- A sulphated flavone glycoside from Livistona australis and its antioxidant and cytotoxic activity
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A new flavone glycoside tricin 7-O - glucopyranoside-2-sulphate sodium salt along with 14 known flavonoid compounds were isolated and identified from the aqueous methanol extract of Livistona australis leaves. Their structures were established on the basis of extensive NMR (1H, 13C, HSQC and H-H COSY) and ESIMS data. Antioxidant and cytotoxicity properties of the methanol extract of the leaves as well as the new compound were investigated.
- Kassem, Mona E.S.,Shoela, Soha,Marzouk, Mona M.,Sleem, Amany A.
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- A novel antimicrobial flavonoidic glycoside from the leaves of Alstonia macrophylla Wall ex A. DC (Apocynaceae)
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A new flavonoidic glycoside, tricin-4′-O-β-l-arabinoside (1) was isolated from the leaves of Alstonia macrophylla along with two known flavonoids, vitexin and myricetin-3′-rhamnoside-3-O-galactoside. Their structures were established by chemical and spectral evidences. The known compounds were reported for the first time from this plant. Moreover compound 1 was tested for antifungal and antibacterial activities.
- Parveen, Mehtab,Khanam, Zakia,Ali, Akhtar,Ahmad, Syed Mohmud
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- Characterization of a Flavonoid 3’/5’/7-O-Methyltransferase from Citrus reticulata and Evaluation of the in Vitro Cytotoxicity of Its Methylated Products
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O-methylation of flavonoids is an important modification reaction that occurs in plants. O-methylation contributes to the structural diversity of flavonoids, which have several biological and pharmacological functions. In this study, an O-methyltransferase gene (CrOMT2) was isolated from the fruit peel of Citrus reticulata, which encoding a multifunctional O-methyltransferase and could effectively catalyze the methylation of 3’-, 5’-, and 7-OH of flavonoids with vicinal hydroxyl substitutions. Substrate preference assays indicated that this recombinant enzyme favored polymethoxylated flavones (PMF)-type substrates in vitro, thereby providing biochemical evidence for the potential role of the enzyme in plants. Additionally, the cytotoxicity of the methylated products from the enzymatic catalytic reaction was evaluated in vitro using human gastric cell lines SGC-7901 and BGC-823. The results showed that the in vitro cytotoxicity of the flavonoids with the unsaturated C2-C3 bond was increased after being methylated at position 3’. These combined results provide biochemical insight regarding CrOMT2 in vitro and indicate the in vitro cytotoxicity of the products methylated by its catalytic reaction.
- Liu, Xiaojuan,Wang, Yue,Chen, Yezhi,Xu, Shuting,Gong, Qin,Zhao, Chenning,Cao, Jinping,Sun, Chongde
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- Flavonoid pattern inheritance in the allopolyploid Spartina anglica – Comparison with the parental species S. maritima and S. alterniflora
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The invasive species Spartina anglica arose in Europe by a cross between the Afro-European species S. maritima (native, paternal ancestor) and the introduced North American S. alterniflora (invasive, maternal ancestor). Aqueous methanolic extracts were prepared from plant tissue for chemotaxonomical comparison between the three species and determination of the phenolic pattern inheritance in S. anglica. A total of 20 phenolic compounds were detected in the aerial tissues of S. anglica and S. alterniflora, but only seven in S. maritima. They were isolated from their respective crude extracts, and their structures were determined according to spectroscopic data analysis and chemical evidence. They all belong to the flavonoid class, with 13 of them identified as C-glycoflavonoid and seven as O-glycoflavonoid. All these products were detected for the first time from S. anglica, fourteen of them for the first time from S. alterniflora, and three of them for the first time from S. maritima. The individual concentrations in the three species were determined by quantitative HPLC. The two parental species were found to differ markedly in their foliar phenolic fingerprint, whereas that of S. anglica showed a clear maternal dominance. Eight of the fourteen major compounds identified were of maternal origin among which, six were over-expressed, only three were from paternal origin but under-regulated, while two originated from the two parents. As far as we know, this work represents the first exhaustive report of the phenolic fingerprints of S. alterniflora and S. anglica and of the phenolic pattern inheritance in S. anglica. The similarity in the phenolic chemistry of the introduced and invasive S. alterniflora to its progeny could play a role in the physiological vigour and invasion success of S. anglica. This work provide a foundation for further studies, considering the reported biological activities of C-glycosidic flavonoids and tricin derivatives, and the lack of knowledge of the ecological chemistry of the genus Spartina.
