DOI QR코드

DOI QR Code

A New Steroidal Glycoside from Allium macrostemon Bunge

  • Kim, Yun Sik (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University) ;
  • Cha, Joon Min (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University) ;
  • Kim, Dong Hyun (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University) ;
  • Lee, Tae Hyun (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University) ;
  • Lee, Kang Ro (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University)
  • Received : 2017.08.17
  • Accepted : 2017.10.31
  • Published : 2018.03.30

Abstract

A phytochemical investigation of Allium macrostemon Bunge (Liliaceae) afforded the new pregnane steroidal glycoside, named allimacroside F (1), along with three known glycosides, benzyl-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranosyl-($1{\rightarrow}6$)-${\beta}-{\text\tiny{D}}$-glucopyranoside (2), phenylethyl-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranosyl-($1{\rightarrow}6$)-${\beta}-{\text\tiny{D}}$-glucopyranoside (3), (Z)-3-hexenyl-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranosyl-($1{\rightarrow}6$)-${\beta}-{\text\tiny{D}}$-glucopyranoside (4). The identification and structural elucidation of a new compound (1) was carried out based on spectral data analyses ($^1H-NMR$, $^{13}C-NMR$, $^1H-^1H$ COSY, HSQC, HMBC, and NOESY) and HR-FAB-MS.

Keywords

References

  1. Usui, A.; Matsuo, Y.; Tanaka, T.; Ohshima, K.; Fukuda, S.; Mine, T.; Nakayama, H.; Ishimaru, K. Nat. Prod. Commun. 2017, 12, 89-91.
  2. Jiangsu New Medical College. Dictionary of Chinese Drugs; Shanghai Science and Technological Publisher: China, 2001, p 2642.
  3. Sobolewska, D.; Michalska, K.; Podolak, I.; Grabowska, K. Phytochem. Rev. 2016, 15, 1-35.
  4. Xie, W.; Zhang, Y.; Wang, N.; Zhou, H.; Du, L.; Ma, X.; Shi, X.; Cai, G. Eur. J. Pharmacol. 2008, 599, 159-165. https://doi.org/10.1016/j.ejphar.2008.09.042
  5. Peng, J.; Yao, X.; Okada, Y.; Okuyama T. Chem. Pharm. Bull. 1994, 42, 2180-2182.
  6. Chen, H. -F.; Wang, N. -L.; Sun, H. -L.; Yang, B. -F.; Yao, X. -S. J. Asian Nat. Prod. Res. 2006, 8, 21-28. https://doi.org/10.1080/10286020500172533
  7. Chen, H.; Wang, G.; Wang, N.; Yang, M.; Wang, Z.; Wang, X.; Yao, X. Pharmazie 2007, 62, 544-548.
  8. Cheng, S. -B.; Wang, Y.; Zhang, Y. -F.; Wang, Y. Zhong cao yao 2013, 44, 1078-1081.
  9. Kim, Y. S.; Suh, W. S.; Park, K. J.; Choi, S. U.; Lee, K. R. Steroids 2017, 118, 41-46. https://doi.org/10.1016/j.steroids.2016.12.002
  10. Hamerski, L.; Bomm, M. D.; Silva, D. H. S.; Young, M. C. M.; Furlan, M.; Eberlin, M. N.; Castro-Gamboa, I.; Cavalheiro, A. J.; da Silva Bolzani, V. Phytochemistry 2005, 66, 1927-1932.
  11. Umehara, K.; Hattori, I.; Miyase, T.; Ueno, A.; Hara, S.; Kageyama, C. Chem. Pharm. Bull. 1988, 36, 5004-5008. https://doi.org/10.1248/cpb.36.5004
  12. Inagaki, J.; Watanabe, N.; Moon, J. -H.; Yagi, A.; Sakata, K.; Ina, K.; Luo, S. Biosci. Biotechnol. Biochem. 1995, 59, 738-739. https://doi.org/10.1271/bbb.59.738
  13. Kishida, M.; Fujii, M.; Ida, Y. Heterocycles 2005, 65, 2127-2137. https://doi.org/10.3987/COM-05-10474
  14. Yokosuka, A.; Mimaki, Y.; Sashida, Y. J. Nat. Prod. 2000, 63, 1239-1243. https://doi.org/10.1021/np000145j
  15. Temraz, A.; El Gindi, O. D.; Kadry, H. A.; De Tommasi, N.; Braca, A. Phytochemistry 2006, 67, 1011-1018. https://doi.org/10.1016/j.phytochem.2006.03.007

Cited by

  1. Recent trends in anti-obesity and anti-inflammatory studies in modern health care vol.27, pp.5, 2018, https://doi.org/10.3233/thc-191736
  2. Natural Antioxidants, Health Effects and Bioactive Properties of Wild Allium Species vol.26, pp.16, 2018, https://doi.org/10.2174/1381612826666200203145851