Chemodiversity of Exudate Flavonoids in Cassinia and Ozothamnus (Asteraceae, Gnaphalieae)

Wollenweber, Eckhard; Fischer, Ralf; Dörr, Marion; Irvine, Kathryn M.; Pereira, Cliff; Stevens, Jan F.

doi:10.1515/znc-2008-9-1019

Cited by 8 publications

(4 citation statements)

References 15 publications

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“…These data, together with ESI-MS/MS and correlations observed in the HSQC and HMBC spectra, are consistent with the structure of the title compound (cf. the figure) confirmed by comparison of spectroscopic data with those reported in the literature for this structure [19,20] and other similar methoxilated flavones [21][22][23].…”

Section: Source Of Materialssupporting

confidence: 84%

Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C₁₉H₁₈O₈

Brito

Bórquez

Simirgiotis

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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C 19 H 18 O 8 , monoclinic, P2 1 /c (no. 14), a = 12.689(2) Å, b = 20.321(4) Å, c = 7.0820(13) Å, β = 105.368(13)°, V = 1760.8(6) Å 3 , Z = 4, R gt = 0.0662, wR ref (F 2 ) = 0.1788, T = 295 K. CCDC no.: 1581467The title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement con- ditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialThe title compound is a highly biologically active polymethoxylated flavonoid, which is anti-inflammatory and antiproliferative [1, 2], can inhibit leukocyte chemotaxis and oxygen free radical formation [3,4] and prevents cyclophosphamide and ifosfamide-induced hemorrhagic cystitis in rats [5]. The title compound was isolated using medium pressure column chromatography (MPCC) from Parastrephia quadrangularis, a medicinal plant used by the Aymara Amerindians [6,7], a known producer of several flavonoids and benzoic acid derivatives with antioxidant activity [8][9][10][11]. Following our program to isolate interesting metabolites from the Atacama Desert Flora, Northern Chile [12][13][14][15][16][17][18], dried aerial parts of P. quadrangularis (1622 g) collected in april 2015 in "El Tatio", Andean mountain range of the of Atacama Desert, II Region, Northern Chile, were defatted with hexane (3 liters, 3 times in the dark, 24 hours each time) and 54.82 g were obtained after evaporation of the solvent. Then the plant material was extracted with ethyl acetate (3 liters, 3 times in the dark, 24 hours each time. After evaporation of the solvent under vacuo at 40 o C, 485 g of a dark gummy extract was obtained. A portion of the extract (10.0 g) was filtered and submitted to a medium pressure column chromatography system composed of an 2.5 cm × 48 cm medium pressure column packed with silicagel using an isocratic solvent system of

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Section: Source Of Materialssupporting

confidence: 84%

Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C₁₉H₁₈O₈

Brito

Bórquez

Simirgiotis

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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“…The side reaction, observed in this case mainly at C-8, is well known with aryl halogens ortho to a methoxy group. 23 The natural flavones 1, 3,4 10, 16,24 and 11 [25][26][27] were identified unambiguously by comparison of their melting points and spectroscopic characteristics with literature values. Formation of the last two flavones, 12 and 13, was rather unexpected.…”

Section: Resultsmentioning

confidence: 99%

Semisynthesis of Natural Flavones Inhibiting Tubulin Polymerization, from Hesperidin

et al. 2010

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Semisynthesis of 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone (1), a natural flavone that binds with high affinity to tubulin, was performed from hesperidin, the very abundant Citrus flavanone, by a five-step sequence. The last step of the synthesis also gave rise to 5,3'-dihydroxy-3,6,7,4'-tetramethoxyflavone (= casticin or vitexicarpin) (10), 5,3'-dihydroxy-3,7,8,4'-tetramethoxyflavone (= gossypetin 3,7,8,4'-tetramethyl ether) (11), and, unexpectedly, 5,7,3'-trihydroxy-3,6,8,4'-tetramethoxyflavone (12) and 5,3'-dihydroxy-8-dimethylamino-3,6,7,4'-tetramethoxyflavone (= 8-dimethylaminocasticin) (13). Cytotoxicity and antitubulin activity of these five flavones, as well as 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (= ayanin) (14) and intermediate 6,8-dibromo-ayanin (8), were evaluated. Comparison of the responses confirmed and clarified the influence of the A-ring substitution pattern on the biological activity.

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“…The individual EtOAc extracts of the roots and fruit of M. integerrimum were separated by various chromatographic techniques to obtain a new compound (1) together with 23 known compounds (2-24), 6-(3-methyl-2-oxobutyroyl)-7-methoxycoumarin (2) (Li et al 2016), phebalosin (3) (Ito et al 1987), murralongin (4) (Talapatra et al 1973), osthenon (5) (Ito et al 1987), microminutin (6) (Suthiwong et al 2014), minutuminolate (7) (Lekphrom et al 2016), murrangatin acetate (8) (Ito et al 1987), (-)-murrangatin (9) (Ito et al 1990), 2′-Oethylmurrangatin (10) (Choudhary et al 2002), minumicrolin (11) (Ito et al 1990), hopeyhopin (12) (Dominguez et al 1977), dehydrogeijerin (13) (Dominguez et al 1977), isoscopoletin (14) (Shafizadeh et al 1970), scopoletin (15) (Cassady et al 1979), citropten (16) (Gray et al 1978), micromelin (17) (Cassady et al 1979), dihydromicromelin B (18) (Das et al 1994), acetyldihydromicromelin A (19) (Das et al 1994), flindulatin (20) (Collins et al 2004), gossypetin 3,7,8,4′-tetramethylether (21) (Wollenber et al 2008), 5,7-dihydroxy-3,4′,6,8-tetramethoxyflavone (22) (Silva et al 2005), 5,7-dihydroxy-3,8,4′-trimethoxyflavone (23) (Tandon et al 1977) and acerosin (24) (Greenham et al 2001).…”

Section: Resultsmentioning

confidence: 99%

Coumarins and flavones from the fruit and root extracts of Micromelum integerrimum

Suthiphasilp

Maneerat

Andersen

et al. 2018

Natural Product Research

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A phytochemical investigation of the fruit and root extracts of Micromelum integerrimum resulted in the isolation and identification of a new compound, integerravone (1), together with 23 known compounds (2-24). Their structures were characterized by spectroscopic methods as well as comparisons made from the literature. Compounds 2, 3-15, 17-18 and 20-23 were evaluated for their cytotoxicities against the colon cancer cell line, HCT116. All of them were inactive at 50 µM. Most of the phenolic compounds were evaluated for their antioxidant activity using the DPPH assay. Compounds 14 and 22-24 showed antioxidant activity with IC50 values ranging from 24.83-135.05 µM.

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Chemodiversity of Exudate Flavonoids in Cassinia and Ozothamnus (Asteraceae, Gnaphalieae)

Cited by 8 publications

References 15 publications

Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C₁₉H₁₈O₈

Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C₁₉H₁₈O₈

Semisynthesis of Natural Flavones Inhibiting Tubulin Polymerization, from Hesperidin

Coumarins and flavones from the fruit and root extracts of Micromelum integerrimum

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Chemodiversity of Exudate Flavonoids in Cassinia and Ozothamnus (Asteraceae, Gnaphalieae)

Cited by 8 publications

References 15 publications

Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C19H18O8

Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C19H18O8

Semisynthesis of Natural Flavones Inhibiting Tubulin Polymerization, from Hesperidin

Coumarins and flavones from the fruit and root extracts of Micromelum integerrimum

Contact Info

Product

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Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C₁₉H₁₈O₈

Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C₁₉H₁₈O₈