Alpha-pyrone glycosides from Scutellaria salviifolia Benth
Alpha-pyrone glycosides from Scutellaria salviifolia Benth
Scutellaria salviifolia Benth. is an endemic species growing in Turkey that belongs to the family Lamiaceae.As a result of a phytochemical study on the aerial parts of S. salviifolia Benth., two new and 10 known compounds were isolated from the aqueous fraction of methanolic extract. The new compounds are methyl-α-pyrone glucosides, 3,4-dihydroxy-6-methylpyran-2-one 3-O-β -glucopyranoside (=scusalvioside A, 1), and 3,4-dihydroxy-6-methylpyran2-one 3-O-β -(6′ -O-E -caffeoyl) glucopyranoside (=scusalvioside B, 2) with new skeletal structures. Along with them, 3 phloroglucinol glucosides [phlorin (3), tadehaginoside (4), and 6′′-O-Z -p-coumaroyl phloroglucinol-1-O-β - glucopyranoside (5)], 6 flavonoids [apigenin (6), apigenin 5-O-β -glucopyranoside (7), isoschaftoside (8), luteolin 7- O-β -glucuronide (9), luteolin 4′ -O-β -glucopyranoside (10), and hispidulin (11)], and one phenylethanoid glycoside [martynoside (12)] were also isolated as known compounds. Compounds 2 and 8 were isolated as a mixture. Structureelucidations of the isolated compounds were carried out using UV, 1 H NMR, 13 C NMR, 2D NMR, and HR-ESI-MS analyses. Moreover, the phenylethanoid glycosides acteoside (13) and leucosceptoside A (14) were also detected in the plant by HPLC-DAD study. Tadehaginoside, 6′′ -O-Z -p-coumaroyl phloroglucinol-1-O-β -glucopyranoside, and luteolin 4 ′-O-β -glucopyranoside were reported for the first time from a Scutellaria species with this study.
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- 1. Senol, F. S.; Orhan, I.; Yilmaz, G.; Cicek, M.; Sener, B. Food Chem. Toxicol. 2010, 48, 781-788.
- 2. Shang, X. F.; He, X. R.; He, X. Y.; Li, M. X.; Zhang, R. X.; Fan, P. C.; Zhang, Q. L.; Jia, Z. P. J. Ethnopharmacol.
2010, 128, 279-313.
- 3. Lin, H.; Zhou, J.; Lin, K.; Wang, H.; Liang, Z.; Ren, X.; Huang, L.; Xia, C. Biomed. Res. Int. 2016, 2016, 5697571.
- 4. Arweiler, N. B.; Pergola, G.; Kuenz, J.; Hellwig, E.; Sculean, A.; Auschill, T. M. Clin. Oral. Invest. 2011, 15,
909-913.
- 5. Seok, J. K.; Kwak, J. Y.; Choi, G. W.; An, S. M.; Kwak, J. H.; Seo, H. H.; Suh, H. J.; Boo, Y. C. Phytother. Res.
2016, 30, 374-379.
- 6. Yin, X. L.; Zhou, J. B.; Jie, C. F.; Xing, D. M.; Zhang, Y. Life Sci. 2004, 75, 2233-2244.
- 7. Cha, Y. Y.; Lee, E. O.; Lee, H. J.; Park, Y. D.; Ko, S. G.; Kim, D. H.; Kim, H. M.; Kang, I. C.; Kim, S. H. Clin.
Chim. Acta 2004, 348, 41-48.
- 8. Shoemaker, M.; Hamilton, B.; Dairkee, S. H.; Cohen, I.; Campbell, M. J. Phytother. Res. 2005, 19, 649-651.
- 9. Chung, C. P.; Park, J. B.; Bae, K. H. Planta Med. 1995, 61, 150-153.
- 10. Yoon, S. B.; Lee, Y. J.; Park, S. K.; Kim, H. C.; Bae, H.; Kim, H. M.; Ko, S. G.; Choi, H. Y.; Oh, M. S.; Park,
W. J. Ethnopharmacol. 2009, 125, 286-290.
- 11. Rugo, H.; Shtivelman, E.; Perez, A.; Vogel, C.; Franco, S.; Tan Chiu, E.; Melisko, M.; Tagliaferri, M.; Cohen, I.;
Shoemaker, M. et al. Breast Cancer Res. Tr. 2007, 105, 17-28.
- 12. Perez, A. T.; Arun, B.; Tripathy, D.; Tagliaferri, M. A.; Shaw, H. S.; Kimmick, G. G.; Cohen, I.; Shtivelman, E.;
Caygill, K. A.; Grady, D. et al. Breast Cancer Res. Tr. 2010, 120, 111-118.
- 13. Zhang, Z. Z.; Lian, X. Y.; Li, S. Y.; Stringer, J. L. Phytomedicine 2009, 16, 485-493.
