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Determine the structure of phosphorylated modification of icariin and its antiviral activity against duck hepatitis virus A.

Xiong W, Ma X, Wu Y, Chen Y, Zeng L, Liu J, Sun W, Wang D, Hu Y - BMC Vet. Res. (2015)

Bottom Line: Anti-DHAV activities of 1 and 2 were compared in duck embryonic hepatocytes (DEHs) cultured in vitro and by artificial infection method in vivo.The compound 2's chemical structure was defined as 8-prenylkaempferol-4'-methylether-3-rhamnosyl-7-(6'''-phosphate)-glycoside. 1 and 2 exhibited anti-virus activity on DHAV.Our results suggest that 1 and 2 might become an anti-virus plant material candidate.

View Article: PubMed Central - PubMed

Affiliation: Institute of Traditional Chinese Veterinary Medicine, College of Veterinary Medicine, Nanjing Agricultural University, Nanjing, 210095, People's Republic of China. pansquito@hotmail.com.

ABSTRACT

Background: Our previous research showed that icariin (1) and its phosphorylated structural modification (2) improved the survival and attenuated oxidative stress and liver dysfunction induced by duck virus hepatitis. In this paper, we were one step closer to determine the structure of phosphorylation icariin (2) by the FT-IR, HRESIMS and (13)C NMR. Anti-DHAV activities of 1 and 2 were compared in duck embryonic hepatocytes (DEHs) cultured in vitro and by artificial infection method in vivo. Additionally, the antiviral mechanisms of replication/release in vitro and the DHAV gene expression in vivo of 1 and 2 were analyzed.

Results: Compound 2's molecular formula was C33H42O18P. The results indicated that 1 and 2 effectively resisted DHAV invading DEHs, that they decreased the mortality of ducklings challenged with DHAV, and that 2 performed more effectively. 1 and 2 performed evenly on DHAV release; however, 2 restrained virus replication far more effectively. Since the anti-DHAV mechanisms of 1 and 2 in vitro probably involve suppression of replication and release, 2's better performance in anti-DHAV may result from its far more effectively inhibiting virus replication.

Conclusions: The compound 2's chemical structure was defined as 8-prenylkaempferol-4'-methylether-3-rhamnosyl-7-(6'''-phosphate)-glycoside. 1 and 2 exhibited anti-virus activity on DHAV. Our results suggest that 1 and 2 might become an anti-virus plant material candidate.

No MeSH data available.


Related in: MedlinePlus

Structure of icariin (1) and 6'''-phosphate icariin (2)
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Fig1: Structure of icariin (1) and 6'''-phosphate icariin (2)

Mentions: Molecular modification of flavonoids and polysaccharide became an important research field along with the increasing pursuit about manifold biological activities of modified. Many studies confirmed that the biological activities of the Chinese herbal ingredients could be improved by the chemical method (sulfated, phosphated, selenylation). In our previous published work, we found that the compound 1 and phosphorylated icariin (C33H42O18P, 2, Fig. 1) could alleviate the oxidative stress and liver injury in ducklings caused by DHAV. These outcomes were better in ducklings treated with 2 than in those treated by 1. In clinical trials, compared with 1, 2 could significantly improve survival rate [13]. This is the most important to the meaning of the actual production application. So we believe that this novel structure resulted in the difference. But between the 1 and 2, their antioxidant effect was similar. It’s suggested that there may be another resistance mechanisms to anti-DHAV infection. To further study its resistance mechanism, we hold the opinion that it is essential to confirm the structure of 2 and study the effect of drug for viral multiplication process. Above on, we determined the chemical structure of 2 by the FT-IR, HRESIMS and 13C NMR and the compound 1 and compound 2 antiviral efficacies against DHAV in vivo and in vitro were investigated.Fig. 1


Determine the structure of phosphorylated modification of icariin and its antiviral activity against duck hepatitis virus A.

Xiong W, Ma X, Wu Y, Chen Y, Zeng L, Liu J, Sun W, Wang D, Hu Y - BMC Vet. Res. (2015)

Structure of icariin (1) and 6'''-phosphate icariin (2)
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC4536795&req=5

Fig1: Structure of icariin (1) and 6'''-phosphate icariin (2)
Mentions: Molecular modification of flavonoids and polysaccharide became an important research field along with the increasing pursuit about manifold biological activities of modified. Many studies confirmed that the biological activities of the Chinese herbal ingredients could be improved by the chemical method (sulfated, phosphated, selenylation). In our previous published work, we found that the compound 1 and phosphorylated icariin (C33H42O18P, 2, Fig. 1) could alleviate the oxidative stress and liver injury in ducklings caused by DHAV. These outcomes were better in ducklings treated with 2 than in those treated by 1. In clinical trials, compared with 1, 2 could significantly improve survival rate [13]. This is the most important to the meaning of the actual production application. So we believe that this novel structure resulted in the difference. But between the 1 and 2, their antioxidant effect was similar. It’s suggested that there may be another resistance mechanisms to anti-DHAV infection. To further study its resistance mechanism, we hold the opinion that it is essential to confirm the structure of 2 and study the effect of drug for viral multiplication process. Above on, we determined the chemical structure of 2 by the FT-IR, HRESIMS and 13C NMR and the compound 1 and compound 2 antiviral efficacies against DHAV in vivo and in vitro were investigated.Fig. 1

Bottom Line: Anti-DHAV activities of 1 and 2 were compared in duck embryonic hepatocytes (DEHs) cultured in vitro and by artificial infection method in vivo.The compound 2's chemical structure was defined as 8-prenylkaempferol-4'-methylether-3-rhamnosyl-7-(6'''-phosphate)-glycoside. 1 and 2 exhibited anti-virus activity on DHAV.Our results suggest that 1 and 2 might become an anti-virus plant material candidate.

View Article: PubMed Central - PubMed

Affiliation: Institute of Traditional Chinese Veterinary Medicine, College of Veterinary Medicine, Nanjing Agricultural University, Nanjing, 210095, People's Republic of China. pansquito@hotmail.com.

ABSTRACT

Background: Our previous research showed that icariin (1) and its phosphorylated structural modification (2) improved the survival and attenuated oxidative stress and liver dysfunction induced by duck virus hepatitis. In this paper, we were one step closer to determine the structure of phosphorylation icariin (2) by the FT-IR, HRESIMS and (13)C NMR. Anti-DHAV activities of 1 and 2 were compared in duck embryonic hepatocytes (DEHs) cultured in vitro and by artificial infection method in vivo. Additionally, the antiviral mechanisms of replication/release in vitro and the DHAV gene expression in vivo of 1 and 2 were analyzed.

Results: Compound 2's molecular formula was C33H42O18P. The results indicated that 1 and 2 effectively resisted DHAV invading DEHs, that they decreased the mortality of ducklings challenged with DHAV, and that 2 performed more effectively. 1 and 2 performed evenly on DHAV release; however, 2 restrained virus replication far more effectively. Since the anti-DHAV mechanisms of 1 and 2 in vitro probably involve suppression of replication and release, 2's better performance in anti-DHAV may result from its far more effectively inhibiting virus replication.

Conclusions: The compound 2's chemical structure was defined as 8-prenylkaempferol-4'-methylether-3-rhamnosyl-7-(6'''-phosphate)-glycoside. 1 and 2 exhibited anti-virus activity on DHAV. Our results suggest that 1 and 2 might become an anti-virus plant material candidate.

No MeSH data available.


Related in: MedlinePlus