A New Cytotoxic Naphthoquinone and Other Chemical Constituents of Sinningia reitzii

Silva, Adson S.; Amorim, Magali S.; Mesquita, Mariana; Salvador, Marcos José; Sá, Eduardo L. de; Stefanello, Maria Élida Alves

doi:10.21577/0103-5053.20190054

Cited by 5 publications

(4 citation statements)

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“…Altogether, 35 jacaranones were isolated from 37 plant species; three-quarters of the compounds are monomers ( n = 26), and the others are dimers ( n = 9) ( Figure 2 and Figure 3 ). Although the best sources of jacaranones are Asteraceae species, certain species of the Acanthaceae [ 3 ], Bignoniaceae [ 1 , 2 , 37 , 38 , 39 , 40 , 41 ], Delesseriaceae [ 42 ], Gesneriaceae [ 43 , 44 ], Oleaceae [ 45 ], and Theaceae [ 4 , 5 ] families were also found to be sources of jacaranones ( Table 2 ). Among Asteraceae species, the genus Senecio is represented by 20 jacaranone derivative-producing plant species [ 36 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 ].…”

Section: Discussionmentioning

confidence: 99%

Jacaranone Derivatives with Antiproliferative Activity from Crepis pulchra and Relevance of This Group of Plant Metabolites

Dávid

Kúsz

Pinke

et al. 2022

Plants

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Jacaranones are a small group of specific plant metabolites with promising biological activities. The occurrence of jacaranones is limited to only a few plant families, with Asteraceae being the most abundant source of these compounds. Therefore, jacaranones can also serve as chemotaxonomic markers. Our phytochemical investigation of Crepis pulchra L. (Asteraceae) resulted in three jacaranone derivatives (jacaranone, 2,3-dihydro-2-hydroxyjacaranone, 2,3-dihydro-2-methoxyjacaranone), and (6R,9S)-3-oxo-α-ionol-β-d-glucopyranoside, fulgidic acid, 12,15-octadecadienoic acid methyl ester, scopoletin and apigenin-7-O-β-d-glucoside. This is the first report on the isolation of jacaranones from a species belonging to the Cichorioideae subfamily of Asteraceae. Jacaranone derivatives were subjected to an in vitro antiproliferative assay against a panel of human cancer cell lines (MCF-7, MDA-MB-231, HeLa, and C33A), revealing high or moderate activities, with IC50 values ranging from 6.3 to 26.5 μM.

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Section: Discussionmentioning

confidence: 99%

Jacaranone Derivatives with Antiproliferative Activity from Crepis pulchra and Relevance of This Group of Plant Metabolites

Dávid

Kúsz

Pinke

et al. 2022

Plants

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“…10,12,13,14,15,16 Phytochemical research on Sinninigia species has mainly reported the identification of terpenes, phenolic glycosides, and compounds from the quinone class, some with documented biological activities such as antioxidant, anti-inflammatory properties, and cytotoxic activity for cancer cell lines. 10,12,14,15,16,17,18,19,20,21,22 Sinningia magnifica (Otto & A. Dietr.)…”

Section: Introductionmentioning

confidence: 99%

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

Serain,

Buitrago‐Mejia,

de Souza

et al. 2023

Photochem & Photobiology

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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.

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“…Compounds based on the structure of 1,4-naphthoquinone are widespread in natural objects [1][2][3][4][5][6][7][8][9]. Among thousands of its derivatives, including dimeric and trimeric products [1][2][3][10][11][12], derivatives of naphthazarin (5,8-dihydroxy-1,4-naphthoquinone) occupy a very prominent place [13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Dimeric (Poly)Hydroxynaphthazarins, Metabolites of Echinoderms and Lichens: The History of the Synthesis and Structure Elucidation

2023

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A New Cytotoxic Naphthoquinone and Other Chemical Constituents of Sinningia reitzii

Cited by 5 publications

References 0 publications

Jacaranone Derivatives with Antiproliferative Activity from Crepis pulchra and Relevance of This Group of Plant Metabolites

Jacaranone Derivatives with Antiproliferative Activity from Crepis pulchra and Relevance of This Group of Plant Metabolites

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

Dimeric (Poly)Hydroxynaphthazarins, Metabolites of Echinoderms and Lichens: The History of the Synthesis and Structure Elucidation

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