The University of Massachusetts Amherst

The Plant Cell Culture Library

Vitis cinerea
Cell Line ID VC-12898
Media Type B105
Lowest Tolerable USDA Zone 4b
Drought Tolerance Average
Availability medium
Order Vitales
Family Vitaceae
Genus Vitis
Antifungal Genus Level ➡ 51 citations
Anticancer Genus Level ➡ 49 citations
Common Names South Westeet Winter Grape
Culture Initiation Site Taastrup IC
Plant Habit liana
Plant Habitat Warm Temperate
Culture Start Material Shoot
Native Range Southeast Virginia-Florida
Plant Supplier Inst/Nat. Plant Germplasm System USDA
Antifungal Citations
  1. De Beer, A. et al., BMC Plant Biol., 2008, 8, 75 (Vv-AMP1) [https://doi.org/10.1186/1471-2229-8-75]
  2. Pryce, R.J. et al., Phytochemistry, 1977, 16, 1452- 1454 (α-Viniferin) [https://doi.org/10.1016/S0031-9422(00)88809-3]
  3. Kitanaka, S. et al., Chem. Pharm. Bull., 1990, 38, 432- 435 (isol, cd, pmr, cmr) [https://doi.org/10.1248/cpb.38.432]
  4. Lee, S.-H. et al., Planta Med., 1998, 64, 204- 207 (isol, pmr, cmr, activity) [https://doi.org/10.1055/s-2006-957409]
  5. Ito, T. et al., Chem. Pharm. Bull., 2000, 48, 1001- 1005 (6'-glucoside) [https://doi.org/10.1248/cpb.48.1001]
  6. Luo, H.-F. et al., Tetrahedron, 2001, 57, 4849- 4854 (Caraphenol A) [https://doi.org/10.1016/S0040-4020(01)00427-6]
  7. Shirataki, Y. et al., Nat. Med. (Tokyo), 2002, 56, 139- 142 (Sophorastilbene A)
  8. Wang, T.-M. et al., J. Chin. Chem. Soc. (Taipei), 2009, 56, 881- 884 (Curcusinol)
  9. Ito, T. et al., Fitoterapia, 2012, 83, 1420- 1429 (Cyperusphenol D) [https://doi.org/10.1016/j.fitote.2012.08.005]
  10. Wright, N.E. et al., Angew. Chem., Int. Ed., 2014, 53, 3409- 3413 (synth)
  11. Langcake, P. et al., Experientia, 1977, 33, 151- 152 (ε-Viniferin, struct, biosynth, phytoalexin,antifungal activity) [https://doi.org/10.1007/BF02124034]
  12. Langcake, P. et al., Phytochemistry, 1977, 16, 1193- 1196 (ε-Viniferin, biosynth) [https://doi.org/10.1016/S0031-9422(00)94358-9]
  13. Sotheeswaran, S. et al., JCS Perkin 1, 1985, 159- 162 (ε-Viniferin, isol) [https://doi.org/10.1039/P19850000159]
  14. Kurihara, H. et al., Phytochemistry, 1991, 30, 649- 653 ((-)-trans-ε-Viniferin, cd, abs config,biosynth, antibacterial activity) [https://doi.org/10.1016/0031-9422(91)83745-7]
  15. Sotheeswaran, S. et al., Phytochemistry, 1993, 32, 1083- 1092 (ε-Viniferin, rev, bibl) [https://doi.org/10.1016/S0031-9422(00)95070-2]
  16. Iinuma, M. et al., Phytochemistry, 1994, 37, 1157- 1159 ((-)-ε-Viniferin, isol) [https://doi.org/10.1016/S0031-9422(00)89549-7]
  17. Engler, T.A. et al., Tet. Lett., 1994, 35, 1661- 1664 (ε-Viniferin, synth) [https://doi.org/10.1016/0040-4039(94)88313-0]
  18. Ohyama, M. et al., CA, 1995, 124, 198124 (7E,7'S,8'R-form)
