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

Department of Biosystems and Biotechnology

Research output: Contribution to journal › Article › peer-review

42 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

ASJC Scopus subject areas

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

Access to Document

10.1021/np800418j

Cite this

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, 01.2009, p. 164-167.

Research output: Contribution to journal › Article › peer-review

@article{c9a10396b08d4f7f9ddf2266aa0eec29,

title = "Prenylated and benzylated flavonoids from the fruits of Cudrania tricuspidata",

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.",

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

year = "2009",

month = jan,

doi = "10.1021/np800418j",

language = "English",

volume = "72",

pages = "164--167",

journal = "Journal of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - Prenylated and benzylated flavonoids from the fruits of Cudrania tricuspidata

AU - Xiang, Hua Han

AU - Seong, Su Hong

AU - Jin, Qinghao

AU - Li, Dayu

AU - Kim, Hyun Kyu

AU - Lee, Jeongrai

AU - Suk, Hyung Kwon

AU - Lee, Dongho

AU - Lee, Chong Kil

AU - Myung, Koo Lee

AU - Bang, Yeon Hwang

PY - 2009/1

Y1 - 2009/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=60549085976&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=60549085976&partnerID=8YFLogxK

U2 - 10.1021/np800418j

DO - 10.1021/np800418j

M3 - Article

C2 - 19113968

AN - SCOPUS:60549085976

VL - 72

SP - 164

EP - 167

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 1

ER -

Prenylated and benzylated flavonoids from the fruits of Cudrania tricuspidata

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this