메뉴 건너뛰기




Volumn 53, Issue 23, 2005, Pages 9010-9016

Isoflavonoids isolated from cuban propolis

Author keywords

( ) liquiritigenin; 1D and 2D NMR spectroscopy; CD; ESI MS MS; Isoflavans; Isoflavonoids; Isoliquiritigenin; Propolis; Pterocarpans

Indexed keywords

FLAVONOID; ISOFLAVONE DERIVATIVE; PROPOLIS;

EID: 28444438591     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0518756     Document Type: Article
Times cited : (111)

References (45)
  • 1
    • 34047229759 scopus 로고
    • Propolis: Chemical composition, biological properties and therapeutic activity
    • Marcucci, M. C. Propolis: chemical composition, biological properties and therapeutic activity. Apidologie 1995, 26, 83-99.
    • (1995) Apidologie , vol.26 , pp. 83-99
    • Marcucci, M.C.1
  • 2
    • 0032489791 scopus 로고    scopus 로고
    • Review of the biological properties and toxicity of bee propolis (propolis)
    • Burdock, G. A. Review of the biological properties and toxicity of bee propolis (propolis). Food Chem. Toxicol. 1998, 36, 347-363.
    • (1998) Food Chem. Toxicol. , vol.36 , pp. 347-363
    • Burdock, G.A.1
  • 3
    • 0034753678 scopus 로고    scopus 로고
    • Recent progress in pharmacological research of propolis
    • Banskota, A. H.; Tezuka, Y.; Kadota, S. Recent progress in pharmacological research of propolis. Phytother. Res. 2001, 15, 561-571.
    • (2001) Phytother. Res. , vol.15 , pp. 561-571
    • Banskota, A.H.1    Tezuka, Y.2    Kadota, S.3
  • 4
    • 0033976532 scopus 로고    scopus 로고
    • Propolis: Recent advances in chemistry and plant origin
    • Bankova, V. B.; De Castro, S. L.; Marcucci, M. C. Propolis: recent advances in chemistry and plant origin. Apidologie 2000, 31, 3-15.
    • (2000) Apidologie , vol.31 , pp. 3-15
    • Bankova, V.B.1    De Castro, S.L.2    Marcucci, M.C.3
  • 6
    • 0032711768 scopus 로고    scopus 로고
    • Studies on the constituents of Brazilian propolis. II
    • Tazawa, S.; Warashina, T.; Noro, T. Studies on the constituents of Brazilian propolis. II. Chem. Pharm. Bull. 1999, 47, 1388-1392.
    • (1999) Chem. Pharm. Bull. , vol.47 , pp. 1388-1392
    • Tazawa, S.1    Warashina, T.2    Noro, T.3
  • 7
    • 0037165536 scopus 로고    scopus 로고
    • Botanical origin and chemical composition of Brazilian propolis
    • Park, Y. K.; Alencar, S. M.; Aguiar, C. L. Botanical origin and chemical composition of Brazilian propolis. J. Agric. Food Chem. 2002, 50, 2502-2506.
    • (2002) J. Agric. Food Chem. , vol.50 , pp. 2502-2506
    • Park, Y.K.1    Alencar, S.M.2    Aguiar, C.L.3
  • 8
    • 0036249452 scopus 로고    scopus 로고
    • Polyisoprenylated benzophenones in Cuban propolis; biological activity of nemorosone
    • Cuesta-Rubio, O.; Frontana-Uribe, B. A.; Ramirez-Apan T.; Cardenas, J. Polyisoprenylated benzophenones in Cuban propolis; biological activity of nemorosone. Z. Naturforsch. 2002, 57C, 372-378.
    • (2002) Z. Naturforsch. , vol.57 C , pp. 372-378
    • Cuesta-Rubio, O.1    Frontana-Uribe, B.A.2    Ramirez-Apan, T.3    Cardenas, J.4
  • 11
    • 0020512371 scopus 로고
    • Naturally occurring isoflavonoids (1855-1981)
    • Ingham, J. L. Naturally occurring isoflavonoids (1855-1981). Prog. Chem. Org. Nat. 1983, 43, 1-266.
    • (1983) Prog. Chem. Org. Nat. , vol.43 , pp. 1-266
    • Ingham, J.L.1
  • 12
    • 0032994684 scopus 로고    scopus 로고
    • Phytoestrogens: The "natural" selective estrogen receptor modulators?
    • Brzezinski, A.; Debi, A. Phytoestrogens: The "natural" selective estrogen receptor modulators? Eur. J. Ob. Gyn. Rep. Biol. 1999, 85, 47-51.
