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Volumn 19, Issue 12, 2014, Pages 19769-19835

Bioinspired syntheses of dimeric hydroxycinnamic acids (Lignans) and hybrids, using phenol oxidative coupling as key reaction, and medicinal significance thereof

Author keywords

4 hydroxycinnamic acids; Biomimetic synthesis; Dihydrobenzofurans; Dihydronaphthalenes; Dilactones; Hybrids; Lignans; Phenol oxidative coupling; Regioselective coupling; Stereoselective coupling

Indexed keywords

4-COUMARIC ACID; BIOMATERIAL; COUMARIC ACID; LIGNAN; PHENOL;

EID: 84919754172     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules191219769     Document Type: Review
Times cited : (25)

References (105)
  • 1
    • 0003547330 scopus 로고
    • Freeman, Cooper & Company: San Francisco, CA, USA Chapter V Chapter XIV, pp. 372-400
    • Geissman, T.A.; Crout, D.H. G. Organic Chemistry of Secondary Plant Metabolism; Freeman, Cooper & Company: San Francisco, CA, USA, 1969; Chapter V, pp. 136-166; Chapter XIV, pp. 372-400.
    • (1969) Organic Chemistry of Secondary Plant Metabolism , pp. 136-166
    • Geissman, T.A.1    Crout, D.H.G.2
  • 3
    • 79955676741 scopus 로고    scopus 로고
    • Cinnamic acid derivatives as anticancer agents - A review
    • De, P.; Baltas, M.; Bedos-Belval, F. Cinnamic acid derivatives as anticancer agents - A review. Curr. Med. Chem. 2011, 18, 1672-1703.
    • (2011) Curr. Med. Chem. , vol.18 , pp. 1672-1703
    • De, P.1    Baltas, M.2    Bedos-Belval, F.3
  • 4
    • 0000351132 scopus 로고    scopus 로고
    • Lignans: Biosynthesis and function
    • Barton, Sir D.H.R., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, UK
    • Lewis, N.G.; Davin, L.B. Lignans: Biosynthesis and function. In Comprehensive Natural Products Chemistry; Barton, Sir D.H.R., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, UK, 1999; Volume 1, pp. 639-712.
    • (1999) Comprehensive Natural Products Chemistry , vol.1 , pp. 639-712
    • Lewis, N.G.1    Davin, L.B.2
  • 5
    • 0040363205 scopus 로고
    • Some biogenetic aspects of phenol oxidation
    • Birkhauser: Basel, Switzerland
    • Barton, D.H.R.; Cohen, T. Some biogenetic aspects of phenol oxidation. In Festschrift Arthur Stoll; Birkhauser: Basel, Switzerland, 1957; pp. 117-143.
    • (1957) Festschrift Arthur Stoll , pp. 117-143
    • Barton, D.H.R.1    Cohen, T.2
  • 7
    • 84941839052 scopus 로고
    • Dehydrierungen in der coniferylreihe. II. Dehydrodi-isoeugenol
    • Erdtman, H. Dehydrierungen in der coniferylreihe. II. Dehydrodi-isoeugenol. Annalen 1933, 503, 283-294.
    • (1933) Annalen , vol.503 , pp. 283-294
    • Erdtman, H.1
  • 8
    • 1542463480 scopus 로고
    • Phenoldehydrogenation as a biosynthetic reaction
    • Birkhauser: Basel, Switzerland
    • Erdtman, H.; Wachtmeister, C.A. Phenoldehydrogenation as a biosynthetic reaction. In Festschrift Arthur Stoll; Birkhauser: Basel, Switzerland, 1957; pp. 144-165.
    • (1957) Festschrift Arthur Stoll , pp. 144-165
    • Erdtman, H.1    Wachtmeister, C.A.2
  • 9
    • 3342986547 scopus 로고
    • Aplleton-Century-Crofts: New York, NY, USA
    • Erdtman, H. Recent Advances in Phytochemistry; Aplleton-Century-Crofts: New York, NY, USA, 1968; Volume 1, p. 29.
    • (1968) Recent Advances in Phytochemistry , vol.1 , pp. 29
    • Erdtman, H.1
  • 10
    • 0001588861 scopus 로고
    • Chemosystematics of the lauraceae
    • Gotlieb, O.R. Chemosystematics of the lauraceae. Phytochemistry 1972, 11, 1537-1570.
    • (1972) Phytochemistry , vol.11 , pp. 1537-1570
    • Gotlieb, O.R.1
  • 11
    • 0000963199 scopus 로고
    • Biochemical aspects of oxidative coupling of phenols
    • Taylor, W.I., Battersby, A.R., Eds.; Edward Arnold Publishers: London, UK
    • Brown, B.R. Biochemical Aspects of Oxidative Coupling of Phenols. In Oxidative Coupling of Phenols; Taylor, W.I., Battersby, A.R., Eds.; Edward Arnold Publishers: London, UK, 1967; pp. 167-201.
    • (1967) Oxidative Coupling of Phenols , pp. 167-201
    • Brown, B.R.1
  • 12
    • 0347219177 scopus 로고
    • Oxidative coupling of phenolic compounds
    • Scott, A.I. Oxidative coupling of phenolic compounds. Q. Rev. (Chem. Soc.) 1965, 19, 1-35.
    • (1965) Q. Rev. (Chem. Soc.) , vol.19 , pp. 1-35
    • Scott, A.I.1
  • 13
    • 84919736370 scopus 로고    scopus 로고
    • ACS Symposium Series; American Chemical Society: Washington, DC, USA
    • Lewis, N.G., Sarkanen, S., Eds. Lignin and Lignan Biosynthesis; ACS Symposium Series; American Chemical Society: Washington, DC, USA, 1998; Volume 697.
