Preparation of C-23 esterified silybin derivatives and evaluation of their lipid peroxidation inhibitory and DNA protective properties

Wang, Feng; Huang, Kuang‐Hua; Yang, Leixiang; Gong, Jing‐Xu; Qiao-feng, Tao; Liu, Hai-Bo; Zhao, Yu; Zeng, Su; Wu, Xiumei; Stöckigt, Joachim

doi:10.1016/j.bmc.2009.07.023

Cited by 20 publications

(14 citation statements)

References 17 publications

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“…The cytotoxicities of S0 and its derivatives (S1 to S5) are shown in Fig. 2A; S0 and its derivatives did not show any significant cytotoxicity in MDCK cells at concentrations up to 400 M. Rather, all of them significantly elevated the viability of cells at concentrations ranging from 6.25 to 100 M. The estimated CC 50 was greater than 400 M. These results were similar to those in previous reports (32)(33)(34).…”

Section: Resultssupporting

confidence: 88%

Identification of 23-( S )-2-Amino-3-Phenylpropanoyl-Silybin as an Antiviral Agent for Influenza A Virus Infection In Vitro and In Vivo

Dai

et al. 2013

Antimicrob Agents Chemother

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It has been reported that autophagy is involved in the replication of many viruses. In this study, we screened 89 medicinal plants, using an assay based on the inhibition of the formation of the Atg12-Atg5/Atg16 heterotrimer, an important regulator of autophagy, and selected Silybum marianum L. for further study. An antiviral assay indicated that silybin (S0), the major active compound of S. marianum L., can inhibit influenza A virus (IAV) infection. We later synthesized 5 silybin derivatives (S1 through S5) and found that 23-(S)-2-amino-3-phenylpropanoyl-silybin (S3) had the best activity. When we compared the polarities of the substituent groups, we found that the hydrophobicity of the substituent groups was positively correlated with their activities. We further studied the mechanisms of action of these compounds and determined that S0 and S3 also inhibited both the formation of the Atg12-Atg5/Atg16 heterotrimer and the elevated autophagy induced by IAV infection. In addition, we found that S0 and S3 could inhibit several components induced by IAV infection, including oxidative stress, the activation of extracellular signal-regulated kinase (ERK)/p38 mitogen-activated protein kinase (MAPK) and IB kinase (IKK) pathways, and the expression of autophagic genes, especially Atg7 and Atg3. All of these components have been reported to be related to the formation of the Atg12-Atg5/Atg16 heterotrimer, which might validate our screening strategy. Finally, we demonstrated that S3 can significantly reduce influenza virus replication and the associated mortality in infected mice. In conclusion, we identified 23-(S)-2-amino-3-phenylpropanoyl-silybin as a promising inhibitor of IAV infection.

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Section: Resultssupporting

confidence: 88%

Identification of 23-( S )-2-Amino-3-Phenylpropanoyl-Silybin as an Antiviral Agent for Influenza A Virus Infection In Vitro and In Vivo

Dai

et al. 2013

Antimicrob Agents Chemother

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“…Because of the well-known biological properties of silibinin and the other compounds of the silymarin complex for protection of liver damage, and for preventing skin tumor promotion, these compounds have attracted efforts on their total synthesis (e.g., isosilybin) [ 6 ] and structural modification [ 5 , 7 – 9 ] to improve their water-solubility, bioavailability and biological activities. Recently, our group has developed a hybrid drug combining silibinin with tacrine (a potent acetylcholinesterase inhibitor for treatment of Alzheimer’s disease), which shows neuro- and hepatoprotective effects exceeding the cytoprotective effects of silibinin and effectively counteracts tacrine’s dose-dependent hepatotoxicity in vitro as well as in vivo [ 10 – 11 ].…”

Section: Introductionmentioning

confidence: 99%

Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

Huang¹,

Schramm

Heilmann

et al. 2016

Beilstein J. Org. Chem.

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SummaryVarious Mitsunobu conditions were investigated for a series of flavonolignans (silybin A, silybin B, isosilybin A, and silychristin A) to achieve either selective esterification in position C-23 or dehydration in a one-pot reaction yielding the biologically important enantiomers of hydnocarpin D, hydnocarpin and isohydnocarpin, respectively. This represents the only one-pot semi-synthetic method to access these flavonolignans in high yields.

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“…[53][54] Furthermore, we have described that the antioxidant capability of the natural products play an important role of many diseases including anti-tumor and anti-virus. [55][56][57] Meanwhile, the free radical scavenging ability is closely related to anti-inflammatory effect of the crude parts of TCM. [58][59] Phenolic compounds are also proved to demonstrate various kinds of biological activities, [60][61] it is obvious more detailed and comprehensive pharmacological mechanism studies of Nidus vespae still await further detailed research.…”

Section: Mechanism Of Action On Antitumor Activitymentioning

confidence: 99%

Research Progress on Nidus Vespae, a Traditional Chinese Medicine Derived From Insects

Wang¹,

Zhang²,

Gao³

et al. 2013

J Pharm Sci Innov.

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Nidus vespae is a drug derived from insects that is commonly used in traditional Chinese medicine (TCM). No systematic review has previously been made about this drug. This paper summarizes previous investigations about the 49 identified chemical constituents and clinical application of Nidus vespae, and explores its pharmacological mechanism of treating disease. Nidus vespae has been reported to be effective in the treatment of rheumatoid arthritis and psoriatic arthritis, intractable skin diseases, dental disease, rhinitis, respiratory disorders, cervical erosion etc. Nidus vespae can be used alone or in combination with other drugs and compounds for a wide range of clinical applications. The objective of this review is to provide a comprehensive reference for further development and utilization of Nidus vespae.

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Preparation of C-23 esterified silybin derivatives and evaluation of their lipid peroxidation inhibitory and DNA protective properties

Cited by 20 publications

References 17 publications

Identification of 23-( S )-2-Amino-3-Phenylpropanoyl-Silybin as an Antiviral Agent for Influenza A Virus Infection In Vitro and In Vivo

Identification of 23-( S )-2-Amino-3-Phenylpropanoyl-Silybin as an Antiviral Agent for Influenza A Virus Infection In Vitro and In Vivo

Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

Research Progress on Nidus Vespae, a Traditional Chinese Medicine Derived From Insects

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