Pharmacological Properties of Lignans

Lignin and Lignans: Advances in Chemistry

Volumn , Issue , 2016, Pages 585-629

  Deyama, Takeshi ^a   Nishibe, Sansei ^b  

^a Research and Development Division   (Japan)

^b HEALTH SCIENCES UNIVERSITY OF HOKKAIDO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84862792315     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/EBK1574444865-21     Document Type: Chapter

References (182)

1. CBS Rao. Chemistry of Lignans. Andhra, India: Andhra University Press, 1978.
2. WD MacRae, GHN Towers. Biological activity of lignans. Phytochem 23:1207-1200, 1984.
3. S Nishibe. Structural elucidation and biological activities of phenylpropanoids, coumarins and lignans from medicinal plants. In: AU Rahman, ed. Studies in Natural Products Chemistry, vol. 5. Structure Elucidation (Part B). Amsterdam: Elsevier, 1989, pp. 505-548.
4. DC Ayres, JD Loike. Lignans. Clinical, Biological and Clinical Properties. Cambridge:Cambridge University Press, 1990, pp. 85-132.
5. S Nishibe. Lignans as Bioactive Components in Traditional Medicines. In: A Scalleert ed. Polyphenolic Phenomena. Paris: INRA Editions, 1993, pp. 247-255.
6. S Nishibe. Bioactive Lignans and Flavonoids from Traditional Medicines. In: R Brouillord, M Jay, A Scalbert, eds. Polyphenols 94, Paris: INRA Editions, 1994, pp. 113-122.
7. J Bruneton. Pharmacognosy, Phytochemistry, Medicinal Plants. Paris:Technique and Documentation-Lavoisier, 1995, pp. 241-254.
8. CT Ho, T Osawa, MT Huang, RT Rosan. ACS Symposium Series 547. Food Phytochemicals for Cancer Prevention II. Washington, DC: American Chemical Society, 1994, pp. 264-280.
9. SD Sarker. Biological activity of magnolol: A review. Fitoterapia 58:3-8, 1997.
10. T Biftu, R Stevenson. Natural 2, 5-bisaryltetrahydrofuran lignans: Platelet-activating factor antagonists. Phytotherapy Research 1:97-106, 1987.
11. Y Damayanthi, JW Lown. Podophyllotoxins: Current status and recent developments. Curr Med Chem 5:205-252, 1998.
12. C Canel, RM Moraes, FE Dayan, D Ferreira. Podophyllotoxin. Phytochem 54:115-120, 2000.
13. M Novelo, JG Cruz, L Hernandez, R Pereda-Misanda, H Chai, W Mar, JM Pezzuto. Cytotoxic constituents from Hyptis verticillata. J Nat Prod 56:728-1736, 1993.
14. GR Pettit, DE Sahaufelberger. Isolation and structure of the cytostatic lignan glycoside phyllanthostatin A. J Nat Prod 51:1104-1112, 1988.
15. SJ Torrance, JJ Hoffmann, JR Cole. Wikstromol, antitumor lignan from Wikstroemia foetida var. oahuensis Gray and Wikstroemia uva-ursi Gray (Thymelaceae). J Pharmaceu Sci 68:664-665, 1979.
16. KH Lee, K Tagahara, H Suzuki, RY Wu, M Haruna, IH Hall, HC Huang. Antitumor agents. 49. Tricin, Kaempherol-3-O-β-D-glucopyranoside and (+)-nortrachelogenin, antileukemic principles from Wikstroemia indica. J Nat Prod 44:530-535, 1981.
17. CY Duh, CH Phoebe, Jr, JM Pezzuto, AD Kinghorn, NR Fansworth. Plant anticancer agents XLII. Cytotoxic constituents from Wikstromia elliptica. Nat Prod 49:706-709, 1986.
18. GV Subbaraju, KKK Kumar, BL Raju, KR Pillai, MC Reddy. Justiciresinol, a new furanoid lignan from Justica glauca. J Nat Prod 54:1639-1641, 991.
19. N Fukamiya, KH Lee. Antitumor agents, 81. Justicidin A and diphyllin, two cytotoxic principles from Justica procumbens. J Nat Prod 49:348-350, 1986.
20. H Joseph, J Gleye, C Moulis, LT Mensah, C Roussakis, C Gratas. Justicidin B, a cytotoxic principle from Justica retoralis. J Nat Prod 51:599-600, 1988.
21. SR Peraza-Sanches, LM Pena-Podriguez. Isolation of picropolygamain from the resin of Bursera simaruba. J Nat Prod 55:1788-1771, 1992.
22. DBM Wickramaratne, W Mar, H Chai, JJ Castillo, NR Farmsworth, DD Soejarto, GA Cordell, JM Pezzuto, AD Kinhhorn. Cytotoxic constituents of Bursera permollis. Planta Medica 61:80-81, 1995.
23. L Luyengi, N Suh, HHS Fong, JM Pezzuto, AD. Kinghorn. A lignan and four terpenoids from Brucea javanica that induce differentiation with cultured HL-60 promyelocytic leukemia cells. Phytochem 43:409-412, 1996.
24. MM Anderson, MJ O’Neill, JD Phillipson, DC Warhurst. In vitro cytotoxicity of a series of quassinoids from Brucera javanica fruits against KB cells. Planta Medica 57:62-64, 1991.
25. A Montagnac, JP Provost, M Litaudon, M Pais. Antimitotic and cytotoxic constituents of Myodocarpus gracilis. Planta Medica 63:365-366, 1997.
26. LBS Kardono, S Tsauri, K Padmawinata, JM Pezzuto, AD Kinghorn. Cytotoxic constituents of the bark of Plumeria rubra collected in Indonesia. J Nat Prod 53:1447-1455, 1990.
