PDF herunterladen
Planta Med 2011; 77(18): 2029-2036
DOI: 10.1055/s-0031-1280024
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Tea Triterpenoidal Saponins from the Roots of Camellia sinensis Have Inhibitory Effects against Alcohol Dehydrogenase

Titto Varughese1 , Md. Maniruzzaman Manir1 , Mozahidur Rahaman1 , Jeong Kee Kim2 , Byeong-Gon Lee2 , Surk-Sik Moon1
  • 1Department of Chemistry, Kongju National University, Gongju, Republic of Korea
  • 2Skin Research Institute, AmorePacific R & D Center, Yongin, Republic of Korea
Weitere Informationen

Publikationsverlauf

received October 31, 2010 revised May 14, 2011

accepted June 2, 2011

Publikationsdatum:
22. Juli 2011 (online)

Auch verfügbar auf
   Lizenzen und Reprints

Abstract

Ten new polyhydroxyolean-12-ene pentacyclic triterpenoidal saponins, named rogchaponins 1–10, were isolated from the methanolic extract of the roots of Camellia sinensis by a series of chromatographic methods (silica gel flash column and C18 MPLC followed by C18 HPLC). Their structures were established by 1D and 2D-NMR techniques along with IR and HR-TOF-MS. Rogchaponins R4 (4) and R5 (5) showed inhibitory activities against yeast alcohol dehydrogenase (ADH) with IC50 values of 16.1 ± 3.2 and 15.4 ± 3.3 µM, respectively. A 4-methylpyrazole positive control exhibited an IC50 of 2750 ± 50 µM. However, the saponins showed no inhibitory activity against yeast aldehyde dehydrogenase (ALDH).

Key words

tea root - Camellia sinensis - Theaceae - triterpenoid saponin - rogchaponin - alcohol dehydrogenase

