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).
Key words
Gastrodia elata
- Orchidaceae - benzofurans - topoisomerases I and II inhibition
References
-
1
D’Arpa P, Liu L F.
Topoisomerase-targeting antitumor drugs.
Biochim Biophys Acta.
1989;
989
163-77.
-
2
Pommier Y.
DNA topoisomerase I and II in cancer chemotherapy: update and perspectives.
Cancer Chemother Pharmacol.
1993;
32
103-8.
-
3
Wang J C.
DNA topoisomerases.
Annu Rev Biochem.
1985;
54
665-79.
-
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.
-
5
Potmesil M.
Camptothecins: from bench research to hospital wards.
Cancer Res.
1994;
54
1431-9.
-
6
Chen A Y, Liu L F.
DNA topoisomerases: essential enzymes and lethal targets.
Annu Rev Pharmacol Toxicol.
1994;
34
191-218.
-
7
Kellner U, Sehested M, Jensen P B, Gieseler F, Rudolph P.
Culprit and victim - DNA topoisomerase II.
Lancet Oncol.
2002;
3
235-43.
-
8
Li Q Y, Zu Y G, Shi R Z, Yao L P.
Review camptothecin: Current perspectives.
Curr Med Chem.
2006;
13
2021-39.
-
9
Liu L F.
DNA topoisomerase poisons as antitumor drugs.
Annu Rev Biochem.
1989;
58
351-75.
-
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.
-
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.
-
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.
-
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.
-
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.
-
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.
-
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.
-
17
Noda N, Kobayashi Y, Miyahara K, Fukahori S.
2,4-Bis(4-hdroxybenzyl)phenol from Gastrodia elata
.
Phytochemistry.
1995;
39
1247-8.
-
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.
-
19
Yun-Choi S H, Pyo M K.
Isolation of 4,4′-dihydroxybenzyl sulfoxide from Gastrodia elata
.
Arch Pharm Res.
1997;
20
91-2.
-
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.
-
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.
-
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.
-
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.
-
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.
-
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.
-
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.
-
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.
-
28
Iwagawa T, Hase T sunao.
A spiro-bis-χ-lactone glucoside from Viburnum dilatatum
.
Phytochemistry.
1984;
23
2299-301.
-
29
Jogia M K, Vakamoce V, Weavers R T.
Synthesis of some furfural and syringic acid derivatives.
Aust J Chem.
1985;
38
1009-16.
Prof. Dr. Jong-Keun Son
College of Pharmacy
Yeungnam University
Gyongsan 712-749
Republic of Korea
Phone: +82-53-810-2817
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