Abstract
Phytochemical study of aerial parts from Sinningia mauroana Chautems (Gesneriaceae) yielded 17 known compounds: sitosterol, stigmasterol, betulinic acid, oleanolic acid, hederagenin, maslinic acid, ursolic acid, pomolic acid, soranjidiol, methyl 4-hydroxyphenylacetate, 6-hydroxy-7-methoxy-α-dunnione, 7-hydroxy-6-methoxy-α-dunnione, jacaranone, calceolarioside A, conandroside, luteolin, and luteolin-7-O-glucoside. Complete NMR data of 6-hydroxy-7-methoxy-α-dunnione and 7-hydroxy-6-methoxy-α-dunnione were obtained in two different solvents. Hexane, ethyl acetate and ethanol extracts were screened for antimicrobial, antioxidant and cytotoxic activities. The antimicrobial activity was assayed against Staphylococcus aureus, S. epidermidis, Escherichia coli, Pseudomonas aeruginosa, Candida albicans, C. parapsilosis, C. dubliniensis, and C. glabrata, using the microdillution method. All extracts were inactive (MIC > 100 µg mL-1). The antioxidant activity was evaluated with the ORAC method; the ethyl acetate and ethanol extracts were active (TE relative > 800 µg g-1). The cytotoxic activity was tested against PC-3 (prostate) and SKMEL-103 (melanoma) human tumor cell lines, and 3T3 fibroblast cell line, using the MTT assay. The hexane extract showed strong activity against PC-3 and SKMEL-103 human tumor cell lines (IC50 50 µg mL-1).
Highlights
Sinningia (Gesneriaceae) is a neotropical genus of herbs and subshrubs, comprising 75 species in Brazil, distributed mainly in Southern and Southeastern regions of the country.1Until the last decade, the knowledge about the chemical constitution of Sinningia species was scant, with only four species investigated: S. aggregata, S. allagophylla, S. cardinalis e S. speciosa.2 Since new phytochemical studies were carried on S. aggregata3 and S. allagophylla,4 and five species were studied for the first time: S. canescens,5,6 S. hatschbachii,7 S. leucotricha,6,8 S. reitzii,9 e S. warmingii.10 The chemical profile that arises from these studies shows that the genus is very chemically diverse, producing anthraquinones, naphthoquinones and derivatives, naphthochromenes, terpenoids, flavonoids, cyclohexylethanoids, and phenylethanoid glycosides.2-10Some compounds isolated from Sinningia spp exhibit biological activity
New phytochemical studies were carried on S. aggregata3 and S. allagophylla,4 and five species were studied for the first time: S. canescens,5,6 S. hatschbachii,7 S. leucotricha,6,8 S. reitzii,9 e S. warmingii
The triterpenes 6-8, the naphthoquinone 11, and the flavonoids 16-17 are being described for the first time in Sinningia (Figure 1)
Summary
Sinningia (Gesneriaceae) is a neotropical genus of herbs and subshrubs, comprising 75 species in Brazil, distributed mainly in Southern and Southeastern regions of the country.1Until the last decade, the knowledge about the chemical constitution of Sinningia species was scant, with only four species investigated: S. aggregata, S. allagophylla, S. cardinalis e S. speciosa.2 Since new phytochemical studies were carried on S. aggregata3 and S. allagophylla,4 and five species were studied for the first time: S. canescens,5,6 S. hatschbachii,7 S. leucotricha,6,8 S. reitzii,9 e S. warmingii.10 The chemical profile that arises from these studies shows that the genus is very chemically diverse, producing anthraquinones, naphthoquinones and derivatives, naphthochromenes, terpenoids, flavonoids, cyclohexylethanoids, and phenylethanoid glycosides.2-10Some compounds isolated from Sinningia spp exhibit biological activity. Dried and powdered aerial parts of S. mauroana (327.0 g) were extracted with hexanes (Hex, mixture of isomers), EtOAc, and EtOH, successively (three successive extraction employing 1.6 L of solvent each time), at room temperature. The extracts of aerial parts of Sinningia mauroana yielded 17 known compounds, which were identified as sitosterol [1],20 stigmasterol [2],20 betulinic acid [3],21 oleanolic acid [4],21 23-hydroxyoleanolic acid (hederagenin, 5),22 2-a-hydroxyoleanolic acid (maslinic acid, 6),22 ursolic acid [7],21 19-a-hydroxyursolic acid (pomolic acid, 8),21 1,6-dihydroxy-2-methylanthraquinone (soranjidiol, 9),23 methyl 4-hydroxyphenylacetate [10],24 6-hydroxy-7-methoxy-a-dunnione
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