  19. Oshima, Y. et al., Experientia, 1995, 51, 63- 66 ((+)-trans-ε-Viniferin, hepatoprotective activity) [https://doi.org/10.1007/BF01964921]
  20. Oshima, Y. et al., Tetrahedron, 1995, 51, 11979- 11986 (ε-Viniferin diol) [https://doi.org/10.1016/0040-4020(95)00757-Y]
  21. Li, W.-W. et al., Phytochemistry, 1996, 42, 1163- 1165 (7E,7'S,8'S-form, struct, cd, abs config) [https://doi.org/10.1016/0031-9422(96)00069-6]
  22. Li, W. et al., Phytochemistry, 1998, 49, 1393- 1394 (Betulifol B) [https://doi.org/10.1016/S0031-9422(97)00905-9]
  23. Huang, K.S. et al., Chin. Chem. Lett., 1999, 10, 817- 820 (Amurensin H, struct, synth)
  24. Ito, J. et al., Tetrahedron, 1999, 55, 2529- 2544 (Viniferifuran) [https://doi.org/10.1016/S0040-4020(99)00039-3]
  25. Baderschneider, B. et al., J. Agric. Food Chem., 2000, 48, 2681- 2686 (Riesling wine diglucosides, antioxidant activity) [https://doi.org/10.1021/jf991348k]
  26. Huang, K.-S. et al., J. Nat. Prod., 2000, 63, 86- 89 (Gnetuhainins A,B, struct) [https://doi.org/10.1021/np990382q]
  27. Bala, A.E.A. et al., J. Phytopathol., 2000, 148, 29- 32 (cis-ε-Viniferin, struct, trans-ε-Viniferin,antifungal activity)
  28. Huang, K.-S. et al., Tetrahedron, 2000, 56, 1321- 1330 (7E,7'R*,8'S*-form, synth) [https://doi.org/10.1016/S0040-4020(99)01034-0]
  29. Kim, H.J. et al., Arch. Pharmacal Res., 2002, 25, 293- 299 (7E,7'S,8'S-form, 7Z,7'R,8'R-form, abs config, cytotoxicity, antimutagenic activity)
  30. Iliya, I. et al., Chem. Pharm. Bull., 2002, 50, 796- 801 (Gnemonoside E) [https://doi.org/10.1248/cpb.50.796]
  31. Iliya, I. et al., Helv. Chim. Acta, 2002, 85, 2394- 2402 (Gnemonoside J) [https://doi.org/10.1002/1522-2675(200208)85:8<2394::AID-HLCA2394>3.0.CO;2-6]
  32. Morikawa, T. et al., Heterocycles, 2002, 57, 1983- 1988 (Longusol B, struct, activity)
  33. Piver, B. et al., Life Sci., 2003, 73, 1199- 1214 (ε-Viniferin, cytochrome P450 inhibition) [https://doi.org/10.1016/S0024-3205(03)00420-X]
  34. Ito, T. et al., Tetrahedron, 2003, 59, 5347- 5363 (Paucifloroside A) [https://doi.org/10.1016/S0040-4020(03)00730-0]
  35. Zhang, Y. et al., J. Agric. Food Chem., 2004, 52, 228- 233 ((+)-ε-Viniferin, COX-1 inhibitor) [https://doi.org/10.1021/jf034616u]
  36. Ito, T. et al., Helv. Chim. Acta, 2005, 88, 23- 34 (Upunoside D)
  37. Szewczuk, L.M. et al., J. Nat. Prod., 2005, 68, 36- 42 (cis-Viniferin, biosynth) [https://doi.org/10.1021/np049702i]
  38. Yanez, M. et al., Eur. J. Pharmacol., 2006, 542, 54- 60 ((-)-trans-ε-Viniferin, antidepressant activity) [https://doi.org/10.1016/j.ejphar.2006.06.005]
  39. Muhtadi, H. et al., Fitoterapia, 2006, 77, 550- 555 ((-)-trans-ε-Viniferin, antileukaemia activity) [https://doi.org/10.1016/j.fitote.2006.07.004]
