Revision of Structures of Flavanoids from Scutellaria indica and Their Protein Tyrosine Phosphatase 1B Inhibitory Activity

  • Published : 2006.12.30

Abstract

The structures of flavonoids, 2(S)-5,7-dihydroxy-8,2'-dimethoxyflavanone (1), wogonin (2), 2(S)-5,7, 2'-trihydroxy-8-methoxyflavanone (3), and 2(S)-5,2',5'-trihydroxy-7,8-dimethoxyflavanone (4), isolated from Scutellaria indica were revised on the basis of 2D NMR spectroscopy, including to gCOSY, gHSQC, and gHMBC. Compounds 1-4 were tested in vitro protein tyrosine phosphatase 1B (PTP1B) inhibitory activity. Compounds 2 and 4 exhibited weak PTP1B inhibitory activity with $IC_{50}$ values of 208 and $337{\mu}M$, respectively.

Keywords

References

  1. Bae, K., Min, B.S., Park, K.R., and Ahn, B.Z., Cytotoxic flavonoids from Scutellaria indica. Planta Med., 60, 280-281 (1994) https://doi.org/10.1055/s-2006-959477
  2. Gaffield, W., Circular dichroism, optical rotatory dispersion and absolute configuration of flavanones, 3-hydroxyflavanones and their glycosides : Determination of aglycone chirality in flavanone glycosides. Tetrahehdron, 26, 4093-4108 (1970) https://doi.org/10.1016/S0040-4020(01)93050-9
  3. Hamaguchi, T., Sudo, T., and Osada, H., RK-682, A potent inhibitor of tyrosine phosphatase arrested the mammalian cell cycle progression at $G_{1}$ phase. FEBS Lett., 372, 54-58 (1995) https://doi.org/10.1016/0014-5793(95)00953-7
  4. Kikuchi, Y., Miyaichi, Y., and Tomimori, T., Studies on Nepalese crude drugs. XIV. New flavonoids from the root of Scutellaria prostrate Jacq. ex Benth. Chem. Pharm. Bull., 39, 1466-1472 (1991) https://doi.org/10.1248/cpb.39.1466
  5. Lin, J.J., Brown, V.K., and Justement, L.B., Regulation of basal tyrosine phosphorylation of the B cell antigen receptor complex by the protein tyrosine phosphatase, CD45. J. Immunol., 149, 3182-3190 (1992)
  6. Min, B.S., Tomiyama, M., Ma, C.M., Nakamura N., and Hattori, M., Kaempferol acetylrhamnosides from the rhizome of Dryopteris crassirhizoma and their inhibitory effects on three different activities of human immunodeficiency virus-1 reverse transcriptase. Chem. Pharm. Bull., 49, 546-550 (2001) https://doi.org/10.1248/cpb.49.546
  7. Miyaichi, Y., Imoto, Y., Tomimori, T., and Lin, C.C., Studies on the constituents of Scutellaria Species. IX. On the flavonoid constituents of the root of Scutellaria indica L. Chem. Pharm. Bull., 35, 3720-3725 (1987) https://doi.org/10.1248/cpb.35.3720
  8. Miyaichi, Y., Imoto, Y., Tomimori, T., and Namba, T., Studies on the Nepales crude drugs. IX. On the flavonoid constituents of the root of Scutellaria scandens Buch.-HAM. ex D. Don. Chem. Pharm. Bull., 36, 2371-2376 (1988) https://doi.org/10.1248/cpb.36.2371
  9. Na, M.K., Cui, L., Min, B.S., Bae K., Yoo, J.K., Kim, B.Y., Oh, W.K., and Ahn, J.S., Protein tyrosine phosphatase 1B inhibitory activity of triterpenes isolated from Astilbe koreana. Bioorg. Med. Chem. Lett., 16, 3273-3276 (2006) https://doi.org/10.1016/j.bmcl.2006.03.036
  10. Shen, C.C., Lin, T.W., Huang, Y.L., Wan, S.T., Shien, B.J., and Chen, C.C., Phenolic constituents of the roots of Sophora flavescens. J. Nat. Prod., 69, 1237-1240 (2006) https://doi.org/10.1021/np060189d
  11. Shirataki, Y., Yokoe, I., Noguchi, M., Tomimori, T., and Komatsu, M., Studies on the constituents of Sophora Species. XXII. Constituents of the root of Sophora moorcroftiang Benth. ex Baker. Chem. Pharm. Bull., 36, 2220-2225 (1988) https://doi.org/10.1248/cpb.36.2220
  12. Tomimori, T., Miyaichi, Y., Imoto, Y., and Kizu, H., Studies on the constituents of Scutellaria Species. On the flavonoid constituents of 'Ban Zhi Lian,' the whole herb of Scutellaria rivularis Wall (I). Shoyakugaku Zasshi, 38, 249-252 (1984)
  13. Tomimori, T., Miyaichi, Y., Imoto, Y., Kizu, H., and Namba, T., Studies on Nepalese crude drugs. V. On the flavonoids constituents of the root of Scutellaria discolor Colebr. Chem. Pharm. Bull., 33, 4457-4463 (1985) https://doi.org/10.1248/cpb.33.4457