81446-30-2Relevant articles and documents
Biopreparation of an anti-inflammatory agent, diarctigenin, from arctiin isolated from Arctium lappa by Rhizoctonia solani AG-4
Kuo, Ping-Chung,Chen, Zi-Yu,Chen, Miao-Fan
, p. 6955 - 6958 (2013)
In the preliminary screening for the plant-derived pesticides against Rhizoctonia solani Kühn AG-4 (RS AG-4), the indicator compounds arctiin (1) and arctigenin (2) in methanol extracts of Arctium lappa L. were consumed and transformed to other compounds. Thus, in the present study RS AG-4 was used as a biocatalyst and the biotransformation of arctiin (1) was investigated. Conversion of arctiin (1) to arctigenin (2) was achieved by the enzymatic hydrolysis of sugar moiety. In addition, an anti-inflammatory lignan dimer reported from the Arctium species, diarctigenin (3) was afforded in good yields. The HPLC monitoring of the biotransformation process indicated the possible mechanism. It would be an excellent method to produce large scale of diarctigenin (3) for the successive medicinal examinations.
Discovery of stereospecific cytotoxicity of (8R,8′R)-trans-arctigenin against insect cells and structure-activity relationship on aromatic ring
Nishi, Kosuke,Nishimoto, Asuka,Nishiwaki, Hisashi,Sugahara, Takuya,Yamauchi, Satoshi
, (2020/04/29)
One of the arctigenin stereoisomers, (8R,8′R)-trans-form 1, showed stereospecific cytotoxicity against insect cells, Sf9 and NIAS-AeAl-2 cells. By the comparison with other stereoisomers, the most importance of the 8′R stereochemistry for the higher activities was clarified. On the other hand, the wider range of activity level among stereoisomers against cancer cells, HL-60, was not observed. The structure-activity relationship research using derivatives bearing (8R,8′R)-trans-form was performed to show the same level of activities of 3-iodo, 4-iodo, and 3,4-methylenedioxy derivatives 28, 29, and 36 as (8R,8′R)-trans-arctigenin 1. In the examination of thiono derivatives, 4-iodo thiono and 3,4-methylenedioxy thiono derivatives 66, 67 showed similar level of activities to that of (8R,8′R)-trans-arctigenin 1. The expression of ribosomal 28S rRNA gene of Sf9 cells was increased by (8R,8′R)-trans-arctigenin 1, whereas a degradation of DNA was not observed.
Identification and characterization of human UDP-glucuronosyltransferases responsible for the in-vitro glucuronidation of arctigenin
Xin, Hong,Xia, Yang-Liu,Hou, Jie,Wang, Ping,He, Wei,Yang, Ling,Ge, Guang-Bo,Xu, Wei
, p. 1673 - 1681 (2016/01/26)
Objectives This study aimed to characterize the glucuronidation pathway of arctigenin (AR) in human liver microsomes (HLM) and human intestine microsomes (HIM). Methods HLM and HIM incubation systems were employed to catalyse the formation of AR glucuronide. The glucuronidation activity of commercially recombinant UGT isoforms towards AR was screened. A combination of chemical inhibition assay and kinetic analysis was used to determine the UGT isoforms involved in the glucuronidation of AR in HLM and HIM. Key findings AR could be extensively metabolized to one mono-glucuronide in HLM and HIM. The mono-glucuronide was biosynthesized and characterized as 4′-O-glucuronide. UGT1A1, 1A3, 1A7, 1A8, 1A9, 1A10, 2B4, 2B7 and 2B17 participated in the formation of 4′-O-G, while UGT2B17 demonstrated the highest catalytic activity in this biotransformation. Both kinetic analysis and chemical inhibition assays demonstrated that UGT1A9, UGT2B7 and UGT2B17 played important roles in AR-4′-O-glucuronidation in HLM. Furthermore, HIM demonstrated moderate efficiency for AR-4′-O-glucuronidation, implying that AR may undergo a first-pass metabolism during the absorption process. Conclusion UGT1A9, UGT2B7 and UGT2B17 were the major isoforms responsible for the 4′-O-glucuronidation of AR in HLM, while UGT2B7 and UGT2B17 were the major contributors to this biotransformation in HIM.