- 14. Gafner, S.; Bergeron, C.; Batcha, L. L.; Reich, J.; Arnason, J. T.; Burdette, J. E.; Pezzuto, J. M.; Angerhofer, C.
K. J. Nat. Prod. 2003, 66, 535-537.
- 15. Awad, R.; Arnason, J. T.; Trudeau, V.; Bergeron, C.; Budzinski, J. W.; Foster, B. C.; Merali, Z. Phytomedicine
2003, 10, 640-649.
- 16. Brock, C.; Whitehouse, J.; Tewfik, I.; Towell, T. Phytother. Res. 2014, 28, 692-698.
- 17. Cakilcioglu, U.; Turkoglu, I. J. Ethnopharmacol. 2010, 132, 165-175.
- 18. Altundag, E.; Ozturk, M. Procd. Soc. Behv. 2011, 19, 756-777.
- 19. Mukemre, M.; Behcet, L.; Cakilcioglu, U. J. Ethnopharmacol. 2015, 166, 361-374.
- 20. Dalar, A.; Mukemre, M.; Unal, M.; Ozgokce, F. J. Ethnopharmacol. 2018, 226, 56-72.
- 21. Quattrocchi, U. CRC World Dictionary of Medicinal and Poisonous Plants: Common Names, Scientific Names,
Eponyms, Synonyms, and Etymology; CRC Press: Boca Raton, FL, USA, 2012.
- 22. Saracoglu, I.; Inoue, M.; Calis, I.; Ogihara, Y. Biol. Pharm. Bull. 1995, 18, 1396-1400.
- 23. Zengin, G.; Llorent-Martinez, E. J.; Molina-Garcia, L.; Fernandez-de Cordova, M. L.; Aktumsek, A.; Uysal, S.;
Rengasamy, K. R. R.; Aumeeruddy, M. Z.; Bahadori, M. B.; Mahomoodally, M. F. J. Pharm. Pharmacol. 2019,
71, 270-280.
- 24. Cicek, M.; Demirci, B.; Yilmaz, G.; Baser, K. H. Nat. Prod. Res. 2011, 25, 1720-1726.
- 25. Foo, L. Y.; Karchesy, J. J. Phytochemistry 1989, 28, 1237-1240.
- 26. Ersöz, T.; Harput, Ü. Ş.; Saracoğlu, İ.; Çalış, İ.; Ogihara, Y. Turk. J. Chem. 2002, 26, 581-588.
- 27. Zhang, X.; Chen, C.; Li, Y.; Chen, D.; Dong, L.; Na, W.; Wu, C.; Zhang, J.; Li, Y. J. Nat. Prod. 2016, 79,
1249-1258.
- 28. Wu, J. N.; Ma, G. X.; Li, H. L.; Wu, C. M.; Tan, Y. F.; Zhang, T. T.; Chen, F.; Guo, P.; Zhang, X. P. Chin. Herb.
Med. 2014, 6, 324-327.
- 29. Malikov, V. M.; Yuldashev, M. P. Chem. Nat. Compd.+ 2002, 38, 358-406.
- 30. Veit, M.; Geiger, H.; Czygan, F. C.; Markham, K. R. Phytochemistry 1990, 29, 2555-2560.
- 31. Zheng, L. H.; Hao, X. J.; Yuan, C. M.; Huang, L. J.; Zhang, J. X.; Dong, F.; Fan, T. Y.; Wu, G. H.; Chen, Y.;
Ma, Y. et al. Zhongguo Zhong Yao Za Zhi 2015, 40, 672-678.
- 32. Xie, C.; Veitch, N. C.; Houghton, P. J.; Simmonds, M. S. J. Chem. Pharm. Bull. 2003, 51, 1204-1207.
- 33. Özgen, U.; Mavi, A.; Terzi, Z.; Kazaz, C.; Aşçı, A.; Kaya, Y.; Seçen, H. Rec. Nat. Prod. 2011, 5, 12-21.
- 34. Ringl, A.; Prinz, S.; Huefner, A.; Kurzmann, M.; Kopp, B. Chem. Biodivers. 2007, 4, 154-162.
- 35. Lee, M. H.; Son, Y. K.; Han, Y. N. Arch. Pharm. Res. 2002, 25, 842-850.
- 36. Guinot, P.; Gargadennec, A.; La Fisca, P.; Fruchier, A.; Andary, C.; Mondolot, L. Ind. Crop. Prod. 2009, 29,
320-325.
- 37. Osei-Safo, D.; Chama, M. A.; Addae-Mensah, I.; Waibel, R. J. Sci. Technol. 2009, 29, 7-15.
- 38. Abdelhalim, A.; Chebib, M.; Aburjai, T.; Johnston, G. A. R.; Hanrahan, J. R. Adv. Biol. Chem. 2014, 4, 148-159.
- 39. Genç, Y. PhD, Hacettepe University, Ankara, 2017.
