Advanced search
Publication Cover
Natural Product Research
Formerly Natural Product Letters
Volume 31, 2017 - Issue 13
Submit an article Journal homepage
241
Views
8
CrossRef citations to date
0
Altmetric
Research Articles

Design and synthesis of 28-hydroxy protopanaxadiol as a novel probe template

Ze-Yun LiuSchool of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University, Yantai, China
,
Heng-Yuan ZhangState Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing, China
,
Yi BiSchool of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University, Yantai, ChinaCorrespondence[email protected]
,
Xian-Xuan LiuSchool of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University, Yantai, China
,
Jing LuSchool of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University, Yantai, China
,
Xiao-Chen ZhangSchool of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University, Yantai, China
,
Jin-Yi XuState Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing, ChinaCorrespondence[email protected]
ORCID Iconhttp://orcid.org/0000-0002-1961-0402
ORCID Icon,
Chong-Zhi WangTang Center for Herbal Medicine Research, University of Chicago, Chicago, IL, USA;Department of Anesthesia and Critical Care, University of Chicago, Chicago, IL, USA
&
Chun-Su YuanTang Center for Herbal Medicine Research, University of Chicago, Chicago, IL, USA;Department of Anesthesia and Critical Care, University of Chicago, Chicago, IL, USA
 show all
Pages 1523-1528 | Received 19 Sep 2016, Accepted 20 Dec 2016, Published online: 20 Jan 2017

References

  • Baldwin JE, Jones RH, Najera C, Yus M. 1985. Functionalisation of unactivated methyl groups through cyclopalladation reactions. Tetrahedron. 41:699–711.10.1016/S0040-4020(01)96448-8
  • Carr K, Saxton HM, Sutherland JK. 1988. The 4α-demethylation of lanostenone. J. Chem. Soc., Perkin Trans. 1. 1:1599–1601.10.1039/P19880001599
  • Constable AG, McDonald WS, Sawkins LC, Shaw BL. 1980. Transition-metal–carbon bonds. Part 45. Attempts to cyclopalladate some aliphatic oximes, NN-dimethylhydrazones, ketazines, and oxime O-allyl ethers. Crystal structures of [Pd2{CH2C(CH3)2C([double bond, length half m-dash]NOH)CH3}2Cl2] and [Pd{CH2C([double bond, length half m-dash]NNMe2)C(CH3)3}(acac)]. J Chem Soc Dalton Trans. 10:1992–2000.10.1039/DT9800001992
  • Duan Y, Nicholson RA. 2008. 20(S)-protopanaxadiol and the ginsenoside Rh2 inhibit Na+ channel-activated depolarization and Na+ channel-dependent amino acid neurotransmitter release in synaptic fractions isolated from mammalian brain. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 147:351–356.10.1016/j.cbpc.2008.01.001
  • Honda T, Janosik T, Honda Y, Han J, Liby KT, Williams CR, Couch RD, Anderson AC, Sporn MB, Gribble GW. 2004. Design, synthesis, and biological evaluation of biotin conjugates of 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid for the isolation of the protein targets. J Med Chem. 47:4923–4932.10.1021/jm049727e
  • Kwak JH, Park JY, Lee D, Kwak JY, Park EH, Kim KH, Park HJ, Kim HY, Jang HJ, Ham J, et al. 2014. Inhibitory effects of ginseng sapogenins on the proliferation of triple negative breast cancer MDA-MB-231 cells. Bioorg Med Chem Lett. 24:5409–5412.10.1016/j.bmcl.2014.10.041
  • Lee JS, Han SY, Kim MS, Yu CM, Kim MH, Kim SH, Min YK, Kim BT. 2006. Synthesis of novel chemical probes for the study of tanshinone binding proteins. Bioorg Med Chem Lett. 16:4733–4737.10.1016/j.bmcl.2006.07.019
  • Leslie BJ, Hergenrother PJ. 2008. Identification of the cellular targets of bioactive small organic molecules using affinity reagents. Chem Soc Rev. 37:1347–1360.10.1039/b702942j
  • Li XJ. 2002. Pharmacoproteomics and drug discovery. Prog Physiol Sci. 33:209–214.
  • Liao J, Sun J, Niu Y, Yu B. 2011. Synthesis of ginsenoside Rh2 and chikusetsusaponin-LT8 via gold(I)-catalyzed glycosylation with a glycosyl ortho-alkynylbenzoate as donor. Tetrahedron Lett. 52:3075–3078.10.1016/j.tetlet.2011.04.003
  • Mochizuki M, Yoo Y, Matsuzawa K, Sato K, Saiki I, Tonooka S, Samukawa K, Azuma I. 1995. Inhibitory effect of tumor metastasis in mice by saponins, ginsenoside-Rb2, 20(R)- and 20(S)-ginsenoside-Rg3, of red ginseng. Biol Pharm Bull. 18:1197–1202.10.1248/bpb.18.1197
  • Nag SA, Qin J, Wang W, Wang MH, Wang H, Zhang R. 2012. Ginsenosides as anticancer agents: in vitro and in vivo activities, structure-activity relationships, and molecular mechanisms of action. Front Pharmacol. 3:1–18.
  • Popovich DG, Kitts DD. 2002. Structure–function relationship exists for ginsenosides in reducing cell proliferation and inducing apoptosis in the human leukemia (THP-1) cell line. Arch Biochem Biophys. 406:1–8.10.1016/S0003-9861(02)00398-3
  • Qi LW, Wang CZ, Yuan CS. 2010. American ginseng: potential structure–function relationship in cancer chemoprevention. Biochem Pharmacol. 80:947–954.10.1016/j.bcp.2010.06.023
  • Saito A, Higgins M, Zheng S, Li W, Ojima I, Dinkova-Kostova AT, Honda T. 2013. Synthesis and biological evaluation of biotin conjugates of (±)-(4bS, 8aR, 10aS)-10a-ethynyl-4b, 8, 8-trimethyl-3, 7-dioxo-3, 4b, 7, 8, 8a, 9, 10, 10a-octahydro-phenanthrene-2, 6-dicarbonitrile, an activator of the Keap1/Nrf2/ARE pathway, for the isolation of its protein targets. Bioorg Med Chem Lett. 23:5540–5543.10.1016/j.bmcl.2013.08.058
  • Sun F, Zhu P, Yao H, Wu X, Xu J. 2012. A partial synthesis of 23-hydroxybetulonic acid and 23-hydroxybetulinic acid starting from betulinic acid. J Chem Res. 36:254–257.10.3184/174751912X13332875186150
  • Xu C, Teng J, Chen W, Ge Q, Yang Z, Yu C, Yang Z, Jia W. 2010. 20(S)-protopanaxadiol, an active ginseng metabolite, exhibits strong antidepressant-like effects in animal tests. Prog Neuro-psychopharmacol Biol Psychiatry. 34:1402–1411.10.1016/j.pnpbp.2010.07.010
  • Xu FX, Yuan C, Wan JB, Yan R, Hu H, Li SP, Zhang QW. 2015. A novel strategy for rapid quantification of 20(S)-protopanaxatriol and 20(S)-protopanaxadiol saponins in Panax notoginseng P. ginseng and P. quinquefolium. Nat Prod Res. 29:46–52.10.1080/14786419.2014.957698
  • Yang HQ, Li XJ. 2011. Chemical proteomics and discovery of drug targets. Acta Pharmacol Sin. 46:877–882.
  • Yu WL, Guizzunti G, Foley TL, Burkart MD, La Clair JJ. 2010. An optimized immunoaffinity fluorescent method for natural product target elucidation. J Nat Prod. 73:1659–1666.10.1021/np100371k

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.