27. YC Wu, GY Chang, FN Ko, CM Teng. Bioactive constituents from the stem of Annona montana. Planta Medica 61:146-149, 1995.
28. N Kaneda, H Chai, JM Pezzuto, AD Kinghorn, NR Farnsworth, P Tuchinda, J Udchachon, T Sunstisuk, V Reutrakul. Cytotoxic activity of cardenolides from Beaumontia brevituba stems. Planta Medica 58:429-431, 1992.
29. T Konoshima, M Kozuka, H Tokuda, H Nishino, A Iwashima, M Haruna, K Ito, M Tanabe. Studies on inhibitors of skin tumor promotion. IX. Neolignans from Magnolia officinalis. J Nat Prod 54:816-822, 1991.
30. DBM Wickramaratne, T Pengsuparp, W Mar, HB Chai, TE Chagwedera, CWW Beecher, NR Farnsworth, AD Kinghorn, JM Pezzuto, GA Cordell. Novel antimitotic dibenzocyclo-octadiene lignan constituents of the stem bark of Steganotaenia araliacea. J Nat Prod 56:2083-2093, 1993.
31. M Taafrout, F Roussac, JP Robin, RP Hicks, DD Shillady, AT Sneden. Neoisostegane, a new bisbenzoylcyclooctadiene lignan lactone from Steganotaenia araliacea. J Nat Prod 47:600-606, 1984.
32. T Suzuki, T Aota, K Endo. The chemical constituents of the leave of Forsythia viridissima Lindley and their cytotoxicity. Proceedings of the 118th Annual Meeting of the Japanese Society of Pharmacology, Kyoto, 1998, p. 162.
33. HC Schröder, H Merz, R Steffen, WEG Müller, PS Sarin, S Trumm, J Schulz, E Eich. Differential in vitro anti-HIV activity of natural lignans. Z Naturforsch 45c:1215-1221, 1990.
34. S Trumm, E Eich. Cytostatic activities of lignanolides from Ipomoea cairica. Planta Medica 55:658-659, 1989.
35. K Pfeifer, H Merz, R Stefen, WEG Müller, S Trumm, J Schulz, E Eich, HC Schröder. In-vitro anti-HIV activity of lignans- differential inhibition of HIV-1 integrase reaction, topoisomerase activity and cellular microtubules. J Pharm Med 2:75-97, 1992.
36. RC Lin, AL Skaltsounis, E Seguin, F Tillequin, M Koch. Phenolic constituents of Selaginella doederleinii. Planta Medica 60:168-170, 1994.
37. V Darias, L Bravo, CCS Mateo, DAM Herrera. Cytostatic and antibcterial activity of some compounds isolated from several Lamiaceae species from the Canary islands. Planta Medica 56:70-72, 1990.
38. AM Rimando, JM Pezzuto, NR Farnsworth, T Suntisuk, V Reutrakul, K Kawanishi. New lignans from Anogeissus acuminata with HIV-1 reverse transcriptase inhibitory activity. J Nat Prod 57:896-904, 1994.
39. T Hirano, K Fukuoka, K Oka, T Naito, K Hosaka, H Mitsuhashi, Y Matsumoto. Antiproliferative activity against the human breast carcinoma cell line, ZR-75-1. Cancer Invest 8:595-602, 1990.
40. K Miyamoto, K Hiramatsu, Y Ohtani, M Kanitani, M Nomura, M Aburada. Effects of gomisin A on the promotor action and serum bile acid concentration in hepatocarcinogenesis induced by 3′-methyl-4-dimethy aminoazobenzene. Biol Pharm Bull 18:1443-1445, 1994.
41. Y Ohtani, M nomura, T Hida, K Miyamoto, M Kanitani, T Aizawa, M Aburada. Inhibition by gomisin A, a lignan compound, of hepatocarcinogenesis by 3′-methyl-4- dimethylaminoazobenzene in rat. Biol Pharm Bull 17:808-814, 1994.
42. M Nomura, M Nakachiyama, T Hida, Y Ohtaki, K Sudo, T Aizawa, M Aburada, K Miyamoto. Gomisin A, a lignan component of Schizandra fruits, inhibits developement of preneoplastic lesions in rat liver by 3′-methyl-4- dimethylamino-azobenzene. Cancer Letters 76:11-18, 1994.
43. K Miyamoto, S Wakusawa, M Nomura, F Sanae, R Sakai, K Sudo, Y Ohtani, S Takeda, Y Fujii. Effect of gomisin A on hepatocarcinogenesis by 3′-methyl-4- dimethylaminoazobenzene in rats. Japan J Pharmacol 57:71-77, 1991.
44. K Yasukawa, Y Ikeya, H Mitsuhashi, M Iwasaki, M Aburada, S Nakagawa, M Takeuchi, M Takido. Gomisin A inhibits tumor promotion by 12-O-tetra-decanoylphorbol-13- acetate in two-stage carcinogenesis in mouse skin. Oncology 49:68-71, 1992.
45. NR Ferringi, JL McLaughlin, RG Powel, CR Smith. Use of potato disk and brine shrimp bioassay to detect activity and isolate piceatanol as the anti-leukemic principle from the seeds of Euphobia lagascae. J Nat Prod 47: 347-352, 1984.
46. JE Anderson, CM Goetz, JL MacLaughlin, M Suffness. A blinde comparison of simple bench-top bioassays and human tumor cell cytotoxicities as anti-tumor prescreenes. Phytochem Anal 2:107-111, 1991.
47. PN Soils, CW Wright, MM Anderson, MPG Gupta, JD Phillipson. A microwell cytotoxicity assay using Artemia salina (Brine shrimp). Planta Medica 59: 250-252, 1993.
