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Inhibitory Constituents against Cyclooxygenases from Aralia cordata Thunb

Dang Nguyen Hai    (College of Pharmacy, Chungnam National University   ); Zhang XinFeng    (College of Pharmacy, Chungnam National University   ); Zheng MingShan    (College of Pharmacy, Chungnam National University   ); Son Kun Ho    (Department of Food and Nutrition, Andong National University   ); Chang Hyeun Wook    (College of Pharmacy, Yeungnam University   ); Kim Hyun Pyo    (College of Pharmacy, Kangwon National University   ); Bae KiHwan    (College of Pharmacy, Chungnam National University   ); Kang Sam Sik    (Natural Products Research Institute and College of Pharmacy, Seoul National University  );
  • 초록

    Seven diterpenes, four polyacetylenes, a lipid glycerol, and two sterols were isolated from the methylene chloride fraction of the root of Aralia cordata. Their chemical structures were determined as (-)-pimara-8(14), 15-dien-19-oic acid (2), pimaric acid (3), (-)-kaur-16-en-19-oic acid (4), 17-hydroxy-ent-kaur-15-en-19-oic acid (9), $7{\alpha}$ -hydroxy-(-)-pimara-8(14), 15-dien-19-oic acid (10), $16\alpha$ , 17 -dihydroxy-(-)-kauran-19-oic acid (11), 16-hydroxy-17-isovaleroyloxy-ent-kauran-19­oic acid (12), falcarindiol (5), dehydrofalcarindiol (6), dehydrofalcarindiol-8-acetate (7), falcarin­diol-8-acetate (8), alpha-mono palmitin (13), stigmasterol (1), and daucosterol (14) by the spectral evidences. These compounds were tested with COX-1 and COX-2 inhibition assays. This study found that compounds 2, 4, 5, 6, 7, 8, and 10 inhibited COX-1 dependent conversion of the exogenous arachidonic acid to $PGE_2$ in a dose-dependent manner with $IC_{50}$ values of $134.2{\mu}M$ , $121.6{\mu}M$ , $170{\mu}M$ , $50.4{\mu}M$ , $11.7{\mu}M$ , $99.6{\mu}M$ , and $69.6{\mu}M$ , respectively. But, most of these compounds weakly inhibited COX-2 dependent $PGE_2$ generation. Among them, only compound 4 showed relatively significant inhibitory activity $(IC_{50}\;:\;127.6{\mu}M)$ .


  • 주제어

    Aralia cordata .   Diterpenoids .   Polyacetylenes .   Lipid glycerol .   Steroids .   Anti-inflammatory .   COX-1 .   COX-2.  

  • 참고문헌 (22)