    • (1999) Eur. J. Ob. Gyn. Rep. Biol. , vol.85 , pp. 47-51
    • Brzezinski, A.1    Debi, A.2
  • 14
    • 0037070032 scopus 로고    scopus 로고
    • Isolation and quantitative analysis of phenolic antioxidants, free sugars, and polyols from mango (Mangifera indica L.) stem bark aqueous decoction used in Cuba as a nutritional supplement
    • Nunez Selles, A.; Velez Castro, H.; Aguero-Aguero, J.; Gonzalez-Gonzalez, J.; Naddeo, F.; De Simone, F.; Rastrelli, L. Isolation and quantitative analysis of phenolic antioxidants, free sugars, and polyols from mango (Mangifera indica L.) stem bark aqueous decoction used in Cuba as a nutritional supplement. J. Agric. Food Chem. 2002, 50, 762-766.
    • (2002) J. Agric. Food Chem. , vol.50 , pp. 762-766
    • Nunez Selles, A.1    Velez Castro, H.2    Aguero-Aguero, J.3    Gonzalez-Gonzalez, J.4    Naddeo, F.5    De Simone, F.6    Rastrelli, L.7
  • 16
    • 0032425577 scopus 로고    scopus 로고
    • Acetophenones, a chalcone, a chromone and flavonoids from Pancratium maritimum
    • Youssef, D. T. A.; Ramadan, M. A.; Khalifa, A. A. Acetophenones, a chalcone, a chromone and flavonoids from Pancratium maritimum. Phytochemistry 1998, 49, 2579-2583.
    • (1998) Phytochemistry , vol.49 , pp. 2579-2583
    • Youssef, D.T.A.1    Ramadan, M.A.2    Khalifa, A.A.3
  • 17
    • 0000436591 scopus 로고
    • Microwave-mediated synthesis of anticarcinogenic isoflavones from soybeans
    • Chang, Y.-C.; Nair, M. G.; Santell, R. C.; Helferich, W. G. Microwave-mediated synthesis of anticarcinogenic isoflavones from soybeans. J. Agric. Food Chem. 1994, 42, 1869-1871.
    • (1994) J. Agric. Food Chem. , vol.42 , pp. 1869-1871
    • Chang, Y.-C.1    Nair, M.G.2    Santell, R.C.3    Helferich, W.G.4
  • 18
    • 0000332380 scopus 로고
    • Occurrence and distribution of free flavonoid aglycons in plants
    • Wollenweber, E.; Dietz, V. H. Occurrence and distribution of free flavonoid aglycons in plants. Phytochemistry 1981, 20, 869-932.
    • (1981) Phytochemistry , vol.20 , pp. 869-932
    • Wollenweber, E.1    Dietz, V.H.2
  • 19
    • 0034003617 scopus 로고    scopus 로고
    • Inhibition of xanthine oxidase by liquiritigenin and isoliquiritigenin isolated from Sinofranchetia chinensis
    • Kong, L. D.; Zhang, Y.; Pan, X.; Tan, R. X.; Cheng, C. H. K. Inhibition of xanthine oxidase by liquiritigenin and isoliquiritigenin isolated from Sinofranchetia chinensis. Cell. Mol. Life Sci. 2000, 57, 500-505.
    • (2000) Cell. Mol. Life Sci. , vol.57 , pp. 500-505
    • Kong, L.D.1    Zhang, Y.2    Pan, X.3    Tan, R.X.4    Cheng, C.H.K.5
  • 20
    • 0031955386 scopus 로고    scopus 로고
    • Three new flavonoids and antiallergic, anti-inflammatory constituents from the heartwood of Dalbergia odorifera
    • Chan, S. C.; Chang, Y. S.; Wang, J. P.; Chen, S. C.; Kuo, S. C. Three new flavonoids and antiallergic, anti-inflammatory constituents from the heartwood of Dalbergia odorifera. Planta Med. 1998, 64, 153-158.
    • (1998) Planta Med. , vol.64 , pp. 153-158
    • Chan, S.C.1    Chang, Y.S.2    Wang, J.P.3    Chen, S.C.4    Kuo, S.C.5
  • 21
    • 1842577637 scopus 로고    scopus 로고
    • Induction of cell cycle arrest and p21CIP1/WAF1 expression in human lung cancer cells by isoliquiritigenin
    • Li, T.; Satomi, Y.; Katoh, D.; Shimada, J.; Baba, M.; Okuyama, T.; Nishino, H.; Kitamura, N. Induction of cell cycle arrest and p21CIP1/WAF1 expression in human lung cancer cells by isoliquiritigenin. Cancer Lett. 2004, 207, 27-35.
    • (2004) Cancer Lett. , vol.207 , pp. 27-35
