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

http://dx.doi.org/10.1351/pac200072081493

INTERNATIONAL UNION OF PURE AND APPLIED CHEMISTRY AND INTERNATIONAL UNION OF BIOCHEMISTRY AND MOLECULAR BIOLOGY
IUPAC-IUB JOINT COMMISSION ON BIOCHEMICAL NOMENCLATURE (JCBN)

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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  • Shi Yiming, Zhong Weimao, Chen Huan, Wang Ruirui, Shang Shanzhai, Liang Chengqin, Gao Zhonghua, Zheng Yongtang, Xiao Weilie, Sun Handong: New Lignans from the Leaves and Stems of Schisandra chinensis and Their Anti-HIV-1 Activities. Chin. J. Chem. 2014, n/a. <http://dx.doi.org/10.1002/cjoc.201400001>
  • Pilkington Lisa I., Barker David: Total Synthesis of (-)-Isoamericanin A and (+)-Isoamericanol A. Eur. J. Org. Chem. 2014, 2014, 1037. <http://dx.doi.org/10.1002/ejoc.201301363>
  • Marconi Ombretta, Calabrò Gabriella, Perretti Giuseppe: Validation of an Electrochemical Detection–High-Performance Liquid Chromatography Method for Simultaneous Determination of Lignans in Flaxseed (Linum usitatissimum L.). Food Anal. Methods 2014, 7, 783. <http://dx.doi.org/10.1007/s12161-013-9681-x>
  • Sathish Kumar B., Singh Aastha, Kumar Amit, Singh Jyotsna, Hasanain Mohammad, Singh Arjun, Masood Nusrat, Yadav Dharmendra K., Konwar Rituraj, Mitra Kalyan, Sarkar Jayanta, Luqman Suaib, Pal Anirban, Khan Feroz, Chanda Debabrata, Negi Arvind S.: Synthesis of neolignans as microtubule stabilisers. Bioorganic & Medicinal Chemistry 2014, 22, 1342. <http://dx.doi.org/10.1016/j.bmc.2013.12.067>
  • Nishiwaki Hisashi, Nakayama Kumiko, Shuto Yoshihiro, Yamauchi Satoshi: Synthesis of All Stereoisomers of 3,3′-Dimethoxy-7,7′-epoxylignane-4,4′-diol and Their Plant Growth Inhibitory Activity. J. Agric. Food Chem. 2014, 62, 651. <http://dx.doi.org/10.1021/jf4046396>
  • Yamauchi Satoshi, Tomiyama Chisato, Wukirsari Tuti, Nishiwaki Hisashi: Syntheses of all the stereoisomers of butanol type 1,7-seco-2,7′-cyclolignane. Bioscience, Biotechnology and Biochemistry 2014, 1. <http://dx.doi.org/10.1080/09168451.2014.877833>
  • Fang Jingjing, Ramsay Aina, Paetz Christian, Tatsis Evangelos C., Renouard Sullivan, Hano Christophe, Grand Eric, Fliniaux Ophélie, Roscher Albrecht, Mesnard Francois, Schneider Bernd: Concentration Kinetics of Secoisolariciresinol Diglucoside and its Biosynthetic Precursor Coniferin in Developing Flaxseed. Phytochem. Anal. 2013, 24, 41. <http://dx.doi.org/10.1002/pca.2377>
  • Pickel Benjamin, Schaller Andreas: Dirigent proteins: molecular characteristics and potential biotechnological applications. Appl Microbiol Biotechnol 2013, 97, 8427. <http://dx.doi.org/10.1007/s00253-013-5167-4>
  • Cheynier Véronique, Comte Gilles, Davies Kevin M., Lattanzio Vincenzo, Martens Stefan: Plant phenolics: Recent advances on their biosynthesis, genetics, and ecophysiology. Plant Physiology and Biochemistry 2013, 72, 1. <http://dx.doi.org/10.1016/j.plaphy.2013.05.009>
  • Wukirsari Tuti, Nishiwaki Hisashi, Hasebe Ayaka, Shuto Yoshihiro, Yamauchi Satoshi: First Discovery of Insecticidal Activity of 9,9′-Epoxylignane and Dihydroguaiaretic Acid against Houseflies and the Structure–Activity Relationship. J. Agric. Food Chem. 2013, 61, 4318. <http://dx.doi.org/10.1021/jf400300n>
  • 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. <http://dx.doi.org/10.1021/jf4015526>
  • Yamauchi Satoshi, Kumamoto Mitsuko, Ochi Yuki, Nishiwaki Hisashi, Shuto Yoshihiro: Structure–Plant Growth Inhibitory Activity Relationship of Lariciresinol. J. Agric. Food Chem. 2013, 61, 12297. <http://dx.doi.org/10.1021/jf404292w>
  • Podloucká Pavlína, Berka Karel, Fabre Gabin, Paloncýová Markéta, Duroux Jean-Luc, Otyepka Michal, Trouillas Patrick: Lipid Bilayer Membrane Affinity Rationalizes Inhibition of Lipid Peroxidation by a Natural Lignan Antioxidant. J. Phys. Chem. B 2013, 117, 5043. <http://dx.doi.org/10.1021/jp3127829>