Supporting Information

References

  • 1 Higdon J V, Frei B. Tea catechin and polyphenols: health effects, metabolism, and antioxidant functions.  Crit Rev Food Sci Nutr. 2003;  43 89-143
    CrossrefPubMedSuche in Google Scholar
  • 2 Friedman M. Overview of antibacterial, antitoxin, antiviral, and antifungal activities of tea flavonoids and teas.  Mol Nutr Food Res. 2007;  51 116-134
    CrossrefPubMedSuche in Google Scholar
  • 3 Gramza A, Korczak J. Tea constituents (Camellia sinensis L.) as antioxidants in lipid systems.  Trends Food Sci Technol. 2005;  16 351-358
    CrossrefPubMedSuche in Google Scholar
  • 4 Yang C S, Lambert J D, Ju J, Lu G, Sang S. Tea and cancer prevention: molecular mechanism and human relevance.  Toxicol Appl Pharmacol. 2007;  224 265-273
    CrossrefPubMedSuche in Google Scholar
  • 5 Yoshikawa M, Nakamura S, Kato Y, Matsuhira K, Matsuda H. Medicinal flowers. XIV. New acylated oleanane-type triterpene oligoglycosides with antiallergic activity from flower buds of Chinese tea plant (Camellia sinensis).  Chem Pharm Bull. 2007;  55 598-605
    CrossrefPubMedSuche in Google Scholar
  • 6 Morikawa T, Nakamura S, Kato Y, Muraoka O, Matsuda H, Yoshikawa M. Bioactive saponins and glycosides. XXVIII. New triterpene saponins, foliatheasaponins I, II, III, IV, and V, from tencha (the leaves of Camellia sinensis).  Chem Pharm Bull. 2007;  55 293-298
    CrossrefPubMedSuche in Google Scholar
  • 7 Yoshikawa M, Morikawa T, Yamamoto K, Kato Y, Nagatomo A, Matsuda H. Floratheasaponins A–C, acylated oleanane-type triterpene oligoglycosides with anti-hyperlipidemic activities from flowers of the tea plant (Camellia sinensis)1.  J Nat Prod. 2005;  68 1360-1365
    CrossrefPubMedSuche in Google Scholar
  • 8 Yoshikawa M, Murakami T, Yoshizumi S, Murakami N, Yamahara J, Matsuda H. Bioactive saponins and glycosides. V. Acylated polyhydroxyolean-12-ene triterpene oligoglycosides, camelliasaponins A1, A2, B1, B2, C1, and C2, from the seeds of Camellia japonica L: structures and inhibitory activity on alcohol absorption.  Chem Pharm Bull. 1996;  44 1899-1907
    CrossrefPubMedSuche in Google Scholar
  • 9 Han L K, Kimura Y, Kawashima M, Takaku T, Taniyama T, Hayashi T, Zheng Y N, Okuda H. Anti-obesity effects in rodents of dietary teasaponin, a lipase inhibitor.  Int J Obes. 2001;  25 1459-1464
    CrossrefPubMedSuche in Google Scholar
  • 10 Yoshikawa M, Morikawa T, Li N, Nagatomo A, Li X, Matsuda H. Bioactive saponins and glycosides. XXIII. Triterpene saponins with gastroprotective effect from the seeds of Camellia sinensis–theasaponins E3, E4, E5, E6, and E7.  Chem Pharm Bull. 2005;  53 1559-1564
    CrossrefPubMedSuche in Google Scholar
  • 11 Morikawa T, Li N, Nagatomo A, Matsuda H, Li X, Yoshikawa M. Triterpene saponins with gastroprotective effects from tea seed (the seeds of Camellia sinensis).  J Nat Prod. 2006;  69 185-190
    CrossrefPubMedSuche in Google Scholar
  • 12 Murakami T, Nakamura J, Matsuda H, Yoshikawa M. Bioactive saponins and glycosides. XV. Saponin constituents with gastroprotective effect from the seeds of tea plant, Camellia sinensis L. var. assamica Pierre, cultivated in Srilanka: structures of assamsaponins A, B, C, D, and E.  Chem Pharm Bull. 1999;  47 1759-1764
    CrossrefPubMedSuche in Google Scholar
  • 13 Ghosh P, Besra S E, Tripathi G, Mitra S, Vedasiromoni J R. Cytotoxic and apoptogenic effect of tea (Camellia sinensis var. assamica) root extract (TRE) and two of its steroidal saponins TS1 and TS2 on human leukemic cell lines K562 and U937 and on cells of CML and ALL patients.  Leuk Res. 2006;  30 459-468
    CrossrefPubMedSuche in Google Scholar
  • 14 Kakuda T, Sakane I, Takihara T, Tsukamoto S, Kanegae T, Nagoya T. Effects of tea (Camellia sinensis) chemical compounds on ethanol metabolism in ICR mice.  Biosci Biotechnol Biochem. 1996;  60 1451-1454
    PubMedSuche in Google Scholar
  • 15 Tsukamoto S, Kanegae T, Nagoya T, Shimamura M, Kato T, Watanabe S, Kawaguchi M. Effects of seed saponins of Thea sinensis L. (Ryokucha saponin) on alcohol absorption and metabolism.  Alcohol Alcohol. 1993;  28 687-692
