DOI QR코드

DOI QR Code

Nitric Oxide Inhibitory Constituents from the Fruits of Amomum tsao-ko

  • 투고 : 2018.12.31
  • 심사 : 2019.03.06
  • 발행 : 2019.03.31

초록

Bioactivity-guided fractionation of MeOH extract of the dried fruits of Amomum tsao-ko led to isolation of nine compounds (1 - 9). Their structures were elucidated by spectroscopic methods including extensive 1D and 2D-NMR, as alpinetin (1), naringenin-5-O-methyl ether (2), naringenin (3), hesperetin (4), 2',4',6'-trihydroxy-4-methoxy chalcone (5), tsaokoin (6), boesenbergin B (7), 4-hydroxyboesenbergin B (8), and tsaokoarylone (9). Of these, compound 8 was isolated from a natural source for the first time, which was previously reported as a synthetic product. The isolated compounds (1 - 9) were tested for their inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages. Among them, three chalcone derivatives (compounds 5, 7, and 8) and a diarylheptanoid (compound 9) exhibited significant inhibitory activity on the NO production with $IC_{50}$ values ranging from 10.9 to $22.5{\mu}M$.

키워드

참고문헌

  1. Tang, W.; Eisenbrand, B. Handbook of Chinese medicinal plants: Chemistry, pharmacology, toxicology; Wiley-VCH; Weinheim, 2011, p 106.
  2. Yang, X.; Kuenzi, P.; Plitzko, I.; Potterat, O.; Hamburger, M. Planta Med. 2009, 75, 543-546. https://doi.org/10.1055/s-0029-1185320
  3. Lee, K. Y.; Kim, S. H.; Sung, S. H.; Kim, Y. C. Planta Med. 2008, 74, 867-869. https://doi.org/10.1055/s-2008-1074552
  4. Starkenmann, C.; Mayenzet, F.; Brauchli, R.; Wunsche, L.; Vial, C. J. Agric. Food Chem. 2007, 55, 10902-10907. https://doi.org/10.1021/jf072707b
  5. Hong, S. S.; Lee, J. H.; Choi, Y. H.; Jeong, W.; Ahn, E. K.; Lym, S. H.; Oh, J. S. Tetrahedron Lett. 2015, 56, 6681-6684. https://doi.org/10.1016/j.tetlet.2015.10.045
  6. Itokawa, H.; Morita, M.; Mihashi, S. Phytochemistry 1981, 20, 2503-2506. https://doi.org/10.1016/0031-9422(81)83082-8
  7. Hammami, S.; Ben Jannet, H.; Bergaoui, A.; Ciavatta, L.; Cimino, G.; Mighri, Z. Molecules. 2004, 9, 602-608. https://doi.org/10.3390/90700602
  8. Jeon, S. H.; Chun, W.; Choi, Y. J.; Kwon, Y. S. Arch. Pharm. Res. 2008, 31, 978-982. https://doi.org/10.1007/s12272-001-1255-9
  9. Ibrahim, A. R.; Galal, A. M.; Ahmed, M. S.; Mossa, G. S. Chem. Pharm. Bull. 2003, 51, 203-206. https://doi.org/10.1248/cpb.51.203
  10. McCormick, S.; Robson, K.; Bohm, B. Phytochemistry 1985, 24, 1614-1616. https://doi.org/10.1016/S0031-9422(00)81081-X
  11. Moon, S. S.; Lee, J. Y.; Cho, S. C. J. Nat. Prod. 2004, 67, 889-891. https://doi.org/10.1021/np030464l
  12. Win, N. N.; Awale, S.; Esumi, H.; Tezuka, Y.; Kadota, S. J. Nat. Prod. 2007, 70, 1582-1587. https://doi.org/10.1021/np070286m
  13. Aigner, L.; Oberbauer-Hofmann, E.; Couillard-Despres, S.; Rivera, F. J.; Riepl, H.; Urmann, C.; Biendl, M. US patents, 2016, 9527860B2.
  14. Moon, S. S.; Cho, S. C.; Lee, J. Y. Bull. Korean Chem. Soc. 2005, 26, 447-450. https://doi.org/10.5012/bkcs.2005.26.3.447
  15. Mariotto, S.; Suzuki, Y.; Persichini, T.; Colasanti, M.; Suzuki, H.; Cantoni, O. Curr. Med. Chem. 2007, 14, 1940-1944. https://doi.org/10.2174/092986707781368531

피인용 문헌

  1. Pyranoflavanones and Pyranochalcones from the Fruits of Amomum tsao-ko vol.82, pp.7, 2019, https://doi.org/10.1021/acs.jnatprod.9b00155
  2. Molecular Networking-based De-replication Strategy Leads to the Isolation of a New Chromone from Pleosporales sp. vol.26, pp.4, 2019, https://doi.org/10.20307/nps.2020.26.4.340
  3. 초과(草果)의 RBL-2H3 세포 항원 유도 탈과립 억제성분 vol.64, pp.1, 2021, https://doi.org/10.3839/jabc.2021.004
  4. Chemistry and bioactivity of plants from the genus Amomum vol.281, 2019, https://doi.org/10.1016/j.jep.2021.114563