J., Rauter Amélia P.: Synthesis of Tetrahydronaphthalene Lignan Esters by Intramolecular Cyclization of Ethyl p-Azidophenyl-2-phenylalkanoates and Evaluation of the Growth Inhibition of Human Tumor Cell Lines. J Med Chem 2011, 54, 3175. <>
  • Rye Claire E., Barker David: Asymmetric Synthesis of (+)-Galbelgin, (−)-Kadangustin J, (−)-Cyclogalgravin and (−)-Pycnanthulignenes A and B, Three Structurally Distinct Lignan Classes, Using a Common Chiral Precursor. J Org Chern 2011, 76, 6636. <>
  • Xiong Liang, Zhu Chenggeng, Li Yanru, Tian Ye, Lin Sheng, Yuan Shaopeng, Hu Jinfeng, Hou Qi, Chen Naihong, Yang Yongchun: Lignans and Neolignans from Sinocalamus affinis and Their Absolute Configurations. J Nat Prod 2011, 74, 1188. <>
  • Li Yanru, Cheng Wei, Zhu Chenggen, Yao Chunsuo, Xiong Liang, Tian Ye, Wang Sujuan, Lin Sheng, Hu Jinfeng, Yang Yongchun: Bioactive Neolignans and Lignans from the Bark of Machilus robusta. J Nat Prod 2011, 74, 1444. <>
  • NISHIWAKI Hisashi, HASEBE Ayaka, KAWAGUCHI Yuya, AKAMATSU Miki, SHUTO Yoshihiro, YAMAUCHI Satoshi: Larvicidal Activity of (−)-Dihydroguaiaretic Acid Derivatives against Culex pipiens. Bioscience Biotechnology & Biochemistry 2011, 75, 1735. <>
  • Siddiqui Bina Shaheen, Butabayeva Kalamkas Zhanarbekovna, Burasheva Gauhar Shahmanovna, Perwaiz Sobiya, Ali Syed Kashif, Bhatti Huma Aslam: A new lignan and a new sesquiterpene from Eurotia ceratoides (L.). Tetrahedron 2010, 66, 1716. <>
  • Rao Maddali L.N., Awasthi Dheeraj K., Banerjee Debasis: An expeditious and convergent synthesis of ailanthoidol. Tetrahetron Lett 2010, 51, 1979. <>
  • Lautié Emmanuelle, Fliniaux Marc‑André, Villarreal Maria Luisa: Updated biotechnological approaches developed for 2,7′-cyclolignan production . Biotechnol Appl Biochem 2010, 55, 139. <>
  • Daquino Carmelo, Rescifina Antonio, Spatafora Carmela, Tringali Corrado: Biomimetic Synthesis of Natural and “Unnatural” Lignans by Oxidative Coupling of Caffeic Esters. Eur J Org Chem 2009, 2009, 6289. <>
  • Struijs Karin, Vincken Jean-Paul, Doeswijk Timo G., Voragen Alphons G.J., Gruppen Harry: The chain length of lignan macromolecule from flaxseed hulls is determined by the incorporation of coumaric acid glucosides and ferulic acid glucosides. Phytochemisry 2009, 70, 262. <>
  • MORITA Masao, YAMAUCHI Satoshi: First Diastereoselective Construction of Butane-Type and Butyrolactone-Type Secocyclolignane Structures. Biosci Biotechnol Biochem 2009, 73, 2445. <>
  • Routier Julie, Calancea Mihaela, David Marion, Vallée Yannick, Denis Jean-Noël: Heterolignans: Stereoselective Synthesis of an 11-Amino Analog of Azaelliptitoxin. Eur J Org Chem 2008, 2008, 5687. <>
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  • Bayindir Ürün, Alfermann August Wilhelm, Fuss Elisabeth: Hinokinin biosynthesis in Linum corymbulosum Reichenb. Plant J 2008, 55, 810. <>
  • TAGO Ryosuke, YAMAUCHI Satoshi, MARUYAMA Masafumi, AKIYAMA Koichi, SUGAHARA Takuya, KISHIDA Taro, KOBA Yojiro: Structure-Antibacterial Activity Relationship for 9-O,9′-O-Demethyl (+)-virgatusin. Biosci Biotechnol Biochem 2008, 72, 1032. <>
  • YAMAUCHI Satoshi, MASUDA Toshiya, SUGAHARA Takuya, KAWAGUCHI Yuya, OHUCHI Maya, SOMEYA Tatsushi, AKIYAMA Jun, TOMINAGA Shiori, YAMAWAKI Manami, KISHIDA Taro: Antioxidant Activity of Butane Type Lignans, Secoisolariciresinol, Dihydroguaiaretic Acid, and 7,7′-Oxodihydroguaiaretic Acid. Biosci Biotechnol Biochem 2008, 72, 2981. <>
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  • Fakhfakh Jawhar Abd’elmonem, Damak Mohamed: Sesquineolignans from the flowers of Centaurea furfuracea Coss. et Dur. (Asteraceae). Nat Prod Res 2007, 21, 1037. <>
  • AKIYAMA Koichi, YAMAUCHI Satoshi, NAKATO Tomofumi, MARUYAMA Masafumi, SUGAHARA Takuya, KISHIDA Taro: Antifungal Activity of Tetra-Substituted Tetrahydrofuran Lignan, (−)-Virgatusin, and Its Structure-Activity Relationship. Biosci Biotechnol Biochem 2007, 71, 1028. <>
  • Raffaelli Barbara, Wähälä Kristiina, Hase Tapio: Asymmetric synthesis, stereochemistry and rearrangement reactions of naturally occurring 7′-hydroxylignano-9,9′-lactones. Org Biomol Chem 2006, 4, 331. <>
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  • Yang Yu-Liang, Chang Fang-Rong, Wu Yang-Chang: Squadinorlignoside: A Novel 7,9′-Dinorlignan from the Stems ofAnnona squamosa. HCA 2005, 88, 2731. <>
  • Li Wen-Wu, Barz Wolfgang: Biotechnological production of two new 8,4′-oxynorneolignans by elicitation of Echinacea purpurea cell cultures. Tetrahetron Lett 2005, 46, 2973. <>
  • Vasilev Nikolay, Ionkova Iliana: Lignan Production by Cell Cultures of Linum setaceum. and Linum campanulatum. phbi 2005, 43, 509. <>
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  • Gordaliza M, Garcı́a P.A, Miguel del Corral J.M, Castro M.A, Gómez-Zurita M.A: Podophyllotoxin: distribution, sources, applications and new cytotoxic derivatives. Toxicon official journal of the International Society on Toxinology 2004, 44, 441. <>
  • Willför S., Reunanen M., Eklund P., Sjöholm R., Kronberg L., Fardim P., Pietarinen S., Holmbom B.: Oligolignans in Norway spruce and Scots pine knots and Norway spruce stemwood. hfsg 2004, 58, 345. <>
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