    • (1998) Lignin and Lignan Biosynthesis , vol.697
    • Lewis, N.G.1    Sarkanen, S.2
  • 14
    • 0034583327 scopus 로고    scopus 로고
    • Nomenclature of lignans and neolignans
    • Moss, G.P. Nomenclature of lignans and neolignans. Pure Appl. Chem. 2000, 72, 1493-1523.
    • (2000) Pure Appl. Chem. , vol.72 , pp. 1493-1523
    • Moss, G.P.1
  • 17
    • 84862792315 scopus 로고    scopus 로고
    • Pharmacological properties of lignans
    • Heitner, C., Dimmel, D.R., Schmidt, J.A., Eds.; CRC Press; Taylor & Francis Group: Boca Raton, FL, USA
    • Deyama, T.; Nishibe, S. Pharmacological properties of lignans. In Lignins and Lignans: Advances in Chemistry; Heitner, C., Dimmel, D.R., Schmidt, J.A., Eds.; CRC Press; Taylor & Francis Group: Boca Raton, FL, USA, 2010; pp. 585-629.
    • (2010) Lignins and Lignans: Advances in Chemistry , pp. 585-629
    • Deyama, T.1    Nishibe, S.2
  • 18
    • 0003111767 scopus 로고
    • The synthesis of lignans and neolignans
    • Ward, R.S. The synthesis of lignans and neolignans. Chem. Soc. Rev. 1982, 11, 75-125.
    • (1982) Chem. Soc. Rev. , vol.11 , pp. 75-125
    • Ward, R.S.1
  • 19
    • 23844444500 scopus 로고    scopus 로고
    • Different strategies for the chemical synthesis of lignans
    • Ward, R.S. Different strategies for the chemical synthesis of lignans. Phytochem. Rev. 2003, 2, 391-400.
    • (2003) Phytochem. Rev. , vol.2 , pp. 391-400
    • Ward, R.S.1
  • 21
    • 0000773034 scopus 로고    scopus 로고
    • Oxidative phenol coupling: A key step for the biommimetic synthesis of many important natural products
    • Pal, T.; Pal, A. Oxidative phenol coupling: A key step for the biommimetic synthesis of many important natural products. Curr. Sci. 1996, 71, 106-108.
    • (1996) Curr. Sci. , vol.71 , pp. 106-108
    • Pal, T.1    Pal, A.2
  • 23
    • 37049166184 scopus 로고
    • Constituents of natural phenolic resins. XIX. Oxidation of ferulic acid
    • Cartwright, N.J.; Haworth, R.D. Constituents of natural phenolic resins. XIX. Oxidation of ferulic acid. J. Chem. Soc. 1944, 535-537.
    • (1944) J. Chem. Soc. , pp. 535-537
    • Cartwright, N.J.1    Haworth, R.D.2
  • 24
    • 0015859475 scopus 로고
    • Synthesis of dl-matairesinol dimethyl ether, dehydrodimethyl conidendrin and dehydrodimethyl retrodendrin from ferulic acid
    • Takei, Y.; Mori, K.; Matsui, M. Synthesis of dl-matairesinol dimethyl ether, dehydrodimethyl conidendrin and dehydrodimethyl retrodendrin from ferulic acid. Agric. Biol. Chem. (Jpn.) 1973, 37, 637-641.
    • (1973) Agric. Biol. Chem. (Jpn.) , vol.37 , pp. 637-641
    • Takei, Y.1    Mori, K.2    Matsui, M.3
  • 26
    • 84981750195 scopus 로고
    • Synthese des syringaresinols und versuche mit sinapinalkohol
    • Freudenberg, K.; Schraube, H. Synthese des syringaresinols und versuche mit sinapinalkohol. Chem. Ber. 1955, 88, 16-23.
    • (1955) Chem. Ber. , vol.88 , pp. 16-23
    • Freudenberg, K.1    Schraube, H.2
  • 29
    • 84971043217 scopus 로고
    • Oxidation of (E)- and (Z)-2,6-dimethoxy-4-propenylphenol with ferric chloride - A facile route to the 2-aryl ethers of 1-arylpropan-1,2-diols
    • Wallis, A.F.A. Oxidation of (E)- and (Z)-2,6-Dimethoxy-4-propenylphenol with ferric chloride - A facile route to the 2-aryl ethers of 1-Arylpropan-1,2-diols. Aust. J. Chem. 1973, 26, 585-594.
    • (1973) Aust. J. Chem. , vol.26 , pp. 585-594
    • Wallis, A.F.A.1
  • 30
    • 84971092344 scopus 로고
    • Oxidative dimerization of methyl (E)-sinapate
    • Wallis, A.F.A. Oxidative dimerization of methyl (E)-sinapate. Aust. J. Chem. 1973, 26, 1571-1576.
    • (1973) Aust. J. Chem. , vol.26 , pp. 1571-1576
    • Wallis, A.F.A.1
  • 32
    • 0000203309 scopus 로고
    • Oxidative coupling of bromoand iodo-ferulic acid derivatives: Synthesis of (±)-veraguensin
    • Ahmed, R.; Schreiber, F.G.; Stevenson, R.; Williams, J.R.; Yeo, H.M. Oxidative coupling of bromoand iodo-ferulic acid derivatives: synthesis of (±)-veraguensin. Tetrahedron 1976, 32, 1339-1344.
