Modification of Sugar Chains in Glycoalkaloids and Variation of Anticancer Activity

Li, S; He, Dajun; Zhang, X; Ni, Wei; Zhou, Yuwei; Zhang, L

doi:10.1016/s1005-9040(07)60065-8

Cited by 8 publications

(8 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Figure shows the hydrolysis products of the principal potato glycoalkaloids α-solanine 1 and α-chaconine 2 , the majority of which have been isolated from nature except β 1 -solanine 38 . The tomato glycoalkaloid α-tomatine 3 exhibits similar pathways of hydrolysis as do the aubergine glycoalkaloids α-solasonine 5 and α-solamargine 6 . Chemical hydrolysis has been performed on a wide range of glycoalkaloids to ascertain the importance of the glycosidic residues for bioactivity.…”

Section: Glycoalkaloid Hydrolysis and Biosynthesismentioning

confidence: 99%

“…Li et al examined α-solamargine 6 and α-solasonine 5 and their hydrolysis products for their antiproliferative activities. They were examined against HCT-8 tumor cells and via a MTT assay.…”

Section: Beneficial Effects Of Glycoalkaloids and Their Aglyconesmentioning

confidence: 99%

“…Higher potency has been demonstrated by α-chaconine 2 in a wide range of test systems when compared with α-solanine 1 , for example, inhibition of acetylcholinesterase, − toxicity in mice, and sodium active transport in frog skin. , A similar trend is observed with the paired aubergine glycoalkaloids α-solamargine 6 and α-solasonine 5 . α-Solamargine 6 consistently displays higher activities in biological systems than α-solasonine 5 , for example, anticancer, development toxicity in frog embryos, , and membrane-disrupting properties …”

Section: Structure−activity Relationship Of Glycoalkaloids and Aglyconesmentioning

confidence: 99%

“…45 The tomato glycoalkaloid R-tomatine 3 exhibits similar pathways of hydrolysis 1 as do the aubergine glycoalkaloids R-solasonine 5 and R-solamargine 6. 79 Chemical hydrolysis has been performed on a wide range of glycoalkaloids to ascertain the importance of the glycosidic residues for bioactivity.…”

Section: ' Structures Of Glycoalkaloids In Solanum Speciesmentioning

confidence: 99%

See 3 more Smart Citations

Bioactivities of Glycoalkaloids and Their Aglycones from Solanum Species

Milner

Brunton

Jones

et al. 2011

J. Agric. Food Chem.

231

236

View full text Add to dashboard Cite

Potatoes, tomatoes, and aubergines are all species of the Solanum genus and contain a vast array of secondary metabolites including calystegine alkaloids, phenolic compounds, lectins, and glycoalkaloids. Glycoalkaloids have been the subject of many literature papers, occur widely in the human diet, and are known to induce toxicity. Therefore, from a food safety perspective further information is required regarding their analysis, toxicity, and bioavailability. This is especially important in crop cultivars derived from wild species to prevent glycoalkaloid-induced toxicity. A comprehensive review of the bioactivity of glycoalkaloids and their aglycones of the Solanum species, particularly focused on comparison of their bioactivities including their anticancer, anticholesterol, antimicrobial, anti-inflammatory, antinociceptive, and antipyretic effects, toxicity, and synergism of action of the principal Solanum glycoalkaloids, correlated to differences of their individual molecular structures is presented.

show abstract

Section: Glycoalkaloid Hydrolysis and Biosynthesismentioning

confidence: 99%

Section: Beneficial Effects Of Glycoalkaloids and Their Aglyconesmentioning

confidence: 99%

Section: Structure−activity Relationship Of Glycoalkaloids and Aglyconesmentioning

confidence: 99%

Section: ' Structures Of Glycoalkaloids In Solanum Speciesmentioning

confidence: 99%

See 2 more Smart Citations

Bioactivities of Glycoalkaloids and Their Aglycones from Solanum Species

Milner

Brunton

Jones

et al. 2011

J. Agric. Food Chem.

231

236

View full text Add to dashboard Cite

show abstract

“…Estudos mostraram que os glicoalcalóides em presença de raminose livre apresentam menor potencial citotóxico, sugerindo a competição por sítios específicos . Li et al, 2007, observaram que a atividade citotóxica frente a linhagens de hepatoma humano era reduzida quando utilizada raminose modificada estruturalmente. Estas observações poderiam explicar a razão pela qual a aglicona, solasodina, não apresenta potencial citotóxico frente às linhagens de células de câncer CHAM et al 1990).…”

