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P57 (glycoside)

P57 (glycoside)

Chemical 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
Chemical formula	C₄₇H₇₄O₁₅
Molecular mass	879.08 g/mol
CAS number	[384329-61-7]
Density	? g/cm³
Melting point	? °C
SMILES	C[C@@]34[C@@](CC[C@@H]4[C@@](C)=O) (O)[C@]2([H])CC=C1C[C@@H](O[C@H]5C [C@@H](OC)[C@H](O[C@H]6C[C@@H](OC) [C@H](O[C@H]7[C@@H](O)[C@H](OC)[C@H] (O)C(C)O7)C(C)O6)C(C)O5)CC[C@@] (C)1[C@]([H])2C[C@H]3OC(/C(C)=C/C)=O
Disclaimer and references

P57 is an oxypregnane steroidal glycoside isolated from the African cactiform Hoodia gordonii. P57 is the only active constituent from this plant that has been reported to be responsible for the potential appetite suppressant activity of Hoodia extracts.

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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. 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%.

References

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.
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. PMID 16792058. Retrieved on 2006-07-11.

Bond:	O-glycosidic bond \| S-glycosidic bond \| N-glycosidic bond
Geometry:	α-Glycoside \| β-Glycoside \| 1,4-Glycoside \| 1,6-Glycoside
Glycone:	Glucoside \| Fructoside \| Glucuronide
Aglycone:	Alcoholic glycoside \| Anthraquinone glycoside \| Coumarin glycoside \| Cyanogenic glycoside \| Flavonoid glycoside \| Phenolic glycoside \| Saponin \| Cardiac glycoside \| Steviol glycoside \| Thioglycoside \| Glycosylamine \| Bufanolide \| Cardenolide