Role of Carbohydrate Side Chains of Potato Glycoalkaloids in Developmental Toxicity

Rayburn, James R.; Bantle, John A.; Friedman, Mendel

doi:10.1021/jf00043a022

Cited by 76 publications

(46 citation statements)

References 17 publications

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“…The results indicated that the glycoalkaloids with chacotriose exhibited greater suppression than the glycoalkaloids with solatriose against Plasmodium yoelii in mice. Our results were similar to those previously reported for the glycoalkaloids chaconine and solanine in disrupting cell membranes (Keukens et al, 1995(Keukens et al, , 1996, antifungal activity (Fewell & Roddick, 1993), blocking of sodium ion active transport in frog skin (Blankemeyer et al, 1995), antitumorigenic activity (Lee et al, 2004;Friedman et al, 2005) and Xenopus embryo teratogenesis (Friedman et al, 1992;Rayburn et al, 1994). As mentioned above, the correlation of solamargine and solasonine in antimalarial activities was similar to that in antifungal activity (Cipollini & Levey, 1997), developmental toxicology in frog embryos (Blankemeyer et al, 1998) and antiproliferative activities against human colon and liver cancer cell lines (Lee et al, 2004).…”

Section: Discussionsupporting

confidence: 91%

In vivoantimalarial activities of glycoalkaloids isolated from Solanaceae plants

Chen¹,

Li²,

Sun³

et al. 2010

Pharmaceutical Biology

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Section: Discussionsupporting

confidence: 91%

In vivoantimalarial activities of glycoalkaloids isolated from Solanaceae plants

Chen¹,

Li²,

Sun³

et al. 2010

Pharmaceutical Biology

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“…The biological activities of SGAs are influenced by both the nature and the number of sugars making up the carbohydrate moiety attached to the C3-OH position of the aglycone (Rayburn et al 1994). Hence, expression of hydrolysing enzymes in tuber tissue to remove the sugar moiety may lead to reduced toxicity of the SGAs.…”

Section: Sga Catabolismmentioning

confidence: 99%

Potato Steroidal Glycoalkaloids: Biosynthesis and Genetic Manipulation

2008

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The potato steroidal glycoalkaloids (SGAs) are important components of plant resistance against pests and pathogens but can be toxic to humans at high levels. SGAs derive their toxicity from anticholinesterase activity affecting the central nervous system and the disruptive effects on cell membrane integrity affecting the digestive system and other organs. Accordingly, current safety regulations limit their content in the edible tuber to 20 mg per 100 g fresh weight. SGA composition and level are genetically determined, with unfavourable growth conditions and inappropriate postharvest management inducing the accumulation of SGAs at levels in the tubers of "safe" cultivars beyond the maximum level set by the industry. Hence, genetic alteration of potato to prevent toxic levels of SGAs in tubers is highly desirable. At the same time, maintaining high SGA levels in other plant organs will contribute to plant resistance against pathogen and pest attacks. To this end, SGA biosynthesis and degradation should be manipulated precisely to exploit tissue-specific expression rather than whole-plant suppression of SGA production, to produce potato cultivars with SGA content enriched in the foliage but diminished in the edible tubers. Only a few details are known about the SGA biosynthetic pathway, its genes and intermediates. Research on factors that regulate SGA biosynthesis and catabolism as well as searches for genetic markers linked to total and specific SGA levels have only recently been pursued. The present review summarizes current data on these issues to encourage further discussion on SGA manipulation for safer food products.

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“…As reported in Scheme 1, the increased production of solasodine leads to the bioformation of the glycoalkaloids solasodenone (m/z 412), solanaviol (m/z 430), solasodiene (m/z 396), solasonine (not observed in our spectra), Note that a strong decrease in the relative abundance of the main potato toxins α-chaconine and α-solanine was observed. This observation can be explained considering that successful pathogens avoid such toxicity by removing sugar chains from the molecule of glycoalkaloids (i.e., hydrolysis) by pH alteration [32]. The hydrolytic degradation of α-solanine and α-chaconine to their catabolic and less toxic β-and γ-forms of m/z 706 and 722, respectively, during sprout colonization by the phytopathogen Rhizoctonia solani has been reported recently by Aliferis et al [7].…”

Section: Resultsmentioning

confidence: 89%

Analysis of Metabolic Changes in Plant Pathosystems by Imprint Imaging DESI-MS

Tata

Pérez

Hamid

et al. 2014

J. Am. Soc. Mass Spectrom.

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Abstract. The response of plants to microbial pathogens is based on the production of secondary metabolites. The complexity of plant-pathogen interactions makes their understanding a challenging task for metabolomic studies requiring powerful analytical approaches. In this paper, the ability of ambient mass spectrometry to provide a snapshot of plant metabolic response to pathogen invasion was tested. The fluctuations of glycoalkaloids present in sprouted potatoes infected by the phytopathogen Pythium ultimum were monitored by imprint imaging desorption electrospray ionization mass spectrometry (DESI-MS). After 8 d from the inoculation, a decrease of the relative abundance of potato glycoalkaloids α-solanine (m/z 706) and α-chaconine (m/z 722) was observed, whereas the relative intensity of solanidine (m/z 398), solasodenone (m/z 412), solanaviol (m/z 430), solasodiene (m/z 396), solaspiralidine (m/z 428), γ-solanine/γ-chaconine (m/z 560) , β-solanine (m/z 706), and β-chaconine (m/z 722) increased. The progression of the disease, expressed by the development of brown necrotic lesions on the potato, led to the further decrease of all the glycoalkaloid metabolites. Therefore, the applicability of imprint imaging DESI-MS in studying the plant metabolic changes in a simple pathosystem was demonstrated with minimal sample preparation.

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Role of Carbohydrate Side Chains of Potato Glycoalkaloids in Developmental Toxicity

Cited by 76 publications

References 17 publications

In vivoantimalarial activities of glycoalkaloids isolated from Solanaceae plants

In vivoantimalarial activities of glycoalkaloids isolated from Solanaceae plants

Potato Steroidal Glycoalkaloids: Biosynthesis and Genetic Manipulation

Analysis of Metabolic Changes in Plant Pathosystems by Imprint Imaging DESI-MS

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