    • Li, T.1    Satomi, Y.2    Katoh, D.3    Shimada, J.4    Baba, M.5    Okuyama, T.6    Nishino, H.7    Kitamura, N.8
  • 22
    • 9944237767 scopus 로고    scopus 로고
    • Studies on cancer chemoprevention by traditional folk medicines. XXV. Inhibitory effect of isoliquiritigenin on azoxymethane-induced murine colon aberrant crypt focus formation and carcinogenesis
    • Baba, M.; Asano, R.; Takigami, I.; Takahashi, T.; Ohmura, M.; Okada, Y.; Sugimoto, H.; Arika, T.; Nishino, H.; Okuyama, T. Studies on cancer chemoprevention by traditional folk medicines. XXV. Inhibitory effect of isoliquiritigenin on azoxymethane-induced murine colon aberrant crypt focus formation and carcinogenesis. Biol. Pharm. Bull. 2002, 25, 247-250.
    • (2002) Biol. Pharm. Bull. , vol.25 , pp. 247-250
    • Baba, M.1    Asano, R.2    Takigami, I.3    Takahashi, T.4    Ohmura, M.5    Okada, Y.6    Sugimoto, H.7    Arika, T.8    Nishino, H.9    Okuyama, T.10
  • 24
    • 0141829776 scopus 로고    scopus 로고
    • Phytoestrogens: A review of the present state of research
    • Osoki, A. L.; Kennelly, E. J. Phytoestrogens: a review of the present state of research. Phytother. Res. 2003, 17, 845-869.
    • (2003) Phytother. Res. , vol.17 , pp. 845-869
    • Osoki, A.L.1    Kennelly, E.J.2
  • 26
    • 28444493579 scopus 로고
    • Chemistry of Brazilian Leguminosae. XXIV. Flavanoids of Dalbergia ecastophyllum
    • Matos, F. J. de Abreu; Gottlieb, O. R.; Ollis, W. D.; Andrade, C. H. Souza. Chemistry of Brazilian Leguminosae. XXIV. Flavanoids of Dalbergia ecastophyllum. An. Acad. Bras. Cienc. 1970, 42, 61-64.
    • (1970) An. Acad. Bras. Cienc. , vol.42 , pp. 61-64
    • Matos, F.J.D.A.1    Gottlieb, O.R.2    Ollis, W.D.3    Souza, A.C.H.4
  • 28
    • 28444480111 scopus 로고
    • Harborne, J. B., Mabry, T. J., Eds.; Chapman and Hall: London, U.K.
    • Dewick, P. M. In The Flavonoids: Advances in Research; Harborne, J. B., Mabry, T. J., Eds.; Chapman and Hall: London, U.K., 1982; p 582.
    • (1982) The Flavonoids: Advances in Research , pp. 582
    • Dewick, P.M.1
  • 31
    • 0028114387 scopus 로고
    • Nematicidal activities of two phytoalexins from Taverniera abyssinica
    • Stadler, M.; Dayne, E.; Anke, H. Nematicidal activities of two phytoalexins from Taverniera abyssinica. Planta Med. 1994, 60, 550-552.
    • (1994) Planta Med. , vol.60 , pp. 550-552
    • Stadler, M.1    Dayne, E.2    Anke, H.3
  • 32
    • 0000202334 scopus 로고
    • Antifungal activity of pterocarpans towards Monilinia fructicola [Schlerotinia fructicola]
    • Perrin, D. R.; Cruickshank, I. A. M. Antifungal activity of pterocarpans towards Monilinia fructicola [Schlerotinia fructicola]. Phytochemistry 1969, 8, 971-978.
    • (1969) Phytochemistry , vol.8 , pp. 971-978
    • Perrin, D.R.1    Cruickshank, I.A.M.2
  • 33
    • 0029139553 scopus 로고
    • Isoflavonoids and neoflavonoids: Naturally occurring o-heterocycles
    • Donnelly, D. M. X.; Boland, G. M. Isoflavonoids and neoflavonoids: naturally occurring o-heterocycles. Nat. Prod. Rep. 1995, 321-338.
    • (1995) Nat. Prod. Rep. , pp. 321-338
    • Donnelly, D.M.X.1    Boland, G.M.2
  • 35
    • 0030272214 scopus 로고    scopus 로고
    • Stereoselective syntheses of substituted pterocarpans with anti-HIV activity and 5-aza-/5-thia-pterocarpan and 2-aryl-2,3-dihydrobenzofuran analogues
    • Engler, T. A.; La Tessa, K. O.; Iyengar, R.; Wenying, C.; Agrios, K. Stereoselective syntheses of substituted pterocarpans with anti-HIV activity and 5-aza-/5-thia-pterocarpan and 2-aryl-2,3-dihydrobenzofuran analogues. Bioorg. Med. Chem. 1996, 4, 1755-1769.