    • (1976) Tetrahedron , vol.32 , pp. 1339-1344
    • Ahmed, R.1    Schreiber, F.G.2    Stevenson, R.3    Williams, J.R.4    Yeo, H.M.5
  • 33
    • 0006651988 scopus 로고
    • Synthesis of tetrahydrofuran lignans, (±)-galbelgin and (±)-grandisin
    • Stevenson, R.; Williams, J.R. Synthesis of tetrahydrofuran lignans, (±)-galbelgin and (±)-grandisin. Tetrahedron 1977, 33, 285-288.
    • (1977) Tetrahedron , vol.33 , pp. 285-288
    • Stevenson, R.1    Williams, J.R.2
  • 34
    • 33745044318 scopus 로고
    • Identification and synthesis of new ferulic acid dehydrodimers present in grass cell walls
    • Ralph, J.; Quideau, S.; Grabber, J.H.; Hatfield, R.D. Identification and synthesis of new ferulic acid dehydrodimers present in grass cell walls. J. Chem. Soc. Perkin Trans. 1 1994, 3485-3498.
    • (1994) J. Chem. Soc. Perkin Trans. 1 , pp. 3485-3498
    • Ralph, J.1    Quideau, S.2    Grabber, J.H.3    Hatfield, R.D.4
  • 35
    • 0017379995 scopus 로고
    • Characterization of the dehydrodicaffeic acid dilactone-forming enzyme and the enzymic and chemical synthesis of this mushroom product
    • Kumada, Y.; Takeuchi, T.; Umezawa, H. Characterization of the dehydrodicaffeic acid dilactone-forming enzyme and the enzymic and chemical synthesis of this mushroom product. Agric. Biol. Chem. 1977, 41, 877-885.
    • (1977) Agric. Biol. Chem. , vol.41 , pp. 877-885
    • Kumada, Y.1    Takeuchi, T.2    Umezawa, H.3
  • 36
  • 38
    • 0006875845 scopus 로고
    • Lignans from Aegilops ovata L. Synthesis of a 2,4- and 2,6-diaryl monoepoxylignanolide
    • Cooper, R.; Gottlieb, H.E.; Lavie, D.; Levy, E.C. Lignans from Aegilops ovata L. Synthesis of a 2,4- and 2,6-diaryl monoepoxylignanolide. Tetrahedron 1979, 35, 861-868.
    • (1979) Tetrahedron , vol.35 , pp. 861-868
    • Cooper, R.1    Gottlieb, H.E.2    Lavie, D.3    Levy, E.C.4
  • 39
    • 2342604742 scopus 로고
    • Thallium in organic synthesis. 60. 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane-4,8-dione lignans by oxidative dimerization of 4-alkoxycinnamic acids with thallium(III) trifluroacetate or cobalt(III) trifluoride
    • Taylor, E.C.; Andrade, J.G.; Rall, G.J.H.; Steliou, K.; Jagdmann, G.E., Jr.; McKillop, A. Thallium in Organic Synthesis. 60. 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane-4,8-dione lignans by oxidative dimerization of 4-alkoxycinnamic acids with thallium(III) trifluroacetate or cobalt(III) trifluoride. J. Org. Chem. 1981, 46, 3078-3081.
    • (1981) J. Org. Chem. , vol.46 , pp. 3078-3081
    • Taylor, E.C.1    Andrade, J.G.2    Rall, G.J.H.3    Steliou, K.4    Jagdmann, G.E.5    McKillop, A.6
  • 40
    • 32644436405 scopus 로고    scopus 로고
    • Simple and efficient asymmetric synthesis of furofuran lignans yangambin and caruilignan A
    • Mori, N.; Watanabe, H.; Kitahara, T. Simple and efficient asymmetric synthesis of furofuran lignans yangambin and caruilignan A. Synthesis 2006, 400-404.
    • (2006) Synthesis , pp. 400-404
    • Mori, N.1    Watanabe, H.2    Kitahara, T.3
  • 41
    • 37049079982 scopus 로고
    • Horse radish peroxidase-catalysed oxidative coupling of methyl sinapate to give diastereomeric spiro dimers
    • Setälä, H.; Pajunen, A.; Kilpelläinen, I.; Brunow, G. Horse radish peroxidase-catalysed oxidative coupling of methyl sinapate to give diastereomeric spiro dimers. J. Chem. Soc. Perkin Trans. 1 1994, 1163-1165.
    • (1994) J. Chem. Soc. Perkin Trans. 1 , pp. 1163-1165
    • Setälä, H.1    Pajunen, A.2    Kilpelläinen, I.3    Brunow, G.4
  • 43
    • 0141516603 scopus 로고    scopus 로고
    • Electrochemical oxidative coupling of 4-hydroxycinnamic ester derivatives: A convenient methodology for the biomimetic synthesis of lignin precursors
    • Neudorffer, A.; Deguin, B.; el Ha, C.; Fleury, M.-B.; Largeron, M. Electrochemical oxidative coupling of 4-hydroxycinnamic ester derivatives: A convenient methodology for the biomimetic synthesis of lignin precursors. Collect. Czechoslov. Chem. Commun. 2003, 68, 1515-1530.
    • (2003) Collect. Czechoslov. Chem. Commun. , vol.68 , pp. 1515-1530
    • Neudorffer, A.1    Deguin, B.2    El Ha, C.3    Fleury, M.-B.4    Largeron, M.5
  • 44
    • 38949121775 scopus 로고    scopus 로고
    • Assymetric biomimetic oxidations of phenols: The mechanism of the diastereo- and enantioselective synthesis of thomasidioic acid
    • Zoia, L.; Bruschi, M.; Orlandi, M.; Tolppa, E.-L.; Rindone, B. Assymetric biomimetic oxidations of phenols: the mechanism of the diastereo- and enantioselective synthesis of thomasidioic acid. Molecules 2008, 13, 129-148.
