Solanidine

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Solanidine

Other names Solatubin; Solatubine; Solanid-5-en-3beta-ol, Solanid-5-en-3-beta-ol
Identifiers
CAS number	80-78-4
PubChem	65727
ChemSpider	59150
ChEBI	CHEBI:28374
Jmol-3D images	{{#if:C[C@@H]1CN2[C@@]3([H])C[C@@]4([H])[C@]5([H])CCC6=C[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@@]3([H])[C@H](C)[C@@]2([H])CC1\|Image 1
SMILES C[C@@H]1CN2[C@@]3([H])C[C@@]4([H])[C@]5([H])CCC6=C[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@@]3([H])[C@H](C)[C@@]2([H])CC1
InChI InChI=1S/C27H43NO/c1-16-5-8-23-17(2)25-24(28(23)15-16)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h6,16-17,19-25,29H,5,7-15H2,1-4H3/t16-,17+,19-,20+,21-,22-,23+,24-,25-,26-,27-/m0/s1 Key: JVKYZPBMZPJNAJ-OQFNDJACSA-N InChI=1/C27H43NO/c1-16-5-8-23-17(2)25-24(28(23)15-16)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h6,16-17,19-25,29H,5,7-15H2,1-4H3/t16-,17+,19-,20+,21-,22-,23+,24-,25-,26-,27-/m0/s1 Key: JVKYZPBMZPJNAJ-OQFNDJACBI
Properties
Molecular formula	C₂₇H₄₃NO
Molar mass	397.64 g mol⁻¹
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Solanidine is a poisonous steroidal alkaloid chemical compound that occurs in plants of the Solanaceae family, such as potato and Solanum americanum.^[1]^[2] Human ingestion of solanidine also occurs via the consumption of the glycoalkaloids, α-solanine and α-chaconine, present in potatoes.^[3]^[4] The sugar portion of these glycoalkaloids hydrolyses in the body, leaving the solanidine portion.^[4] Solanidine occurs in the blood serum of normal healthy people who eat potato, and serum solanidine levels fall markedly once potato consumption ceases.^[5] Solanidine from food is also stored in the human body for prolonged periods of time, and it's been suggested by researchers that it could be released during times of metabolic stress with the potential for deleterious consequences.^[6] Solandine is responsible for neuromuscular syndromes via cholinesterase inhibition.^[7]^[8]

Uses

Solanidine is a very important precursor for the synthesis of hormones and some pharmacologically active compounds.^[1]

References

↑ 1.0 1.1 Nikolic, NC; Stankovic, MZ (2003). "Solanidine hydrolytic extraction and separation from the potato (Solanum tuberosum L.) vines by using solid-liquid-liquid systems". Journal of agricultural and food chemistry 51 (7): 1845–9. doi:10.1021/jf020426s. PMID 12643640.
↑ Mohy-ud-dint, A., Khan,Z., Ahmad, M., Kashmiri, M.A. (2010). "Chemotaxonomic value of alkaloids in Solanum nigrum complex". Pakistan Journal of Botany 42 (1): 653–660.
↑ Friedman, M; Henika, PR; MacKey, BE (2003). "Effect of feeding solanidine, solasodine and tomatidine to non-pregnant and pregnant mice". Food and chemical toxicology 41 (1): 61–71. PMID 12453729.
↑ 4.0 4.1 Kuiper-Goodman, T., Nawrot, P.S., Solanine and Chaconine, IPCS Inchem
↑ Harvey, M.H.; McMillan, M.; Morgan, M.R.A.; Chan, H. W. S. (1985). "Solanidine is Present in Sera of Healthy Individuals and in Amounts Dependent on their Dietary Potato Consumption". Human & Experimental Toxicology 4 (2): 187. doi:10.1177/096032718500400209.
↑ Claringbold, W. D. B.; Few, J. D.; Renwick, J. H. (1982). "Kinetics and retention of solanidine in man". Xenobiotica 12 (5): 293–302. doi:10.3109/00498258209052469. PMID 7135998.
↑ Bushway, R.J., Savage, S.A., Ferguson, B.S., Inhibition of acetyl cholinesterase by solanaceous glycoalkaloids and alkaloids, American Potato Journal, Aug. 1987, Volume 64, Issue 8, pp 409-413
↑ Everist, S.L., Poisonous Plants of Australia, Angus and Robertson, 1974, ISBN 0207142289.

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