48. C Spatafora, C Tringali. Bioactive metabolites from the bark of Fagara macrophylla. Phytochem Anal 8:139-142, 1997.
49. YH Hui, CJ Chang, JL McLaughlin, RG Powell. Justicidin B, a bioactive trace lignan from the seeds of Sesbania drummondii. J Nat Prod 46:1175-1178, 1986.
50. TL Bachmann, F Ghia, KBG Tarssell. Lignans and lactones from Phyllanthus anisolobus. Phytochem 33:189-191, 1993.
51. K He, G Shi, L Zeng, Q Ye, JL McLaughlin. Konishiol, a new sesquiterpene, and bioactive components from Cunninghamia konishii. Planta Medica 63: 58-160, 1997.
52. K Umehara, A Sugawa, M Kuroyanagi, A Ueno, T Taki. Studies on differentiationinducers from Arctium fructus. Chem Pharm Bull 41:1774-1779, 1993.
53. K Umehara, M Nakamura, T Miyase, M Kuroyanagi, A Ueno. Studies on differentiation inducersVI. Lignan derivatives from Arctium fructus (2). Chem Pharm Bull 44:2300-2304, 1996.
54. T Hirano, K Fukuoka, K Oka, Y Matsumoto. Differential sensitivity of human gastric cancer ATPase and normal gastric mucosa ATPase to the synthetic mammalian lignan analogue 2, 3-dibenzylbutane-1, 4-diol (hattalin). Cancer Invest 9:145-150, 1991.
55. A Kamal, M Daneshtalab, K Atchison, RG Micetich. Synthesis of ring-A-opened isopicropodophyllins as potential DNA topoisomerase II inhibitors. Bioorg Medic Chem Lett 4:1513-1518, 1994.
56. A Kamal, M Daneshtalab, RG Micetich. A rapid entry into podophyllotoxin congeners:Synthesis of justicidin B. Tetrahedron Letters 35:3879-3882, 1994.
57. PT Anastas, R Stevenson. Synthesis of natural lignan arylnaphthalene-lactones, daurinol and retrochinensin. J Nat Prod 54:1687-1691, 1991.
58. YL Zhang, YC Shen, ZQ Wang, HX Chen, X Guo, YC Chen, KH Lee. Antitumor agents, 130. Novel 4β-arylamino derivatives of 3′, 4′-didemethoxy-3′, 4′-dioxo-4- deoxypodophyllotoxin as potent inhibitors of human DNA topoisomerase II. J Nat Prod 55:1100-1111, 1992.
59. A Kamal, K Atchison, M Daneshtalab, RG Micetich. Synthesis of podophyllotoxin congeners as potential DNA topoisomeraseII inhibitors. Anti-Cancer Drug Design 10:545-554, 1995.
60. H Saito, H Yoshikawa, Y Nishimura, S Kondo, T Takeuchi, H Umezawa. Studies on lignan lactone antitumor agents.I. Synthesis of aminoglycosidic lignan variants related to podophyllotoxin. Chem Pharm Bull 34: 3733-3740, 1986.
61. H Saito, H Yoshikawa, Y nishimura, S Kondo, T Takeuchi, H Umezawa. Studies on lignan lactone antitumor agents. II. Synthesis of N-alkylamino-and 2, 6-dideoxy-2- aminoglycosidic lignan variants related to podophyllotoxin. Chem Pharm Bull 34:3741-3746, 1986.
62. Y Hitotsuyanagi, K Yamagami, A Fujii, Y Naka, Y Ito, T Tahara. Synthesis and biological properties of novel aza-podophyllotoxin analogs possessing pronounced antitumor activity. Bioorg Medic Chem Lett 5:1039-1042, 1995.
63. AS Feliciano, M Medarde, RP Lamamie de Clairac, JL Lopez, P Puebla, MDG Gravalos, PR Lazaro, MT Garcia de Quesada. Synthesis and biological activity of bromolignans and cyclolignans. Arch Pharm (Weinheim) 326:421-426, 1993.
64. F Zavala, D Guenard, JP Robin, E Brown. Structure-antitubulin activity relationships in steganacin congeners and analogues. Inhibition of tubulin polymerization in vitro by (±)-isodeoxypodophyllotoxin. J Med Chem 23:546-549, 1980.
65. EW Sutherland, TW Rall. Fractionation and characterization of a cyclic adenine ribonucleotide formed by tissue particles. J Bio Chem 232:1077-1091, 1958.
66. T Nikaido, T Ohmoto, T Kinoshita, U Sankawa, S Nishibe, S Hisada. Inhibition of cyclic AMP phosphodiesterase by lignans. Chem Pharm Bull 29:3586-3592, 1981.
67. T Deyama, S Nishibe, S Kitagawa, Y Ogihara, T Takeda, T Ohmoto, T Nikaido, U Sankawa. Inhibition of adenosine 3′, 5′-cyclic monophosphate phosphodiesterase by lignan glucosides of Eucommia bark. Chem Pharm Bull 36:435-439, 1988.
68. S Nishibe H Tsukamoto, S Hisada, T Nikaido, T Ohmoto, U sankawa. Inhibition of cyclic AMP phosphodiesterase by lignans and coumarins of Olea and Fraxinus barks. Shoyakugaku Zasshi 40:89-94, 1986.
69. II Brekhman, IV Dardymov. Pharmacological investigation of glycosides from Ginseng and Eleutherococcus. Lloydia 32:46-51, 1969.
70. T Deyama. The constituents of Eucommia ulmoides Oliv. I. Isolation of (+)-medioresinol di-O-β-D-glucopyranoside. Chem Pharm Bull 31:2993-2997, 1983.
