Cytotoxic activity of dietary lignan and its derivatives: Structure-cytotoxic activity relationship of dihydroguaiaretic acid

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 23, 2014, Pages 5305-5315

  Wukirsari, Tuti ^a   Nishiwaki, Hisashi ^a   Nishi, Kosuke ^a   Sugahara, Takuya ^a   Akiyama, Koichi ^a   Kishida, Taro ^a   Yamauchi, Satoshi ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

cytotoxic activity; dihydroguaiaretic acid; lignan; secoisolariciresinol

Indexed keywords

STEREOCHEMISTRY;

ARYL GROUP; CYTOTOXIC ACTIVITIES; DIHYDROGUAIARETIC ACID; HYDROPHOBIC GROUPS; LIGNAN; SECOISOLARICIRESINOL; STRUCTURE ACTIVITY RELATIONSHIPS; VERO CELLS;

CYTOTOXICITY;

CYTOTOXIN; DIHYDROGUAIARETIC ACID; GUAIACOL; LIGNAN;

ANALOGS AND DERIVATIVES; ANIMAL; CELL PROLIFERATION; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; CHLOROCEBUS AETHIOPS; DRUG EFFECTS; HL 60 CELL LINE; HUMAN; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TOXICITY; VERO CELL LINE;

ANIMALS; CELL PROLIFERATION; CELL SURVIVAL; CERCOPITHECUS AETHIOPS; CYTOTOXINS; GUAIACOL; HL-60 CELLS; HUMANS; LIGNANS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; VERO CELLS;

EID: 84902279630     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf5010572     Document Type: Article

References (19)

1. Penalvo, J. L.; Adlercreutz, H.; Uehara, M.; Ristimaki, A.; Watanabe, S. Lignan content of selected foods from Japan J. Agric. Food Chem. 2008, 56, 401-409
2. Ayres, D. C.; Loike, J. D. Biological and clinical properties of podophyllotoxin and other lignans. Lignans; Cambridge University Press: Cambridge, U.K., 1990; pp 85-112.
3. Osawa, T. Phenolic antioxidants on dietary plants as antimutagens. In Phenolic compounds in food and their effects on health II, antioxidants and cancer prevention; Huang, M.-T; Ho, C.-T; Lee, C. Y., Eds.; American Chemical Society: Washington, DC, 1992; pp 135-149.
4. Kawahara, S.; Iwata, I.; Fujita, E.; Yamawaki, M.; Nishiwaki, H.; Sugahara, T.; Yamauchi, S.; Akiyama, K.; Kishida, T. IgE-suppressive activity of (-)-matairesinol and its structure-activity relationship Biosci. Biotechnol. Biochem. 2010, 74, 1878-1883
5. Yamawaki, M.; Nishi, K.; Nishimoto, S.; Yamauchi, S.; Akiyama, K.; Kishida, T.; Maruyama, M.; Nishiwaki, H.; Sugahara, T. Immunomodulatory effect of (-)-matairesinol in vivo and ex vivo Biosci. Biotechnol. Biochem. 2011, 75, 859-863
6. Tominaga, S.; Sugahara, T.; Nishimoto, S.; Yamawaki, M.; Nakashima, Y.; Kishida, T.; Akiyama, K.; Maruyama, M.; Yamauchi, S. Biosci. Biotechnol. Biochem. 2009, 73, 35-39
7. Yamauchi, S.; Kishida, T.; Sugahara, T.; Yamawaki, M.; Nishimoto, S.; Shinomiya, Y.; Yamamoto, T. Inhibition of the discoloration of yellowtail dark muscle by lignan Biosci. Biotechnol. Biochem. 2009, 73, 1718-1721
8. Yamauchi, S.; Kawahara, S.; Wukirsari, T.; Nishiwaki, H.; Nishi, K.; Sugahara, T.; Akiyama, K.; Kishida, T. Structure-cytotoxic activity relationship of sesquilignan, morinol A Bioorg. Med. Chem. Lett. 2013, 23, 4923-4930
9. Niemeyer, H. B.; Honig, D. M.; Kulling, S. E.; Metzler, M. Studies on the metabolism of the plant lignans secoisolariciresinol and matairesinol J. Agric. Food Chem. 2003, 51, 6317-6325
10. Struijs, K.; Vincken, J.-P; Gruppen, H. Bacterial conversion of secoisolariciresinol and anhydrosecoisolariciresinol J. Appl. Microbiol. 2009, 107, 308-317
11. Ho, S. S. H.; Go, M. L. Restraining the flexibility of the central linker in terameprocol results in constrained analogs with improved growth inhibitory activity Bioorg. Med. Chem. Lett. 2013, 23, 6127-6133
12. Mansoor, T. A.; Ramalho, R. M.; Rodrigues, C. M. P.; Ferreira, M.-J. U. Dibenzylbutane- and butyrolactone-type lignans as apoptosis inducers in human hepatoma HuH-7 cells Phytother. Res. 2012, 26, 692-696
13. Yamauchi, S.; Sugahara, T.; Matsugi, J.; Someya, T.; Masuda, T.; Kishida, T.; Akiyama, K.; Maruyama, M. Effect of the benzylic structure of lignan on antioxidant activity Biosci. Biotechnol. Biochem. 2007, 71, 2283-2290
14. Yamauchi, S.; Hayashi, Y.; Nakashima, Y.; Kirikihira, T.; Yamada, K.; Masuda, T. Effect of benzylic oxygen on the antioxidant activity of phenolic lignans J. Nat. Prod. 2005, 68, 1459-1470
15. Yamauchi, S.; Masuda, T.; Sugahara, T.; Kawaguchi, Y.; Ohuchi, M.; Someya, T.; Akiyama, J.; Tominaga, S. Biosci. Biotechnol. Biochem. 2008, 72, 2981-2986
16. Kawaguchi, Y.; Yamauchi, S.; Masuda, K.; Nishiwaki, H.; Akiyama, K.; Maruyama, M.; Sugahara, T.; Kishida, T.; Koba, Y. Antimicrobial activity of stereoisomers of butane-type lignans Biosci. Biotechnol. Biochem. 2009, 73, 1806-1810
17. Nishiwaki, H.; Hasebe, A.; Kawaguchi, Y.; Akamatsu, M.; Shuto, Y.; Yamauchi, S. Larvicidal activity of (-)-dihydroguaiaretic acid derivatives against Culex pipiens Biosci. Biotechnol. Biochem. 2011, 75, 1735-1739
18. Hasebe, A.; Nishiwaki, H.; Akiyama, K.; Sugahara, T.; Kishida, T.; Yamauchi, S. Quantitative structure-activity relationship analysis of antifungal (+)-dihydroguaiaretic acid using 7-phenyl derivatives J. Agric. Food Chem. 2013, 61, 8548-8555
19. Moss, G. P. Nomenclature of lignans and neolignans (IUPAC recommendations 2000) Pure Appl. Chem. 2000, 72, 1493-1523