    • (2008) Molecules , vol.13 , pp. 129-148
    • Zoia, L.1    Bruschi, M.2    Orlandi, M.3    Tolppa, E.-L.4    Rindone, B.5
  • 45
    • 33751500205 scopus 로고
    • Characterization of the products of non-enzymic autoxidative phenolic reactions in a caffeic acid model system
    • Cilliers, J.J.L.; Singleton, V.L. Characterization of the products of non-enzymic autoxidative phenolic reactions in a caffeic acid model system. J. Agric. Food Chem. 1991, 39, 1298-1303.
    • (1991) J. Agric. Food Chem. , vol.39 , pp. 1298-1303
    • Cilliers, J.J.L.1    Singleton, V.L.2
  • 46
    • 0028817132 scopus 로고
    • Studies on the preparation of bioactive lignans by oxidative coupling reaction. IV. Oxidative coupling reaction of methyl (E)-3-(3,4-dihydroxy-2-methoxyphenyl)propenoate and lipid peroxidation inhibitory effects of the produced lignans
    • Maeda, S.; Masuda, H.; Tokoroyama, T. Studies on the preparation of bioactive lignans by oxidative coupling reaction. IV. Oxidative coupling reaction of methyl (E)-3-(3,4-dihydroxy-2-methoxyphenyl)propenoate and lipid peroxidation inhibitory effects of the produced lignans. Chem. Pharm. Bull. 1995, 43, 84-90.
    • (1995) Chem. Pharm. Bull. , vol.43 , pp. 84-90
    • Maeda, S.1    Masuda, H.2    Tokoroyama, T.3
  • 47
    • 0028566687 scopus 로고
    • Studies on the preparation of bioactive lignans by oxidative coupling reaction. II. Oxidative coupling reaction of methyl (E)-3-(4,5-dihydroxy-2-methoxyphenyl)propenoate and lipid peroxidation inhibitory effects of the produced lignans
    • Maeda, S.; Masuda, H.; Tokoroyama, T. Studies on the preparation of bioactive lignans by oxidative coupling reaction. II. Oxidative coupling reaction of methyl (E)-3-(4,5-dihydroxy-2-methoxyphenyl)propenoate and lipid peroxidation inhibitory effects of the produced lignans. Chem. Pharm. Bull. 1994, 42, 2506-2513.
    • (1994) Chem. Pharm. Bull. , vol.42 , pp. 2506-2513
    • Maeda, S.1    Masuda, H.2    Tokoroyama, T.3
  • 48
    • 0343639922 scopus 로고
    • Rabdosiin, a new rosmarinic acid dimer with a lignan skeleton from rabdosia japonica
    • Agata, I.; Hatano, T.; Nishibe, S.; Okuda, T. Rabdosiin, a new rosmarinic acid dimer with a lignan skeleton from Rabdosia japonica. Chem. Pharm. Bull. 1988, 36, 3223-3225.
    • (1988) Chem. Pharm. Bull. , vol.36 , pp. 3223-3225
    • Agata, I.1    Hatano, T.2    Nishibe, S.3    Okuda, T.4
  • 49
    • 0000025780 scopus 로고
    • A tetrameric derivative of caffeic acid from rabdosia japonica
    • Agata, I.; Hatano, T.; Nishibe, S.; Okuda, T. A tetrameric derivative of caffeic acid from Rabdosia japonica. Phytochemistry 1989, 28, 2447-2450.
    • (1989) Phytochemistry , vol.28 , pp. 2447-2450
    • Agata, I.1    Hatano, T.2    Nishibe, S.3    Okuda, T.4
  • 50
  • 51
    • 0028919791 scopus 로고
    • Novel lignan derivatives as selective inhibitors of DNA topoisomerase II
    • Kashiwada, Y.; Bastow, K.F.; Lee, K. Novel lignan derivatives as selective inhibitors of DNA topoisomerase II. Bioorg Med. Chem. Lett. 1995, 5, 905-908.
    • (1995) Bioorg Med. Chem. Lett. , vol.5 , pp. 905-908
    • Kashiwada, Y.1    Bastow, K.F.2    Lee, K.3
  • 52
    • 0031427199 scopus 로고    scopus 로고
    • A non-enzymatic synthesis of (S)-(-)-rosmarinic acid and a study of a biomimetic route to (+)-rabdosiin
    • Bogucki, D.E.; Charlton, J.L. A non-enzymatic synthesis of (S)-(-)-rosmarinic acid and a study of a biomimetic route to (+)-rabdosiin. Can. J. Chem. 1997, 75, 1783-1794.
    • (1997) Can. J. Chem. , vol.75 , pp. 1783-1794
    • Bogucki, D.E.1    Charlton, J.L.2
  • 53
    • 0032329959 scopus 로고    scopus 로고
    • Synthese der enantiomeren (+)- and (-)-rosmarinsäuremethylester
    • Reimann, E.; Pflug, T. Synthese der enantiomeren (+)- and (-)-rosmarinsäuremethylester. Monatsch. Chem. 1998, 129, 187-193.
    • (1998) Monatsch. Chem. , vol.129 , pp. 187-193
    • Reimann, E.1    Pflug, T.2
  • 54
    • 33748637567 scopus 로고    scopus 로고
    • Total synthesis and biological evaluation of (+)- and (-)-butyl ester of rosmarinic acid
    • Huang, L.-J.; Li, C.-H.; Lu, Z.-M.; Ma, Z.-B.; Yu, D.-Q. Total synthesis and biological evaluation of (+)- and (-)-butyl ester of rosmarinic acid. J. Asian Nat. Prod. Res. 2006, 8, 561-566.
