Skip to main content
Log in

Anti-hyperlipidemic constituents from the bark of Shorea roxburghii

  • Original Paper
  • Published:
Journal of Natural Medicines Aims and scope Submit manuscript

Abstract

The methanol extract from the bark of Shorea roxburghii (Dipterocarpaceae, “Phayom” in Thai) was found to suppress plasma triglyceride elevation in olive oil-treated mice, and also to inhibit pancreatic lipase activity (IC50 = 31.6 μg/ml). From the extract, two new 3-acetyl-4-phenyl-3,4-dihydroisocoumarins, phayomphenols A1 (1) and A2 (2) were isolated, together with 22 known compounds. The structures of 1 and 2 were elucidated on the basis of chemical and spectroscopic evidence, including X-ray crystallographic analysis. Among the isolates, several oligostilbenoids, including (−)-hopeaphenol (3) and (+)-isohopeaphenol (4), showed inhibitory effects on plasma triglyceride elevation at a dose of 200 mg/kg p.o. and pancreatic lipase inhibitory activity (IC50 = 32.9 and 26.5 μM, respectively).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Patcharamun W, Sichaem J, Siripong P, Khumkratok S, Jong-aramruang J, Tip-pyang S (2011) A new dimeric resveratrol from the roots of Shorea roxburghii. Fitoterapia 82:489–492

    Article  PubMed  CAS  Google Scholar 

  2. Morikawa T, Xie Y, Asao Y, Okamoto M, Yamashita C, Muraoka O, Matsuda H, Pongpiriyadacha Y, Yuan D, Yoshikawa M (2009) Oleanane-type triterpene oligoglycosides with pancreatic lipase inhibitory activity from the pericarps of Sapindus rarak. Phytochemistry 70:1166–1172

    Article  PubMed  CAS  Google Scholar 

  3. Asao Y, Morikawa T, Xie Y, Okamoto M, Hamao M, Matsuda H, Muraoka O, Yuan D, Yoshikawa M (2009) Structures of acetylated oleanane-type triterpene saponins, rarasaponins IV, V, and VI, and anti-hyperlipidemic constituents from the pericarps of Sapindus rarak. Chem Pharm Bull 57:198–203

    Article  PubMed  CAS  Google Scholar 

  4. Matsuda H, Asao Y, Nakamura S, Hamao M, Sugimoto S, Hongo M, Pongpiriyadacha Y, Yoshikawa M (2009) Antidiabetogenic constituents from the Thai traditional medicine Cotylelobium melanoxylon. Chem Pharm Bull 57:487–494

    Article  PubMed  CAS  Google Scholar 

  5. Matsuda H, Ninomiya K, Morikawa T, Yasuda D, Yamaguchi I, Yoshikawa M (2009) Hepatoprotective amide constituents from the fruit of Piper chaba: structural requirements, mode of action, and new amides. Bioorg Med Chem 17:7313–7323

    Article  PubMed  CAS  Google Scholar 

  6. Muraoka O, Morikawa T, Miyake S, Akaki J, Ninomiya K, Pongpiriyadacha Y, Yoshikawa M (2011) Quantitative analysis of neosalacinol and neokotalanol, another two potent α-glucosidase inhibitors from Salacia species, by LC–MS with ion pair chromatography. J Nat Med 65:142–148

    Article  PubMed  CAS  Google Scholar 

  7. Ito T, Abe N, Oyama M, Iinuma M (2008) Oligostilbenoids from Dipterocarpaceaeous plants: a new resveratrol tetramer from Vateria indica and the revised structure of isohopeaphenol. Helv Chim Acta 91:1989–1998

    Article  CAS  Google Scholar 

  8. Ito T, Abe N, Masuda Y, Nasu M, Oyama M, Sawa R, Takahashi Y, Iinuma M (2009) Two novel resveratrol derivatives from the leaves of Vateria indica. Helv Chim Acta 92:195–208