71. S Nishibe, H Kinosita, H Takeda, G Okano. Phenolic compounds from stem bark of Acanthopanax senticosus and their pharmacological effect in chronic swimming stressed rats. Chem Pharm Bull 38:1783-1785, 1990.
72. N Takasugi, T moriguchi, T Fuwa, S Sanada, Y Ida, J Shoji, H Saito. Effect of Eleutherococcus senticosus and its components on rectal temperature, body and grip tones, motor coordination, and exploratory and spontaneous movements in acute stressed mice. Shoyakugaku Zasshi 39:232-237, 1985.
73. T Deyama, T Ikawa, S Kitagawa, S Nishibe. The constituents of Eucommia ulmoides Oliv. V. Isolation of dihydroxydehydrodiconiferyl alcohol isomers and phenolic compounds. Chem Pharm Bull 35:1785-1789, 1987.
74. T Deyama, T Ikawa, S Nishibe. The constituents of Eucommia ulmoides Oliv II. Isolation and structures of three new lignan glycosides. Chem Pharm Bull 33:3651-3657, 1985.
75. T Deyama, T Ikawa, S Kitagawa, S Nishibe. The constituents of Eucommia ulmoides Oliv III. Isolation and structure of a new lignan glycoside. Chem Pharm Bull 34:523-527, 1986.
76. T Deyama, T Ikawa, S Kitagawa, S Nishibe. The constituents of Eucommia ulmoides Oliv IV. Isolation of a new sesquilignan glycoside and iridoids. Chem Pharm Bull 34:4933-4938, 1986.
77. T Deyama, T Ikawa, S Kitagawa, S Nishibe. The constituents of Eucommia ulmoides Oliv VI. Isolation of a new sesquilignan and neolignan glycosides Chem Pharm Bull 35:1803-1807, 1987.
78. Y Oshima, S Tanaka, H Hikino, T Deyama, G Kinoshita. Anticomplementary activity of the constituents of Eucommia ulmoides bark. J Ethnopharmacol 23:159-164, 1988.
79. A Fleckenstein. Specific pharmacology of calcium in myocardium pacemakers, and vascular smooth muscle. Ann Rev Pharmacol Toxicol 17:149-166, 1977.
80. K Ichikawa, T Kinosita, S Nishibe, U Sankawa. The Ca2 + antagonist activity of lignans. Chem Pharm Bull 34:3514-3517, 1986.
81. P Braquet, N Senn, JP Robin, A Esanu, T Godfraind, R Garay. Inhibition of the erythrocyte Na+, K+ -pump by mammalian lignans. Pharmacol Res Commun 18:227-239, 1986.
82. M Fagoo, P Braquet, JP Robin, A Esanu, T Godfraind. Biochem. Biophys Res Commun 134:1064-1070, 1986.
83. T Hirano, K Oka, T Naitoh, K Hosaka, H Mitsuhashi. Endogeneous digoxin-like activity of mammalian-lignans and their derivatives. Res Commun Chem Pathol Pharmacol 64:227-240, 1989.
84. 2+ antagonistic principle of the flower buds of Magnolia fargesii. Planta Medica: 438-440, 1988.
85. YL Huang, CC Chen, YP Chen, HY Hsu, YH Kuo. (-)-Fargesol, a new lignan from the flower buds of Magnolia fargesii. Planta Medica 56:237-238, 1990.
86. N Lami, S Kadota, T Kikuchi, Y Momose. Constituents of the roots of Boerhaavia diffuse L. III. Identification of Ca2+ channel antagonistic compound from the methanol extract. Chem Pharm Bull 39:1551-1555, 1991.
87. T Tsuruga, Y Ebizuka, J Nakajima, YT Chun, H Noguchi, Y Iitaka, U Sankawa. Biologically active constituents of Magnolia salicifolia: Inhibitors of induced histamin release from rat mast cells. Chem Pharm Bull 39:3265-3271, 1991.
88. TY Shen. Chemical and biological characterization of lignan analogs as novel PAF receptor antagonists. Lipids 26:1154-1156, 1991.
89. P Braquet, JJ Goldfroid. PAF-acether specific binding sites:2. Design of specific antagonists. Trends in Pharmacol Sci 397-403, 1986.
90. S Iwakami, Y Ebizuka, U Sankawa. Lignans and sesquiterpenoids as PAF antagonist. Heterocycle 30:795-798, 1990.
91. T Fujimoto, M Nose, T Takeda, Y Ogihara, S Nishibe, M Minami. Studies on the Chinese crude drug “Luoshiteng”(II) On the biologically active components in the stem part of Luoshiteng originating from rachelospermum jasminoides. Shoyakugaku Zasshi 46:224-249, 1992.
92. HCCF Neto, PT Bozza, HN Crurz, CLM Silva, FA Violante, JMB Filho, G Thomas, MA Martins, EV Tibirica, F Noel, RSB Cordeiro. Yangambin: A new naturally occurring platelet-activating factor receptor antagonist: Binding and in vitro functional studies. Planta Medica 61:101-105, 1995.
93. MF Serra, BL Diaz, EO Barreto, APB P antagonist yangambin. Planta Medica 63:207-212, 1997.
94. HCCF Neto, MA Martins, PMR Silva, PT Bozza, HN Cruz, MQ Paulo, MAC Kaplan, RSB Cordeiro. Pharmacological profile of epiyangambin: A frofrun lignan with PAF antagonist activity. J Lipid Mediators 7:1-9, 1993.
95. TS Wu, YL Leu, YY Chan, SM Yu, CM Teng, JD Su. Lignans and an aromatic acid from Cinnamomum philippinense. Phytochem 36:785-788, 1994.
96. CC Chen, WC Hsin, FN Ko, YL Huang, JC Ou, CM Teng. Antiplatelet arylnaphthalide lignans from Justicia procumbens. J Nat Prod 59:1149-1150, 1996.
