Four New Benzofurans from Seeds of Styrax perkinsiae

Abstract

Four new benzofurans trans-5-(3-hydroxypropyl)-7-methoxy-2-[2,3-dihydro-3-hydroxymethyl-7-methoxy-2-(3-methoxy-4-hydroxyphenyl)-benzofuran-5-yl]benzofuran (1), (E)-5-(2-formylvinyl)-7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran (2), 5-(3-butanoyloxypropyl)-7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran (3), and 5-(3-hydroxypropyl)-7-hydroxy-2-(3,4-methylenedioxyphenyl) benzofuran (4) were isolated from the seeds of Styrax perkinsiae, together with egonol (5), demethoxyegonol (6), egonol acetate (7), demethoxyegonol acetate (8), egonol glucoside (9), egonol gentiobioside (10), egonol gentiotrioside (11), β-sitosterol (12), and β-daucosterol (13). Their structures were established by spectroscopic and chemical methods. Compounds 1 and 4 exhibited cytotoxic activity in vitro using two breast cancer cell lines MCF-7 and MDA-MB-231.

Key words

Styrax perkinsiae - Styracaceae - cytotoxic activity - benzofurans

References

• 1 Delectis Florae Reipublicae Popularis Sinicae Agendae Academiae Sinicae Edita. Flora Reipublicae Popularis Sinicae. Vol 60 Beijing; Science Press 1987: pp 77-89
• 2 Akgul Y Y, Anil H. Benzofurans and another constituent from seeds of Styrax officinalis .  Phytochemistry. 2003;  63 939-43
• 3 Yayla Y, Alankus-Caliskan O, Anil H, Bates R B, Stessman C C, Kane V V. Saponins from Styrax officinalis .  Fitoterapia. 2002;  73 320-6
• 4 Yoshikawa K, Hiral H, Tanaka M, Arihara S. Antisweet natural products, structures of jegosaponins A - D from Styrax japonica .  Chem Pharm Bull. 2000;  48 1093-6
• 5 Anil H. 21-Benzoyl-barringtogenol C, a sapogenin from Styrax officinalis .  Phytochemistry. 1979;  18 1760-1
• 6 Anil H. Four benzofuran glycosides from Styrax officinalis .  Phytochemistry. 1980;  19 2784-6
• 7 Takanashi M, Takizawa Y, Mitsuhashi T. 5-(3-Hydroxypropyl)-2-(3′,4′-methylenedioxyphenyl)benzofuran: a new benzofuran from Styrax obassia Sieb. et Zucc. Chem Lett 1974: 869-71
• 8 Takanashi M, Takizawa Y. New benzofurans related to egonol from immature seeds of Styrax obassia .  Phytochemistry. 1988;  27 1224-6
• 9 Ranjith H, Dharmaratne W, Nishanthi W M, Wijesinghe M. A trioxygenated diprenylated chromenxanthone from Calophyllum moonii .  Phytochemistry. 1997;  46 1293-5
• 10 Iinuma M, Tosa H, Toriyama N, Tanaka T, Ito T, Chelladurai V. Six xanthones from Calophyllum austroindicum .  Phytochemistry. 1996;  43 681-5
• 11 Skehan P, Storing R, Scudiero D, Monk A, McMahon J, Visica D. New colorimetric cytotoxity assay for anticancer-drug-screen.  J Natl Cancer Inst. 1990;  82 1107-12
• 12 Rubinstein L V, Shoemaker R H, Paul K D, Tosini S, Skehan P, Scudiero D A. et al . Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines.  J Natl Cancer Inst. 1990;  82 1113-8
• 13 Agrawal P K, Rastogi R P, Osterdahl B G. ¹³C NMR spectral analysis of dihydrobenzofuran lignans.  Org Magn Resonance. 1983;  21 119-21
• 14 Fang J M, Lee C K, Cheng Y S. Lignans from leaves of Juniperus chinensis .  Phytochemistry. 1992;  31 3659-61
• 15 Ito K, Ichino K, Iida T, Lai J. Neolignans from Magnolia kachirachirai .  Phytochemistry. 1984;  23 2643-5
• 16 Nabeta K, Hirata M, Ohke Y, Ananda Samaraweera S W, Okuyama H. Lignans in cell cultures of Picea glehnii .  Phytochemistry. 1994;  37 409-13
• 17 Hopkins C Y, Ewing D F, Chisholm M J. Egonol spectrometric properties and derivatives.  Can J Chem. 1967;  45 1425-9
• 18 Venturini M, Durando A, Garrone O. et al . Capecitabine in combination with docetaxel and epirubicin in patients with previously untreated, advanced breast carcinoma.  Cancer. 2003;  97 1174-80
• 19 Berruti A, Bitossi R, Bottini A, Bonardi S, Donadio M, Nigro C. et al . Combination regimen of epirubicin, vinorelbine and 5-fluorouracil continuous infusion as first-line chemotherapy in anthracycline-naive metastatic breast cancer patients.  Eur J Cancer. 2005;  41 249-55
• 20 Tokunaga E, Oda S, Fukushima M, Maehara Y, Sugimachi K. Differential growth inhibition by 5-fluorouracil in human colorectal carcinoma cell lines.  Eur J Cancer. 2000;  36 1998-2006
• 21 Tsai I L, Hsieh C F, Duh C Y. Additional cytotoxic neolignans from Persea obovatifolia .  Phytochemistry. 1998;  48 1371-5
• 22 Tsai I L, Hsieh C F, Duh C Y, Chen I S. Cytotoxic neolignans from Persea obovatifolia .  Phytochemistry. 1996;  43 1261-3
• 23 Cui B, Chai H, Santisuk T, Reutrakul V, Farnsworth N R, Cordell G A, Kinghorn A D. Novel cytotoxic 1H-cyclopenta[b]benzofuran lignans from Aglaia elliptica .  Tetrahedron. 1997;  53 17 625-32
• 24 Hayakawa I, Shioya R, Agatsuma T, Furukawa H, Sugano Y. Thienopyridine and benzofuran derivatives as potent anti-tumor agents possessing different structure-activity relationships.  Bioorg Med Chem Lett. 2004;  14 3411-4
• 25 Hayakawa I, Shioya R, Agatsuma T, Furukawa H, Naruto S, Sugano Y. 4-Hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as potent anti-tumor agents.  Bioorg Med Chem Lett. 2004;  14 55-8
• 26 Ballarin L, Cima F, Sabbadin A. Phenoloxidase and cytotoxicity in the compound ascidian Botryllus schlosseri .  Dev Comp Immunol. 1998;  22 479-92
• 27 Passi S, Picardo M, Nazzaro-Porro M. Comparative cytotoxicity of phenols in vitro .  Biochem J. 1987;  245 537-42
• 28 Terao M, Tomita K, Oki T, Tabe L, Gianni M, Garattini E. Inhibition of melanogenesis by BMY-28 565, a novel compound depressing tyrosinase activity in B16 melanoma cells.  Biochem Pharmacol. 1992;  43 183-9
• 29 Prezioso J A, Epperly M W, Wang N, Bloomer W D. Effects of tyrosinase activity on the cytotoxicity of 4-S-cysteaminylphenol and N-acetyl-4-S-cysteaminylphenol in melanoma cells.  Cancer Lett. 1992;  63 73-9
• 30 Yamada I, Seki S, Suzuke S, Matsubara O, Kasuga T. The killing effect of 4-S-cysteaminylphenol, a newly synthesised melanin precursor, on B16 melanoma cell lines.  Br J Cancer. 1991;  63 187-90