Anguivine and isoanguivine steroid alkaloid glycosides fromSolanum anguivi

doi:10.1016/S0031-9422(00)89600-4

Phytochemistry

Volume 37, Issue 6, December 1994, Pages 1725-1727

https://doi.org/10.1016/S0031-9422(00)89600-4 Get rights and content

Abstract

In addition to solamargine, two new steroid alkaloid glycosides, anguivine and isoanguivine, have been isolated from the roots ofSolanum anguivi,

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Cited by (21)

Influence of ripeness stage on the bioactive compounds’ contents and antioxidant activities of Solanum anguivi Lam. fruits accessions
2023, Heliyon
Solanum anguivi Lam. fruits (SALF) possess bioactive compounds, such as phenolics, alkaloids, saponins, flavonoids, and vitamin C, that are beneficial for preventing oxidative stress-related diseases. It has been documented that ripeness stage influences the nutritional quality of fruits. However, there is limited information on the effect of the ripeness stages (unripe, yellow, orange and red) on the bioactive compounds' contents (BCC) and antioxidant activity (AA) of SALF. We investigated the effect of ripening on the BCC and AA of different SALF accessions. Spectrophotometry was used to determine SALF's total contents of phenolics, flavonoids, saponins, vitamin C, and AA and gravimetry for total alkaloids. The AA was determined as free radical scavenging activity (FRSC) and total antioxidant capacity (TAC). The total phenolics (7.6–22.6 mg gallic acid equivalent/g DW), flavonoids (1.3–4.1 mg quercetin equivalent (QE)/g DW), saponins (44.8–152.5 mg diosgenin equivalent/g DW), vitamin C (2.2–6.4 mg ascorbic acid equivalent/g DW), alkaloids (141.2–296.9 mg/g DW), FRSC (1.5–66.2 %) and TAC (0.1–14.2 mg QE/g DW) significantly differed among the ripeness stages. Fruits in the unripe stage were rich in phenolics, flavonoids, and AA; in the red stage in alkaloids and vitamin C; and in the orange stage, in saponins and flavonoids. The AA had strong positive correlations with total flavonoids and phenolics (r = 0.72 and 0.81, respectively) and a moderate negative correlation with total alkaloids (r = −0.67). Overall, unripe stage fruits had the highest AA and total phenolics and thus may have the highest health-promoting properties. Botanists and farmers may, therefore, focus on harvesting and trading SALF to markets/consumers while still unripe.
Solanum steroidal glycoalkaloids: Structural diversity, biological activities, and biosynthesis
2021, Natural Product Reports
Covering: up to 1 October 2020
Solanum steroidal glycoalkaloids (SGA), characterized by nitrogenous steroidal aglycone and glycoside residues, mainly occur in the Solanum species, including economically important edible plants such as potato, tomato, and eggplant. To date, 107 SGA assigned to six total skeletons have been identified from Solanum plants. SGA have unique structures and display significant pharmacological activities such as cytotoxic, antimicrobial, anticholesterol, and some are well-known poisons. The biosynthesis pathway, transcriptional regulation, and the evolution of SGA are also examined in detail. This report updates the chemical knowledge of the naturally occurring SGA from Solanum species, thereby providing an in-depth analysis of their diversity, biological activities, and biosynthesis.
Chemical constituents from the fruits of Solanum incanum L
2020, Biochemical Systematics and Ecology
Citation Excerpt :
W2C2 (52 mg) was purified by preparative HPLC with an isocratic mobile phase system of acetonitrile: water (9:91) to furnish compounds 6 (tR = 23.1 min, 2.0 mg) and 7 (tR = 26.6 min, 3.0 mg). The isolated compounds (Fig. 1) were identified as solamargine (1) (Tian et al., 1997), solaverine I (2) (Yamashita et al., 1990), (23S)-23-hydroxyanguivine (3) (Ripperger, 1997), sisymbrifolin (4) (Li et al., 2019a,b; Chakravarty et al., 1996), sisymbrifolin 4-O-glucopyranoside (5) (Eom et al., 2016), benzyl-glucopyranoside (6) (Li et al., 2019a,b), syringin (7) (Zhou et al., 2019), citroside B (8) (Osorio et al., 1999), fraxinol-6-β-D-galactopyranoside (9) (Yu et al., 2015), by comparison of their spectroscopic data with literature values. The isolated compounds from S. incanum are classified as steroidal alkaloids (1–3), lignans (4–5), and simple phenolic compounds (6–9).
Phytochemical investigation of the fruits of Solanum incanum L. resulted in the isolation of nine compounds, including three steroidal glycoalkaloids (1-3), two neolignans (4–5), two simple phenolics (6–7), one monoterpene glycoside (8), and one coumarin glucoside (9). The structure elucidation of isolated compounds was determined based on NMR and mass spectral data. Compounds 4 and 9 were isolated for the first time from the genus Solanum and their chemotaxonomic significance was discussed.
Hypoglycemic, antiperoxidative and antihyperlipidemic effects of saponins from Solanum anguivi Lam. fruits in alloxan-induced diabetic rats