    • (1996) Bioorg. Med. Chem. , vol.4 , pp. 1755-1769
    • Engler, T.A.1    La Tessa, K.O.2    Iyengar, R.3    Wenying, C.4    Agrios, K.5
  • 36
    • 0001528214 scopus 로고
    • Structures of cabenegrins A-I and A-II, potent anti-snake venoms
    • Nakagawa, M.; Nakanishi, K.; Darko, L. L.; Vick, J. A. Structures of cabenegrins A-I and A-II, potent anti-snake venoms. Tetrahedron Lett. 1982, 23, 3855-3858.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 3855-3858
    • Nakagawa, M.1    Nakanishi, K.2    Darko, L.L.3    Vick, J.A.4
  • 37
    • 2342608961 scopus 로고    scopus 로고
    • A new cyclooxygenase (COX) inhibitory pterocarpan from Indigofera aspalathoides: Structure elucidation and determination of binding orientations in the active sites of the enzyme by molecular docking
    • Selvam, C.; Jachak, Sanjay M.; Oli, R. Gnana; Thilagavathi, Ramasamy; Chakraborti, Asit K.; Bhutani, K. K. A new cyclooxygenase (COX) inhibitory pterocarpan from Indigofera aspalathoides: Structure elucidation and determination of binding orientations in the active sites of the enzyme by molecular docking. Tetrahedron Lett. 2004, 45, 4311-4314.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 4311-4314
    • Selvam, C.1    Jachak Sanjay, M.2    Gnana, O.R.3    Thilagavathi, R.4    Chakraborti Asit, K.5    Bhutani, K.K.6
  • 38
    • 0033105204 scopus 로고    scopus 로고
    • Stereoselective synthesis of isoflavonoids. (R)- and (S)-isoflavans
    • Versteeg, M.; Bezuidenhoudt, B. C. B.; Ferreira, D. Stereoselective synthesis of isoflavonoids. (R)- and (S)-isoflavans. Tetrahedron 1999, 55, 3365-3376.
    • (1999) Tetrahedron , vol.55 , pp. 3365-3376
    • Versteeg, M.1    Bezuidenhoudt, B.C.B.2    Ferreira, D.3
  • 40
    • 0035855281 scopus 로고    scopus 로고
    • Synthesis of isoflavonoids. Enantiopure cis- and trans-6a- hydroxypterocarpans and a racemic trans-pterocarpan
    • van Aardt, T. G.; van Rensburg, H.; Ferreira, D. Synthesis of isoflavonoids. Enantiopure cis- and trans-6a-hydroxypterocarpans and a racemic trans-pterocarpan. Tetrahedron 2001, 57, 7113-7126.
    • (2001) Tetrahedron , vol.57 , pp. 7113-7126
    • Van Aardt, T.G.1    Van Rensburg, H.2    Ferreira, D.3
  • 43
    • 0034899720 scopus 로고    scopus 로고
    • Chiroptical properties of 2,3-dihydrobenzo[b]furan and chromane chromophores in naturally occurring O-heterocycles
    • Antus, S.; Kurtan, T.; Juhasz, L.; Kiss, L.; Hollosi, M.; Majer, Z. S. Chiroptical properties of 2,3-dihydrobenzo[b]furan and chromane chromophores in naturally occurring O-heterocycles. Chirality 2001, 13, 493-506.
    • (2001) Chirality , vol.13 , pp. 493-506
    • Antus, S.1    Kurtan, T.2    Juhasz, L.3    Kiss, L.4    Hollosi, M.5    Majer, Z.S.6
  • 44
    • 0000029584 scopus 로고
    • Mass spectra of oxygen heterocycles. II. Mass spectra of some flavonoids
    • Pelter, A.; Stainton, P.; Barber, M. J. Mass spectra of oxygen heterocycles. II. Mass spectra of some flavonoids. Heterocycl. Chem. 1965, 2, 262-271.
    • (1965) Heterocycl. Chem. , vol.2 , pp. 262-271
    • Pelter, A.1    Stainton, P.2    Barber, M.J.3
  • 45
    • 0034536051 scopus 로고    scopus 로고
    • Mass spectrometric studies of the pterocarpan skeleton
    • Toth, E.; Dinya, Z.; Antus, S. Mass spectrometric studies of the pterocarpan skeleton. Rapid Commun. Mass Spectrom. 2000, 14, 2367-2372.
    • (2000) Rapid Commun. Mass Spectrom. , vol.14 , pp. 2367-2372
    • Toth, E.1    Dinya, Z.2    Antus, S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.