P57 (glycoside)

P57 (glycoside)

Names
IUPAC name (3β,12β,14β)-3-[(O-6-Deoxy-3-O-methyl-β-D-glucopyranosyl-(1→4)-O-2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl)oxy]-14-hydroxy-12-[[(2E)-2-methyl-1-oxo-2-butenyl]]oxy]pregn-5-en-20-one
Other names P57 P57AS3
Identifiers
CAS Number	384329-61-7
3D model (Jmol)	Interactive image
ChemSpider	8138385
PubChem	9962786
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 Key: CBMQKMMZBOSHHP-VXXSQTRDSA-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	879.08 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

P57 is an oxypregnane steroidal glycoside isolated from the African cactiform Hoodia gordonii. P57 is thought to be the main active constituent from this plant that may be responsible for the possible appetite suppressant activity of Hoodia extracts.^[1][2][3]

In a rat study at Brown Medical School, intracerebroventricular injections of the purified P57 demonstrated that the compound has a likely central nervous system (CNS) mechanism of action.^[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

• Hoodia gordonii, for additional information about Hoodia gordonii
• Anorectic, for additional information about appetite suppressants

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. 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:10.5555/jaoi.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.