    • (2006) J. Asian Nat. Prod. Res. , vol.8 , pp. 561-566
    • Huang, L.-J.1    Li, C.-H.2    Lu, Z.-M.3    Ma, Z.-B.4    Yu, D.-Q.5
  • 55
    • 79953174578 scopus 로고    scopus 로고
    • Contribution of cinnamic acid analoues in rosmarinic acid to inhibition of snake venom induced hemorrhage
    • Aung, H.T.; Furukawa, T.; Nikai, T.; Niwa, M.; Takaya, Y. Contribution of cinnamic acid analoues in rosmarinic acid to inhibition of snake venom induced hemorrhage. Bioorg. Med. Chem. 2011, 19, 2392-2396.
    • (2011) Bioorg. Med. Chem. , vol.19 , pp. 2392-2396
    • Aung, H.T.1    Furukawa, T.2    Nikai, T.3    Niwa, M.4    Takaya, Y.5
  • 56
    • 67849092818 scopus 로고    scopus 로고
    • Explorations into neolignan biosynthesis: Concise total syntheses of helicterin B, helisorin, and helisterculin A from a common intermediate
    • Snyder, S.A.; Kontes, F. Explorations into neolignan biosynthesis: Concise total syntheses of Helicterin B, Helisorin, and Helisterculin A from a common intermediate. J. Am. Chem. Soc. 2009, 131, 1745-1752.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 1745-1752
    • Snyder, S.A.1    Kontes, F.2
  • 58
    • 55549135728 scopus 로고    scopus 로고
    • Lignanamides and sesquiterpenoids from stems of mitrephora thorelii
    • Ge, F.; Tang, C.-P.; Ye, Y. Lignanamides and sesquiterpenoids from stems of Mitrephora thorelii. Helv. Chim. Acta 2008, 91, 1023-1030.
    • (2008) Helv. Chim. Acta , vol.91 , pp. 1023-1030
    • Ge, F.1    Tang, C.-P.2    Ye, Y.3
  • 59
    • 71849101048 scopus 로고    scopus 로고
    • Biomimetic synthesis of natural and "unnatural" lignans by oxidative coupling of caffeic esters
    • Daquino, C; Rescifina, A.; Spatafora, C.; Tringali, C. Biomimetic synthesis of natural and "unnatural" lignans by oxidative coupling of caffeic esters. Eur. J. Org. Chem. 2009, 2009, 6289-6300.
    • (2009) Eur. J. Org. Chem. , vol.2009 , pp. 6289-6300
    • Daquino, C.1    Rescifina, A.2    Spatafora, C.3    Tringali, C.4
  • 61
    • 0027162370 scopus 로고
    • A general asymmetric synthesis of (-)-a-dimethylretrodendrin and its diastereomers
    • Maddaford, S.P.; Charlton, J.L. A general asymmetric synthesis of (-)-a-dimethylretrodendrin and its diastereomers. J. Org. Chem. 1993, 58, 4132-4138.
    • (1993) J. Org. Chem. , vol.58 , pp. 4132-4138
    • Maddaford, S.P.1    Charlton, J.L.2
  • 63
    • 84970627023 scopus 로고
    • Oxidative coupling of lignans III. Non-phenolic oxidative coupling of deoxypodorhizon and related compounds
    • Cambie, R.C.; Craw, P.A.; Rutledge, P.S.; Woodgate, P.D. Oxidative coupling of lignans III. Non-phenolic oxidative coupling of deoxypodorhizon and related compounds. Aust. J. Chem. 1988, 41, 897-918.
    • (1988) Aust. J. Chem. , vol.41 , pp. 897-918
    • Cambie, R.C.1    Craw, P.A.2    Rutledge, P.S.3    Woodgate, P.D.4
  • 64
    • 37049118551 scopus 로고
    • Oxidative dimerization of methyl (E)-4-hydroxy-3,5-di-t-butylcinnamate with potassium ferricyanide
    • Sarkanen, K.V.; Wallis, A.F.A. Oxidative dimerization of methyl (E)-4-hydroxy-3,5-di-t-butylcinnamate with potassium ferricyanide. J. Chem. Soc. Perkin Trans. 1 1973, 1878-1881.
    • (1973) J. Chem. Soc. Perkin Trans. 1 , pp. 1878-1881
    • Sarkanen, K.V.1    Wallis, A.F.A.2
  • 65
    • 33646569066 scopus 로고    scopus 로고
    • An efficient method for the synthesis of lignans
    • Wang, Q.; Yang, Y.; Li, Y.; Yu, W.; Hou, Z.H. An efficient method for the synthesis of lignans. Tetrahedron 2006, 62, 6107-6112.
    • (2006) Tetrahedron , vol.62 , pp. 6107-6112
    • Wang, Q.1    Yang, Y.2    Li, Y.3    Yu, W.4    Hou, Z.H.5
  • 67
    • 48449088236 scopus 로고    scopus 로고
    • Hanultarin, a cytotoxic lignan as an inhibitor of actin cytoskeleton polymerization from the seeds of trichosanthes kirilowii
    • Moon, S.-S.; Rahman, A.A.; Kim, J.-Y.; Kee, S.-H. Hanultarin, a cytotoxic lignan as an inhibitor of actin cytoskeleton polymerization from the seeds of Trichosanthes kirilowii. Bioorg. Med. Chem. 2008, 16, 7264-7269.