2013, South African Journal of Botany
Citation Excerpt :
The dried powders of the fruits were used in the medication for high blood pressure. Phytochemical reports on S. anguivi indicated that the stem, fruits, roots, flowers and leaves contain glycoalkaloids (anguivine and isoanguivine), steroidal alkaloids (solamargine and solasoline), steroidal glycosides (anguiviosides A–C, anguiviosides 1–4) (Chopra et al., 1994; Ripperger and Himmelreich, 1994; Zhu et al., 2000; Honbu et al., 2000). The domesticated species are consumed as leafy and/or fruit vegetables that are rich in essential minerals and vitamins (Bukenya-Ziraba, 2004), and are recommended as a dietary staple supplements for nursing mothers, the young, the aged, and anemic patients (Jansen, 2004).
The present study evaluates the hypoglycemic, antiperoxidative and antihyperlipidemic activities of saponins from Solanum anguivi fruits in alloxan induced diabetes rats. Diabetic rats were treated with saponin (20–100 mg/kg) for 21 days. Results indicated that administration of saponins significantly reduced the elevated levels of glucose, decreased total cholesterol (TC), total triglycerides (TG), low density lipoprotein (LDL) and increased high density lipoprotein (HDL) in the serum towards normalcy when compared to the diabetic control (p < 0.05). In addition, saponins exhibited strong inhibition of lipid peroxidation and increased the levels of antioxidant enzymes (superoxide dismutase and catalase) in the serum, liver and pancreas when compared to the diabetic control (p < 0.05). Our results suggest that saponins from S. anguivi fruit can enhance the hypoglycemic, hypolipidemic and antioxidant properties in alloxan-induced diabetic rats, and may have the potential to be used in the prevention or in the management of diabetes.
Toxicological studies on a standardized extract of Solanum indicum ssp. distichum
2011, Food and Chemical Toxicology
Citation Excerpt :
The fruits are used as nutritious vegetables on account of their high content of starch, calcium, vitamin A, ascorbic acid and phosphate. The fruits also contain steroid glycosides as well as glyco-alkaloids (Abouzid et al., 2008; Honbu et al., 2002; Ripperger and Himmelreich, 1994; Zhu et al., 2000). The fruits have been claimed in folk medicine to have anti-hypertensive properties (Rubaihayo, 1995), a fact that led us to investigate the efficacy of a standardized fruit extract in lowering blood pressure and found it effective in an animal model of L-NAME induced hypertension (Bahgat et al., 2008).
A standardized extract of the fruits of Solanum distichum has previously been shown to possess anti-hypertensive activity in rats (ED50 about 1 mg/kg). Earlier acute toxicity studies had shown that single doses up to 2 g/kg orally or intraperitoneally failed to show any signs of morbidity. To study its potential long-term toxicity, rats of either sex were fed orally 1 g/kg of the extract daily over a period of 4 weeks to 6 months. The extract did not affect food intake or rate of growth of the animals. Blood counts and other hematological parameters remained unaffected. Treatment for 4 weeks had no effect on plasma cholesterol or blood urea nitrogen in both sexes, but extended treatment to 6 months tended to lower both parameters. Plasma creatinine, liver enzymes and fasting blood sugar, plasma electrolytes, total protein and albumin were not altered. Gross necropsy showed a 20% increase in liver to body weight ratios after 6 months. None of the body organs tested showed any histopathological changes. Bearing in mind that the dose of the extract used in this study was several 100 times greater than its ED50, the present findings point to the wide safety margin of the extract.
Evaluation of biological activity of crude extracts from plants used in Yucatecan traditional medicine part I. Antioxidant, antimicrobial and β-glucosidase inhibition activities
2001, Phytomedicine
Bioactivity of extracts from leaves, stems and roots of twelve plants commonly used in Yucatecan traditional medicine were evaluated in four bioassays. Crude extracts from ten plants showed significant activity in the inhibition of bleaching of β-carotene assay, while thirteen extracts showed activity in the reduction of 2, 2- diphenyl-1-picrylhydrazyl radical (DPPH) assay. In the antimicrobial bioassay, the major activity was presented by the root extract of Jatropha gaumeri and in the β-glucosidase inhibition activity assay the strongest activity was observed in the stem and root extracts of Solanum hirtum.

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: Part 129 in the series ‘Solanum Alkaloids’. For Part 128, see ref. [1].

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Anguivine and isoanguivine steroid alkaloid glycosides fromSolanum anguivi

Abstract

Phytochemistry

Liebigs Ann. Chem.

Chem. Pharm. Bull.