Flindulatin

Flindulatin

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Flindulatin
Category Others
Catalog number BBF-05426
CAS 521-44-8
Molecular Weight 358.34
Molecular Formula C19H18O7
Purity 98%

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Specification

Synonyms 5-Hydroxy-3,4',7,8-tetramethoxy-flavone; 5-hydroxy-3,7,8-trimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one; NSC 678105; 3,7,8,4'-Tetramethylherbacetin
IUPAC Name 5-hydroxy-3,7,8-trimethoxy-2-(4-methoxyphenyl)chromen-4-one
Canonical SMILES COC1=CC=C(C=C1)C2=C(C(=O)C3=C(O2)C(=C(C=C3O)OC)OC)OC
InChI InChI=1S/C19H18O7/c1-22-11-7-5-10(6-8-11)16-19(25-4)15(21)14-12(20)9-13(23-2)17(24-3)18(14)26-16/h5-9,20H,1-4H3
InChI Key SQOMVBRIXCJFKW-UHFFFAOYSA-N

Properties

Boiling Point 590.8±50.0°C at 760 mmHg
Density 1.4±0.1 g/cm3

Reference Reading

1. Antifungal Quinoline Alkaloids from Waltheria indica
Sylvian Cretton, Stéphane Dorsaz, Antonio Azzollini, Quentin Favre-Godal, Laurence Marcourt, Samad Nejad Ebrahimi, Francine Voinesco, Emilie Michellod, Dominique Sanglard, Katia Gindro, Jean-Luc Wolfender, Muriel Cuendet, Philippe Christen J Nat Prod. 2016 Feb 26;79(2):300-7. doi: 10.1021/acs.jnatprod.5b00896. Epub 2016 Feb 5.
Chemical investigation of a dichloromethane extract of the aerial parts of Waltheria indica led to the isolation and characterization of five polyhydroxymethoxyflavonoids, namely, oxyanin A (1), vitexicarpin (3), chrysosplenol E (4), flindulatin (5), 5-hydroxy-3,7,4'-trimethoxyflavone (6), and six quinolone alkaloids, waltheriones M-Q (2, 7, 8, 10, 11) and 5(R)-vanessine (9). Among these, compounds 2, 7, 8, 10, and 11 have not yet been described in the literature. Their chemical structures were established by means of spectroscopic data interpretation including (1)H and (13)C, HSQC, HMBC, COSY, and NOESY NMR experiments and UV, IR, and HRESIMS. The absolute configurations of the compounds were established by ECD. The isolated constituents and 10 additional quinoline alkaloids previously isolated from the roots of the plant were evaluated for their in vitro antifungal activity against the human fungal pathogen Candida albicans, and 10 compounds (7, 9, 11-16, 18, 21) showed growth inhibitory activity on both planktonic cells and biofilms (MIC ≤ 32 μg/mL). Their spectrum of activity against other pathogenic Candida species and their cytotoxicity against human HeLa cells were also determined. In addition, the cytological effect of the antifungal isolated compounds on the ultrastructure of C. albicans was evaluated by transmission electron microscopy.

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