Teratogenicity of the solatium alkaloid solasodine and of ‘Kennebec’ potato sprouts in hamsters

Keeler, Richard F.; Brown, Dennis A.; Douglas, Dexter R.; Stallknecht, G. F.; Young, Stuart

doi:10.1007/bf01685698

Cited by 43 publications

(15 citation statements)

References 9 publications

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“…This aglycone as well as its parent glycoalkaloid compound solanine are naturally present in all members of the solanum plant family, including solanum tuberosum (potatoes) and are likely to be present in extremely high and toxic concentrations in blighted potatoes. In addition to these recorded acute toxicities, solasodine was also found to be teratogenic in mammals (Keeler et al, 1976). Therefore, the reduced ability of "atypical" BuChE to bind the solanoid poisons can clearly have a survival advantage, particularly in heterozygotes to this mutation where scavenging and catalytic activities may be retained under intoxication.…”

Section: Discussionmentioning

confidence: 99%

Aspartate‐70 to glycine substitution confers resistance to naturally occurring and synthetic anionic‐site ligands on inovo produced human butyrylcholinesterase

Neville

Gnatt

Loewenstein

et al. 1990

J of Neuroscience Research

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The "atypical" allelic variant of human butyrylcholinesterase (BuChE) can be characterized by its failure to bind the local anesthetic dibucaine, the muscle relaxant succinylcholine, and the naturally occurring steroidal alkaloid solanidine, all assumed to bind to the charged anionic site component within the normal BuChE enzyme. A single nucleotide substitution conferring a change of aspartate-70 into glycine was recently reported in the CHE gene encoding BuChE from several individuals having the "atypical" BuChE phenotype, whereas in two other DNA samples, this mutation appeared together with a second alteration conferring a change of serine-425 into proline. To separately assess the contribution of each of these mutations toward anionic site interactions in BuChE, three transcription constructs were engineered with each of these substitutions alone or both of them together. Xenopus oocyte microinjection of normal or mutated synthetic BuChEmRNA transcripts was employed in conjunction with biochemical analyzes of the resultant recombinant BuChE variants. The presence of the Gly-70 mutation alone was found to render the enzyme resistant to 100 microM solanidine and 5 mM succinylcholine; concentrations sufficient to inhibit the "normal," Asp-70 containing BuChE by over 50%. Furthermore, when completely inhibited by the organophosphorous poison diisopropylfluorophosphate (DFP), Gly-70 BuChE failed to be reactivated by 10 mM of the cholinesterase-specific oxime pyridine 2-aldoxime methiodide (2-PAM); a concentration restoring about 50% of activity in the "normal" Asp-70 recombinant enzyme. The Pro-425 mutation alone had no apparent influence on BuChE interactions with any of these ligands. However, it conferred synergistic effects on some of the anionic site changes induced by the Gly-70 mutation.(ABSTRACT TRUNCATED AT 250 WORDS)

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Section: Discussionmentioning

confidence: 99%

Aspartate‐70 to glycine substitution confers resistance to naturally occurring and synthetic anionic‐site ligands on inovo produced human butyrylcholinesterase

Neville

Gnatt

Loewenstein

et al. 1990

J of Neuroscience Research

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“…In later experiments, sprout material from the 'Kennebec' potato produced terata in offspring from hamster dams gavaged with that material (35). The alkaloid concentration was usually up to 1,000 times higher in sprouts than in tuber material.…”

Section: Teratogenicity Of Potato Preparationsmentioning

confidence: 95%

Cyclopamine and related steroidal alkaloid teratogens: Their occurrence, structural relationship, and biologic effects

Keeler

1978

Lipids

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A spontaneous congenital deformity is produced in lambs whose dams consume Veratrum californicum on the 14th day of gestation. The deformity is generally expressed as cyclopia, cebocephaly, anophthalmia, or microphthalmia. This teratogenic effect is produced by certain steroidal alkaloid teratogens from the plant - most notably the compound cyclopamine. Cyclopamine is a C-nor-D-homo steroid with fused furanopiperidine rings E and F at right angles to the plane of the steroid because of spiro attachment at C-17 of the steroid. Among veratrum alkaloids, only those with an intact furan ring E were teratogenic in sheep, whereas those in which the peperidine ring is not rigidly positioned at right angles to the steroid were not. Many ruminants and laboratory animals are susceptible to the teratogen. It has wide species and tissue specificity and appears to have a direct effect on the embryo, not as a consequence of metabolic alteration of its structure nor as an indirect effect through a maternal influence. Other plant sources, notably potatoes, tomatoes, and eggplant contain related spirosolane steroidal alkaloids. Among naturally occurring spirosolanes, solasodine is teratogenic in hamsters, but neither tomatidine not diosgenin, the non-nitrogen containing analog of solasodine, is teratogenic. Results of these and other studies suggest that a basic nitrogen positioned alpha with respect to the steroidal plane and at appropriate distance beyond the D ring confers the teratogenicity on the molecule. Potato sprouts with high alkaloid content are teratogenic in hamsters, but tubers and peels are not.