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 7264-7269
    • Moon, S.-S.1    Rahman, A.A.2    Kim, J.-Y.3    Kee, S.-H.4
  • 69
    • 0036179960 scopus 로고    scopus 로고
    • Lignanamides and nonalkaloidal components of hyoscyamus Niger seeds
    • Ma, C.-Y.; Liu, W.K.; Che, C.-T. Lignanamides and nonalkaloidal components of Hyoscyamus niger seeds. J. Nat. Prod. 2002, 65, 206-209.
    • (2002) J. Nat. Prod. , vol.65 , pp. 206-209
    • Ma, C.-Y.1    Liu, W.K.2    Che, C.-T.3
  • 73
    • 0028567205 scopus 로고
    • Studies on the preparation of bioactive lignans by oxidative coupling reaction. I. Preparation and lipid peroxidation inhibitory effect of benzofuran lignans related to schizotenuins
    • Maeda, S.; Masuda, H.; Tokoroyama, T. Studies on the preparation of bioactive lignans by oxidative coupling reaction. I. Preparation and lipid peroxidation inhibitory effect of benzofuran lignans related to schizotenuins. Chem. Pharm. Bull. 1994, 42, 2500-2505.
    • (1994) Chem. Pharm. Bull. , vol.42 , pp. 2500-2505
    • Maeda, S.1    Masuda, H.2    Tokoroyama, T.3
  • 74
    • 0028609070 scopus 로고
    • Studies on the preparation of bioactive lignans by oxidative coupling reaction. III. Synthesis of polyphenolic benzofuran and coumestan derivatives by oxidative coupling reaction of methyl (E)-3-(4-hydroxy-2-methoxyphenyl)propenoate and their inhibitory effect on lipid peroxidation
    • Maeda, S.; Masuda, H.; Tokoroyama, T. Studies on the preparation of bioactive lignans by oxidative coupling reaction. III. Synthesis of polyphenolic benzofuran and coumestan derivatives by oxidative coupling reaction of methyl (E)-3-(4-hydroxy-2-methoxyphenyl)propenoate and their inhibitory effect on lipid peroxidation. Chem. Pharm. Bull. 1994, 42, 2536-2545.
    • (1994) Chem. Pharm. Bull. , vol.42 , pp. 2536-2545
    • Maeda, S.1    Masuda, H.2    Tokoroyama, T.3
  • 77
    • 0033619997 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of dihydrobenzofuran lignans and related compounds as potentia antitumor agents that inhibit tubulin polymerization
    • Pieters, L.; van Dyck, S.; Gao, M.; Bai, R.; Hamel, E.; Vlietinck, A.; Lemière, G. Synthesis and biological evaluation of dihydrobenzofuran lignans and related compounds as potentia antitumor agents that inhibit tubulin polymerization. J. Med. Chem. 1999, 42, 5475-5481.
    • (1999) J. Med. Chem. , vol.42 , pp. 5475-5481
    • Pieters, L.1    Van Dyck, S.2    Gao, M.3    Bai, R.4    Hamel, E.5    Vlietinck, A.6    Lemière, G.7
  • 78
    • 0035800642 scopus 로고    scopus 로고
    • Oxidation of ferulic acid by laccase: Identification of the products and inhibitory effect of some dipeptides
    • Carunchio, F.; Crescenzi, C.; Girelli, A.M.; Messina, A.; Tarola, A.M. Oxidation of ferulic acid by laccase: Identification of the products and inhibitory effect of some dipeptides. Talanta 2001, 55, 189-200.
    • (2001) Talanta , vol.55 , pp. 189-200
    • Carunchio, F.1    Crescenzi, C.2    Girelli, A.M.3    Messina, A.4    Tarola, A.M.5
  • 79
    • 0029895941 scopus 로고    scopus 로고
    • Synthesis of 5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)-3-benzo[b]furancarbaldehyde, a novel adenosine A1 receptor ligand from the root of salvia miltiorrhiza
    • Kuo, Y.-H.; Wu, C.-H. Synthesis of 5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)-3-benzo[b]furancarbaldehyde, a novel adenosine A1 receptor ligand from the root of Salvia miltiorrhiza. J. Nat. Prod. 1996, 59, 625-628.
    • (1996) J. Nat. Prod. , vol.59 , pp. 625-628
    • Kuo, Y.-H.1    Wu, C.-H.2
  • 80
    • 1642495631 scopus 로고    scopus 로고
    • Salvinal, a novel microtubule inhibitor isolated from salvia miltiorrhizae bunge (Danshen), with antimitotic activity in multi-drug-sensitive and-resistant human tumor cells
    • Chang, J.Y.; Chang, C.-Y.; Kuo, C.-C.; Chen, L.-T.; Wein, Y.-S.; Kuo, Y.-H. Salvinal, a novel microtubule inhibitor isolated from Salvia miltiorrhizae Bunge (Danshen), with antimitotic activity in multi-drug-sensitive and-resistant human tumor cells. Mol. Pharmacol. 2004, 65, 77-84.
    • (2004) Mol. Pharmacol. , vol.65 , pp. 77-84
    • Chang, J.Y.1    Chang, C.-Y.2    Kuo, C.-C.3    Chen, L.-T.4    Wein, Y.-S.5    Kuo, Y.-H.6
  • 82
    • 63349095764 scopus 로고    scopus 로고
    • Ferulate-coniferyl alcohol cross-coupled products formed by radical coupling reactions
    • Zhang, A.; Lu, F.; Sun, R.; Ralph, J. Ferulate-coniferyl alcohol cross-coupled products formed by radical coupling reactions. Planta 2009, 229, 1099-1108.