    PubMedSuche in Google Scholar
  • 16 Swift R, Davidson D. Alcohol hangover: mechanism and mediators.  Alcohol Health Res World. 1998;  22 54-60
    PubMedSuche in Google Scholar
  • 17 Wiese J G, Shlipak M G, Browner W S. The alcohol hangover.  Ann Intern Med. 2000;  132 897-902
    PubMedSuche in Google Scholar
  • 18 Eriksson C J P. The role of acetaldehyde in the actions of alcohol.  Alcohol Clin Exp Res. 2001;  25 15-32
    CrossrefPubMedSuche in Google Scholar
  • 19 Poschl G, Seitz H K. Alcohol and cancer.  Alcohol Alcohol. 2004;  39 155-165
    PubMedSuche in Google Scholar
  • 20 Varughese T, Rahaman M, Kim N S, Cho S C, Moon S S. Gamnamoside, a phenylpropanoid glycoside from persimmon leaves (Diospyros kaki) with an inhibitory effect against an alcohol metabolizing enzyme.  Bull Korean Chem Soc. 2009;  30 1035-1038
    CrossrefPubMedSuche in Google Scholar
  • 21 Song J, Manir M M, Moon S S. Cytotoxic grifolin derivatives isolated from the wild mushroom Boletus pseudocalopus (Basidiomycetes).  Chem Biodivers. 2009;  6 1435-1442
    CrossrefPubMedSuche in Google Scholar
  • 22 Oshima R, Kumanotani J. Determination of configuration of monosaccharides by HPLC on diastereoisomeric 1–deoxy–1–(N–acetyl–α–methylbenzylamino) alditol acetates.  Chem Lett. 1981;  10 943-946
    PubMedSuche in Google Scholar
  • 23 Zheng Q, Koike K, Han L K, Okuda H, Nikaido T. New biologically active triterpenoid saponins from Scabiosa tschiliensis.  J Nat Prod. 2004;  67 604-613
    CrossrefPubMedSuche in Google Scholar
  • 24 Yin S J, Bosron W F, Magnes L J, Li T K. Human liver alcohol dehydrogenase: purification and kinetic characterization of the β 2 β 2, β 2 β 1, αβ 2 and β 2 γ 1 “Oriental” isoenzymes.  Biochemistry. 1984;  23 5847-5853
    CrossrefPubMedSuche in Google Scholar
  • 25 Traves C, Camps L, Lopez-Tejero D. Liver alcohol dehydrogenase activity and ethanol levels during chronic ethanol intake in pregnant rats and their offspring.  Pharmacol Biochem Behav. 1995;  52 93-99
    CrossrefPubMedSuche in Google Scholar
  • 26 Yosioka I, Hino K, Matsuda A, Kitagawa I. Saponin and sapogenol. VI. Sapogenols constituents of leaves of Pittosporum tobira AIT.  Chem Pharm Bull. 1972;  20 1499-1506
    CrossrefPubMedSuche in Google Scholar
  • 27 Yu L, Yang J Z, Chen X G, Shi J G, Zhang D M. Cytotoxic triterpenoid glycosides from the roots of Gordonia chrysandra.  J Nat Prod. 2009;  72 866-870
    CrossrefPubMedSuche in Google Scholar
  • 28 Zhang Z, Li S. Cytotoxic triterpenoid saponins from the fruits of Aesculus pavia L.  Phytochemistry. 2007;  68 2075-2086
    CrossrefPubMedSuche in Google Scholar
  • 29 Lu Y, Umeda T, Yagi A, Sakata K, Chaudhuri T, Ganguly D K, Sharma S. Triterpenoid saponins from the roots of tea plant (Camellia sinensis var. assamica).  Phytochemistry. 2000;  53 941-946
    CrossrefPubMedSuche in Google Scholar
  • 30 Yosioka I, Nishimura T, Matsuda A, Kitagawa I. Saponin and sapogenol. II. Seeds sapogenols of Thea sinensis L. (2). Theasapogenol A.  Chem Pharm Bull. 1970;  18 1621-1632
    CrossrefPubMedSuche in Google Scholar
  • 31 Ghosh P, Besra S E, Tripathi G, Mitra S, Vedasiromoni J R. Cytotoxic and apoptogenic effect of tea (Camellia sinensis var. assamica) root extract (TRE) and two of its steroidal saponins TS1 and TS2 on human leukemic cell lines K562 and U937 and on cells of CML and ALL patients.  Leuk Res. 2006;  30 459-468
    CrossrefPubMedSuche in Google Scholar
  • 32 Chattopadhyay P, Besra S E, Gomes A, Das M, Sur P, Mitra S, Vedasiromoni J R. Anti-inflammatory activity of tea (Camellia sinensis) root extract.  Life Sci. 2004;  74 1839-1849
    CrossrefPubMedSuche in Google Scholar
  • 33 Kobayashi K, Teruya T, Suenaga K, Matsui Y, Masuda H, Kigoshi H. Isotheasaponins B1–B3 from Camellia sinensis var. sinensis tea leaves.  Phytochemistry. 2006;  67 1385-1389
    CrossrefPubMedSuche in Google Scholar

Prof. Dr. Surk-Sik Moon

Department of Chemistry
Kongju National University

Gongju 314-701

Republic of Korea

Telefon: +82 4 18 50 84 95

Fax: +82 4 18 50 84 79

eMail: ssmoon@kongju.ac.kr