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“…1) are detected in tissues of tubers except in the pith or center portion (Maga, 1980). It has been reported that these glycoalkaloids show acute toxicity (Jellema et al, 1980; McMillan & Thompson, 1980), chronic toxicity (Mun et al, 1975;Keeler et al, 1976), and have a bitter taste (Sinden & Deahl, 1976; Woolfe, 1987). The intrinsic glycoalkaloid content in tubers of commercial potato cultivars is low due to selection in breeding, but the content may increase in response to environmental stress conditions, such as light (Friedman, 1997;Griffiths et al, 1994;Kozukue et al, 1993;Maga, 1980;Percival & Dixon, 1994;Percival, 1999; Sinden et al, 1984; Woolfe, 1987), frost and hail damage, and wounding during harvesting or postharvest handling (Woolfe, 1987).…”

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confidence: 99%

Quantification of Light-Induced Glycoalkaloids, .ALPHA.-Solanine and .ALPHA.-Chaconine, in Four Potato Cultivars (Solanum tuberosum L.) Distributed in Japan by LC/MS

Chuda¹,

Tsuda

Ohara-Takada

et al. 2004

FSTR

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The major glycoalkaloids, a-solanine and a-chaconine, in potato tubers were determined by LC/ESI-MS. The average recoveries from spiked samples by the method used in this study were more than 94% with RSD of analytical values less than 5% for both oe-solanine and a-chaconine. The total glycoalkaloid contents in tubers of four potato cultivars distributed in Japan, cv. Irish Cobbler, Touya, May Queen, and Sayaka, were compared. There was no significant difference in glycoalkaloid content between immature and mature tubers among all the cultivars tested. There was also no significant difference among cultivars in glycoalkaloid content at either the immature or mature stage, except for May Queen, which had higher glycoalkaloid contents at both stages. Glycoalkaloid content increased significantly in cv. May Queen and Touya with 7 days of light exposure immediately after harvest. The light exposure increased glycoalkaloid content in the long-term stored tubers of all four cultivars tested and that in the short-term stored tubers, except for Sayaka.Keywords: solanum tuberosum, potato, glycoalkaloids, oe-solanine, oe-chaconine, LC/MS, Iight. IntroductionToxic glycoalkaloids have been found in plants of the Solanaceae family, such as tomato, eggplant and potato. The major potato glycoalkaloids, namely, oc-solanine and cr-chaconine, (Fig. 1) are detected in tissues of tubers except in the pith or center portion (Maga, 1980). It has been reported that these glycoalkaloids show acute toxicity (Jellema et al., 1980; McMillan & Thompson, 1980), chronic toxicity (Mun et al., 1975;Keeler et al., 1976), and have a bitter taste (Sinden & Deahl, 1976; Woolfe, 1987). The intrinsic glycoalkaloid content in tubers of commercial potato cultivars is low due to selection in breeding, but the content may increase in response to environmental stress conditions, such as light (Friedman, 1997;Griffiths et al., 1994;Kozukue et al., 1993;Maga, 1980;Percival & Dixon, 1994;Percival, 1999; Sinden et al., 1984; Woolfe, 1987), frost and hail damage, and wounding during harvesting or postharvest handling (Woolfe, 1987). Among these stress conditions, the stimulation of glycoalkaloid accumulation with light exposure is a major problem for farmers, packers, suppliers, and vendors of potato (Percival & Dixon, 1994). This is because potato is exposed to various lights and illuminations, such as daylight, fluorescent light, and incandescent light, during harvest, transport, and marketing. The E-mail: chuda @ affrc . go . j p increase in glycoalkaloid content lowers the quality of potato tubers for market.The intrinsic glycoalkaloid content and the accumulation of glycoalkaloids with light exposure in potato tubers vary with physiological stages, i.e., immaturity, full maturity and aging (stored potato) as well as with cultivars (Griffiths et al., 1994; Sinden et al., 1984). In Japan, some potato tubers are harvested before full maturity and consumed without storage. Most of them, however, are harvested at full maturity and stored for various periods, ...

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Teratogenicity of the solatium alkaloid solasodine and of ‘Kennebec’ potato sprouts in hamsters

Cited by 43 publications

References 9 publications

Aspartate‐70 to glycine substitution confers resistance to naturally occurring and synthetic anionic‐site ligands on inovo produced human butyrylcholinesterase

Aspartate‐70 to glycine substitution confers resistance to naturally occurring and synthetic anionic‐site ligands on inovo produced human butyrylcholinesterase

Cyclopamine and related steroidal alkaloid teratogens: Their occurrence, structural relationship, and biologic effects

Quantification of Light-Induced Glycoalkaloids, .ALPHA.-Solanine and .ALPHA.-Chaconine, in Four Potato Cultivars (Solanum tuberosum L.) Distributed in Japan by LC/MS

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