  40. Barjot, C. et al., Life Sci., 2007, 81, 1565- 1574 ((-)-trans-ε-Viniferin, anticancer activity) [https://doi.org/10.1016/j.lfs.2007.08.047]
  41. He, S. et al., JOC, 2009, 74, 7966- 7969 ((+)-ε-Viniferin, antioxidant activity) [https://doi.org/10.1021/jo901354p]
  42. Farag, S.F. et al., Phytochem. Lett., 2009, 2, 148- 151 (Tingitanol A, struct, activity) [https://doi.org/10.1016/j.phytol.2009.05.001]
  43. Kraus, G.A. et al., Tet. Lett., 2009, 50, 7180- 7183 (Amurensin H, synth) [https://doi.org/10.1016/j.tetlet.2009.10.040]
  44. Yim, N. et al., Bioorg. Med. Chem. Lett., 2010, 20, 1165- 1168 (trans-ε-Viniferin,anticariogenic activity) [https://doi.org/10.1016/j.bmcl.2009.12.020]
  45. Riviere, C. et al., Bioorg. Med. Chem. Lett., 2010, 20, 3441- 3443 (ε-Viniferin-13-glucoside,amyloid-β fibril inhibitor) [https://doi.org/10.1016/j.bmcl.2009.09.074]
  46. Choi, C.W. et al., Bull. Korean Chem. Soc., 2010, 31, 3448- 3450 (Vitis vinifera 3'-glucoside) [https://doi.org/10.5012/bkcs.2010.31.11.3448]
  47. Morikawa, T. et al., Chem. Pharm. Bull., 2010, 58, 1379- 1385 (Logusol B) [https://doi.org/10.1248/cpb.58.1379]
  48. Abe, N. et al., J. Nat. Prod., 2010, 73, 1499- 1506 (Vatalbinoside C, struct, cd, abs config) [https://doi.org/10.1021/np1002675]
  49. Mattivi, F. et al., J. Agric. Food Chem., 2011, 59, 5364- 5375 ((+)-E,Z-ε-Viniferins, E,Z-ω-Viniferins) [https://doi.org/10.1021/jf200771y]
  50. Choi, C.W. et al., Planta Med., 2011, 77, 374- 376 (cis-ε-Viniferin) [https://doi.org/10.1055/s-0030-1250370]
  51. Lindgren, A.E.G. et al., Eur. J. Org. Chem., 2016, 426- 429 (synth)
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Anticancer Citations
  1. Langcake, P. et al., Experientia, 1977, 33, 151- 152 (ε-Viniferin, struct, biosynth, phytoalexin,antifungal activity) [https://doi.org/10.1007/BF02124034]
  2. Langcake, P. et al., Phytochemistry, 1977, 16, 1193- 1196 (ε-Viniferin, biosynth) [https://doi.org/10.1016/S0031-9422(00)94358-9]
  3. Sotheeswaran, S. et al., JCS Perkin 1, 1985, 159- 162 (ε-Viniferin, isol) [https://doi.org/10.1039/P19850000159]
  4. Kurihara, H. et al., Phytochemistry, 1991, 30, 649- 653 ((-)-trans-ε-Viniferin, cd, abs config,biosynth, antibacterial activity) [https://doi.org/10.1016/0031-9422(91)83745-7]
  5. Sotheeswaran, S. et al., Phytochemistry, 1993, 32, 1083- 1092 (ε-Viniferin, rev, bibl) [https://doi.org/10.1016/S0031-9422(00)95070-2]
  6. Iinuma, M. et al., Phytochemistry, 1994, 37, 1157- 1159 ((-)-ε-Viniferin, isol) [https://doi.org/10.1016/S0031-9422(00)89549-7]
  7. Engler, T.A. et al., Tet. Lett., 1994, 35, 1661- 1664 (ε-Viniferin, synth) [https://doi.org/10.1016/0040-4039(94)88313-0]
  8. Ohyama, M. et al., CA, 1995, 124, 198124 (7E,7'S,8'R-form)