- Grignon-Dubois, Micheline,De Montaudouin, Xavier,Rezzonico, Bernadette
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- Synthesis method of 5,7,4'-trihydroxy-3',5'-dimethoxyflavone
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The invention discloses a synthesis method of 5,7,4'-trihydroxy-3',5'-dimethoxyflavone (I), and belongs to the technical field of preparation methods of chemical medicinal intermediates. The synthesismethod comprises the following steps: with 1,3,5-trihydroxybenzene (II) and ethyl cyanoacetate as raw materials, performing a condensation reaction to obtain 2-(2-chloro-1-iminoethyl)benzene-1, 3, 5-triphenol (III), then hydrolyzing the (III) in dilute hydrochloric acid to obtain 2-chloro-1-(2,4,6-trihydroxyphenyl)ethanone (IV), and then cyclizing the IV with 3,5-dimethoxy-4-hydroxybenzaldehyde in the presence of alkali to obtain the 5,7,4'-trihydroxy-3',5'-dimethoxyflavone (I). The used raw materials are relatively cheap and easy to obtain, the method is easy and convenient to operate, the product yield is relatively high, and a relatively high industrialization value is achieved.
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Paragraph 0012; 0020-0036
(2019/10/01)
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- A new synthesis for acacetin, chrysoeriol, diosmetin, tricin and other hydroxylated flavones by modified Baker-Venkataraman transformation
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Baker-Venkataraman (BV) rearrangement is the method of choice for the synthesis of flavones. The major limitation of BV is that it requires extensive protections and deprotections of hydroxyl groups which make the process lengthy and cumbersome. In the present study, a three step efficient method has been developed using simple protecting groups and easily available starting materials. New syntheses for acacetin, chrysoeriol, diosmetin, tricin and other hydroxylated flavones are described.
- Pandurangan
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p. 225 - 229
(2014/05/20)
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- Increased bioavailability of tricin-amino acid derivatives via a prodrug approach
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Tricin (4′,5,7-trihydroxy-3′,5′-dimethoxyflavone) has demonstrated diverse biological activities. This compound has a high anti-human cytomegalovirus (HCMV) activity; however, its oral availability is low. To improve its bioavailability, we synthesized tricin-amino acid derivatives as prodrugs and investigated their cell permeability, stability in vitro, and oral availability in vivo. The results demonstrated that the tricin-alanine-glutamic acid conjugate exhibited enhanced permeability, stability in MDCK cells, and excellent bioavailability after oral administration in Crl:CD (SD) male rats. Tricin-alanine-glutamic acid conjugate is a potential new anti-HCMV drug.
- Ninomiya, Masayuki,Tanaka, Kaori,Tsuchida, Yuzo,Muto, Yoshinori,Koketsu, Mamoru,Watanabe, Kunitomo
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p. 1529 - 1536
(2011/05/12)
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- ANTI-VIRAL AGENT
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Provided is an antiviral agent with high antiviral activities and low side effects (cytotoxicity). Specifically provided is an antiviral agent comprising as an effective component at least one member selected from the group consisting of 5,7,4'-trihydroxy-3',5'-dimethoxyflavone, 3-hydroxypyridine, p-hydroxybenzaldehyde and vanillin.
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- Tricin from a Malagasy connaraceous plant with potent antihistaminic activity
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The bioassay-guided separation of a Malagasy plant, Agelaea pentagyna, led to the isolation of a flavonoid, tricin (1), with potent inhibitory activity toward exocytosis from antigen-stimulated rat leukemia basophils (RBL-2H3). The structure-activity relationships among structurally related natural and synthetic flavonoids are also discussed.
- Kuwabara, Hidenori,Mouri, Kyoko,Otsuka, Hideaki,Kasai, Ryoji,Yamasaki, Kazuo
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p. 1273 - 1275
(2007/10/03)
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- Isolation and identification of the probing stimulants in the rice plant for the white-back planthopper, Sogatella furcifera (Homoptera: Delphacidae)
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Adult females of the white-back planthopper, Sogatella furcifera, showed characteristic behavior of stylet sheath deposit on a parafilm membrane when fed on a 2% aqueous crude rice leaf and stem extract containing 15% sucrose. Subsequent bioassays revealed that the butanol-soluble fraction of the extract was highly active against the insects. When the butanol fraction was chromatographed on an ODS open column and eluted in sequence with a mixture of an increasing concentration of methanol in water, the 40 % methanol fraction was separated as the most active. A further bioassay of the HPLC components in the active fraction revealed that two major components (1 and 3) stimulated the high probing activity of the white-back planthopper only when they were combined. Of the active components, one component (3) was identified to be tricin 5-O-glucoside by spectroscopic analyses.
- Adjei-Afriyie, Francis,Kim, Chul-Sa,Takemura, Masami,Ishikawa, Masahiro,Horiike, Michio
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p. 443 - 446
(2007/10/03)
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- A Short and Facile Synthetic Route to Hydroxylated Flavones. New Syntheses of Apigenin, Tricin, and Luteolin
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Reaction of lithium polyanions generated from o-hydroxyacetophenones 3a-f with O-silyloxylated benzoates 2a-d gave 1-aryl-3-(2-hydroxyphenyl)-1,3-propanediones 4a-n, which on treatment with acetic acid containing 0.5percent H2SO4 at 95 - 100 deg C afforded hydroxylated flavones 5-18 in high yields (76 - 92percent).
- Nagarathnam, Dhanapalan,Cushman, Mark
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p. 4884 - 4887
(2007/10/02)
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