Isoapetalic acid - CAS 34366-34-2
Catalog number: 34366-34-2
Not Intended for Therapeutic Use. For research use only.
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Isoapetalic acid isolated from the leaves of Calophyllum brasiliense. It exhibit cytotoxic activities towards both cancer cell lines and both Gram-positive bacteria.
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(7S,βR)-7,8-Dihydro-5-hydroxy-2,2,7β,8α-tetramethyl-6-oxo-β-propyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-10-propanoic acid
cytotoxic activities
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1.Chromanones and dihydrocoumarins from Calophyllum blancoi.
Shen YC;Wang LT;Khalil AT;Kuo YH Chem Pharm Bull (Tokyo). 2004 Apr;52(4):402-5.
Chromatographic fractionation of the acetone extract of the seeds of Calophyllum blancoi yielded six pyranochromanone derivatives; apetalic acid (1), isoapetalic acid (2), apetalic acid methyl ester (3), apetalic acid 5-O-acetate (4), isoapetalic methyl ester (5), and isoapetalic acid 5-O-acetate (6). In addition, one new dihydrocoumarin derivative, isorecedensolide (7), was also isolated together with recedensolide (8). The structures of the isolated compounds were established through analysis of NMR spectral data including 2D techniques as well as other physical and spectroscopic methods. Compounds 3, 4, 5, 7, and 8 showed mild activity against KB (human oral epidermoid carcinoma) and Hela (human cervical epitheloid carcinoma) tumor cell lines.
2.Antimicrobial Assessment of Resins from Calophyllum Antillanum and Calophyllum Inophyllum.
Cuesta-Rubio O;Oubada A;Bello A;Maes L;Cos P;Monzote L Phytother Res. 2015 Dec;29(12):1991-4. doi: 10.1002/ptr.5506. Epub 2015 Oct 30.
The Calophyllum genus is well-known for its antimicrobial and cytotoxic activities, and therefore, we analyzed these biological activities for resins of Calophyllum antillanum and Calophyllum inophyllum growing in Cuba. C. antillanum resins showed a potent activity against Plasmodium falciparum (IC50  = 0.3 ± 0.1 µg/mL), while its cytotoxicity against MRC-5 cells was much lower (IC50  = 21.6 ± 1.1 µg/mL). In contrary, the resin of C. inophyllum showed an unspecific activity. The presence of apetalic acid, isoapetalic acid, calolongic acid, pinetoric acid I, pinetoric acid II, isocalolongic acid, pinetoric acid III, and isopinetoric acid III in C. antillanum resins was also confirmed. These results demonstrated for the first time the potential activity of C. antillanum resins against P. falciparum.
3.Antifungal chromans inhibiting the mitochondrial respiratory chain of pea seeds and new xanthones from Calophyllum caledonicum.
Hay AE;Guilet D;Morel C;Larcher G;Macherel D;Le Ray AM;Litaudon M;Richomme P Planta Med. 2003 Dec;69(12):1130-5.
Two new xanthones, caledonixanthone M 1 and caloxanthone L 2, and one new acid, caledonic acid 6 were isolated from the hexane-soluble extract of the stem bark of Calophyllum caledonicum. In the course of this phytochemical study, seven other known compounds - calothwaitesixanthone, calozeyloxanthone, allanxanthone, isoapetalic acid 3, calolongic acid 4, apetalic acid 5 and isocalolongic acid 7 - were isolated. Their antifungal activity against the growth of the human pathogenic fungus Aspergillus fumigatus was then investigated. The results indicated that the crude extract, calolongic acid 4 and isocalolongic acid 7 exhibited strong inhibitory effects with MIC (80) values of 8, 4, 2 microg/mL, respectively. Besides, calolongic acid 4, its lactone derivative 4a and isocalolongic acid 7 markedly reduced the respiration of pea seed mitochondria.
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CAS 34366-34-2 Isoapetalic acid

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