Two New Benzofurans from Gastrodia elata and their DNA Topoisomerases I and II Inhibitory Activities

 

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Abstract

Two new benzofurans, 1-furan-2-yl-2-(4-hydroxyphenyl)-ethanone (1) and 5-(4-hydroxybenzyloxymethyl)-furan-2-carbaldehyde (2), together with five known compounds, 4-hydroxybenzyl methyl ether (3), 5-(hydroxymethyl)-furfural (4), gastrodin (5), β-sitosterol (6) and β-sitosterol glucoside (7) were isolated from the rhizome of Gastrodia elata Blume. In DNA topoisomerase I and II inhibition assays in vitro at a concentration of 20 μM, 1 showed potent inhibitory activity, 66 % and 71 % inhibition, respectively, compared to the positive control compounds, camptothecin and etoposide, 71 % and 22 % inhibition, respectively. All of these compounds exhibited weak or no cytotoxicities against human colon carcinoma cell line (HT-29), human breast carcinoma cell line (MCF-7) and human hepatocellular carcinoma cell line (HepG-2).

References

• 1 D’Arpa P, Liu L F. Topoisomerase-targeting antitumor drugs.  Biochim Biophys Acta. 1989;  989 163-77.
  PubMedGoogle Scholar
• 2 Pommier Y. DNA topoisomerase I and II in cancer chemotherapy: update and perspectives.  Cancer Chemother Pharmacol. 1993;  32 103-8.
  CrossrefPubMedGoogle Scholar
• 3 Wang J C. DNA topoisomerases.  Annu Rev Biochem. 1985;  54 665-79.
  CrossrefPubMedGoogle Scholar
• 4 Slichenmyer W J, Rowinsky E K, Donehower R C, Kaufmann S H. The current status of camptothecin analogues as antitumor agents.  J Natl Cancer Inst. 1993;  85 271-91.
  CrossrefPubMedGoogle Scholar
• 5 Potmesil M. Camptothecins: from bench research to hospital wards.  Cancer Res. 1994;  54 1431-9.
  PubMedGoogle Scholar
• 6 Chen A Y, Liu L F. DNA topoisomerases: essential enzymes and lethal targets.  Annu Rev Pharmacol Toxicol. 1994;  34 191-218.
  PubMedGoogle Scholar
• 7 Kellner U, Sehested M, Jensen P B, Gieseler F, Rudolph P. Culprit and victim - DNA topoisomerase II.  Lancet Oncol. 2002;  3 235-43.
  CrossrefPubMedGoogle Scholar
• 8 Li Q Y, Zu Y G, Shi R Z, Yao L P. Review camptothecin: Current perspectives.  Curr Med Chem. 2006;  13 2021-39.
  CrossrefPubMedGoogle Scholar
• 9 Liu L F. DNA topoisomerase poisons as antitumor drugs.  Annu Rev Biochem. 1989;  58 351-75.
  PubMedGoogle Scholar
• 10 Hus H Y, Chen Y P, Hsu S J, Hsu C S. Oriental Materia Medica: a concise guide.  California: Oriental Health Art. Institute;  1986 662.
  PubMedGoogle Scholar
• 11 Tang W, Eisenbrand G. Chinese drugs of plant origin, chemistry, pharmacology, and use in traditional and modern medicine.  Berlin Heidelberg: Springer. Verlag;  1992 545-8.
  PubMedGoogle Scholar
• 12 Hayashi J, Sekine T, Deguchi S, Lin Q, Horie S, Tsuchiya S. et al . Phenolic compounds from Gastrodia rhizome and relaxant effects of related compounds on isolated smooth muscle preparation.  Phytochemistry. 2002;  59 513-9.
  CrossrefPubMedGoogle Scholar
• 13 Hsieh M T, Wu C R, Chen C F. Gastrodin and p-hydroxybenzyl alcohol facilitate memory consolidation and retrieval but not acquisition on the passive avoidance task in rats.  J Ethnopharmacol. 1997;  56 45-54.
  CrossrefPubMedGoogle Scholar
• 14 Wu C R, Hsieh M T, Huang S C, Peng W H, Chang Y S, Chen C F. Effects of Gastrodia elata and its active compounds on scopolamine-induced amnesia in rats.  Planta Med. 1996;  62 317-21.
