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Turkish Journal of Chemistry

Author ORCID Identifier

DANIELLE BOGO: 0000-0003-0233-3047

ISABEL MÁXIMO C. ALCÂNTARA: 0000-0003-2036-6758

GLAUCIA BRAZ ALCANTARA: 0000-0003-2549-3000

ANA CAMILA MICHELETTI: 0000-0002-0797-6669

NELI HONDA: 0000-0001-9417-4885

MARIA DE FÁTIMA CEPA MATOS: 0000-0003-4240-0849

DOI

10.55730/1300-0527.3694

Abstract

Structural modifications in lichen phenolic compounds have been one of the tools to potentiate their biological activity. In the present work, seven alkyl derivatives of norstictic acid were prepared and evaluated against eight cell lines. Norstictic acid was isolated from the lichen Ramalina anceps and the alkyl derivatives were obtained through reactions with alcohols. Cytotoxicity was evaluated against the 786-0 (kidney carcinoma), MCF7 (breast carcinoma), HT-29 (colon carcinoma), PC-03 (prostate carcinoma), HEP2 (laryngeal carcinoma), B16-F10 (murine melanoma), UACC-62 (human melanoma), and NIH/3T3 (mouse embryonic fibroblast) cell lines using the sulforhodamine B assay. Norstictic acid exhibited poor activity, while the 8'-O-n-butyl-norstictic acid and 8'-O-sec-butyl-norstictic acid derivatives showed potential activity (GI50 values of 6.37–45.0 μM and 6.8–52.40 μM, respectively) and high selectivity (selectivity index (SI) values of 13.88–98.11 and SI 11.30–87.40, respectively) against all tumor cells. The 8'-O-n-hexyl-norstictic acid showed good activity (5.96–9.53 μM) and moderate selectivity (SI 9.2–5.76) against MCF7, HT-29, PC-03, and HEP2 cells, while 8'-O-isopropyl-norstictic acid demonstrated high activity and selectivity against PC-03 cells ( GI50 1.28 μM and SI 33.8), and was highly active but moderately selective against UACC, HEP2, and B16-F10 cells (GI50 6.2, 7.78, and 9.65 μM; SI 7.0, 5.5, and 4.5, respectively). Additionally, 8'-O-n-pentyl- and 8'-O-tert-butyl-norstictic acids were active and selective against PC-03 cells (GI50 8.77 and 7.60 μM; SI 6.53 and 5.0, respectively). Chemometric analysis revealed a clear relationship between all compounds and their biological activities. The insertion of a four-carbon alkyl chain (n-butyl and sec-butyl) produced potentially active compounds on all tested tumor cells.

Keywords

Cytotoxic activity, selectivity index, alkyl derivatives, lichens, phenols

First Page

748

Last Page

755

Creative Commons License

Creative Commons Attribution 4.0 International License
This work is licensed under a Creative Commons Attribution 4.0 International License.

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