97. SB Hwang, MH Lam, T Biftu, TR Beattie, TY Shen. Trans-2, 5-Bis(3, 4, 5-trimethoxyphenyl) tetrahydrofuran. J Biol Chem 260:15639-15645, 1985.
98. JM Prieto, MC Recio, RM Giner, S Manez, A Massmanian, PG Waterman, JL Rios. Topical anti-inflammatory lignans from Haplophyllum hispanicum. Z Naturforsch 51C:618-622, 1996.
99. K Yoshikawa, H Kinoshita, Y Kan, S Arihara. Neolignans and phenylpropanoids from the rhizomes of Coptis japonica var dissecta. Chem Pharm Bull 43:578-581, 1995.
100. JY Cho, J Park, ES Yoo, K Yoshikawa, KU Baik, J Lee, MH Park. Inhibitory effect of lignans from the rhizomes of Coptis japonica var dissecta on tumor necrosis factor-α production in lipopolysaccharide-stimulated RAW 264.7 cells. Arch Pharm Res 21:12-16, 1998.
101. Y Fukuyama, K Mizuta, K Nakagawa, Q Wenjuan, W Xiue. A new neo-lignan, a prostaglandin I2 inducer from the leaves of Zizyphus jujuba. Planta Medica, 501-502, 1986.
102. M Abe, M Morikawa, M Inoue, A Nakajima, M Tsuboi, T Naito, K Hosaka, HMitsuhashi. Effect of 2, 3-dibenzylbutane-1, 4-diol on vascular smooth muscle of rabbit aorta. Arch Int Pharmacodyn 301:40-50, 1989.
103. E Okuyama, K Suzumura, M Yamazaki. Pharmacologically active components of Todopon Puok(Fargracea racemosa), a medicinal plant from Borneo. Chem Pharm Bull 32:2200-2204, 1995.
104. HB Wan, DC Ju, ST Lian, S Watanabe, M Tamai, S Okuyama, S Kitsukawa, S Omura. JP Patent 01242596, 1989.
105. S Watanabe, M Tamai, S Okuyama, S Kitsukawa, S Omura. JP Patent 01290693, 1989.
106. E Okuyama, S Fujimori, M Yamazaki, T Deyama. Pharmacologically active components of Viticis fructus (Vitex rotundifolia).II. The components having analgestic effect. Chem Pharm Bull 46:655-662, 1998.
107. CJ Sih, PR Ravikumar, FC Huang, C Buchner, H Whitelock Jr. Isolation and synthesis of pinoresinol diglucoside, a new antihypertensive principle of Tu-Chang (Eucommia ulmoides Oliver). J Am Chem Soc 98:5412-5413, 1976.
108. T Deyama. Studies on the constituents of Eucommia ulmoides Oliver. Doctoral thesis of Nagoya City University, 1987.
109. Y Matsumura, S Kita, S Morimoto, K Akimoto, M Furuya, N Oka, T Tanaka. Antihypertensive effect of sesamine. I. Protection against deoxycorticosterone acetatesalt- induced hypertension and cardiovascular hypertrophy. Biol Pharm Bull 18:1016-1019, 1995.
110. S Kita, Y Matsumura, S Morimoto, K Akimoto, M Furuya, N Oka, T Tanaka. Antihypertensive effect of sesamine II. Protection against two-kidney, one-clip renal hypertension and cardiovascular hypertrophy. Biol Pharm Bull 18:1283-1285, 1995.
111. K Matsunaga, M Shibuya, Y Ohizumi. Graminone B, a novel lignan with vasodilative activity from Imperata cylindrica. J Nat Prod 57:1734-1736, 1994.
112. M Therien, BJ Fitzsimmons, J Scheigetz, D Macdonald, LY Choo, J Guay, JP Falgueyret, D Riendeau. Justicidin E: A new leukotriene biosynthesis inhibitor. Bioorg Medic Chem Lett 3:2063-2066, 1993.
113. Y Ducharme, C Brideau, D Dube’, CC Chan, JP Falgueyret, JW Gillard, J Guay, JH Hutchinson, CS McFarlane, D Riendeau, J Scheigetz, Y Girad. Naphthalenic lignan lactones as selective, nonredox 5-lipoxygenase inhibitors. Synthesis and biological activity of (methylalkyl)thiazole and methoxytetrahydrofuran hybrids. J Med Chem 37: 512-518, 1994.
114. D Delorme, Y Ducharme, C Brideau, CC Chan, N Chauret, S Desmarais, D Dubé, JP Falgueyret, R Fortin, J Guay, P Hamel, TR Jones, C Lépine, C Li, M McAuliffe, CS McFarlane, DA Nicoll-Griffith, D Riendeau, JA Yergey, Y Girad. Dioxabicyclooctanyl naphthalenenitriles as nonredox 5-lipoxygenase inhibitors: Structure-activity relationship study directed toward the improvement of metabolic stability. J Med Chem 39:3951-3970, 1996.
115. N Hirose, F Doi, T Ueki, K Akazawa, K Chijiiwa, M Sugano, K Akimoto, S Shimizu, H Yamada. Suppressive effect of sesamin against 7, 12-dimethyl-benz[a]-anthracene induced rat mammary carcinogensis. Anticancer Res 12:1259-1265, 1992.
116. Y Fukuda, M Nagata, T Osawa, M Namiki. Contribution of lignan analogues to antioxidative activity of refined unroasted sesame seed oil. J Am Oil Chem Soc 63:1027-1031, 1986.
117. Y Fukuda, M Namiki. Recent studies on sesame seed and oil. Nippon Shokuhin Kogyo Gakkaishi 35:525-562, 1988.
118. T Osawa. Aging, investigation from anti-oxidants. Genndai Iryo 25:3327-3332, 1993.
119. K Kuriyama, T Murai. Inhibition effects of lignan glucosides on lipid peroxidation. Nippon Nogei Kagaku Kaishi 70:161-167, 1996.
