First total synthesis of prasinic acid and its anticancer activity

Chakor, Narayan S.; Patil, Ganapathi; Writer, Diana; Periyasamy, Giridharan; Sharma, Rajiv; Roychowdhury, Abhijit; Prabhu, K. Narayan

doi:10.1016/j.bmcl.2012.08.116

Cited by 3 publications

(3 citation statements)

References 7 publications

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“…To our knowledge, biological activity of prasinic acid has not been previously described in the literature, and its antibacterial activity against S. aureus is presented here for the first time. A demethoxylated derivative of prasinic acid was found to exhibit moderate antitumor activity against different cancer cell lines [28]. Our results showed that the antibacterial activity of C. incrassata acetone extract against S. aureus can be attributed to the combined activities of the different compounds described above.…”

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confidence: 55%

Uncommon Chlorinated Xanthone and Other Antibacterial Compounds from the Lichen Cladonia incrassata

et al. 2014

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Bioassay-guided fractionation of an extract of the lichen Cladonia incrassata against Staphylococcus aureus led to a novel compound, 1,5-dihydroxy-2,4,6-trichloro-7-methylxanthone (1), along with six known compounds: (-)-usnic acid (2), didymic acid (3), condidymic acid (4), squamatic acid (5), thamnolic acid (6), and prasinic acid (7). Didymic, condidymic, and prasinic acids were isolated for the first time from C. incrassata. Didymic, condidymic, and (-)-usnic acids were active against S. aureus (a minimum inhibitory concentration of 7.5 µg/mL).

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confidence: 55%

Uncommon Chlorinated Xanthone and Other Antibacterial Compounds from the Lichen Cladonia incrassata

et al. 2014

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“…In the case of 1 , a third biosynthetic unit is also incorporated. Other fungal depsides containing alkyl side-chains have reportedly exhibited anti-inflammatory , and antitumor activities . Depsides are most commonly found in lichens and plants, although their production by nonlichenized ascomycetes has been reported occasionally.…”

Section: Resultsmentioning

confidence: 99%

“…Other fungal depsides containing alkyl sidechains have reportedly exhibited anti-inflammatory 20,21 and antitumor activities. 22 Depsides are most commonly found in lichens and plants, although their production by nonlichenized ascomycetes has been reported occasionally. The presence of a sugar substituent is uncommon in depsides, but glucose, galactose, and glucuronic acid derivatives are found in metabolites such as TPI-1 to TPI-5, 23 exophilic acid, 24 aquastatin, 25 CRM646-A/B, 26 and KS-501/KS-502.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Arenicolins: C-Glycosylated Depsides from Penicillium arenicola

Perlatti

Earp

et al. 2020

J. Nat. Prod.

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During investigation of the secondary metabolism of four strains of Penicillium arenicola, two new depsides, arenicolins A (1) and B (2), were isolated and characterized. Their structures were established mainly by analysis of NMR and HRMS data and by comparison with known compounds. These depsides incorporate intriguing structural features, including dual alkyl side chains and a C-glycosyl unit, with 1 also containing an acylated 2-hydroxymethyl-4,5,6-trihydroxycyclohexenone moiety. Although the arenicolins were produced by all strains tested, arenicolin A (1) was obtained using only one of five medium compositions employed, while arenicolin B (2) was produced in all media tested. Neither compound showed antibacterial or antifungal activity, but 1 exhibited cytotoxicity toward mammalian cell lines, including colorectal carcinoma (HCT-116), neuroblastoma (IMR-32), and ductal carcinoma (BT-474), with IC 50 values of 7.3, 6.0, and 9.7 μM, respectively.

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ChemInform Abstract: First Total Synthesis of Prasinic Acid and Its Anticancer Activity.

et al. 2013

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First Total Synthesis of Prasinic Acid and Its Anticancer Activity. -A ten-step synthesis of prasinic acid (I) starting from readily available and cheap materials is presented. Compound (I) shows moderate antitumor activity in different cancer cell lines. -(CHAKOR, N.; PATIL, G.; WRITER, D.; PERIYASAMY, G.; SHARMA, R.; ROYCHOWDHURY, A.; MISHRA*, P. D.; Bioorg. Med. Chem. Lett. 22 (2012) 21, 6608-6610, http://dx.

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First total synthesis of prasinic acid and its anticancer activity

Cited by 3 publications

References 7 publications

Uncommon Chlorinated Xanthone and Other Antibacterial Compounds from the Lichen Cladonia incrassata

Uncommon Chlorinated Xanthone and Other Antibacterial Compounds from the Lichen Cladonia incrassata

Arenicolins: C-Glycosylated Depsides from Penicillium arenicola

ChemInform Abstract: First Total Synthesis of Prasinic Acid and Its Anticancer Activity.

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