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Planta Med 2013; 79(18): 1742-1748
DOI: 10.1055/s-0033-1351051
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Anti HSV-1 Flavonoid Derivatives Tethered with Houttuynin from Houttuynia cordata

Shao-Dan Chen
1   Institute of Traditional Chinese Medicine & Natural Products, Jinan University, Guangzhou, Peopleʼs Republic of China
3   The second clinical college of Guangzhou university of Chinese medicine, Guangzhou, Peopleʼs Republic of China
,
Ting Li
2   State Key Laboratory for Respiratory Disease, Laboratory of Viral Immunology, Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou, Peopleʼs Republic of China
,
Hao Gao
1   Institute of Traditional Chinese Medicine & Natural Products, Jinan University, Guangzhou, Peopleʼs Republic of China
,
Qin-Chang Zhu
2   State Key Laboratory for Respiratory Disease, Laboratory of Viral Immunology, Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou, Peopleʼs Republic of China
,
Chuan-Jian Lu
3   The second clinical college of Guangzhou university of Chinese medicine, Guangzhou, Peopleʼs Republic of China
,
Hong-Ling Wu
2   State Key Laboratory for Respiratory Disease, Laboratory of Viral Immunology, Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou, Peopleʼs Republic of China
,
Tao Peng
2   State Key Laboratory for Respiratory Disease, Laboratory of Viral Immunology, Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou, Peopleʼs Republic of China
,
Xin-Sheng Yao
1   Institute of Traditional Chinese Medicine & Natural Products, Jinan University, Guangzhou, Peopleʼs Republic of China
› Author Affiliations
Further Information

Publication History

received 14 May 2013
revised 23 September 2013

accepted 13 October 2013

Publication Date:
28 November 2013 (online)

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Abstract

This paper reports the phytochemical investigation of the 50 % aq. EtOH extract of Houttuynia cordata, an effective TCM and functional food in China, which led to the isolation of 17 flavonoids including four new ones. The four new compounds were flavonoid derivatives tethered with houttuynin (3-oxododecanal). Each of the new compounds was obtained as a pair of inseparable diasteriomeric epimers due to the chiral carbon of hemiketal at C-3″. This phenomenon is rooted in the ring-chain tautomerism of the hemiketal functional group in solution, which was proved by dynamic NMR experiments. The new compounds 1–4 displayed inhibitory activities against herpes simplex virus 1, with respective IC50 values of 38.46, 14.10, 62.00 and 70.76 µM, which was associated with the medicinal functions of H. cordata.

Key words

Houttuynia cordata - Saururaceae - flavonoids - HSV-1 - diasteriomeric epimers

Supporting Information

 

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