120. K Kuriyama, T Murai. Scavenging of hydroxy radicals by lignan glucosides in germinated sesame seeds. Nippon Nogei Kagaku Kaishi 69:703-705, 1995.
121. H Katsuzaki, M Kawasumi, S Kawakishi, T Osawa. Structure of novel antioxidative lignan glucosides isolated from sesame seeds. Biosci Biotech Biochem 56:2087-2088, 1992.
122. H Katsuzaki, S Kawakishi, T Osawa. Structure of novel antioxidative lignan triglucoside isolated from sesame seeds. Heterocycles 36:933-936, 1993.
123. H Katsuzaki, S Kawakishi, T Osawa. Sesaminol glucosides in sesame seeds. Phytochem 35:773-776, 1994.
124. S Maeda, H Masuda, T Tokoroyama. Studies on preparation of bioactive lignans by oxidative coupling reaction. I. Preparatiom and lipid peroxidation inhibitory effect of benzofuran lignans related to schizotenuins. Chem Pharm Bull 42:2500-2505, 1994.
125. H Hirano, T Tokuhira, T Yokoi, T Shingu. Isolation of free radical scavenger from Coptidis rhizoma. Natural Medicines 51:539-540, 1997.
126. S Toda, M Kimura, M Ohnishi, K Nakashima, Y Ikeya, H Taguchi, H Mitsuhashi. Natural Antioxidant (IV). Antioxidative components isolated from Schizandra fruit. Shoyakugaku Zasshi 42:156-159, 1988.
127. Y Kiso, M Tohkin, H Hikino, Y Ikeya, H Taguchi. Mechanism of antihepatotoxic activity of wuweizisu C and gomisin A. Planta Medica 331-334, 1985.
128. JP Wang, SL Raung, MF Hsu, CC Chen. Inhibition by gomisin C (a lignan from Schizandra chinensis) of the respiratory burst of rat neutrophils. Br J Pharmacol 113:945-953, 1994.
129. XW Yang, H Miyashiro, M Hattori, T Namba, Y Tezuka, T Kikuchi, DF Chen, GJ Xu, T Hori, M Extine, H Mizuno. Isolation of novel lignans, heteroclitins F and G, from the stem of Kadsura heteroclita, and anti-lipid peroxidative actions of heteroclitins A-G and related compounds in the in vitro rat liver homogenate system. Chem Pharm Bull 40:1510-1516, 1992.
130. XW Yang, M Hattori, T Namba, DF Chen, GJ Xu. Anti-lipid peroxidative effect of an exract of the stem of Kadsura heteroclita and its major constituent, kadsurin, in mice. Chem Pharm Bull 40:406-409, 1992.
131. AD Muir, ND Westcott. Flax seed lignans, stereochemistry, quantitation and biological activity. Proceedings of Phytochemical Society of North America for “Phytochemicals in Human Health Protection, Nutrition and Plant Defense.” Pullman, USA, 1998, pp. 29.
132. S Maeda, K Sudo, Y Miyamoto, S Takeda, M Shinbo, M Aburada, Y Ikeya, H Taguchi, M Harada. Pharmacological studies on Schizandra fruits. II. Effect of constituents of Schizandra fruits on drugs hepatic damage in rats. Yakugaku Zasshi 102:579-588, 1982.
133. S Maeda, S Takeda, Y Miyamoto, M Aburada, M Harada. Effect of gomisin A on liver function in hepatotoxic chemicals-treated rats. Japan J Pharmacol 38:347-353, 1985.
134. S Takeda, S Maemura, K Sudo, Y Kase, I Arai, Y Ohkura, S Funo, Y Fujii, M Aburada, E Hosoya. Effects of gomisin A, a lignan component of Schizandra fruits, on experimental liver injuries and liver microsomal drug-metabolizing enzymes. Folia Pharmacol Japan 87:169-187, 1986.
135. S Takeda, I Arai, Y Kase, Y Ohkura, M Hasegawa, Y Sekiguchi, K Sudo, M Aburada, E Hosoya. Pharmacological studies on antihepatotoxic action of (+)-(6S, 7S, R-biar)-5, 6, 7, 8-tetrahydro-1, 2, 3, 12-tetramethoxy-6, 7-dimethyl-10, 11-methylenedioxy-6- dibenzo[a, c] cyclooctenol(TJN-101), a lignan component of Schizandra fruits. Influence of resolvents on the efficacy of TJN-101 in the experimental acute hepatic injuries. Yakugaku Zasshi 107:517-524, 1987.
136. S Takeda, Y Kase, I Arai, M Hasegawa, Y Sekiguchi, S Funo, M Aburada, E Hosoya, Y Mizoguchi, S Morisawa. Effects of TJN-101((+)-(6S, 7S, R-biar)-5, 6, 7, 8- tetrahydro-1, 2, 3, 12- tetramethoxy-6, 7-dimethyl-10, 11-methylenedioxy-6-dibenzo[a, c] cyclooctenol) on liver regeneration after partial hepatectomy, and on regional hepatic blood flow and fine structure of the liver in normal rats. Folia Pharmacol Japan 88:321-330, 1986.
137. S Takeda, Y Kase, I Arai, Y Ohkura, M Hasegawa, Y Sekiguchi, A Tatsugi, S Funo, M Aburada, E Hosoya. Effect of TJN-101, a lignan compound isolated from Schizandra fruits, on liver fibrosis and on liver regeneration after partial hepatectomy in rats with chronic liver injury induced by CCl4. Folia Pharmacol Japan 90:51-65, 1987.
