30021-77-3Relevant academic research and scientific papers
Synthesis and Bioevaluation of Diphyllin Glycosides as Novel Anticancer Agents
Zhao, Yu,Ni, Chunyan,Zhang, Yuting,Zhu, Li
, p. 622 - 628 (2012)
A series of diphyllin glycosides were synthesized from diphyllin by phase transfer catalysis glycosylation, deprotection, and etherification, and the structures were established by 1H NMR, 13C NMR, and HRMS. These glycosides were evaluated for their in vitro cytotoxicity against HCT-116, A549, and A549T cancer cell lines by MTT assay, and most of them were cytotoxic at submicromolar concentrations. They were also effective against the paclitaxel-resistant cell line A549T. The kDNA decatenation assay indicated that most of these compounds inhibited topoisomerase IIα-mediated kDNA decatenation. In addition, the in vitro tubulin polymerization study showed that compounds 5 and 6 had antimicrotubule activity with a paclitaxel-like mode of action. Taken together, these results suggest that these diphyllin glycosides act on both TopoII and tubulin. Copyright
Patentiflorin A Analogs as Antiviral Agents
-
Paragraph 0111; 0357; 0362; 0369, (2021/03/05)
The present disclosure relates to patentiflorin A analogs that are useful as antivirals, such as anti-HIV, anti-coronaviral, anti-Ebola viral, and anti-influenza viral agents and methods of use thereof.
Synthesis and antiproliferative activity of derivatives of the phyllanthusmin class of arylnaphthalene lignan lactones
Woodard, John L.,Huntsman, Andrew C.,Patel, Pratiq A.,Chai, Hee-Byung,Kanagasabai, Ragu,Karmahapatra, Soumendrakrishna,Young, Alexandria N.,Ren, Yulin,Cole, Malcolm S.,Herrera, Denisse,Yalowich, Jack C.,Kinghorn, A. Douglas,Burdette, Joanna E.,Fuchs, James R.
, p. 2354 - 2364 (2018/04/16)
A series of arylnaphthalene lignan lactones based on the structure of the phyllanthusmins, a class of potent natural products possessing diphyllin as the aglycone, has been synthesized and screened for activity against multiple cancer cell lines. SAR exploration was performed on both the carbohydrate and lactone moieties of this structural class. These studies have revealed the importance of functionalization of the carbohydrate hydroxy groups with both acetylated and methylated analogues showing increased potency relative to those with unsubstituted sugar moieties. In addition, the requirement for the presence and position of the C-ring lactone has been demonstrated through reduction and selective re-oxidation of the lactone ring. The most potent compound in this study displayed an IC50 value of 18 nM in an HT-29 assay with several others ranging from 50 to 200 nM. In an effort to elucidate their potential mechanism(s) of action, the DNA topoisomerase IIa inhibitory activity of the most potent compounds was examined based on previous reports of structurally similar compounds, but does not appear to contribute significantly to their antiproliferative effects.
Potent Inhibitor of Drug-Resistant HIV-1 Strains Identified from the Medicinal Plant Justicia gendarussa
Zhang, Hong-Jie,Rumschlag-Booms, Emily,Guan, Yi-Fu,Wang, Dong-Ying,Liu, Kang-Lun,Li, Wan-Fei,Nguyen, Van H.,Cuong, Nguyen M.,Soejarto, Djaja D.,Fong, Harry H. S.,Rong, Lijun
, p. 1798 - 1807 (2017/06/28)
Justicia gendarussa, a medicinal plant collected in Vietnam, was identified as a potent anti-HIV-1 active lead from the evaluation of over 4500 plant extracts. Bioassay-guided separation of the extracts of the stems and roots of this plant led to the isolation of an anti-HIV arylnaphthalene lignan (ANL) glycoside, patentiflorin A (1). Evaluation of the compound against both the M-and T-Tropic HIV-1 isolates showed it to possess a significantly higher inhibition effect than the clinically used anti-HIV drug AZT. Patentiflorin A and two congeners were synthesized, de novo, as an efficient strategy for resupply as well as for further structural modification of the anti-HIV ANL glycosides in the search for drug leads. Subsequently, it was determined that the presence of a quinovopyranosyloxy group in the structure is likely essential to retain the high degree of anti-HIV activity of this type of compounds. Patentiflorin A was further investigated against the HIV-1 gene expression of the R/U5 and U5/gag transcripts, and the data showed that the compound acts as a potential inhibitor of HIV-1 reverse transcription. Importantly, the compound displayed potent inhibitory activity against drug-resistant HIV-1 isolates of both the nucleotide analogue (AZT) and non-nucleotide analogue (nevaripine). Thus, the ANL glycosides have the potential to be developed as novel anti-HIV drugs.
Design, synthesis and biological evaluation of novel glycosylated diphyllin derivatives as topoisomerase II inhibitors
Shi, Da-Kuo,Zhang, Wei,Ding, Ning,Li, Ming,Li, Ying-Xia
, p. 424 - 431 (2012/02/14)
Recently, a novel glycosylated diphyllin derivative 11 which exhibiting potent anticancer activity by targeting topoisomerase IIα was reported by our group. In order to provide more molecules for structure-activity relationship (SAR) studies, 12 new glyco