  Article in Thieme ConnectPubMedGoogle Scholar
• 15 Zhou J, Yang Y B, Yang T R. The chemistry of Gastrodia elata Bl, 1. The isolation and identification of chemical constituents of Gastrodia elata Bl.  Acta Chim Sin. 1979;  37 183-9.
  PubMedGoogle Scholar
• 16 Taguchi H, Yoshioka I, Yamasaki K, Kim I H. Studies on the constituents of Gastrodia elata Blume.  Chem Pharm Bull. 1981;  29 55-62.
  PubMedGoogle Scholar
• 17 Noda N, Kobayashi Y, Miyahara K, Fukahori S. 2,4-Bis(4-hdroxybenzyl)phenol from Gastrodia elata .  Phytochemistry. 1995;  39 1247-8.
  CrossrefPubMedGoogle Scholar
• 18 Lin J H, Liu Y C, Hau J P, Wen K C. Parishins B and C from rhizomes of Gastrodia elata .  Phytochemistry. 1996;  42 549-51.
  CrossrefPubMedGoogle Scholar
• 19 Yun-Choi S H, Pyo M K. Isolation of 4,4′-dihydroxybenzyl sulfoxide from Gastrodia elata .  Arch Pharm Res. 1997;  20 91-2.
  PubMedGoogle Scholar
• 20 Yun-Choi S H, Pyo M K, Park K M. Isolation of 3-O-(4′-hydroxybenzyl)-beta-sitosterol and 4-[4′-(4″-dihydroxybenzyloxy) benzyloxy] methyl ether from fresh tubers of Gastrodia elata .  Arch Pharm Res. 1998;  21 357-60.
  PubMedGoogle Scholar
• 21 Liu X Q, Baek W S, Ahn D K, Choi H Y, Yook C S. The constituents of the aerial part of Gastrodia elata Blume.  Nat Prod Sci. 2002;  8 137-40.
  PubMedGoogle Scholar
• 22 Ishida H, Seri K I. Catalytic activity of lanthanoide (III) ions for dehydration of d-glucose to 5-(hydroxymethyl) furfural.  J Mol Catal A Chem. 1996;  112 L163-5.
  CrossrefPubMedGoogle Scholar
• 23 Baek N I, Choi S Y, Park J K, Cho S W, Ahn E M, Jeon S G. et al . Isolation and identification of succinic semialdehyde dehydrogenase inhibitory compound from the rhizome of Gastrodia elata Blume.  Arch Pharm Res. 1999;  22 219-24.
  PubMedGoogle Scholar
• 24 Chang I M, Yun H S, Yamasaki K. β-Sitosterol and β-sitosteryl-3-O-β-d-glucopyranoside isolated from Plantago asiatica seed.  Korean J Pharmcognosy. 1981;  12 12-24.
  PubMedGoogle Scholar
• 25 Fukuda M, Nishio K, Kanzawa F, Ogasawara H, Ishida T, Arioka H. et al . Synergism between cisplatin and topoisomerase I inhibitors, NB-506 and SN-38, in human small cell lung cancer cells.  Cancer Res. 1996;  56 789-93.
  PubMedGoogle Scholar
• 26 Li G, Lee C S, Woo M H, Lee S H, Chang H W, Son J K. Lignans from the bark of Machilus thunbergii and their DNA topoisomerases I and II inhibition and cytotoxicity.  Biol Pharm Bull. 2004;  27 147-50.
  CrossrefPubMedGoogle Scholar
• 27 Rubinstein L V, Shoemaker R H, Paull K D, Simon R M, Tosini S, Skehan P. et al . Comparison of in vitro anticancer-drug-screening data generated with a lines.  J Nat Cancer Inst. 1990;  82 1113-8.
  CrossrefPubMedGoogle Scholar
• 28 Iwagawa T, Hase T sunao. A spiro-bis-χ-lactone glucoside from Viburnum dilatatum .  Phytochemistry. 1984;  23 2299-301.
  CrossrefPubMedGoogle Scholar
• 29 Jogia M K, Vakamoce V, Weavers R T. Synthesis of some furfural and syringic acid derivatives.  Aust J Chem. 1985;  38 1009-16.
  PubMedGoogle Scholar

Prof. Dr. Jong-Keun Son

College of Pharmacy

Yeungnam University

Gyongsan 712-749

Republic of Korea

Phone: +82-53-810-2817

Fax: +82-53-810-4654

Email: jkson@yu.ac.kr

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