Antitumoral photoinduced effects of crude extract, fractions, and naphthoquinones from Sinningia magnifica (Otto & A. Dietr.) Wiehler (Gesneriaceae) in a bioguided study

• Published in: Photochemistry and photobiology Vol. 100; no. 1; pp. 190 - 203
• Main Authors: Serain, A. F., Buitrago‐Mejia, A. J., Souza, G. C. A., Corrêa, W. R., Stefanello, M. E. A., Salvador, M. J.
• Format: Journal Article
• Language: English
• Published: United States Blackwell Publishing Ltd 01.01.2024
• Subjects: Anthraquinones; Anthraquinones - chemistry; Anthraquinones - pharmacology; Anticancer properties; Biological activity; Complex Mixtures; Gesneriaceae; Glycosides; Humans; Melanoma; Melanoma - drug therapy; naphthoquinones; Naphthoquinones - chemistry; Naphthoquinones - pharmacology; Naphthoquinones - therapeutic use; natural photosensitizers; Oxygen production; Phenolic compounds; Phenols; Photochemotherapy; Photodegradation; Photodynamic therapy; Photosensitization; Photosensitizing Agents - pharmacology; Photosensitizing Agents - therapeutic use; Prostate; Prostate cancer; Side effects; Singlet oxygen; Sinningia; Tandem Mass Spectrometry; Tropical forests; Tumor cell lines; natural photosensitizers; naphthoquinones; Sinningia; photodynamic therapy
• ISSN: 0031-8655; 1751-1097
• DOI: 10.1111/php.13830

Photodynamic therapy (PDT) has been used for various purposes, including as an antitumor resource in a noninvasive therapy with minimal side effects. Sinningia magnifica (Otto & A. Dietr.) Wiehler is a rupicolous plant found in rock crevices in Brazilian tropical forests. Initial studies indicate the presence of phenolic glycosides and anthraquinones in species of the genus Sinningia (Generiaceae family). It is known that anthraquinones are natural photosensitizers with potential PDT applications. This led us to investigate the potential compounds of S. magnifica for use as a natural photosensitizer against the melanoma (SK‐MEL‐103) and the prostate cancer (PC‐3) cell lines in a bioguided study. Our results showed that singlet oxygen production by the 1,3‐DPBF photodegradation assay greatly increased in the presence of crude extract and fractions. The biological activity evaluation showed photodynamic action against melanoma cell line SK‐MEL‐103 and prostate cell line PC‐3. These results suggest the presence of potential photosensitizing substances, as demonstrated in this in vitro antitumor PDT study by the naphthoquinones Dunniol and 7‐hydroxy‐6‐methoxy‐α‐dunnione for the first time. Naphthoquinones, anthraquinones and phenolic compounds were identified in the crude extract by UHPLC–MS/MS analysis, motivating us to continue with the bioguided phytochemical study aiming to discover more photochemically bioactive substances in Gesneriaceae plants. The bioguided study of Sinningia magnifica (Otto & A. Dietr.) Wiehler crude extract and fractions reveals naphthoquinones by UHPLC–MS/MS identification as Dunniol and 7‐hydroxy‐6‐methoxy‐α‐dunnione. In the photodegradation assay, singlet oxygen production was enhanced, showing the potential of this plant for use of its substances as natural photosensitizers against melanoma (SK‐MEL‐103) and prostate cancer (PC‐3) cell lines, as demonstrated by our study for the first time.