  9. Oshima, Y. et al., Experientia, 1995, 51, 63- 66 ((+)-trans-ε-Viniferin, hepatoprotective activity) [https://doi.org/10.1007/BF01964921]
  10. Oshima, Y. et al., Tetrahedron, 1995, 51, 11979- 11986 (ε-Viniferin diol) [https://doi.org/10.1016/0040-4020(95)00757-Y]
  11. Li, W.-W. et al., Phytochemistry, 1996, 42, 1163- 1165 (7E,7'S,8'S-form, struct, cd, abs config) [https://doi.org/10.1016/0031-9422(96)00069-6]
  12. Li, W. et al., Phytochemistry, 1998, 49, 1393- 1394 (Betulifol B) [https://doi.org/10.1016/S0031-9422(97)00905-9]
  13. Huang, K.S. et al., Chin. Chem. Lett., 1999, 10, 817- 820 (Amurensin H, struct, synth)
  14. Ito, J. et al., Tetrahedron, 1999, 55, 2529- 2544 (Viniferifuran) [https://doi.org/10.1016/S0040-4020(99)00039-3]
  15. Baderschneider, B. et al., J. Agric. Food Chem., 2000, 48, 2681- 2686 (Riesling wine diglucosides, antioxidant activity) [https://doi.org/10.1021/jf991348k]
  16. Huang, K.-S. et al., J. Nat. Prod., 2000, 63, 86- 89 (Gnetuhainins A,B, struct) [https://doi.org/10.1021/np990382q]
  17. Bala, A.E.A. et al., J. Phytopathol., 2000, 148, 29- 32 (cis-ε-Viniferin, struct, trans-ε-Viniferin,antifungal activity)
  18. Huang, K.-S. et al., Tetrahedron, 2000, 56, 1321- 1330 (7E,7'R*,8'S*-form, synth) [https://doi.org/10.1016/S0040-4020(99)01034-0]
  19. Kim, H.J. et al., Arch. Pharmacal Res., 2002, 25, 293- 299 (7E,7'S,8'S-form, 7Z,7'R,8'R-form, abs config, cytotoxicity, antimutagenic activity)
  20. Iliya, I. et al., Chem. Pharm. Bull., 2002, 50, 796- 801 (Gnemonoside E) [https://doi.org/10.1248/cpb.50.796]
  21. Iliya, I. et al., Helv. Chim. Acta, 2002, 85, 2394- 2402 (Gnemonoside J) [https://doi.org/10.1002/1522-2675(200208)85:8<2394::AID-HLCA2394>3.0.CO;2-6]
  22. Morikawa, T. et al., Heterocycles, 2002, 57, 1983- 1988 (Longusol B, struct, activity)
  23. Piver, B. et al., Life Sci., 2003, 73, 1199- 1214 (ε-Viniferin, cytochrome P450 inhibition) [https://doi.org/10.1016/S0024-3205(03)00420-X]
  24. Ito, T. et al., Tetrahedron, 2003, 59, 5347- 5363 (Paucifloroside A) [https://doi.org/10.1016/S0040-4020(03)00730-0]
  25. Zhang, Y. et al., J. Agric. Food Chem., 2004, 52, 228- 233 ((+)-ε-Viniferin, COX-1 inhibitor) [https://doi.org/10.1021/jf034616u]
  26. Ito, T. et al., Helv. Chim. Acta, 2005, 88, 23- 34 (Upunoside D)
  27. Szewczuk, L.M. et al., J. Nat. Prod., 2005, 68, 36- 42 (cis-Viniferin, biosynth) [https://doi.org/10.1021/np049702i]
  28. Yanez, M. et al., Eur. J. Pharmacol., 2006, 542, 54- 60 ((-)-trans-ε-Viniferin, antidepressant activity) [https://doi.org/10.1016/j.ejphar.2006.06.005]
  29. Muhtadi, H. et al., Fitoterapia, 2006, 77, 550- 555 ((-)-trans-ε-Viniferin, antileukaemia activity) [https://doi.org/10.1016/j.fitote.2006.07.004]
