Synthesis of all stereoisomers of 3,3′-dimethoxy-7,7′- epoxylignane-4,4′-diol and their plant growth inhibitory activity

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 3, 2014, Pages 651-659

  Nishiwaki, Hisashi ^a   Nakayama, Kumiko ^a   Shuto, Yoshihiro ^a   Yamauchi, Satoshi ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

3,3 dimethoxy 7,7 epoxylignane 4,4 diol; Italian ryegrass; lettuce; lignan; plant growth inhibitory activity

Indexed keywords

DEHYDROXYLATIONS; HIGHER PLANTS; INHIBITORY ACTIVITY; ITALIAN RYEGRASS; LETTUCE; LIGNAN; STRUCTURAL MODIFICATIONS; TETRA-HYDROFURAN; 3 3-DIMETHOXY-7 7-EPOXYLIGNANE-4 4-DIOL;

CHEMISTRY;

STEREOCHEMISTRY;

EMBRYOPHYTA; LACTUCA; LOLIUM; LOLIUM MULTIFLORUM;

LIGNAN; PHYTOHORMONE;

CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; GROWTH, DEVELOPMENT AND AGING; LETTUCE; LOLIUM; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

LETTUCE; LIGNANS; LOLIUM; MOLECULAR STRUCTURE; PLANT GROWTH REGULATORS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84892998549     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf4046396     Document Type: Article

References (36)