  • Zhu Ruyi, Wei Jiangbo, Shi Zhangjie: Benzofuran synthesis via copper-mediated oxidative annulation of phenols and unactivated internal alkynes. Chem. Sci. 2013, 4, 3706. <http://dx.doi.org/10.1039/c3sc51489g>
  • Bu Peng-Bin, Li Yan-Ru, Jiang Ming, Wang Fang, Wang Xiao-Liang, Lin Sheng, Zhu Cheng-Gen, Shi Jian-Gong: Glycosides from the bark of Machilus robusta. Journal of Asian Natural Products Research 2013, 15, 482. <http://dx.doi.org/10.1080/10286020.2013.785530>
  • Renouard Sullivan, Corbin Cyrielle, Lopez Tatiana, Montguillon Josiane, Gutierrez Laurent, Lamblin Frédéric, Lainé Eric, Hano Christophe: Abscisic acid regulates pinoresinol–lariciresinol reductase gene expression and secoisolariciresinol accumulation in developing flax (Linum usitatissimum L.) seeds. Planta Berl 2012, 235, 85. <http://dx.doi.org/10.1007/s00425-011-1492-y>
  • Bae Jong-Sup, Kim Tae Hoon: Enzymatic transformation of caffeic acid with enhanced cyclooxygenase-2 inhibitory activity. Bioog Med Chem Lett 2012, 22, 793. <http://dx.doi.org/10.1016/j.bmcl.2011.12.072>
  • Castro Ma Ángeles, Miguel del Corral José Ma., García Pablo A., Rojo Ma Victoria, Bento Ana C., Mollinedo Faustino, Francesch Andrés M., San Feliciano Arturo: Lignopurines: A new family of hybrids between cyclolignans and purines. Synthesis and biological evaluation. European Journal of Medicinal Chemistry 2012, 58, 377. <http://dx.doi.org/10.1016/j.ejmech.2012.10.026>
  • Abad Andrés, López-Pérez José L., del Olmo Esther, García-Fernández Luis F., Francesch Andrés, Trigili Chiara, Barasoain Isabel, Andreu José M., Díaz J. Fernando, San Feliciano Arturo: Synthesis and Antimitotic and Tubulin Interaction Profiles of Novel Pinacol Derivatives of Podophyllotoxins. J. Med. Chem. 2012, 55, 6724. <http://dx.doi.org/10.1021/jm2017573>
  • Arias Leire, Vara Yosu, Cossío Fernando P.: Regioselective Preparation of Benzo[b]furans from Phenols and α-Bromoketones. J Org Chern 2012, 77, 266. <http://dx.doi.org/10.1021/jo201841y>
  • Pilkington Lisa I., Barker David: Asymmetric Synthesis and CD Investigation of the 1,4-Benzodioxane Lignans Eusiderins A, B, C, G, L, and M. J. Org. Chem. 2012, 77, 8156. <http://dx.doi.org/10.1021/jo3015006>
  • 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. <http://dx.doi.org/10.1021/np200974e>
  • 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. <http://dx.doi.org/10.1016/j.phytochem.2011.04.007>
  • 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. <http://dx.doi.org/10.1016/j.tetlet.2011.01.083>
  • 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. <http://dx.doi.org/10.1021/jf203222w>
  • 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. <http://dx.doi.org/10.1021/jm101182s>
  • 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. <http://dx.doi.org/10.1021/jo200968f>
  • 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. <http://dx.doi.org/10.1021/np200117y>
  • 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. <http://dx.doi.org/10.1021/np2001896>
  • 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. <http://dx.doi.org/10.1271/bbb.110269>
  • 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. <http://dx.doi.org/10.1016/j.tet.2010.01.016>
  • Rao Maddali L.N., Awasthi Dheeraj K., Banerjee Debasis: An expeditious and convergent synthesis of ailanthoidol. Tetrahetron Lett 2010, 51, 1979. <http://dx.doi.org/10.1016/j.tetlet.2010.02.018>
  • Lautié Emmanuelle, Fliniaux Marc‑André, Villarreal Maria Luisa: Updated biotechnological approaches developed for 2,7′-cyclolignan production . Biotechnol Appl Biochem 2010, 55, 139. <http://dx.doi.org/10.1042/BA20090253>
  • 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. <http://dx.doi.org/10.1002/ejoc.200900804>