Section: Mecanismo De Ação Dos Glicoalcalóidesunclassified

Obtenção de extrato padronizado de Solanum lycicarpum A. St.-Hil. contendo glicoalcalóides, desenvolvimento de método analítico por CLAE e de forma farmacêutica de uso tópico

Tiossi¹

View full text Add to dashboard Cite

Solanum lycocarpum A. St.-Hil. (Solanaceae-Solanum), popular wolf-fruit is a native shrub species and characteristic of the Brazilian Cerrado vegetation. Its fruits are used in folk medicine as diuretic, sedative, anti-spasmodic, antiepileptic and antiophidic. This species belongs to the genus Solanum, known to produce alkaloid heterosides, which possess antitumor activity, including skin anticancer. Skin cancer has concerned the authorities in the world because of its growing rates. Therefore, the search for new active anticancer is paramount. The wolf-fruit furnish an alkaloidic extract, which is rich in a mixture of heteroside alkaloids and composed mostly of solasonine and solamargine. Such compounds have been studied as potential anticancer, because they are relatively selective for tumor cells and, consequently, have low toxicity to health cell. For these reasons, the antitumor potential of this species should be investigated. For that, the fruits were collected, dried and crushed. The dried plant biomass was submitted to acid-base extraction to obtain the alkaloidic extract. The analytical method for the quantitation of the alkaloids in both crude alkaloid extract and plant biomass was developed and validated by HPLC-UV. From the alkaloidic extract, formulations were developed for topical use. These formulations were evaluated by in vitro tests of skin permeation and retention in Franz diffusion cell, for which an analytical method for quantifying solasonine and solamargine was developed, as well. The selection of the most promising formulation for anticancer assay in vivo was based in both, the permeation performance of the formulation in vitro and its skin retention in vivo in hairless health mice. The formulation B, containing crude alkaloid extract 1%, Monoolein 5%, propyleneglycol 5% in Natrosol gel (pH 6.5), showed total dermal retention, which is suitable for future trials of skin anticancer in animal models.

show abstract

In vitro Leishmanicidal and Cytotoxic Activities of the Glycoalkaloids from Solanum lycocarpum (Solanaceae) Fruits

Miranda

Tiossi

Silva

et al. 2013

Chemistry & Biodiversity

View full text Add to dashboard Cite

Leishmaniasis is an infection caused by a protozoan parasite of the genus Leishmania and is the second most prevalent parasitic protozoal disease after malaria in the world. We report the in vitro leishmanicidal activity on promastigote forms of Leishmania amazonensis and cytotoxicity, using LLCMK2 cells, of the glycoalkaloids from the fruits of Solanum lycocarpum, determined by colorimetric methods. The alkaloidic extract was obtained by acid-base extraction; solamargine and solasonine were isolated by silica-gel chromatography, followed by reversed-phase HPLC final purification. The alkaloidic extract, solamargine, solasonine, as well as the equimolar mixture of the glycoalkaloids solamargine and solasonine displayed leishmanicidal activity against promastigote forms of L. amazonensis, whereas the aglycone solasodine was inactive. After 24 and 72 h of incubation, most of the samples showed lower cytotoxicities (IC50 6.5 to 124 μM) as compared to leishmanicidal activity (IC50 1.1 to 23.6 μM). The equimolar mixture solamargine/solasonine was the most active with an IC50 value of 1.1 μM, after 72 h. Likewise, solamargine was the most active after 24 h with an IC50 value of 14.4 μM, both in comparison with the positive control amphotericin B.

show abstract

Modification of Sugar Chains in Glycoalkaloids and Variation of Anticancer Activity

Cited by 8 publications

References 16 publications

Bioactivities of Glycoalkaloids and Their Aglycones from Solanum Species

Bioactivities of Glycoalkaloids and Their Aglycones from Solanum Species

Obtenção de extrato padronizado de Solanum lycicarpum A. St.-Hil. contendo glicoalcalóides, desenvolvimento de método analítico por CLAE e de forma farmacêutica de uso tópico

In vitro Leishmanicidal and Cytotoxic Activities of the Glycoalkaloids from Solanum lycocarpum (Solanaceae) Fruits

Contact Info

Product

Resources

About