34170-18-8Relevant academic research and scientific papers
Semisynthesis of polymethoxyflavonoids from naringin and hesperidin
Li, Yue,Cai, Shuanglian,He, Kailin,Wang, Qiuan
, p. 287 - 290 (2014)
Polymethoxyflavonoids (PMFs) possess important biological activities, notably as anticancer agents. Semisynthesis of a series of PMFs were performed by glycoside hydrolysis, dehydrogenation, bromination, aromatic nucleophilic substitution, O-methylation, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. A new synthetic method for selective methylation using CuBr catalysed and microwave-assisted reaction was developed, and the dimethyl dioxirane oxidation of flavones to flavonols was much improved. The new semisynthetic route has the advantages of easy availability of starting materials, simple operation and good yields.
Synthesis of Citrus polymethoxyflavonoids and their antiproliferative activities on Hela cells
Nguyen, Van-Son,Li, Wei,Li, Yue,Wang, Qiuan
, p. 1585 - 1592 (2017/06/05)
Abstract: A series of polymethoxyflavonoids (3–16) were synthesized through dehydrogenation, O-methylation, glycoside hydrolysis, bromination, microwave-assisted aromatic nucleophilic substitution, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. All the synthetic compounds were test for antiproliferative activities on human cervical carcinoma Hela cell line by the standard CCK-8 assay, the result showed that most of the target compounds exhibited moderate to potent antiproliferative activities on Hela cells comparable with the positive control cis-Platin. Among them, 5-hydroxypolymethoxy flavonoid 13 showed the strongest activity (IC50 0.791 μM). Graphical Abstract: [InlineMediaObject not available: see fulltext.].
Cytotoxic and anti-HIV-1 constituents of Gardenia obtusifolia and their modified compounds
Tuchinda, Patoomratana,Pompimon, Wilart,Reutrakul, Vichai,Pohmakotr, Manat,Yoosook, Chalobon,Kongyai, Natedao,Sophasan, Samaisukh,Sujarit, Kulawee,Upathum, Suchart E,Santisuk, Thawatchai
, p. 8073 - 8086 (2007/10/03)
5α-Cycloart-24-ene-3,23-dione (1), 5α-cycloart-24-ene-3,16,23-trione (2) and methyl 3,4-seco-cycloart-4(28),24-diene-29-hydroxy-23-oxo-3-oate (3), together with five known flavones 5,7,4′-trihydroxy-3,8-dimethoxyflavone (4), 5,7,4′-trihydroxy-3,8,3′-tri-methoxyflavone (5), 5,7,4′-trihydroxy-3,6,8-trimethoxyflavone (6), 5,4′-dihydroxy-3,6,7,8-tetramethoxyflavone (7) and 5,3′-dihydroxy-3,6,7,8,4′-pentamethoxyflavone (8) have been isolated from the leaves and twigs of Gardenia obtusifolia. The structures were assigned on the basis of spectroscopic methods. Compounds 3-8 and some of the modified compounds showed significant cytotoxic activities in several mammalian cell lines, especially 8 and its diacetate 21 which exhibited potent cytotoxicities (compound 8: P-388 0.05μg/mL, KB 0.09μg/mL, BCA-1 0.63μg/mL, Lu-1 0.09μg/mL, ASK 0.70μg/mL; its diacetate: P-388 0.27μg/mL, KB 0.06μg/mL, BCA-1 0.53μg/mL, Lu-1 0.49μg/mL). It was also found that 5, 8 and 21 showed antimitotic acitivity in the ASK assay. Compounds 2, 4, 6, 7 and some of the modified compounds displayed interesting anti-HIV activity in the syncytium assay, but were inactive or exhibited weak activity in the HIV-1 RT assay; while compound 3 was found to be active in the HIV-1 RT assay (99.9 % inhibition at 200μg/mL), but cytotoxic in the syncytium assay.
Studies of the selective O-alkylation and dealkylation of flavonoids. XIX. A convenient method for synthesizing 3,5,6,7,8-pentaoxygenated flavones
Horie,Kawamura,Yamamoto,Yamashita
, p. 2054 - 2063 (2007/10/03)
The methoxymethyl ethers of 6-hydroxy-5,7,8-trimethoxyflavones, which were derived from 2',5'dihydroxy-3',4',6'-trimethoxyacetophenone, were oxidized with dimethyldioxirane to give the corresponding 3-hydroxyflavones. Selective O-alkylation and dealkylation of the 3-hydroxyflavones were examined and a convenient method for synthesizing the following ten kinds of 3,5,6,7,8- pentaoxygenated flavones was established: 3-hydroxy-5,6,7,8- tetramethoxyflavones, 3,5-dihydroxy-6,7,8-trimethoxyflavones, 3,6-dihydroxy- 5,7,8-trimethoxyflavones, 3,5,6-trihydroxy-7,8-dimethoxyflavones, 3,5,6,7- tetrahydroxy-8-methoxyflavones, and their 3-methyl ethers. Furthermore, 3,5,8-trihydroxy-4',6,7-trimethoxyflavone, 3,8-dihydroxy-4',5,6,7- tetramethoxyflavone, and 5,8-dihydroxy-3,6,7-trimethoxyflavones were similarly synthesized and their spectral properties were examined. Additionally, the proposed structures of three natural flavones were revised.
