P57 (glycoside)

P57 (glycoside)

Names
IUPAC name 14-Hydroxy-3β-[(3-O-methyl-β-D-quinovopyranosyl)-(1→4)-(3-O-methyl-2-deoxy-β-D-ribo-hexopyranosyl)-(1→4)-3-O-methyl-2-deoxy-β-D-ribo-hexopyranosyloxy]-20-oxo-14β-pregn-5-en-12β-yl (2E)-2-methylbut-2-enoate
Systematic IUPAC name (11S,13aS,13bR,17S,19aR,19bS,111R,111aS,32R,34S,35R,36R,52S,54S,55R,56R,72S,73R,74S,75R,76R)-11-Acetyl-13a,73,75-trihydroxy-34,54,74-trimethoxy-19a,111a,36,56,76-pentamethyl-12,13,13a,14b,14,16,17,18,19,19a,19b,110,111,111a-tetradecahydro-11H-2,4,6-trioxa-3,5(2,5),7(2)-tris(oxana)-1(7)-cyclopenta[a]phenanthrenaheptaphan-111-yl (2E)-2-methylbut-2-enoate
Other names P57 P57AS3
Identifiers
CAS Number	384329-61-7  Y
3D model (JSmol)	Interactive image
ChemSpider	8138385  N
PubChem CID	9962786
UNII	870A6Q6XVJ  Y
CompTox Dashboard (EPA)	DTXSID20433336
InChI InChI=1S/C47H74O15/c1-12-23(2)43(51)60-35-20-32-31(47(52)18-16-30(24(3)48)46(35,47)8)14-13-28-19-29(15-17-45(28,32)7)59-36-21-33(53-9)40(26(5)56-36)61-37-22-34(54-10)41(27(6)57-37)62-44-39(50)42(55-11)38(49)25(4)58-44/h12-13,25-27,29-42,44,49-50,52H,14-22H2,1-11H3/b23-12+/t25-,26-,27-,29+,30-,31-,32+,33+,34+,35-,36+,37+,38-,39-,40-,41-,42+,44+,45+,46+,47+/m1/s1 N Key: CBMQKMMZBOSHHP-VXXSQTRDSA-N N InChI=1/C47H74O15/c1-12-23(2)43(51)60-35-20-32-31(47(52)18-16-30(24(3)48)46(35,47)8)14-13-28-19-29(15-17-45(28,32)7)59-36-21-33(53-9)40(26(5)56-36)61-37-22-34(54-10)41(27(6)57-37)62-44-39(50)42(55-11)38(49)25(4)58-44/h12-13,25-27,29-42,44,49-50,52H,14-22H2,1-11H3/b23-12+/t25-,26-,27-,29+,30-,31-,32+,33+,34+,35-,36+,37+,38-,39-,40-,41-,42+,44+,45+,46+,47+/m1/s1 Key: CBMQKMMZBOSHHP-VXXSQTRDBA
SMILES O=C(C)[C@H]1CC[C@@]7(O)[C@]1(C)[C@H](OC(=O)/C(=C/C)C)C[C@H]6[C@H]7C/C=C5/C[C@@H](O[C@@H]4O[C@H](C)[C@@H](O[C@@H]3O[C@@H]([C@@H](O[C@@H]2O[C@@H]([C@@H](O)[C@H](OC)[C@H]2O)C)[C@@H](OC)C3)C)[C@@H](OC)C4)CC[C@@]56C
Properties
Chemical formula	C47H74O15
Molar mass	879.094 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

P57 is an oxypregnane steroidal glycoside isolated from the traditional African medicine Hoodia gordonii . P57 is hypothesized to be the chemical constituent responsible for the putative appetite suppressant activity of Hoodia. ^{[1] [2] [3]}

In a study on rats at Brown Medical School, intracerebroventricular injections of the purified P57 demonstrated that the compound has a likely central nervous system (CNS) mechanism of action like that of neuroactive steroids. ^[4] The studies demonstrated that the compound increases the content of ATP by 50-150% in hypothalamic neurons. In addition, third ventricle administration of P57 reduced subsequent 24-hour food intake by 40-60%.

See also

• Anorectic, for additional information about appetite suppressants
• Neuroactive steroid

References

1. van Heerden FR, Marthinus Horak R, Maharaj VJ, Vleggaar R, Senabe JV, Gunning PJ (Oct 2007). "An appetite suppressant from Hoodia species". Phytochemistry. 68 (20): 2545–53. Bibcode:2007PChem..68.2545V. doi:10.1016/j.phytochem.2007.05.022. PMID   17603088.
2. van Heerden FR (Oct 2008). "Hoodia gordonii: a natural appetite suppressant". Journal of Ethnopharmacology. 119 (3): 134–137. doi:10.1016/j.jep.2008.08.023. PMID   18804523.
3. Avula, Bharathi; Yan-Hong Wang; Rahul S. Pawar; Yatin J. Shukla; Brian Schaneberg; Ikhlas A. Khan (May–June 2006). "Determination of the appetite suppressant P57 in Hoodia gordonii plant extracts and dietary supplements by liquid chromatography/electrospray ionization mass spectrometry (LC-MSD-TOF) and LC-UV methods". Journal of AOAC International. 89 (3): 606–611. doi: 10.1093/jaoac/89.3.606 . PMID   16792058 . Retrieved 2006-07-11.
4. MacLean, David B.; Lu-Guang Luo (September 2004). "Increased ATP content/production in the hypothalamus may be a signal for energy-sensing of satiety: studies of the anorectic mechanism of a plant steroidal glycoside". Brain Research. 1020 (1–2): 1–11. doi:10.1016/j.brainres.2004.04.041. PMID   15312781. S2CID   1994748.