DOI QR코드

DOI QR Code

Structure-Guided Identification of Novel Phenolic and Phenolic Amide Allosides from the Rhizomes of Cimicifuga heracleifolia

  • Yim, Soon-Ho (College of Pharmacy and Research Institute of Drug Development, Chonnam National University) ;
  • Kim, Hyun-Jung (College of Pharmacy, Mokpo National University) ;
  • Jeong, Na-Ri (Genophile Co., Ltd.) ;
  • Park, Ki-Deok (Gwangju Center, Korea Basic Science Institute) ;
  • Lee, Young-Ju (Gwangju Center, Korea Basic Science Institute) ;
  • Cho, Sung-Dong (Department of Chemistry, College of Natural Science) ;
  • Lee, Ik-Soo (College of Pharmacy and Research Institute of Drug Development, Chonnam National University)
  • Received : 2011.12.20
  • Accepted : 2012.01.12
  • Published : 2012.04.20

Abstract

Two phenolic allopyranosides and two phenolic amide allopyranosides, along with eight known phenolic compounds, including cimicifugic acids, shomaside B, fukiic acid, isoferulic acid, and piscidic acid, were isolated from the n-butanolic extract of rhizomes of Cimicifuga heracleifolia. On-line spectroscopic data for UV, NMR, and MS from a combination of LC-NMR and LC-MS techniques directly and rapidly provided sufficient structural information to identify and confirm all the structures of major phenolic compounds in the extract, in addition to their HPLC profiles. This combined analytic information was then used as a dereplication tool for structure-guided screening in order to isolate unknown phenolic compounds in the extract. Successive fractionation and purification using semi-preparative HPLC acquired four unknown allopyranosides, and their structures were identified as cis-ferulic acid 4-O-${\beta}$-D-allopyranoside, trans-ferulic acid 4-O-${\beta}$-D-allopyranoside, trans-feruloyltyramine 4-O-${\beta}$-D-allopyranoside, and trans-feruloyl-(3-O-methyl)dopamine 4-O-${\beta}$-D-allopyranoside, based on a subsequent spectroscopic interpretation.

Keywords

References

  1. Jiang, J. W.; Qi, C. D. Dictionary of Medicinal Plants; Tianjin Science and Technology Press: Tianjin, China, 2005; p 175.
  2. Li, J. X.; Yu, Z. Y. Curr. Med. Chem. 2006, 13, 2927. https://doi.org/10.2174/092986706778521869
  3. Shibata, M.; Sakurai, N.; Onoda, M. Yakugaku Zasshi 1977, 97, 911.
  4. Shibata, M.; Yamatake, Y.; Amagaya, Y.; Fukushima, M. Yakugaku Zasshi 1975, 95, 539.
  5. Hirabayashi, T.; Ochiai, H.; Sakai, S.; Nakajima, K.; Terasawa, K. Planta Med. 1995, 61, 221. https://doi.org/10.1055/s-2006-958060
  6. Lee, K. H.; Lee, W. J.; Yang, S. J.; Huh, J. W.; Choi, J.; Hong, H. N.; Hwang, O.; Cho, S. W. Mol. Cells 2004, 17, 509.
  7. Li, J. X.; Kadota, S.; Hattori, M.; Yoshimachi, S.; Shiro, M.; Oogami, N.; Mizuno, H.; Namba, T. Chem. Pharm. Bull. 1993, 41, 832. https://doi.org/10.1248/cpb.41.832
  8. Vogler, B.; Klaiber, I.; Roos, G.; Walter, C. U.; Hiller, W.; Sandor, P.; Kraus, W. J. Nat. Prod. 1998, 61, 175. https://doi.org/10.1021/np970416z
  9. Holtzel, A.; Schlotterbeck, G.; Albert, G.; Bayer, E. Chromatographia 1996, 42, 499. https://doi.org/10.1007/BF02290283
  10. Schneider, B.; Zhao, Y.; Blitzke, T.; Schmitt, B.; Nookandeh, A.; Sun, X.; Stockigt, J. Phytochem. Anal. 1998, 9, 237. https://doi.org/10.1002/(SICI)1099-1565(199809/10)9:5<237::AID-PCA411>3.0.CO;2-U
  11. Spring, O.; Buschmann, H.; Vogler, B; Schilling, E. E.; Spraul, M.; Hoffmann, M. Phytochemistry 1995, 39, 609. https://doi.org/10.1016/0031-9422(95)00084-K
  12. Gu, Z. M.; Zhaou, D.; Wu, J.; Shi, G.; Zeng, L.; McLaughlin, J. L. J. Nat. Prod. 1997, 60, 242. https://doi.org/10.1021/np960487i
  13. Hostettmann, K.; Potterat, O.; Wolfender, J. L. Pharm. Ind. 1997, 59, 339.
  14. Wolfender, J. L.; Ndjoko, K.; Hostettmann, K. Phytochem. Anal. 2001, 12, 2. https://doi.org/10.1002/1099-1565(200101/02)12:1<2::AID-PCA552>3.0.CO;2-K
  15. Wolfender, J. L.; Ndjoko, K.; Hostettmann, K. Curr. Org. Chem. 1998, 2, 575.
  16. Takahira, M.; Kusano, A.; Shibano, M.; Kusano, G.; Sacurai, N.; Nagai, M.; Miyase, T. Chem. Pharm. Bull. 1998, 46, 362. https://doi.org/10.1248/cpb.46.362
  17. Iwanaga, A.; Kusano, G.; Warashina, T.; Miyase, T. J. Nat. Prod. 2010, 73, 573. https://doi.org/10.1021/np900675n
  18. Kruse, S. O.; Lohning, A.; Pauli, G. F.; Winterhoff, H.; Nahrstedt, A. Planta Med. 1999, 65, 763. https://doi.org/10.1055/s-2006-960862
  19. Seigler, D. D.; Pauli, G. F.; Nahrstedt, A.; Leen, R. Phytochemistry 2002, 60, 873. https://doi.org/10.1016/S0031-9422(02)00170-X

Cited by

  1. Phenylethanoid Glycosides from the Fruits of Magnolia obovata vol.51, pp.4, 2015, https://doi.org/10.1007/s10600-015-1379-4
  2. Dereplication strategies in natural product research: How many tools and methodologies behind the same concept? vol.16, pp.1, 2017, https://doi.org/10.1007/s11101-015-9448-7
  3. Feruloyl dopamine-O-hexosides are efficient marker compounds as orthogonal validation for authentication of black cohosh (Actaea racemosa)—an UHPLC-HRAM-MS chemometrics study vol.409, pp.10, 2017, https://doi.org/10.1007/s00216-017-0205-1
  4. Two new compounds from Aconitum tanguticum vol.16, pp.7, 2014, https://doi.org/10.1080/10286020.2014.904292
  5. Glucosylation of the phytoalexin N‐feruloyl tyramine modulates the levels of pathogen‐responsive metabolites in Nicotiana benthamiana vol.100, pp.1, 2012, https://doi.org/10.1111/tpj.14420
  6. Two new glycoalkaloids from Stephania succifera vol.34, pp.None, 2019, https://doi.org/10.1016/j.phytol.2019.10.001
  7. Systematically identifying the anti‐inflammatory constituents of Cimicifuga dahurica by UPLC–Q/TOF–MS combined with network pharmacology analysis vol.35, pp.12, 2021, https://doi.org/10.1002/bmc.5177