protopanaxatriol

{{Short description|Ginseng plant extract}}

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| verifiedrevid = 424890248

| ImageFile=Protopanaxatriol.svg

| ImageSize=200px

| IUPACName = (20R)-Dammar-24-ene-3β,6α,12β,20-tetrol

| SystematicName = (1S,3aR,3bR,5S,5aR,7S,9aR,9bR,11R,11aR)-1-[(2R)-2-Hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-5,7,11-triol

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|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo= 34080-08-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = ZMK19P3WMP

| PubChem=9847853

| KEGG=C20716

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 8023566

| SMILES = O[C@H]4[C@@H]1[C@H](CC[C@]1([C@]2([C@@H]([C@]3(C)[C@@H]([C@@H](O)C2)C(C)(C)[C@@H](O)CC3)C4)C)C)[C@@](O)(C)CC\C=C(/C)C

| InChI = 1/C30H52O4/c1-18(2)10-9-13-30(8,34)19-11-15-28(6)24(19)20(31)16-22-27(5)14-12-23(33)26(3,4)25(27)21(32)17-29(22,28)7/h10,19-25,31-34H,9,11-17H2,1-8H3/t19-,20+,21-,22+,23-,24-,25-,27+,28+,29+,30+/m0/s1

| InChIKey = SHCBCKBYTHZQGZ-DLHMIPLTBT

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C30H52O4/c1-18(2)10-9-13-30(8,34)19-11-15-28(6)24(19)20(31)16-22-27(5)14-12-23(33)26(3,4)25(27)21(32)17-29(22,28)7/h10,19-25,31-34H,9,11-17H2,1-8H3/t19-,20+,21-,22+,23-,24-,25-,27+,28+,29+,30+/m0/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = SHCBCKBYTHZQGZ-DLHMIPLTSA-N

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|Section2={{Chembox Properties

| C=30 | H=52 | O=4

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|Section3={{Chembox Hazards

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Protopanaxatriol (PPT) is an organic compound that is an aglycone of ginsenosides, a group of steroid glycosides.{{cite journal | doi = 10.1016/0024-3205(95)00124-o | title = Ginsenosides of the protopanaxatriol group cause endothelium-dependent relaxation in the rat aorta | date = 1995 | last1 = Kang | first1 = Soo Yeon | last2 = Schini-Kerth | first2 = Valérie B. | last3 = Kim | first3 = Nak Doo | journal = Life Sciences | volume = 56 | issue = 19 | pages = 1577–1586 | pmid = 7723586 }} It is a dammarane-type tetracyclic triterpene sapogenins found in ginseng (Panax ginseng) and in notoginseng (Panax pseudoginseng).

In rats, the oral bioavailbility is about 3.7% and the half-life is 0.80 hours (when given as a PPD-PPT mixture). PPT is unstable in acid, showing 40% degradation after 4 hours at 37°C both in pH 1.2 buffer solution and rat stomach contents.{{cite journal |last1=Kong |first1=LT |last2=Wang |first2=Q |last3=Xiao |first3=BX |last4=Liao |first4=YH |last5=He |first5=XX |last6=Ye |first6=LH |last7=Liu |first7=XM |last8=Chang |first8=Q |title=Different pharmacokinetics of the two structurally similar dammarane sapogenins, protopanaxatriol and protopanaxadiol, in rats. |journal=Fitoterapia |date=April 2013 |volume=86 |pages=48–53 |doi=10.1016/j.fitote.2013.01.019 |pmid=23391424}} It is extensively metabolized in mice.{{cite journal |last1=Wang |first1=YZ |last2=Wang |first2=YS |last3=Chu |first3=SF |last4=Chen |first4=NH |last5=Zhang |first5=JT |title=Protopanaxatriol metabolites identified by LC-MS/MS after oral administration in mice. |journal=International Journal of Clinical Pharmacology and Therapeutics |date=April 2010 |volume=48 |issue=4 |pages=282–90 |doi=10.5414/cpp48282 |pmid=20353750}}