摘要: P57和果同尼皂苷F是從南非火地亞仙人掌中分離得到的孕甾皂苷類化合物，具有抑制食欲的活性。主要針對P57和果同尼皂苷F的化學(xué)合成、生物活性和作用機(jī)制研究進(jìn)行綜述，旨在為相關(guān)的健康產(chǎn)品和藥物研發(fā)提供參考。

Abstract: P57 and Gordonoside F are pregnane saponins isolated from a South African cactus-like Hoodia gordonii with appetite-suppressive activity. This article reviews the advances in research on the chemical synthesis, biological activities and action mechanisms of P57 and Gordonoside F, so as to provide some reference for the development of relevant health products and drugs.

[1]

Van Heerden F R. Hoodia gordonii:a natural appetite suppressant[J]. J Ethnopharmacol, 2008, 119(3):434-437.

[2]

Vermaak I, Hamman J H, Viljoen A M. Hoodia gordonii:an up-to-date review of a commercially important anti-obesity plant[J]. Planta Med, 2011, 77(11):1149-1160.

[3]

Van Heerden F R, Vleggaar R, Horak R M, et al. Pharmaceutical compositions having appetite suppressant activity:WO 98/34624[P]. 1998-10-22.

[4]

Raskin I, O'neal J M, III. Appetite-suppressing compositions and methods:US 7265101 B2[P]. 2006-04-20.

[5]

Rubin I D, Cawthorne M A, Bindra J S. Extracts, compounds & pharmaceutical compositions having anti-diabetic and their use:US 7033616 B2[P]. 2002-02-01.

[6]

Horak R M, Maharaj V, Hakkinen J. A composition comprising a pregnenone derivative and an NSAID:GB 2396815[P]. 1999-10-27.

[7]

Van Heerden F R, Marthinus Horak R, Maharaj V J, et al. An appetite suppressant from Hoodia species[J]. Phytochemistry, 2007, 68(20):2545-2553.

[8]

Dall'acqua S, Innocenti G. Steroidal glycosides from Hoodia gordonii[J]. Steroids, 2007, 72(6/7):559-568.

[9]

Pawar R S, Shukla Y J, Khan I A. New calogenin glycosides from Hoodia gordonii[J]. Steroids, 2007, 72(13):881-891.

[10]

Pawar R S, Shukla Y J, Khan S I, et al. New oxypregnane glycosides from appetite suppressant herbal supplement Hoodia gordonii[J]. Steroids, 2007, 72(6/7):524-534.

[11]

Shukla Y J, Pawar R S, Ding Y, et al. Pregnane glycosides from Hoodia gordonii[J]. Phytochemistry, 2009, 70(5):675-683.

[12]

Smith C, Krygsman A. Hoodia gordonii:to eat, or not to eat[J]. J Ethnopharmacol, 2014, 155(2):987-991.

[13]

Zhang S, Ma Y, Li J, et al. Molecular matchmaking between the popular weight-loss herb Hoodia gordonii and GPR119, a potential drug target for metabolic disorder[J]. Proc Natl Acad Sci USA, 2014, 111(40):14571-14576.

[14]

Geoffroy P, Ressault B, Marchioni E, et al. Synthesis of Hoodigogenin A, aglycone of natural appetite suppressant glycosteroids extracted from Hoodia gordonii[J]. Steroids, 2011, 76(7):702-708.

[15]

Zhang J, Shi H, Ma Y, et al. Expeditious synthesis of saponin P57, an appetite suppressant from Hoodia plants[J]. Chem Commun, 2012, 48(69):8679-8681.

[16]

Li Y, Yang Y, Yu B. An efficient glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors under the catalysis of Ph3PAuOTf[J]. Tetrahedron Lett, 2008, 49(22):3604-3608.

[17]

Li Y, Yang X, Liu Y, et al. Gold(I)-catalyzed glycosylation with glycosyl ortho-alkynylbenzoates as donors:general scope and application in the synthesis of a cyclic triterpene saponin[J]. Chem Eur J, 2010, 16(6):1871-1882.

[18]

Zhu Y, Yu B. Characterization of the isochromen-4-yl-gold(I) intermediate in the gold(I)-catalyzed glycosidation of glycosyl ortho-alkynylbenzoates and enhancement of the catalytic efficiency thereof[J]. Angew Chem Int Ed, 2011, 50(36):8329-8332.

[19]

Yu B, Sun J, Yang X. Assembly of naturally occurring glycosides, evolved tactics, and glycosylation methods[J]. Acc Chem Res, 2012, 45(8):1227-1236.

[20]

Tang Y, Li J, Zhu Y, et al. Mechanistic insights into the gold(I)-catalyzed activation of glycosyl ortho-alkynylbenzoates for glycosidation[J]. J Am Chem Soc, 2013, 135(49):18396-18405.

[21]

Li W, Yu B. Gold-catalyzed glycosylation in the synthesis of complex carbohydrate-containing natural products[J]. Chem Soc Rev, 2018, 47(21):7954-7984.

