Hepatoprotective and Antioxidant Arylbenzofurans and Flavonoids from the Twigs of Morus mesozygia

Abstract

The chemical investigation of the twigs of Morus mesozygia resulted in the isolation of three new prenylated 2-arylbenzofurans, named moracin KM, LM, and SC (1–3), nine known 2-arylbenzofurans (4–12), and two known flavonoids (13–14). The structures of the new compounds were established as [2′′,3′′:6,7]-(6-(S)-hydroxymethyl-6-methylpyrano)-2-(3,5-dihydroxyphenyl)benzofuran-5-ol (1), [2′′,3′′:6,7]- (4,7-dihydro-6-methyloxepine)-2-(3-hydroxy-5-methoxyphenyl)benzofuran-5-ol (2), and [2′′,3′′:6,7]-(6,6-dimethylpyrano)-2-(3,5-dihydroxyphenyl)benzofuran (3). One of the new compounds, moracin LM (2), displayed modest antioxidant activity, whereas known compounds 4, 13, and 14 showed significant hepatoprotective and antioxidant activities.

arylbenzofurans - flavonoids - hepatoprotective - Moraceae - Morus mesozygia

References

• 1 Kapche G D W F, Fozing C D, Donfack J H, Fotso G W, Amadou D, Tchana A N, Bezabih M, Moundipa P F, Ngadjui B T, Abegaz B M. Prenylated arylbenzofuran derivatives from Morus mesozygia with antioxidant activity.  Phytochemistry. 2009;  70 216-221
• 2 Oh H, Ko J E K, Jun Y, Oh M H, Park S U, Kang K H, Lee H S, Kim Y C. Hepatoprotective and free radical scavenging activities of prenylflavonoids, coumarins and stibenes from Morus alba.  Planta Med. 2002;  68 932-934
• 3 Kang J, Ruo-Yun C, De-Quan Y. Five new diels-alder type adducts from the stem bark and roots bark of Morus mongolica (mongolicins A–E).  Planta Med. 2006;  72 52-59
• 4 Sheng-Jun D, Zhong-Mao M, Zhi-Bo M, Shuai L, Ruo-Yun C, De-Quan Y. Bioactive diels-alder type adducts from the stem bark of Morus macroura.  Planta Med. 2004;  70 758-763
• 5 Oshima Y, Namao K, Kamijou A, Matsuoka S, Nakano M, Terao K, Ohizumi Y. Powerful hepatoprotective and hepatotoxic plant oligostilbenes, isolated from the Oriental medicinal plant Vitis coignetiae (Vitaceae).  Cell Mol Life Sci. 1995;  51 63-66
• 6 Mann I S, Widdowson D A, Clough J M. Transition metal directed synthesis of moracin M.  Tetrahedron. 1991;  47 7991-8000
• 7 Lee D, Bhat K P L, Fong H H S, Farnsworth N R, Pezzuto J M, Kinghorn A D. Aromatase inhibitors from Broussonetia papyrifera.  J Nat Prod. 2001;  64 1286-1293
• 8 Noguchi A, Yoshihara T, Ichihara A, Sugihara S, Koshino M, Kojima M, Masaoka Y. Iron-deficiency stress ferric phosphate-dissolving compound, alfafuran, from Alfalfa (Medicago sativa L.) in response to iron-deficiency stress.  Biosci Biotechnol Biochem. 2000;  58 2312-2313
• 9 Takasugi M, Nagao S, Munoz L, Ishikawa S. Moracin E, F, G, and H, new phytoalexins from diseased mulberry.  Tetrahedron Lett. 1979;  48 4675-4678
• 10 Matsuyama S, Kuwahara Y, Nakamura S, Suzuki T. Oviposition stimulants for the lesser mulberry pyralid, Glyphodes pyloalis (Walker), in mulberry leaves; rediscovery of phytoalexin components as insect kairomones.  Agric Biol Chem. 1991;  55 1333-1341
• 11 Meragelman K M, McKee T C, Boyd M R. Anti-HIV prenylated flavonoids from Monotes africanus.  J Nat Prod. 2001;  64 546-548
• 12 Nomura T, Fukai T. Phenylflavonoids from the root bark of the cultivated mulberry tree.  Heterocycles. 1982;  15 1531-1567
• 13 Pacher T, Seger C, Engelmeier D, Vajrodaya S, Hofer O, Greger H. Antifungal stilbenoids from Stemona collinsae.  J Nat Prod. 2002;  65 820-827
• 14 Velozo L S M, Ferreira M J P, Santos M S, Moreira D L, Emerenciano V P, Kaplan M A C. Unusual chromenes from Peperomia blanda.  Phytochemistry. 2006;  67 492-496
• 15 Bruggisser R, von Daeniken K, Jundt G, Schaffner W, Tullberg-Reinert H. Interference of plant extracts, phytoestrogens and antioxidants with the MTT tetrazolium assay.  Planta Med. 2002;  68 445-448