138. S Kubo, Y Ohkura, Y Mizoguchi, I Matsui-Yuasa, S Otani, S Morisawa, H Kinoshita, S Takeda, M Aburada, E Hosoya. Effect of gomisin A(TJN-101) on liver regeneration. Planta Medica 58:489-492, 1992.
139. Y Mizoguchi, N Kawada, Y Ichikawa, H Tsutsui. Effect of gomisin A in the prevention of acute hepatic failure induction. Planta Medica 57:320-324, 1991.
140. H Nagai, I Yakuo, M Aoki, K Teshima, Y Ono, T Sengoku, T Shimazawa, M Aburada, A Koda. The effect of gomisin A on immunologic liver injury in mice. Planta Medica 55:13-17, 1989.
141. Y Ohkura, Y Mizoguchi, Y Sakagami, K Kobayashi, S Yamamoto, S Morisawa, S Takeda, M Aburada. Inhibitory effect of TJN-101((+)-(6S, 7S, R-biar)-5, 6, 7, 8- tetrahydro-1, 2, 3, 12- tetramethoxy-6, 7-dimethyl-10, 11-methylenedioxy-6-dibenzo[a, c] cyclooctenol) on immunologically induced liver injuries. Japan J Pharmacol 44:179-185, 1987.
142. S Takeda, I Arai, M Hasegawa, A Tatsugi, M Aburada, E Hosoya. Effect of gomisin A(TJN-101), a lignan compound isolated from Schizandra fruits, on liver function in rats. Folia Pharmacol Japan 91:237-244, 1988.
143. K Akimoto, Y Kitagawa, T Akamatsu, N Hirose, M Sugano, S Shimizu, H Yamada. Protective effects of sesamin against liver damage caused by alcohol or carbon tetrachloride in rodents. Ann Nutr Metab 37:218-224, 1993.
144. N Hirose, T Inoue, K Nishihara, M Sugano, K Akimoto, S Shimizu, H Yamada. Inhibition of cholesterol absorption and synthesis in rat by sesamin. J Lipid Res 32:629-638, 1991.
145. F Hirata, K Fujita, Y Ishikura, K Hosoda, T Ishikawa, H Nakamura. Hypocholesterolemic effect of sesame lignan in humans. Atherosclerosis 122:135-136, 1996.
146. T Iwasaki, K Kondo, T Nishitani, T Kuroda, K Hirakoso, A Ohtani, K Takashima. Arylnaphthalene lignans as novel series of hypolipidemic agents raising high-density lipoprotein level. Chem Pharm Bull 43:1701-1705, 1995.
147. T Kuroda, K Kondo, T Iwasaki, A Ohtani, K Takashima. Synthesis and hypolipidemic activity of diesters of arylnaphthalene lignan and their heteroaromatic analogs. Chem Pharm Bull 45:678-684, 1997.
148. BM Kwon, MK Kim, SH Lee, JA Kim, IR Lee, YK Kim, SH Bok. Acyl-CoA: Cholesterol acyltransferase inhibitors from Magnolia obovata. Planta Medica 63:550-551, 1997.
149. RJ Fletcher. Food sources of phytoestrogens and their precursors in Europe. Br J Nutr 89:Supple 1, S39-S43, 2003.
150. J Liggins, R Grimwood, SA Bingham. Extraction and quantification of lignan phytoestrogens in food and human samples. Anal Biochem 287:102-109, 2000.
151. T Nurmi, S Heinonen, W Mazur, T Deyama, S Nishibe, H Adlercreutz. Analytical, nutritional and clinical methods. Lignans in selected wines. Food Chem 83:303-309, 2003.
152. S Heinonen, T Nurmi, K Liukkonen, K Potanen, K Wähälä, T Deyama, S Nishibe, Adlercreutz. In Vitro Metabolism of plant lignans: New precursors of mammalian lignans enterolactone and enterodiol. J Agric Food Chem 49:3178-3186, 2001.
153. NM Saarinen, A Smeds, SI Mäkelä, J Ämmälä, K Hakala, JM Pihlava, EL Ryhänen, R Sjöholm, R Santti. Structural determination of plant lignans for the formation of enterolactone in vivo. J Chromatogr B 25:311-319, 2002.
154. L Valentin-Blasini, BC Blount, HS Rogers, LL Needham. HPLC-MS/MS method for the measurement of seven phytoestrogens in human serum and urine. Journal of Exposure Analysis and Environmental Epidemiology 10:799-807, 2000.
155. LH Xie, EM Ahn, T Akao, AA Abdel-Hafez, N Nakamura, M Hattori. Transformation of arctiin to estragenic and antiestragenic substances by human intestinal bacteria. Chem Pharm Bull 51:378-384, 2003.
156. LH Xie, T Akao, K Hamasaki, T Deyama, M Hattori. Biotransformation of pinoresinol diglucoside to mammalian lignans by human intestinal microflora, and Isolation of enterococcus faecalis strain PDG-1 responsible for the transformation of (+)-pinoresinol to (+)-lariciresinol. Chem Pharm Bull 51:508-515, 2003.
157. K Hamasaki, K Furukawa, M Hattori, S Nishibe, H Adlercreutz, T Deyama. Metabolism of lignans by intestinal bacteria II. Metabolism of lignans from Eucomiae Cortex and other herbal medicines. Proceeding of the 50th Annual Meeting of the Japanese Society of Pharmacognosy, Tokyo, 2003, p. 69.
158. S Nishibe, T Deyama, K Hamasaki, T Kawamura, T Tanaka, E Sakai, S Heinonen, H Adlercreutz. Use of Forsythia leaves as phytoestrogen source. Abstract books of the 1st internatuional conference on polyphenols and health, Vichy-France, 2003, p. 225.