    Article  CAS  Google Scholar 

  9. Tanaka T, Ito T, Nakaya K, Iinuma M, Takahashi Y, Naganawa H, Riswan S (2001) Six new heterocyclic stilbene oligomers from stem bark of Shorea hemsleyana. Heterocycles 55:729–740

    Article  CAS  Google Scholar 

  10. Tanaka T, Ito T, Nakaya K, Iinuma M, Riswan S (2000) Oligostilbenoids in stem bark of Vatica rassak. Phytochemistry 54:63–69

    Article  PubMed  CAS  Google Scholar 

  11. Ito T, Tanaka T, Iinuma M, Iliya I, Nakaya K, Ali Z, Takahashi Y, Sawa R, Shirataki Y, Murata J, Darnaedi D (2003) New resveratrol oligomers in the stem bark of Vatica pauciflora. Tetrahedron 59:5347–5363

    Article  CAS  Google Scholar 

  12. Ito T, Tanaka T, Ido Y, Nakaya K, Iinuma M, Takahashi Y, Naganawa H, Riswan S (2001) Five new oligostilbenes with one or two dihydrofurans from the stem bark of Vatica rassak. Heterocycles 55:557–567

    Article  CAS  Google Scholar 

  13. Ito T, Tanaka T, Nakaya K, Iinuma M, Takahashi Y, Naganawa H, Ohyama M, Nakanishi Y, Bastow KF, Lee K-H (2001) A novel bridged stilbenoid trimer and four highly condensed stilbenoid oligomers in Vatica rassak. Tetrahedron 57:7309–7321

    Article  CAS  Google Scholar 

  14. Kitanaka S, Ikezawa T, Yasukawa K, Yamanouchi S, Takido M, Sung HK, Kim IH (1990) (+)-α-Viniferin, an anti-inflammatory compound from Caragana chamlagu root. Chem Pharm Bull 38:432–435

    Article  PubMed  CAS  Google Scholar 

  15. Tanaka T, Ito T, Ido Y, Nakaya K, Iinuma M, Chelladurai V (2001) Hopeafuran and a C-glucosyl resveratrol isolated from stem wood of Hopea utilis. Chem Pharm Bull 49:785–787

    Article  PubMed  CAS  Google Scholar 

  16. Diyasena MNC, Sotheeswaran S, Surendrakumar S, Balasubramanian S, Bokel M, Kraus W (1985) Balanocarpol a new polyphenol from Balanocarpus zeylanicus (Trimen) and Hopea jucunda (Thw.) (Dipterocarpaceae). J Chem Soc Perkin Trans I:1807–1809

    Article  Google Scholar 

  17. Tanaka T, Ito T, Ido Y, Son T-K, Nakaya K, Iinuma M, Ohyama M, Chelladurai V (2000) Stilbenoids in the stem bark of Hopea parviflora. Phytochemistry 53:1015–1019

    Article  PubMed  CAS  Google Scholar 

  18. Dai J-R, Hallock YF, Cardellina JH II, Boyd MR (1998) HIV-inhibitory and cytotoxic oligostilbenes from the leaves of Hopea malibato. J Nat Prod 61:351–353

    Article  PubMed  CAS  Google Scholar 

  19. Baderschneider B, Winterhalter P (2000) Isolation and characterization of novel stilbene derivatives from Riesling wine. J Agric Food Chem 48:2681–2686

    Article  PubMed  CAS  Google Scholar 

  20. Jayatilake GS, Jayasuriya H, Lee E-S, Koonchanok NM, Geahlen RL, Ashendel CL, McLaughlin JL, Chang C-J (1993) Kinase inhibitors from Polygonum cuspidatum. J Nat Prod 56:1805–1810

    Article  PubMed  CAS  Google Scholar 

  21. Markham KR, Ternai B, Stanley R, Geiger H, Mabry TJ (1978) Carbon-13 NMR studies of flavonoids-III naturally occurring flavonoid glycosides and their acylated derivatives. Tetrahedron 34:1389–1397

    Article  CAS  Google Scholar 

  22. Yamano Y, Ito M (2005) Synthesis of optically active vomifoliol and roseoside stereoisomers. Chem Pharm Bull 53:541–546