- 40. Veit, M.; Geiger, H.; Kast, B.; Beckert, C.; Horn, C.; Markham, K. R.; Wong, H.; Czygan, F. C. Phytochemistry
1995, 39, 915-917.
- 41. Demuner, A. J.; Valente, V. M. M.; Barbosa, L. C. A.; Rathi, A. H.; Donohoe, T. J.; Thompson, A. L. Molecules
2009, 14, 4973-4986.
- 42. Tempone, A. G.; Ferreira, D. D.; Lima, M. L.; Costa Silva, T. A.; Borborema, S. E. T.; Reimao, J. Q.; Galuppo,
M. K.; Guerra, J. M.; Russell, A. J.; Wynne, G. M. et al. Eur. J. Med. Chem. 2017, 139, 947-960.
- 43. Zha, W.; Shao, Z.; Frost, J. W.; Zhao, H. J. Am. Chem. Soc. 2004, 126, 4534-4535.
- 44. Kwon, S. J.; Lee, M. Y.; Ku, B.; Sherman, D. H.; Dordick, J. S. ACS Chem. Biol. 2007, 2, 419-425.
- 45. Paton, A. Kew Bull. 1990, 45, 399-450.
- 46. Kikuchi, Y.; Miyaichi, Y.; Yamaguchi, Y.; Kizu, H.; Tomimori, T.; Vetschera, K. Chem. Pharm. Bull. 1991, 39,
199-201.
- 47. Wang, W. S.; Zhou, Y. W.; Ye, Y. H.; Du, N. Zhongguo Zhong Yao Za Zhi 2004, 29, 957-959.
- 48. Miyaichi, Y.; Kizu, H.; Tomimori, T.; Lin, C. C. Chem. Pharm. Bull. 1989, 37, 794-797.
- 49. Kuroda, M.; Iwabuchi, K.; Mimaki, Y. Nat. Prod. Commun. 2012, 7, 471-474.
- 50. Hussain, H.; Ahmad, V. U.; Anwar, S.; Miana, G. A.; Krohn, K. Biochem. Syst. Ecol. 2008, 36, 490-492.
- 51. Oganesyan, G. B. Chem. Nat. Compd.+ 2010, 46, 466-467.
- 52. Nicollier, G. F.; Thompson, A. C.; Salin, M. L. J. Agr. Food Chem. 1981, 29, 1179-1181.
- 53. Miyaichi, Y.; Morimoto, T.; Yaguchi, K.; Kizu, H. J. Nat. Med. 2006, 60, 157-158.
- 54. Xiao, H. T.; Li, X. Shenyang Yao Ke Da Xue Xue Bao 2006, 23, 637-640.
- 55. Marques, M. R.; Stuker, C.; Kichik, N.; Tarrago, T.; Giralt, E.; Morel, A. F.; Dalcol, I. I. Fitoterapia 2010, 81,
552-556.
- 56. Gousiadou, C.; Karioti, A.; Heilmann, J.; Skaltsa, H. Phytochemistry 2007, 68, 1799-1804.
- 57. Saracoğlu, İ.; Ersöz, T.; Calış, İ. Hacettepe University Journal of the Faculty of Pharmacy 1992, 12, 65-70.
- 58. Zhou, Z. H.; Zhang, Y. J.; Yang, C. R. Stud. Plan. S. 1999, 6, 305-310.
- 59. Grzegorczyk-Karolak, I.; Kuzma, L.; Wysokinska, H. Acta Physiol. Plant. 2015, 37, 1736-1744.
- 60. Bardakci, H.; Skaltsa, H.; Milosevic-Ifantis, T.; Lazari, D.; Hadjipavlou-Litina, D.; Yesilada, E.; Kirmizibekmez,
H. Ind. Crop. Prod. 2015, 77, 196-203.
- 61. Calis, I.; Saracoglu, I.; Basaran, A. A.; Sticher, O. Phytochemistry 1993, 32, 1621-1623.
- 62. Mousavi, S. N. M.; Delazar, A.; Nazemiyeh, H.; Khodaie, L. Iran. J. Pharm. Res. 2015, 14, 215-223.
- 63. Olennikov, D. N.; Chirikova, N. K. Chem. Nat. Compd.+ 2013, 49, 124-126.
- 64. Cha, J. H.; Kim, H. W.; Kim, S.; Jung, S. H.; Whang, W. K. Yakhak Hoechi 2006, 50, 136-143.
- 65. Wang, T.; Wang, S.; Xiao, D. L. J. Med. Plants Res. 2012, 6, 4259-4275.
- 66. Karimov, A.; Botirov, E. K. Chem. Nat. Compd.+ 2015, 51, 764-765.
- 67. Siddikov, G. U.; Yuldashev, M. P.; Abdullaev, S. V. Chem. Nat. Compd.+ 2007, 43, 324-325.