159. M Nose, T Fujimoto, T Takeda, S Nishibe, Y Ogihara. Structural transformation of lignan compounds in rat gastrointestinal tract. Planta Medica 58:520-523, 1992.
160. M Nose, T Fujimoto, S Nishibe, Y Ogihara. Structural transformation of lignan compounds in rat gastrointestinal tract II. Serum concentration of lignans and their metabolites. Planta Medica 59:131-134, 1993.
161. R Kasper, G Ganßer, J Doehmer. Biotransformation of the naturally occurring lignan (-)-arctigenin in mammalian cell lines genetically engineered for expression of single cytochrome P450 isoforms. Planta Medica 60:441-444, 1994.
162. SP Borriello, KDR Setchell, M Axelson, AM Lawson. Production and metabolism of lignans by human faecal flora. J Appl Bacteriol 58:37-43, 1985.
163. PI Musey, H Adlercreutz, KG Gould, DC Collins, T Fotsis, C Bannwart, T Mäkelä, K Wähälä, G Brunow, T Hase. Effect of diet lignans and isoflavonoid phytoestrogens in chimpanzees. Life Sciences 57:655-664, 1995.
164. KDR Setchell, AM Lawson, FL Mitchell, H Adlercreutz, DN Kirk, M Axelson. Lignans in man and in animal species. Nature 287:740-742, 1980.
165. M Axelson, J Sjövall, BE Gustafsson, KDR Setchell. Origin of lignans in mammals and identification of a precursor from plants. Nature 298:659-660, 1982.
166. TD Shultz, WR Bonorden, WR Seaman. Effect of short-term flaxseed comsumption on lignan and sex hormone metabolism in men. Nutrition Res 11:1089-1100, 1991.
167. D Ganßer, G Spiteller. Plant constituents interfering with human sex hormone-binding globulin. Evaluation of a test method and its application to Urtica dioica root extracts. Z Naturforsch C Biosci 50:98-104, 1995.
168. M Schöttner, D Ganßer, G Spiteller. Lignans from the root of Urtica dioica and their metabolites bind to human sex hormone binding globulin (SHBG). Planta Medica 63:529-632, 1997.
169. ME Martin, M Haourigui, C Pelissero, C Benassayag, EA Nunez. Interacxtion between phytoestrogens and human sex steroid binding protein. Life Sciences 58:429-436, 1996.
170. M Schöttner, D Ganßer, G Spiteller. Interaction of lignans with human sex hormone binding Globulin (SHBG). J Biosci 52:834-843, 1997.
171. H Adlercreutz, C Bannwart, K Wähälä, T Mäkelä, G Brunow, T Hase, PJ Arosemena, JT Kellis Jr, LE Vickery. Inhibition of human aromatase by mammalian lignans and isoflavonoid phytoestrogens. J Steroid Biochem Molec Biol 44:147-153, 1993.
172. C Wang, T Mäkelä, T Hase, H Adlercreutz, MS Kurzer. Lignans and flavonoids inhibit aromatase enzyme in human preadipocytes. J Steroid Biochem Molec Biol 50:205-212, 1994.
173. DF Chen, SX Zhang, K Chen, BN Zhou, P Wang, LM Cosentino, KH Lee. Two new lignans, interiotherins A and B, as anti-HIV principles from Kadsura interior. J Nat Prod 59:1066-1068, 1996.
174. K Yamashita, Y Nohara, K Katayama, M Namiki. Sesame seed lignans and γ-tochopherol act synergistically to produce vitamine E activity in rats. Nutr 122:2240-2246, 1992.
175. T Kawai, K Kinoshita, K Koyama, K Takahashi. Anti-emetic principles of Magnolia obovata bark and Zingiber officinale rhizome. Planta Medica 60: 17-20, 1994.
176. C Konno, ZZ Lu, HZ Xue, CAJ Erdelmeier, D Meksuriyen, CT Che, GA Cordell, DD Soejarto, DP Waller, HHS Fong. Furanoid lignans from Larrea tridentata. J Nat Prod 53:396-406, 1990.
177. T Namba, M Tsunezuka, KH Bae, M Hattori. Studies on dental caries prevention by traditional Chinese medicines(Part I) Screening of crude drugs for antibacterial action against Streptcoccus mutans. Shoyakugaku Zasshi 35:295-302, 1981.
178. K Ito, T Iida, K Ichino, M Tsunezuka, M Hattori, T Namba. Obovatol and obovatal, novel biphenyl ether lignans from leaves of Magnolia obovata Thunb. Chem Pharm Bull 30:3347-3353, 1982.
179. JK Nitao, MG Nair, DL Thorogood, KS Johnson, JM Scriber. Bioactive neolignans from the leaves of Magnolia virginiana. Phytochem 30:2193-2195, 1991.
180. J Luo, T Chuang, J Cheung, J Quan, J Tsai, C Sullivan, RF Hector, MJ Reed, K Meszaros, SR King, TJ Carlson, GM Reaven. Masoprocol (nordihydroguaiaretic acid): A new antihyperglycemic agent isolated from the creosote bush(Larrea tridentata). Eur J Pharmacol 346:77-79, 1998.
181. T Fujikawa, A Yamaguchi, I Morita, H Takeda, S Nishibe. Protective effects of Acanthopanax sencticosus Harms from Hokkaido and its components on gastric ulcer in restrained cold water stressed rats. Biol Pharm Bull 19:1227-1230, 1996.
182. T Fujikawa, N Kanda, A Shimada, M Ogata, I Suzuki, I Hayashi, K Nakashima. Effects of sesamin in Acanthopanax sencticosus Harms on behavioral dysfunction in rotenoneinduced Parkinsonian rats. Biol Pharm Bull 28:169-172, 2005.