    Article  PubMed  CAS  Google Scholar 

  23. Magid AA, Voutquenne-Nazabadioko L, Moroy G, Moretti C, Lavaud C (2007) Dihydroisocoumarin glucosides from stem bark of Caryocar glabrum. Phytochemistry 68:2439–2443

    Article  PubMed  CAS  Google Scholar 

  24. Duan W-J, Jin X, Chen L-X, Zhang X, Yao X-S, Qiu F (2009) Four new compounds from Paeonia albiflora. J Asian Nat Prod Res 11:297–303

    Google Scholar 

  25. Hashimoto T, Tori M, Asakawa Y (1987) Three dihydroisocoumarin glucosides from Hydrangea macrophylla subsp. serrata. Phytochemistry 26:3323–3330

    Article  CAS  Google Scholar 

  26. Speranza G, Manitto P, Cassara P, Monti D (1993) Feralolide, a dihydroisocoumarin from Cape aloe. Phytochemistry 33:175–178

    Article  CAS  Google Scholar 

  27. Krohn K, Bahramsari R, Flörke U, Ludewig K, Kliche-Spory C, Michel A, Aust H-J, Draeger S, Schulz B, Antus S (1997) Dihydroisocoumarins from fungi: isolation, structure elucidation, circular dichroism and biological activity. Phytochemistry 45:313–320

    Article  PubMed  CAS  Google Scholar 

  28. Ito C, Mishina Y, Litaudon M, Cosson J-P, Furukawa H (2000) Xanthone and dihydroisocoumarin from Montrouziera sphaeroidea. Phytochemistry 53:1043–1046

    Article  PubMed  CAS  Google Scholar 

  29. Kurosaki Y, Fukuda T, Iwao M (2005) Asymmetric synthesis of 3-substituted 3,4-dihydroisocoumarins via stereoselective addition of laterally lithiated chiral 2-(o-tolyl)oxazolines to aldehydes followed by diastereomer-selective lactonization. Tetrahedron 61:3289–3303

    Article  CAS  Google Scholar 

  30. Zidorn C, Lohwasser U, Pschorr S, Salvenmoser D, Ongania K-H, Ellmerer EP, Börner A, Stuppner H (2005) Bibenzyls and dihydroisocoumarins from white salsify (Tragopogon porrifolius subsp. porrifolius). Phytochemistry 66:1691–1697

    Article  PubMed  CAS  Google Scholar 

  31. McNeely W, Benfield P (1998) Orlistat. Drugs 56:241–249

    Article  PubMed  CAS  Google Scholar 

  32. Morikawa T, Li X, Nishida E, Ito Y, Matsuda H, Nakamura S, Muraoka O, Yoshikawa M (2008) Perennisosides I–VII, acylated triterpene saponins with antihyperlipidemic activities from the flowers of Bellis perennis. J Nat Prod 71:828–835

    Article  PubMed  CAS  Google Scholar 

  33. Morikawa T, Li X, Nishida E, Nakamura S, Ninomiya K, Matsuda H, Oda Y, Muraoka O, Yoshikawa M (2010) Medicinal flowers. Part 29. acylated oleanane-type triterpene bisdesmosides: perennisaponins G, H, I, J, K, L, and M with pancreatic lipase inhibitory activity from the flowers of Bellis perennis. Helv Chim Acta 93:573–586

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by High-tech Research Center Project for Private Universities: matching fund subsidy from MEXT (The Ministry of Education, Culture, Sports, Science and Technology), 2007-2011 and also supported by a Grant-in Aid for Scientific Research by JSPS (Japan Society for the Promotion of Science).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Osamu Muraoka.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Morikawa, T., Chaipech, S., Matsuda, H. et al. Anti-hyperlipidemic constituents from the bark of Shorea roxburghii . J Nat Med 66, 516–524 (2012). https://doi.org/10.1007/s11418-011-0619-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-011-0619-6

Keywords

Navigation