1. Finefield, J. M.; Sherman, D. H.; Kreitman, M.; Williams, R. M. Enantiomeric natural products: occurrence and biogenesis Angew. Chem., Int. Ed. 2012, 51, 4802-4836
2. Nishiwaki, H.; Kumamoto, M.; Shuto, Y.; Yamauchi, S. Stereoselective syntheses of all stereoisomers of lariciresinol and their plant growth inhibitory activities J. Agric. Food Chem. 2011, 59, 13089-13095
3. Rimando, A.; Dayan, F. E.; Mikell, J. R.; Moraes, R. M. Phytotoxic lignans of Leucophyllum frutescens Nat. Toxins 1999, 7, 39-43
4. Carillo, P.; Cozzolino, C.; D'Abrosca, B.; Nacca, F.; DellaGreca, M.; Fiorentio, A.; Fuggi, A. Effects of the allelochemicals dihydrodiconiferyl alcohol and lariciresinol on metabolism of Lactuca sativa Open Bioact. Compd. J. 2010, 3, 18-24
5. Sartorelli, P.; Young, M. C. M.; Kato, M. J. Antifungal lignans from the arils of Virola oleifera Phytochemistry 1998, 47, 1003-1006
6. Giang, P. M.; Son, P. T.; Matsunami, K.; Otsuka, H. New neolignans and lignans from vietnamese medicinal plant Machilus odoratissima Nees Chem. Pharm. Bull. 2006, 54, 380-383
7. Hattori, M.; Hada, S.; Kawata, Y.; Tezuka, Y.; Kikuchi, T.; Namba, T. New 2,5-bis-aryl-3,4-dimethyltetrahydrofuran lignans from the aril of Myristica fragrans Chem. Pharm. Bull. 1987, 35, 3315-3322
8. Schöttner, M.; Reiner, J.; Tayman, F. K. (+)- neo -Olivil from roots of Urtica dioica Phytochemistry 1997, 46, 1107-1109
9. Rao, K. V.; Oruganty, R. S. An improved method for the isolation of the lignan constituents of Saururus cernuus by reverse phase column chromatography J. Liq. Chromatogr. Relat. Technol. 1997, 20, 3121-3134
10. Nguyen, P. H.; Le, T. V. T.; Kang, H. W.; Chae, J.; Kim, S. K.; Kwon, K.; Seo, D. B.; Lee, S. J.; Oh, W. K. AMP-activated protein kinase (AMPK) activators from Myristica fragrans (nutmeg) and their anti-obesity effect Bioorg. Med. Chem. Lett. 2010, 20, 4128-4131
11. Hernandez, A.; Pascual, C.; Valverde, S. Neo-olivil, a new lignan from Thymus longiflorus Phytochemistry 1981, 20, 181-182
12. Shimomura, H.; Sashida, Y.; Oohara, M. Lignan from Machilus thunbergii Phytochemistry 1988, 27, 634-636
13. 2-promoted reductive deoxygenation/epimerization of cyclic hemiketal: synthesis of (-)-odoratisol C, (-)-futokadsurin A, (-)-veraguensin, (+)-fragransin A2, (+)-gabelgin, and (+)-talaumidin Org. Lett. 2007, 9, 3965-3968
14. 1 Org. Lett. 2006, 8, 5477-5480
15. Kim, H.; Kasper, A. C.; Moon, E. J.; Park, Y.; Wooten, C. M.; Dewhirst, M. W.; Hong, J. Nucleophilic addition of organozinc reagents to 2-sulfonyl cyclic ethers: stereoselective synthesis of manassantins A and B Org. Lett. 2009, 11, 89-92
16. Kraus, R.; Spiteller, G. Lignanglucoside aus wurzeln von Urtica dioica Liebigs Ann. Chem. 1990, 1205-1213
17. Yamauchi, S.; Okazaki, M.; Akiyama, K.; Sugahara, T.; Kishida, T.; Kashiwagi, T. First enantioselective synthesisof (-)- and (+)-virgatusin, tetra-substituted tetrahydrofuran lignan Org. Biomol. Chem. 2005, 3, 1670-1675
18. Yamauchi, S.; Nakato, T.; Tsuchiya, M.; Akiyama, K.; Maruyama, M.; Sugahara, T.; Kishida, T. Use of the benzyl mesylate for the synthesis of tetrahydrofuran lignan: syntheses of 7,8- trans, 7′,8′- trans, 7,7′- cis, and 8,8′- cis -virgatusin stereoisomers Biosci., Biotechnol., Biochem. 2007, 71, 2248-2255
19. Nakato, T.; Yamauchi, S.; Tago, R.; Akiyama, K.; Maruyama, M.; Sugahara, T.; Kishida, T.; Koba, Y. Syntheses and antimicrobial activity of tetrasubstituted tetrahydrofuran lignan stereoisomers Biosci., Biotechnol., Biochem. 2009, 73, 1608-1617
20. Moss, G. P. Nomenclature of lignans and neolignans (IUPAC recommendations 2000) Pure Appl. Chem. 2000, 72, 1493-1523
21. Chaurasia, V. N.; Wichtl, M. Phenylpropane und lignane aus der wurzel von Urtica dioica Dtsch. Apoth. Ztg. 1986, 126, 1559-1563
22. Akiyama, K.; Tone, J.; Yamauchi, S.; Sugahara, T.; Maruyama, M.; Kakinnuma, Y. Disruption of ion homeostasis by verrucosin and a related compound Biosci., Biotechnol., Biochem. 2011, 75, 1000-1002
23. Nguyen, P. H.; Kang, H. W.; Le, T. V. T.; Chae, J.; Kim, S. K.; Kwon, K. I.; Lim, S. I.; Oh, W. K. Simple process for the decrease of myristicin content from Myristica fragrans (nutmeg) and its activity with AMP-activated protain kinase (AMPK) J. Food Biochem. 2011, 35, 1715-1722
24. Hien, T. T.; Oh, W. K.; Nguyen, P. H.; Oh, S. J.; Lee, M. Y.; Kang, K. W. Nectandrin B activates endothelial nitric-oxide synthase phosphorylation in endothelial cells: role of the AMP-activated protein kinase/estrogen receptor α/phosphatidylinositol 3-kinase/Akt pathway Mol. Pharmacol. 2011, 80, 1166-1178
25. Na, C. S.; Hong, S. S.; Choi, Y.-H.; Lee, Y. H.; Hong, S. H.; Lim, J.-Y.; Kang, B. H.; Park, S.-Y.; Lee, D. Neuroprotective effects of constituents of Eragrostis ferruginea against a β-induced toxicity in PC 12 cells Arch. Pharm. Res. 2010, 33, 999-1003
26. Zhai, H.; Inoue, T.; Moriyama, M.; Esumi, T.; Mitsumoto, Y.; Fukuyama, Y. Neuroprotective effects of 2,5-diaryl-3,4-dimethyltetrahydrofuran neolignans Biol. Pharm. Bull. 2005, 28, 289-293
27. Cho, J. Y.; Choi, G. J.; Son, S. W.; Jang, K. S.; Lim, H. K.; Lee, S. O.; Sung, N. D.; Cho, K. Y.; Kim, J.-C. Isolation and antifungal activity of lignans from Myristica fragrans against various plant pathogenic fungi Pest Manag. Sci. 2007, 63, 935-940
28. Davis, R. A.; Carroll, A. R.; Duffy, S.; Avery, V. M.; Guymer, G. P.; Forster, P. I.; Quinn, R. J. Endiandrin A, a potent glucocorticoid receptor binder isolated from the Australian plant Endiandra anthropophagorum J. Nat. Prod. 2007, 70, 1118-1121
29. Lee, J. W.; Choi, Y. H.; Yoo, M. Y.; Choi, S. U.; Hong, K.-S.; Lee, B. H.; Yon, G. H.; Ryu, S. Y. Inhibitory effects of the seed extract of Myristicae semen on the proliferation of human tumor cell line (II) Kor. J. Pharmacog. 2006, 37, 206-211
30. Filleur, F.; Le Bail, J. C.; Duroux, J. L.; Simon, A.; Chulia, A. J. Antiproliferative, anti-aromatase, anti-17β-HSD and antioxidant activity of lignans isolated from Myristica argentea Planta Med. 2001, 67, 700-704
31. Li, G.; Lee, C.-S.; Woo, M.-H.; Lee, S.-H.; Chang, H.-W.; Son, J.-K. Lignans from the bark of Machilus thunbergii and their DNA topoisomerases I and II inhibition and cytotoxicity Biol. Pharm. Bull. 2004, 27, 1147-1150
32. Li, G.; Ju, H. K.; Chang, H. W.; Jahng, Y.; Lee, S.-H.; Son, J.-K. Melanin biosynthesis inhibitors from the bark of Machilus thunbergii Biol. Pharm. Bull. 2003, 26, 1039-1041
33. Sadhu, S. K.; Okuyama, E.; Fujimoto, H.; Ishibashi, M. Separation of Leucas aspera, a medicinal plant of Bangladesh, guided by prostaglandin inhibitory and antioxidant activities Chem. Pharm. Bull. 2003, 51, 595-598
34. Wang, B.-G.; Hong, X.; Li, L.; Zhou, J.; Hao, X.-J. Chemical constituents of two Chinese Magnoliaceae plants, Tsoongiodendron odorum and Manglietiastrum sinicum, and their inhibition of platelet aggregation Planta Med. 2000, 66, 511-515
35. Satake, H.; Ono, E.; Murata, J. Recent advances in the metabolic engineering of lignan biosynthesis pathways for the production of transgenic plant-based foods and supplements J. Agric. Food Chem. 2013, 61, 11721-11729
36. DellaGreca, M.; Zuppolini, S.; Zarrelli, A. Isolation of lignans as seed germination and plant growth inhibitors from Mediterranean plants and chemical synthesis of some analogues Phytochem. Rev. 2013, 12, 717-731