Prenylated and benzylated flavonoids from the fruits of Cudrania tricuspidata

Hua Han Xiang; Su Hong Seong; Qinghao Jin; Dayu Li; Hyun Kyu Kim; Jeongrai Lee; Hyung Kwon Suk; Dongho Lee; Chong Kil Lee; Koo Lee Myung; Yeon Hwang Bang

doi:10.1021/np800418j

Prenylated and benzylated flavonoids from the fruits of Cudrania tricuspidata

Hua Han Xiang, Su Hong Seong, Qinghao Jin, Dayu Li, Hyun Kyu Kim, Jeongrai Lee, Hyung Kwon Suk, Dongho Lee, Chong Kil Lee, Koo Lee Myung, Yeon Hwang Bang

Division of Biotechnology

Research output: Contribution to journal › Article

34 Citations (Scopus)

Abstract

Three new prenylated isoflavones, 5,7-dihydroxy-6-(2″-hydroxy- 3″-methylbut-3″-enyl)-4′-methoxylisoflavone (1), 5,4′-dihydroxy-6-(3″-methylbut-2′-enyl)-2‴-(4‴- hydroxy-4‴-methylethyl)-3‴-methoxydihydrofurano-[4‴, 5‴;7,8]isoflavone (2), and 5,4′-dihydroxy-8-(3″-methylbut- 2″-enyl)-2‴-(4‴-hydroxy-4‴-methylethyl) furano-[4‴,5‴;6,7]isoflavone (3), a benzylated dihydroflavonol, 5,7,4′-trihydroxy-8-p-hydroxybenzyldihydroflavonol (4), and eight known flavonoids (5-12) were isolated from the fruits of Cudrania tricuspidata. The structures of these compounds were determined on the basis of MS and ¹H and ¹³C NMR spectroscopic data, including 2D NMR experiments. Compounds 2, 3, 6, 7, 8, 10, 11, and 12 inhibited LPS-induced nitric oxide production, with IC₅₀ values of 11.8-41.8 μM.

Original language	English
Pages (from-to)	164-167
Number of pages	4
Journal	Journal of Natural Products
Volume	72
Issue number	1
DOIs	https://doi.org/10.1021/np800418j
Publication status	Published - 2009 Jan 1

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ASJC Scopus subject areas

Complementary and alternative medicine
Molecular Medicine
Organic Chemistry
Analytical Chemistry
Pharmaceutical Science
Pharmacology
Drug Discovery

Cite this

Xiang, H. H., Seong, S. H., Jin, Q., Li, D., Kim, H. K., Lee, J., Suk, H. K., Lee, D., Lee, C. K., Myung, K. L., & Bang, Y. H. (2009). Prenylated and benzylated flavonoids from the fruits of Cudrania tricuspidata. Journal of Natural Products, 72(1), 164-167. https://doi.org/10.1021/np800418j

Prenylated and benzylated flavonoids from the fruits of Cudrania tricuspidata. / Xiang, Hua Han; Seong, Su Hong; Jin, Qinghao; Li, Dayu; Kim, Hyun Kyu; Lee, Jeongrai; Suk, Hyung Kwon; Lee, Dongho; Lee, Chong Kil; Myung, Koo Lee; Bang, Yeon Hwang.

In: Journal of Natural Products, Vol. 72, No. 1, 01.01.2009, p. 164-167.

Research output: Contribution to journal › Article

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abstract = "Three new prenylated isoflavones, 5,7-dihydroxy-6-(2″-hydroxy- 3″-methylbut-3″-enyl)-4′-methoxylisoflavone (1), 5,4′-dihydroxy-6-(3″-methylbut-2′-enyl)-2‴-(4‴- hydroxy-4‴-methylethyl)-3‴-methoxydihydrofurano-[4‴, 5‴;7,8]isoflavone (2), and 5,4′-dihydroxy-8-(3″-methylbut- 2″-enyl)-2‴-(4‴-hydroxy-4‴-methylethyl) furano-[4‴,5‴;6,7]isoflavone (3), a benzylated dihydroflavonol, 5,7,4′-trihydroxy-8-p-hydroxybenzyldihydroflavonol (4), and eight known flavonoids (5-12) were isolated from the fruits of Cudrania tricuspidata. The structures of these compounds were determined on the basis of MS and 1H and 13C NMR spectroscopic data, including 2D NMR experiments. Compounds 2, 3, 6, 7, 8, 10, 11, and 12 inhibited LPS-induced nitric oxide production, with IC50 values of 11.8-41.8 μM.",

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10.1021/np800418j