    • (2009) Planta , vol.229 , pp. 1099-1108
    • Zhang, A.1    Lu, F.2    Sun, R.3    Ralph, J.4
  • 83
    • 34548230986 scopus 로고    scopus 로고
    • Justicia lignans: Part 10-synthesis of tiruneesiin, the first neolignan from justicia species
    • Subbaraju, G.; Kavitha, J.; Rajasekhar, D.; Hsu, F.-L.; Cheng, K.-T. Justicia lignans: Part 10-Synthesis of tiruneesiin, the first neolignan from Justicia species. Ind. J. Chem. 2007, 46B, 357-359.
    • (2007) Ind. J. Chem. , vol.46 B , pp. 357-359
    • Subbaraju, G.1    Kavitha, J.2    Rajasekhar, D.3    Hsu, F.-L.4    Cheng, K.-T.5
  • 87
    • 84986703472 scopus 로고
    • Total synthesis of two naturally occurring neolignans of potential biological activity
    • Antus, S.; Gottsegen, A.; Kolonits, P.; Wagner, H. Total synthesis of two naturally occurring neolignans of potential biological activity. Liebigs Ann. Chem. 1989, 1989, 593-594.
    • (1989) Liebigs Ann. Chem. , vol.1989 , pp. 593-594
    • Antus, S.1    Gottsegen, A.2    Kolonits, P.3    Wagner, H.4
  • 88
    • 33846556705 scopus 로고    scopus 로고
    • Asymmetric biomimetic oxidations of phenols using oxazolidines as chiral auxiliaries: The enantioselective synthesis of (+)- and (-)-dehydrodiconiferyl alcohol
    • Bruschi, M.; Orlandi, M.; Rindone, B.; Rummakko, P.; Zoia, L. Asymmetric biomimetic oxidations of phenols using oxazolidines as chiral auxiliaries: the enantioselective synthesis of (+)- and (-)-dehydrodiconiferyl alcohol. J. Phys. Org. Chem. 2006, 19, 592-596.
    • (2006) J. Phys. Org. Chem. , vol.19 , pp. 592-596
    • Bruschi, M.1    Orlandi, M.2    Rindone, B.3    Rummakko, P.4    Zoia, L.5
  • 89
    • 33645105879 scopus 로고    scopus 로고
    • Modeling suberization with peroxidase-catalyzed polymerization of hydroxycinnamic acids: Cross-coupling and dimerization reactions
    • Arrieta-Baez, D.; Stark, R.E. Modeling suberization with peroxidase-catalyzed polymerization of hydroxycinnamic acids: Cross-coupling and dimerization reactions. Phytochemistry 2006, 67, 743-753.
    • (2006) Phytochemistry , vol.67 , pp. 743-753
    • Arrieta-Baez, D.1    Stark, R.E.2
  • 90
    • 79959518232 scopus 로고    scopus 로고
    • Horseradish peroxidase catalyzed oxidative cross-coupling reactions: The synthesis of "unnatural" dihydrobenzofuran lignans
    • Saliu, F.; Tolppa, E.-L.; Zoia, L.; Orlandi, M. Horseradish peroxidase catalyzed oxidative cross-coupling reactions: The synthesis of "unnatural" dihydrobenzofuran lignans. Tetrahedron Lett. 2011, 52, 3856-3860.
    • (2011) Tetrahedron Lett. , vol.52 , pp. 3856-3860
    • Saliu, F.1    Tolppa, E.-L.2    Zoia, L.3    Orlandi, M.4
  • 91
    • 0035908217 scopus 로고    scopus 로고
    • New reagent for oxidative phenol coupling. The transformation of the monocyclic spermine base (S)-dihydroverbacine to the bicyclic alkaloid (S,S,S)-aphelandrine by cell free extract of barley seedlings
    • Nezbedovà, L.; Hesse, M.; Drandarov, K.; Werner, C. New reagent for oxidative phenol coupling. The transformation of the monocyclic spermine base (S)-dihydroverbacine to the bicyclic alkaloid (S,S,S)-aphelandrine by cell free extract of barley seedlings. Tetrahedron Lett. 2001, 42, 4139-4141.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 4139-4141
    • Nezbedovà, L.1    Hesse, M.2    Drandarov, K.3    Werner, C.4
  • 92
    • 49149137295 scopus 로고
    • The biosynthesis of coumarylagmantine in barley seedings
    • Bird, C.R.; Smith, T.A. The biosynthesis of coumarylagmantine in barley seedings. Phytochemistry 1981, 20, 2345-2346.
    • (1981) Phytochemistry , vol.20 , pp. 2345-2346
    • Bird, C.R.1    Smith, T.A.2
  • 93
    • 84863607222 scopus 로고    scopus 로고
    • Synthesis of anti-HIV lithospermic acid by two divergent strategies
    • For a very informative short introduction on the isolation, characterization, biological properties and synthesis of (+)-lithospermic acid see: Varadaraju, T.G.; Hwu, J.R. Synthesis of anti-HIV lithospermic acid by two divergent strategies. Org. Biomol. Chem. 2012, 10, 5456-5465.
    • (2012) Org. Biomol. Chem. , vol.10 , pp. 5456-5465
    • Varadaraju, T.G.1    Hwu, J.R.2
  • 94
    • 33845560030 scopus 로고
    • Total synthesis of heptamethyl lithospermate
    • Jacobson, R.M.; Raths, R.A. Total synthesis of heptamethyl lithospermate. J. Org. Chem. 1979, 44, 4013-4014.
