Antigenotoxic and Antioxidant Properties of <i>Solanum cernuum</i> and Its Alkaloid, Cernumidine

Abstract

Solanum cernuum VELL. has been used extensively for the treatment of urinary disorders, gonorrhea and skin infections; cernumidine is a major component of S. cernuum (SC) hydroalcoholic extract. The micronucleus test in V79 cells was used to evaluate the genotoxic and antigenotoxic potential of SC and cernumidine. For antigenotoxicity assessment, methyl methanesulfonate (MMS, 44 µg/mL) and hydrogen peroxide (H 2 O 2 , 3.5 µg/mL) were added as inducers of chromosome damage. Antioxidant activity was evaluated by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) test. Significantly higher frequencies of micronuclei were observed in cell cultures treated with SC concentrations of 160 and 320 µg/mL in comparison with the negative control, demonstrating a genotoxic effect. There was no significant difference in the frequency of micronuclei between cell cultures treated with a combination of SC and MMS and those treated only with MMS. On the other hand, a significant reduction in the frequency of micronuclei was observed for V79 cells treated with SC or cernumidine plus H 2 O 2 compared to those treated only with H 2 O 2 . Furthermore, SC and cernumidine were able to scavenge free radicals in the DPPH assay. Thus, the protective effect of SC and cernumidine against H 2 O 2 can be attributed to antioxidant activity.

The Genus Solanum: An Ethnopharmacological, Phytochemical and Biological Properties Review

“…Spanish: tamarillo, tomate de árbol, tomate SerranoEcuador, Colombia, Peru, Bolivia, Rwanda, South Africa, India, Nepal China, United States, Chile, Australia, New Zealand, Malaysia, Philippines, Puerto Rico, Bhutan [71–74]Ripe fruit edible, preservative [71, 72], antioxidant [75]13 S. buddleifolium UnknownBrazil [79]Unknown14 S. caavurana Laranjinha do mato, ‘jurubebarana’ or ‘jurubeba-branca’Brazil (Ceará, Bahia, Mato Grosso do Sul, Paraná,Santa Catarina States), Paraguay, ArgentinaAnemia, liver disorders, digestion [80]15 S. capsicoides Cockroach berry, polohauai’i (Polynesia), devil’s appleBrazil, Central America, Australia, Brooklyn, New York [81–84]Ornamental [83], anti-inflammatory [85], anticancer [86], antihypertensive [87]16 S. cathayanum ChinaAnti-inflammatory, anti-bacterial [102], antitumor, anti-neurodegenerative [102–106]17S. cernuum“Panaceia”BrazilGastric ulcers, hepatic injuries, skin disorders, anti-tumor, depurative, diuretic, antihemorrhagic, antiblennorrhoea, cardiac disorders, analgesic, anti-inflammatory, urinary disorders, gastric cancer, gonorrhea [107–112]18 S. chrysotrichum “Sosa”MexicoAnti-mycotic, anti-inflammatory [113–120]19 S. cornifolium Latin AmericaAnti-mycotic [121]20 S. crinitum “jurubeba” and “fruto-de-lobo”Brazil, ColombiaAnti-tumor [122, 123]…”

“…(Fig. 10), comprising types of cyclic guanidine alkaloids, e.g., cernumidine ( 446 ) and isocernumidine ( 447 ) from the leaves of S. cernuum [109, 111, 112]. Bioactive long chain amides, 454 – 456 , exhibiting antimicrobial activity against Escherichia coli and Candida albicans were isolated from aerial parts of S. schimperianum [277].…”

Exploring the synthesis of aminal guanidine-based molecules: synthesis of cernumidine and analogues, and survey of its anti-inflammatory activity

“…This conclusion arises from the clear dominance of the dextro isomer, which is evident through its measured optical rotation of [a] 20 D +10.9 (c 0.84, MeOH). Like many of the members of the genus Solanum, 2 cernumidine (1) displays antioxidant 3,4 and antitumor activity. 1,5 The latter is probably owned to its ability to inhibit the production of interleukin-8 (IL-8), as showed in 2011 on colorectal carcinoma cells (HT-29).…”

Synthetic Approaches to a Challenging and Unusual Structure—An Amino-Pyrrolidine Guanine Core

“…Cernumidine (1) ( Figure 1) is an alkaloid isolated in 2011 [17] presenting an unusual cyclic-guanidine core and displaying inhibition of interleukine-8 production by HT-29 colon carcinoma cells [18][19][20][21]. Cernumidine and other isomeric compounds isolated from the Brazilian native tree used in folk medicine, Solanum cernuum Vell., present a never reported 2-aminopyrrolidine-1-carboxamidine unit with five consecutive C-N bonds that, although structurally very simple and with only a labile stereogenic center, presents a major synthetic challenge to a synthetic chemist [22,23]. Previous efforts on the synthesis of a cyclic-guanidine core were reported in the work of Ascenzi et al who described the biological synthesis of the hemiaminal, 2-hydroxopyrrolidin-1-yl carboxamidine from agmatine ((4-aminobutyl)guanidine) using copper aminoxidase from Pisum sativum L. in an oxidative deamination process.…”