[22]

Yu B. Gold(I)-catalyzed glycosylation with glycosyl o-alkynylbenzoates as donors[J]. Acc Chem Res, 2018, 51(2):507-516.

[23]

Templeton J F, Ling Y, Jin J, et al. Synthesis of 3β,14-dihydroxy-5β,14β-pregnan-20-one C-3 derivatives:ozonolysis of digitoxin and digitoxigenin and their derivatives followed by zinc-acetic acid reduction to the C-21 methyl ketone[J]. J Chem Soc, Perkin Trans 1, 1991(4):823-829.

[24]

Zhu Y, Yu B. Highly stereoselective beta-mannopyranosylation via the 1-alpha-glycosyloxy-isochromenylium-4-gold(I) intermediates[J]. Chem Eur J, 2015, 21(24):8771-8780.

[25]

Zhu Y, Shen Z, Li W, et al. Stereoselective synthesis of β-rhamnopyranosides via gold(i)-catalyzed glycosylation with 2-alkynyl-4-nitro-benzoate donors[J]. Org Biomol Chem, 2016, 14(5):1536-1539.

[26]

Shen Z, Mobarak H, Li W, et al. Synthesis of β-(1→2)-linked 6-deoxy-L-altropyranose oligosaccharides via gold(I)-catalyzed glycosylation of an ortho-hexynylbenzoate donor[J]. J Org Chem, 2017, 82(6):3062-3071.

[27]

Liu C, Ma Y, Pei C, et al. A glycal approach to the synthesis of pregnane glycoside P57[J]. Chin J Chem, 2018, 36(11):1007-1010.

[28]

Zhang X, Zhou Y, Zuo J, et al. Total synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects[J]. Nat Commun, 2015, 6:5879. Doi: 10.1038/ncomms6879.

[29]

Zhang X, Yu B. Tackling the challenge of the total synthesis of periploside A[J]. Synlett, 2018, 29(13):1683-1692.

[30]

Ma Y, Li Z, Shi H, et al. Assembly of digitoxin by gold(I)-catalyzed glycosidation of glycosyl o-alkynylbenzoates[J]. J Org Chem, 2011, 76(23):9748-9756.

[31] 馬玉勇. 洋地黃毒苷和果同尼皂苷F的全合成[D]. 上海:中國科學(xué)院上海有機(jī)化學(xué)研究所, 2013. [32]

Maclean D B, Luo L G. 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[J]. Brain Res, 2004, 1020(1/2):1-11.

[33]

Le Neve B, Foltz M, Daniel H, et al. The steroid glycoside H.g.-12 from Hoodia gordonii activates the human bitter receptor TAS2R14 and induces CCK release from HuTu-80 cells[J]. Am J Physiol Gastrointest Liver Physiol, 2010, 299(6):G1368-G1375.

[34]

Chen M C, Wu S V, Reeve J R, Jr., et al. Bitter stimuli induce Ca2+ signaling and CCK release in enteroendocrine STC-1 cells:role of L-type voltage-sensitive Ca2+ channels[J]. Am J Physiol Cell Physiol, 2006, 291(4):C726-C739.

[35]

Crovesy L, Rosado E L. Interaction between genes involved in energy intake regulation and diet in obesity[J]. Nutrition, 2019, 67/68:110547. Doi: 10.1016/j.nut.2019.06.027.

[36]

Johnson K O, Shannon O M, Matu J, et al. Differences in circulating appetite-related hormone concentrations between younger and older adults:a systematic review and meta-analysis[J]. Aging Clin Exp Res, 2020, 32(7):1233-1244.

[37]

Liaset B, Oyen J, Jacques H, et al. Seafood intake and the development of obesity, insulin resistance and type 2 diabetes[J]. Nutr Res Rev, 2019, 32(1):146-167.

[38]

Smith C, Krygsman A. Hoodia gordonii extract targets both adipose and muscle tissue to achieve weight loss in rats[J]. J Ethnopharmacol, 2014, 155(2):1284-1290.

[39]

Tsoukalas M, Muller C D, Lobstein A, et al. Pregnane glycosides from Cynanchum marnierianum stimulate GLP-1 secretion in STC-1 cells[J]. Planta Med, 2016, 82(11/12):992-999.

[40]

Sakamoto Y, Inoue H, Kawakami S, et al. Expression and distribution of Gpr119 in the pancreatic islets of mice and rats:predominant localization in pancreatic polypeptide-secreting PP-cells[J]. Biochem Biophys Res Commun, 2006, 351(2):474-480.

[41]

Chu Z L, Jones R M, He H, et al. A role for beta-cell-expressed G protein-coupled receptor 119 in glycemic control by enhancing glucose-dependent insulin release[J]. Endocrinology, 2007, 148(6):2601-2609.

[42]

Overton H A, Babbs A J, Doel S M, et al. Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small-molecule hypophagic agents[J]. Cell Metab, 2006, 3(3):167-175.

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