  30. Barjot, C. et al., Life Sci., 2007, 81, 1565- 1574 ((-)-trans-ε-Viniferin, anticancer activity) [https://doi.org/10.1016/j.lfs.2007.08.047]
  31. He, S. et al., JOC, 2009, 74, 7966- 7969 ((+)-ε-Viniferin, antioxidant activity) [https://doi.org/10.1021/jo901354p]
  32. Farag, S.F. et al., Phytochem. Lett., 2009, 2, 148- 151 (Tingitanol A, struct, activity) [https://doi.org/10.1016/j.phytol.2009.05.001]
  33. Kraus, G.A. et al., Tet. Lett., 2009, 50, 7180- 7183 (Amurensin H, synth) [https://doi.org/10.1016/j.tetlet.2009.10.040]
  34. Yim, N. et al., Bioorg. Med. Chem. Lett., 2010, 20, 1165- 1168 (trans-ε-Viniferin,anticariogenic activity) [https://doi.org/10.1016/j.bmcl.2009.12.020]
  35. Riviere, C. et al., Bioorg. Med. Chem. Lett., 2010, 20, 3441- 3443 (ε-Viniferin-13-glucoside,amyloid-β fibril inhibitor) [https://doi.org/10.1016/j.bmcl.2009.09.074]
  36. Choi, C.W. et al., Bull. Korean Chem. Soc., 2010, 31, 3448- 3450 (Vitis vinifera 3'-glucoside) [https://doi.org/10.5012/bkcs.2010.31.11.3448]
  37. Morikawa, T. et al., Chem. Pharm. Bull., 2010, 58, 1379- 1385 (Logusol B) [https://doi.org/10.1248/cpb.58.1379]
  38. Abe, N. et al., J. Nat. Prod., 2010, 73, 1499- 1506 (Vatalbinoside C, struct, cd, abs config) [https://doi.org/10.1021/np1002675]
  39. Mattivi, F. et al., J. Agric. Food Chem., 2011, 59, 5364- 5375 ((+)-E,Z-ε-Viniferins, E,Z-ω-Viniferins) [https://doi.org/10.1021/jf200771y]
  40. Choi, C.W. et al., Planta Med., 2011, 77, 374- 376 (cis-ε-Viniferin) [https://doi.org/10.1055/s-0030-1250370]
  41. Lindgren, A.E.G. et al., Eur. J. Org. Chem., 2016, 426- 429 (synth)
  42. Mattivi, F. et al., Bull. Liaison-Groupe Polyphenols, 1992, 16, 116- 119 (r-Viniferin, struct)
  43. Oshima, Y. et al., Tetrahedron, 1995, 51, 11979- 11986 (Vitisin B, cis-Vitisin B, struct, rel stereochem) [https://doi.org/10.1016/0040-4020(95)00757-Y]
  44. Ito, J. et al., Tetrahedron, 1996, 52, 9991- 9998 (Vitisins B,C, cis-Vitisin B, struct, abs config,biosynth) [https://doi.org/10.1016/0040-4020(96)00543-1]
  45. Ito, J. et al., Tetrahedron, 1999, 55, 2529- 2544 (Vitisfuran B, struct, abs config) [https://doi.org/10.1016/S0040-4020(99)00039-3]
  46. Takaya, Y. et al., Tetrahedron, 2002, 58, 9265- 9271 (Vitisins B,C, abs config, biosynth) [https://doi.org/10.1016/S0040-4020(02)01191-2]
  47. Huang, Y.-L. et al., J. Nat. Prod., 2005, 68, 217- 220 ((+)-Vitisin C, platelet aggregation inhibitor, free radical scavenging activity) [https://doi.org/10.1021/np049686p]
  48. Pat. Coop. Treaty (WIPO), 2006, 2006 025 708, ( UNIGEN) (γ-Viniferin, pmr, AChE inhibitor)
  49. Choi, C.W. et al., Bull. Korean Chem. Soc., 2010, 31, 3448- 3450 (Vitisin B, antiproliferative activity) [https://doi.org/10.5012/bkcs.2010.31.11.3448]
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