    • (1979) J. Org. Chem. , vol.44 , pp. 4013-4014
    • Jacobson, R.M.1    Raths, R.A.2
  • 95
    • 25844469333 scopus 로고    scopus 로고
    • Total synthesis of (+)-lithospermic acid by asymmetric intramolecular alkylation via catalytic C-H bond activation
    • O'Malley, S.J.; Tan, K.L.; Watzke, A.; Bergman, R.G.; Ellman, J.A. Total synthesis of (+)-lithospermic acid by asymmetric intramolecular alkylation via catalytic C-H bond activation. J. Am. Chem. Soc. 2005, 127, 13496-13497.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 13496-13497
    • O'Malley, S.J.1    Tan, K.L.2    Watzke, A.3    Bergman, R.G.4    Ellman, J.A.5
  • 96
    • 79954505975 scopus 로고    scopus 로고
    • Highly convergent total synthesis of (+)-lithospermic acid via a late-stage intermolecular C-H olefination
    • Wang, D.-H.; Yu, J.-Q. Highly convergent total synthesis of (+)-lithospermic acid via a late-stage intermolecular C-H olefination. J. Am. Chem. Soc. 2011, 133, 5767-5769.
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 5767-5769
    • Wang, D.-H.1    Yu, J.-Q.2
  • 97
    • 79959754849 scopus 로고    scopus 로고
    • A concise route to dehydrobenzo[b]furans: Formal total synthesis of (+)-lithospermic acid
    • Fischer, J.; Savage, G.P.; Coster, M.J. A concise route to dehydrobenzo[b]furans: Formal total synthesis of (+)-lithospermic acid. Org. Lett. 2011, 13, 3376-3379.
    • (2011) Org. Lett. , vol.13 , pp. 3376-3379
    • Fischer, J.1    Savage, G.P.2    Coster, M.J.3
  • 98
    • 33745508516 scopus 로고    scopus 로고
    • Isolation and characterization of rosmarinic acid oligomers in celastrus hindsii benth leaves and their antioxidative activities
    • Ly, T.N.; Shimoyamada, M.; Yamauchi, R. Isolation and characterization of rosmarinic acid oligomers in Celastrus hindsii Benth leaves and their antioxidative activities. J. Agric. Food Chem. 2006, 54, 3786-3793.
    • (2006) J. Agric. Food Chem. , vol.54 , pp. 3786-3793
    • Ly, T.N.1    Shimoyamada, M.2    Yamauchi, R.3
  • 99
    • 84865639363 scopus 로고    scopus 로고
    • Rapid synthesis of dehydrodiferulates via biomometic radical coupling reactions of ethyl ferulate
    • Lu, F.; Wei, L.; Azarpira, A.; Ralph, J. Rapid synthesis of dehydrodiferulates via biomometic radical coupling reactions of ethyl ferulate. J. Agric. Food Chem. 2012, 60, 8272-8277.
    • (2012) J. Agric. Food Chem. , vol.60 , pp. 8272-8277
    • Lu, F.1    Wei, L.2    Azarpira, A.3    Ralph, J.4
  • 100
    • 0027489313 scopus 로고
    • Melitric acids A and B, new trimeric caffeic acid derivatives from meliss officinalis
    • Agata, I.; Kusakabe, H.; Hatano, T.; Nishibe, S.; Okuda, T. Melitric acids A and B, new trimeric caffeic acid derivatives from Meliss officinalis. Chem. Pharm. Bull. 1993, 41, 1608-1611.
    • (1993) Chem. Pharm. Bull. , vol.41 , pp. 1608-1611
    • Agata, I.1    Kusakabe, H.2    Hatano, T.3    Nishibe, S.4    Okuda, T.5
  • 101
    • 0032954489 scopus 로고    scopus 로고
    • Rosmarinic acid derivatives from salvia officinalis
    • Lu, Y.; Foo, L.Y. Rosmarinic acid derivatives from Salvia officinalis. Phytochemistry 1999, 51, 91-94.
    • (1999) Phytochemistry , vol.51 , pp. 91-94
    • Lu, Y.1    Foo, L.Y.2
  • 102
    • 0033401722 scopus 로고    scopus 로고
    • Sagecoumarin, a novel caffeic acid trimer from salvia officinalis
    • Lu, Y.; Foo, L.Y.; Wong, H. Sagecoumarin, a novel caffeic acid trimer from Salvia officinalis. Phytochemistry 1999, 52, 1149-1152.
    • (1999) Phytochemistry , vol.52 , pp. 1149-1152
    • Lu, Y.1    Foo, L.Y.2    Wong, H.3
  • 104
    • 79251607360 scopus 로고    scopus 로고
    • Salvianolic acid B, a potential chemoprotective agent, for head and necksquamous cell cancer
    • Zhao, Y.; Guo, Y.; Gu, X. Salvianolic acid B, a potential chemoprotective agent, for head and necksquamous cell cancer. J. Oncol. 2011, 2011, doi:10.1155/2011/534548.
    • (2011) J. Oncol. , vol.2011
    • Zhao, Y.1    Guo, Y.2    Gu, X.3
  • 105
    • 0242518089 scopus 로고    scopus 로고
    • A novel spiro compound formed by oxidative cross coupling of methyl sinapate with a syringyl lignin model compound. A model system for the β-1 pathway in lignin biosynthesis
    • Setälä, H.; Pajunen, A.; Rummakko, P.; Sipilä, J.; Brunow, G. A novel spiro compound formed by oxidative cross coupling of methyl sinapate with a syringyl lignin model compound. A model system for the β-1 pathway in lignin biosynthesis. J. Chem. Soc. Perkin Trans. 1 1999, 461-464.
    • (1999) J. Chem. Soc. Perkin Trans. 1 , pp. 461-464
    • Setälä, H.1    Pajunen, A.2    Rummakko, P.3    Sipilä, J.4    Brunow, G.5


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