Skip to main content
Erschienen in: Journal of Natural Medicines 3/2012

01.07.2012 | Original Paper

Anti-hyperlipidemic constituents from the bark of Shorea roxburghii

verfasst von: Toshio Morikawa, Saowanee Chaipech, Hisashi Matsuda, Makoto Hamao, Yohei Umeda, Hiroki Sato, Haruka Tamura, Kiyofumi Ninomiya, Masayuki Yoshikawa, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka

Erschienen in: Journal of Natural Medicines | Ausgabe 3/2012

Einloggen, um Zugang zu erhalten

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).
Literatur
1.
Zurück zum Zitat 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 82:489–492PubMedCrossRef 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 82:489–492PubMedCrossRef
2.
Zurück zum Zitat 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 70:1166–1172PubMedCrossRef 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 70:1166–1172PubMedCrossRef
3.
Zurück zum Zitat 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 57:198–203PubMedCrossRef 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 57:198–203PubMedCrossRef
4.
Zurück zum Zitat 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 57:487–494PubMedCrossRef 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 57:487–494PubMedCrossRef
5.
Zurück zum Zitat 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 17:7313–7323PubMedCrossRef 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 17:7313–7323PubMedCrossRef
6.
Zurück zum Zitat 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 65:142–148PubMedCrossRef 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 65:142–148PubMedCrossRef
7.
Zurück zum Zitat 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 91:1989–1998CrossRef 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 91:1989–1998CrossRef
8.
Zurück zum Zitat 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 92:195–208CrossRef 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 92:195–208CrossRef
9.
Zurück zum Zitat 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 55:729–740CrossRef 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 55:729–740CrossRef
10.
Zurück zum Zitat Tanaka T, Ito T, Nakaya K, Iinuma M, Riswan S (2000) Oligostilbenoids in stem bark of Vatica rassak. Phytochemistry 54:63–69PubMedCrossRef Tanaka T, Ito T, Nakaya K, Iinuma M, Riswan S (2000) Oligostilbenoids in stem bark of Vatica rassak. Phytochemistry 54:63–69PubMedCrossRef
11.
Zurück zum Zitat 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 59:5347–5363CrossRef 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 59:5347–5363CrossRef
12.
Zurück zum Zitat 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 55:557–567CrossRef 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 55:557–567CrossRef
13.
Zurück zum Zitat 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 57:7309–7321CrossRef 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 57:7309–7321CrossRef
14.
Zurück zum Zitat 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 38:432–435PubMedCrossRef 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 38:432–435PubMedCrossRef
15.
Zurück zum Zitat 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 49:785–787PubMedCrossRef 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 49:785–787PubMedCrossRef
16.
Zurück zum Zitat 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:1807–1809CrossRef 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:1807–1809CrossRef
17.
Zurück zum Zitat 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 53:1015–1019PubMedCrossRef 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 53:1015–1019PubMedCrossRef
18.
Zurück zum Zitat 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 61:351–353PubMedCrossRef 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 61:351–353PubMedCrossRef
19.
Zurück zum Zitat Baderschneider B, Winterhalter P (2000) Isolation and characterization of novel stilbene derivatives from Riesling wine. J Agric Food Chem 48:2681–2686PubMedCrossRef Baderschneider B, Winterhalter P (2000) Isolation and characterization of novel stilbene derivatives from Riesling wine. J Agric Food Chem 48:2681–2686PubMedCrossRef
20.
Zurück zum Zitat 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 56:1805–1810PubMedCrossRef 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 56:1805–1810PubMedCrossRef
21.
Zurück zum Zitat 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 34:1389–1397CrossRef 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 34:1389–1397CrossRef
22.
Zurück zum Zitat Yamano Y, Ito M (2005) Synthesis of optically active vomifoliol and roseoside stereoisomers. Chem Pharm Bull 53:541–546PubMedCrossRef Yamano Y, Ito M (2005) Synthesis of optically active vomifoliol and roseoside stereoisomers. Chem Pharm Bull 53:541–546PubMedCrossRef
23.
Zurück zum Zitat Magid AA, Voutquenne-Nazabadioko L, Moroy G, Moretti C, Lavaud C (2007) Dihydroisocoumarin glucosides from stem bark of Caryocar glabrum. Phytochemistry 68:2439–2443PubMedCrossRef Magid AA, Voutquenne-Nazabadioko L, Moroy G, Moretti C, Lavaud C (2007) Dihydroisocoumarin glucosides from stem bark of Caryocar glabrum. Phytochemistry 68:2439–2443PubMedCrossRef
24.
Zurück zum Zitat 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 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
25.
Zurück zum Zitat Hashimoto T, Tori M, Asakawa Y (1987) Three dihydroisocoumarin glucosides from Hydrangea macrophylla subsp. serrata. Phytochemistry 26:3323–3330CrossRef Hashimoto T, Tori M, Asakawa Y (1987) Three dihydroisocoumarin glucosides from Hydrangea macrophylla subsp. serrata. Phytochemistry 26:3323–3330CrossRef
26.
Zurück zum Zitat Speranza G, Manitto P, Cassara P, Monti D (1993) Feralolide, a dihydroisocoumarin from Cape aloe. Phytochemistry 33:175–178CrossRef Speranza G, Manitto P, Cassara P, Monti D (1993) Feralolide, a dihydroisocoumarin from Cape aloe. Phytochemistry 33:175–178CrossRef
27.
Zurück zum Zitat 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 45:313–320PubMedCrossRef 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 45:313–320PubMedCrossRef
28.
Zurück zum Zitat Ito C, Mishina Y, Litaudon M, Cosson J-P, Furukawa H (2000) Xanthone and dihydroisocoumarin from Montrouziera sphaeroidea. Phytochemistry 53:1043–1046PubMedCrossRef Ito C, Mishina Y, Litaudon M, Cosson J-P, Furukawa H (2000) Xanthone and dihydroisocoumarin from Montrouziera sphaeroidea. Phytochemistry 53:1043–1046PubMedCrossRef
29.
Zurück zum Zitat 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 61:3289–3303CrossRef 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 61:3289–3303CrossRef
30.
Zurück zum Zitat 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 66:1691–1697PubMedCrossRef 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 66:1691–1697PubMedCrossRef
32.
Zurück zum Zitat 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 71:828–835PubMedCrossRef 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 71:828–835PubMedCrossRef
33.
Zurück zum Zitat 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 93:573–586CrossRef 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 93:573–586CrossRef
Metadaten
Titel
Anti-hyperlipidemic constituents from the bark of Shorea roxburghii
verfasst von
Toshio Morikawa
Saowanee Chaipech
Hisashi Matsuda
Makoto Hamao
Yohei Umeda
Hiroki Sato
Haruka Tamura
Kiyofumi Ninomiya
Masayuki Yoshikawa
Yutana Pongpiriyadacha
Takao Hayakawa
Osamu Muraoka
Publikationsdatum
01.07.2012
Verlag
Springer Japan
Erschienen in
Journal of Natural Medicines / Ausgabe 3/2012
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-011-0619-6

Weitere Artikel der Ausgabe 3/2012

Journal of Natural Medicines 3/2012 Zur Ausgabe