  • 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. <http://dx.doi.org/10.1016/j.phytochem.2008.12.015>
  • MORITA Masao, YAMAUCHI Satoshi: First Diastereoselective Construction of Butane-Type and Butyrolactone-Type Secocyclolignane Structures. Biosci Biotechnol Biochem 2009, 73, 2445. <http://dx.doi.org/10.1271/bbb.90401>
  • 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. <http://dx.doi.org/10.1002/ejoc.200800880>
  • Costantin Mara B., Ferreira Marcelo J. P., Rodrigues Gilberto V., Emerenciano Vicente P.: Computer-Assisted Approach to Structural Elucidation of Lignans. Spectrosc Lett 2008, 41, 405. <http://dx.doi.org/10.1080/00387010802371817>
  • Bayindir Ürün, Alfermann August Wilhelm, Fuss Elisabeth: Hinokinin biosynthesis in Linum corymbulosum Reichenb. Plant J 2008, 55, 810. <http://dx.doi.org/10.1111/j.1365-313X.2008.03558.x>
  • 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. <http://dx.doi.org/10.1271/bbb.70783>
  • 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. <http://dx.doi.org/10.1271/bbb.80461>
  • Suzuki Shiro, Umezawa Toshiaki: Biosynthesis of lignans and norlignans. J Wood Sci 2007, 53, 273. <http://dx.doi.org/10.1007/s10086-007-0892-x>
  • Federolf Katja, Alfermann A. Wilhelm, Fuss Elisabeth: Aryltetralin-lignan formation in two different cell suspension cultures of Linum album: Deoxypodophyllotoxin 6-hydroxylase, a key enzyme for the formation of 6-methoxypodophyllotoxin. Phytochemisry 2007, 68, 1397. <http://dx.doi.org/10.1016/j.phytochem.2007.02.031>
  • Fakhfakh Jawhar Abd’elmonem, Damak Mohamed: Sesquineolignans from the flowers of Centaurea furfuracea Coss. et Dur. (Asteraceae). Nat Prod Res 2007, 21, 1037. <http://dx.doi.org/10.1080/14786410701483028>
  • 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. <http://dx.doi.org/10.1271/bbb.60696>
  • 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. <http://dx.doi.org/10.1039/b513303c>
  • Giannellini Valerio, Bambagiotti-Alberti Massimo, Bruni Bruno, Di Vaira Massimo: Structural and conformational study of two solvates of a fulgenic acid derivative. New J Chem 2006, 30, 647. <http://dx.doi.org/10.1039/b515266f>
  • Yang Yu-Liang, Chang Fang-Rong, Wu Yang-Chang: Squadinorlignoside: A Novel 7,9′-Dinorlignan from the Stems ofAnnona squamosa. HCA 2005, 88, 2731. <http://dx.doi.org/10.1002/hlca.200590212>
  • 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. <http://dx.doi.org/10.1016/j.tetlet.2005.03.036>
  • Vasilev Nikolay, Ionkova Iliana: Lignan Production by Cell Cultures of Linum setaceum. and Linum campanulatum. phbi 2005, 43, 509. <http://dx.doi.org/10.1080/13880200500220631>
  • Noguera B., Dı́az E., Garcı́a M.V., Feliciano A.San, López-Perez J.L., Israel A.: Anti-inflammatory activity of leaf extract and fractions of Bursera simaruba (L.) Sarg (Burseraceae). J Ethopharmacol 2004, 92, 129. <http://dx.doi.org/10.1016/j.jep.2004.02.009>
  • 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. <http://dx.doi.org/10.1016/j.toxicon.2004.05.008>
  • 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. <http://dx.doi.org/10.1515/HF.2004.053>
  • Waibel Reiner, Benirschke Gerd, Benirschke Monika, Achenbach Hans: Sesquineolignans and other constituents from the seeds of Joannesia princeps. Phytochemisry 2003, 62, 805. <http://dx.doi.org/10.1016/S0031-9422(02)00357-6>
  • Willför S., Hemming J., Reunanen M., Holmbom B.: Phenolic and Lipophilic Extractives in Scots Pine Knots and Stemwood. hfsg 2003, 57, 359. <http://dx.doi.org/10.1515/HF.2003.054>
  • Van Dyck Stefaan M.O., Lemière Guy L.F., Jonckers Tim H.M., Dommisse Roger, Pieters Luc, Buss Volker: Kinetic resolution of a dihydrobenzofuran-type neolignan by lipase-catalysed acetylation. Tet Asymm 2001, 12, 785. <http://dx.doi.org/10.1016/S0957-4166(01)00135-5>