Content deleted Content added
m →Physical and chemical properties: fixed CS1 error & added more info to citation & ce |
m Open access bot: doi added to citation with #oabot. |
||
Line 139:
RLA may function ''in vivo'' like a B-vitamin and at higher doses like plant-derived nutrients, such as [[curcumin]], [[sulforaphane]], [[resveratrol]], and other nutritional substances that induce [[Drug metabolism#Phase II – conjugation|phase II detoxification enzymes]], thus acting as cytoprotective agents.<ref name="Shay in Packer">{{cite book |last1= Shay |first1= KP |last2= Shenvi |first2= S |last3= Hagen |first3= TM |chapter= Ch. 14 Lipoic Acid as an Inducer of Phase II Detoxification Enzymes Through Activation of Nr-f2 Dependent Gene Expression|title=Lipoic Acid: Energy Production, Antioxidant Activity and Health Effects|pages= 349–71}} In {{harvnb|Packer|Patel|2008}}.</ref><ref>{{cite journal |last1=Lii |first1= CK |last2= Liu |first2= KL |last3= Cheng |first3= YP |last4= Lin |first4= AH |last5= Chen |first5= HW |last6= Tsai |first6= CW |display-authors= 4 |title= Sulforaphane and alpha-lipoic acid upregulate the expression of the pi class of glutathione S-transferase through c-jun and Nrf2 activation |journal= [[Journal of Nutrition]] |volume= 140 |issue= 5 |pages= 885–92 |date= May 2010 |pmid= 20237067 |doi= 10.3945/jn.110.121418 |doi-access= free }}</ref> This stress response indirectly improves the antioxidant capacity of the cell.<ref name= "Shay08">{{cite journal |pmid= 18409172 |last1= Shay |first1= KP |doi= 10.1002/iub.40 |last2= Moreau |first2= RF |last3= Smith |first3= EJ |last4= Hagen |first4= TM |title= Is alpha-lipoic acid a scavenger of reactive oxygen species in vivo? Evidence for its initiation of stress signaling pathways that promote endogenous antioxidant capacity |journal= IUBMB Life |volume= 60 |issue= 6 |date= June 2008 |pages= 362–7 |s2cid= 33008376 |doi-access= free }}</ref>
The (''S'')-enantiomer of LA was shown to be toxic when administered to thiamine-deficient rats.<ref>{{cite journal |doi= 10.1016/0003-9861(60)90051-5 |pmid= 13825981 |last1= Gal |first1= EM |last2= Razevska |first2= DE |title= Studies on the in vivo metabolism of lipoic acid. 1. The fate of DL-lipoic acid-S35 in normal and thiamine-deficient rats |journal= [[Archives of Biochemistry and Biophysics]] |volume= 89 |date= August 1960 |pages= 253–61 |issue= 2}}</ref><ref name="Gal1965">{{cite journal |doi= 10.1038/207535a0 |pmid= 5328673 |last1= Gal |first1= EM |title= Reversal of selective toxicity of (-)-alpha-lipoic acid by thiamine in thiamine-deficient rats |journal= [[Nature (journal)|Nature]] |volume= 207 |issue= 996 |date= July 1965 |page= 535|bibcode= 1965Natur.207..535G |s2cid= 4146866 |doi-access= free }}</ref>
Several studies have demonstrated that SLA either has lower activity than RLA or interferes with the specific effects of RLA by [[competitive inhibition]].<ref>{{cite patent |inventor1-last= Ulrich |inventor1-first= H |inventor2-last= Weischer |inventor2-first= CH |inventor3-last= Engel |inventor3-first= J |inventor4-last= Hettche |inventor4-first= H |title= Pharmaceutical compositions containing R-alpha-lipoic acid or S-alpha.-lipoic acid as active ingredient |country= US |number= 6271254 |gdate= 2001-08-07 |status= patent |assign1= ASTA Pharma |fdate= 1998-02-02 |pridate= 1989-11-09 |postscript= .}}</ref><ref>{{cite journal |pmid= 8673020 |last1= Kilic |first1= F |last2= Handelman |first2= GJ |last3= Serbinova |first3= E |last4= Packer |first4= L |last5= Trevithick |first5= JR |display-authors= 4 |title= Modelling cortical cataractogenesis 17: In vitro effect of a-lipoic acid on glucose-induced lens membrane damage, a model of diabetic cataractogenesis |journal= Biochemistry and Molecular Biology International |volume= 37 |issue= 2 |date= October 1995 |pages= 361–70}}</ref><ref>{{cite conference |last1= Artwohl |first1= M |last2= Schmetterer |first2= L |last3= Rainer |first3= G |last4= unknown |display-authors= 3 |date= September 2000|title= Modulation by antioxidants of endothelial apoptosis, proliferation, & associated gene/protein expression |conference= 36th Annual Meeting of the European Association for the Study of Diabetes, 17–21 September 2000, Jerusalem, Israel. |journal= [[Diabetologia]] |volume= 43 |issue= Suppl 1 |page= Abs 274 |publication-date= August 2000 |no-pp= yes |pmid= 11008622}}</ref><ref>{{cite journal |pmid= 9252495 |last1= Streeper |first1= RS |last2= Henriksen |first2= EJ |last3= Jacob |first3= S |last4= Hokama |first4= JY |last5= Fogt |first5= DL |last6= Tritschler |first6= HJ |display-authors= 4 |title= Differential effects of lipoic acid stereoisomers on glucose metabolism in insulin-resistant skeletal muscle |journal= [[American Journal of Physiology|AJP: Endocrinology and Metabolism]] |volume= 273 |issue= 1 Pt 1 |date= July 1997 |pages= E185–91|doi= 10.1152/ajpendo.1997.273.1.E185 }}</ref><ref>{{cite journal |pmid= 14991456 |last1= Frölich |first1= L |last2= Götz |first2= ME |last3= Weinmüller |first3= M |last4= Youdim |first4= MB |last5= Barth |first5= N |last6= Dirr |first6= A |last7= Gsell |first7= W |last8= Jellinger |first8= K |last9= Beckmann |first9= H |last10= Riederer |first10= P |display-authors= 4 |title= (r)-, but not (s)-alpha lipoic acid stimulates deficient brain pyruvate dehydrogenase complex in vascular dementia, but not in Alzheimer dementia |journal = Journal of Neural Transmission |volume= 111 |issue= 3 |date= March 2004 |pages= 295–310 |doi= 10.1007/s00702-003-0043-5|s2cid= 20214857 }}</ref>
| |||