    1. Bernart, W. M., Cardellina, H. J., Balaschak, S. M., Alexander, R. M., Shoemaker, H. R., and Boyd, R. M., Cytotoxic falcarinol oxylipins from Dendropanax arboreus. J. Nat. Prod., 59, 748-753 (1996) 
    2. Matsuo, A., Uto, S., Nakayama, M., Hayashi, S., Yamasaki, K., Kasai, R., and Tanaka, O., (-)-Thermarol. A new ent-pimaraneclass diterpene diol from Jungermannia thermerum (liverwort). Tetrahedron Letters, 28, 2451-2454 (1976) 
    3. Okuyama, E., Nishimura, S., and Yamazaki, M., Analgesic principles from Aralia cordata Thunb. Chem. Pharm. Bull., 39, 405-407 (1991) 
    4. Shibata, S., Mihashi, S., and Tanaka, O., The occurrence of (-) pimarane-type diterpene in Aralia cordata Thunb. Tetrahedron Lett., 51, 5241-5243 (1967) 
    5. Zheng, G., Lu, W., and Cai, J., Stereoselective total synthesis of (3R, 8S)-falcarindiol, a common polyacetylene compound from Umbellifers. J. Nat. Prod., 62, 626-628 (1999) 
    6. Emery, P., COX-1, COX-2: So what? Scand. J. Rheumatol., 28, 6-9 (1999) 
    7. Kim, J. S. and Kang, S. S., Saponins from the aerial parts of Aralia continentalis. Natural Products Sciences, 4, 45-50 (1998) 
    8. Rahman, A. and Ahmad, V. Q., $^{13}$C-NMR of natural products. Plenum Press, 2, 258 (1992) 
    9. Sang, S. M., Kikuzaki, H., Lapsley, K., Rosen, R. T., Nakatani, N., and Ho, C. T., Sphingolipid and other constituents from almond nuts (Prunus amygdalucs Batsch). J. Agric. Food Chem., 50, 4709-4712 (2002) 
    10. Yahara, S., Ishida, M., Yamazaki, K., Tanaka, O., and Mihashi, S., Minor diterpenes of Aralia cordata Thunb: 17-hydroxyent- kaur-15-en-19-oic acid and grandifloric acid. Chem. Pharm. Bull., 22, 1629-1631 (1974) 
    11. Silva, E. A., Takashi, J. A., Boaventura, M. A. D., Oliveira, A. B., The biotransformation of ent-kaur-16-en-19-oic acid by Rhizopus stolonifer. Phytochemistry, 52, 397-400 (1999) 
    12. Zhang, Y. M., Yang, J. S., and Xu, X. D., A new kaurane derivative from Aralia fargesii. Chinese Chemical Letters, 10, 673-674 (1999) 
    13. Ylva, N., Therese, R., Premila, P., Helena, D., and Lars, B., Development of a Radiochemical Cyclooxygenase-1 and 2 in vitro assay for identification of natural products as inhibitor of prostaglandin biosynthesis. J. Nat. Prod., 61, 2-7 (1998) 
    14. Hung, C. Y. and Yen, G. C., Extraction and identification of antioxidative components of Hsian-tsao (Mesona procumbens Hemsl.). Lebensm.-Wiss. u.-Technol., 34, 306-311 (2001) 
    15. Mihashi, S., Yanagisawa, I., Tanaka, O., and Shibata, S., Further study on the diterpenes of Aralia spp. Tetrahedron Lett., 21, 1683-1686 (1969) 
    16. Andreas, C. and Thomas, H., Structural and sensory characterization of compounds contributing to the bitter off-taste of carrots (Daucus carota L.) and carrot puree. J. Agric. Food Chem., 51, 3865-3873 (2003) 
    17. Park, S. Y. and Kim, J. W., Cytotoxic polyacetylenes from Aralia cordata. Yakhak Hoeji, 39, 681-688 (1995) 
    18. Kwon, H. C. and Lee, K. R., Phytochemical constituents of Artemisia japonica ssp. littoricola. Arch. Pharm. Res., 24, 194-197 (2001) 
    19. Chang, F. R., Yang, P. Y., Lin, J. Y., Lee, K. H., and Wu, Y. C., Bioactive kaurane diterpenoids from Annona glabra. J. Nat. Prod., 61, 437-439 (1998) 
    20. Okuyama, E., Nishimura, S., Ohmori, S., Ozaki, Y., Satake, M., and Yamazaki, M., Analgesic components of Notopterygium incisum Ting. Chem. Pharm. Bull., 41, 926-929 (1993) 
    21. Tanaka, O., Mihashi, S., Yanagisawa, I., Niaido, T., and Shibata, S., Diterpenes of Aralia cordata: Oxidative transformation of 4-axial aldehyde of some diterpenes and a note to the naturally occurring 4-hydroxy-18 (or 19) norditerpenes. Tetrahedron, 28, 4523-4537 (1972) 
    22. Han, B. H., Han, Y. N., Han, L. A., Park, M. H., and Lee, E. O., Studies on the anti-inflammatory activity of Aralia continentalis (I). Arch. Pharm. Res., 6, 17-23 (1983) 
  • 이 논문을 인용한 문헌 (14)

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    3. 2007. "" 동의생리병리학회지 = Journal of physiology & pathology in Korean Medicine, 21(6): 1576~1580     
    4. 2007. "" International journal of oral biology : official journal of the Korean Academy of Oral Biology and the UCLA Dental Research Institute, 32(2): 75~78     
    5. 2008. "" International journal of oral biology : official journal of the Korean Academy of Oral Biology and the UCLA Dental Research Institute, 33(4): 213~216     
    6. Yang, Seun-Ah ; Im, Nam-Kyung ; Jhee, Kwang-Hwan ; Lee, In-Seon 2008. "Effects of Aralia continentalis Kitagawa on Antiplatelet and Antioxidative Activities." 생명과학회지 = Journal of life science, 18(3): 357~362     
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    12. Shin, Ye-Ji ; Beak, Yong-Hyeon ; Park, Dong-Suk ; Kim, Jae-Kyu ; Koh, Hyung-Kyun 2010. "The Effect of Aralia Cordata Thunb and Cimicifuga Heracleifolia on Cartilage Protection by the Regulation of Metabolism in Human Osteoarthric Chondrocytes" 大韓鍼灸學會誌= The journal of Korean Acupuncture & Moxibustion Society, 27(4): 39~53     
    13. 2011. "" Journal of the Korean Society for Applied Biological Chemistry, 54(1): 54~58     
    14. Jung, Young-Mi ; Lee, Dong-Sub ; Kwon, Ki-Sang 2016. "Anti-Inflammatory Effects of Fusion-Fermented Aralia continentalis Radix (fACR) on THP-1 cells" 디지털융복합연구 = Journal of digital convergence, 14(1): 353~361     

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