35154-55-3

Usage

Uses

Used in Pharmaceutical Industry:
Natsudaidain is used as a potential therapeutic agent for its antioxidant and anti-inflammatory properties, which may help reduce oxidative stress, inflammation, and age-related cognitive decline.
Used in Cardiovascular Disease Prevention:
Natsudaidain is used as a protective agent against cardiovascular diseases due to its potential to reduce inflammation and oxidative stress, which are risk factors for these conditions.
Used in Cancer Prevention and Treatment:
Natsudaidain is used as a potential chemopreventive and therapeutic agent in cancer research, as it has shown promise in protecting against cancer development and progression.
Used in Neurodegenerative Disorder Prevention:
Natsudaidain is used as a potential protective agent against neurodegenerative disorders, such as Alzheimer's and Parkinson's diseases, due to its potential to reduce oxidative stress and inflammation in the brain.

InChI:InChI=1/C21H22O9/c1-24-11-8-7-10(9-12(11)25-2)16-15(23)14(22)13-17(26-3)19(27-4)21(29-6)20(28-5)18(13)30-16/h7-9,23H,1-6H3

Upstream product

• 478-01-3 nobiletin 
• 114021-60-2 2'-hydroxy-3,4,4',6'-tetramethoxychalcone 
• 76650-20-9 1-(2,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone 
• 2306-27-6 sinensetin 
• 21763-80-4 5-desmethylsinensetin 
• 683278-67-3 5,8-dihydroxy-6,7-dimethoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 520-27-4 diosmin 
• 10544-05-5 2-(3,4-dimethoxy-phenyl)-7-hydroxy-5-methoxy-chromen-4-one 

Downstream Products

• 1178-24-1 3,3',4',5,6,7,8-heptamethoxyflavone 
• 1176-88-1 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone 

Relevant academic research and scientific papers

Studies on the differentiation inducers of myeloid leukemic cells from Citrus species

An attempt was made to isolate differentiation inducers from Aurantii Nobilis Pericarpium and the fruit peel of Citrus reticulata Blanco (Rutaceae). Twenty-seven kinds of flavones, including five new flavones, were isolated after repeated chromatography from methanol extracts of these plants and their structures were established, from their physicochemical data, to be highly methoxylated flavones. Each compound, except for two flavone glucosides, showed the differentiation inducing activity toward mouse myeloid leukemia cells (M1), and the cells came to have phagocytic activity. Furthermore, differentiation inducing activity was tested using human acute promyelocytic leukemia cell line (HL-60).

Synthesis of Citrus polymethoxyflavonoids and their antiproliferative activities on Hela cells

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.].

Semisynthesis of polymethoxyflavonoids from naringin and hesperidin

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.

Isolation and syntheses of polymethoxyflavones and hydroxylated polymethoxyflavones as inhibitors of HL-60 cell lines

Fifteen polymethoxyflavones (PMFs) and hydroxylated PMFs were isolated from sweet orange (Citrus sinensis) peel extract and synthesized to investigate their biological activity. All obtained compounds were tested in HL-60 cancer cell proliferation and apoptosis induction assays. While some PMFs and hydroxylated PMFs had moderate anti-carcinogenic activities, 5-hydroxy-6,7,8,3′,4′-pentamethoxyflavone and 5-hydroxy-3,6,7,8,3′,4′-hexamethoxyflavone showed strong inhibitory activities against the proliferation and induced apoptosis of HL-60 cell lines.

Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids

The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3′,4′,5,6,7,8- heptamethoxyflavone, quercetin and its derivatives were synthesized.