Preparation, purification and regioselective functionalization of protoescigenin-the main aglycone of escin complex

Molecules

Volumn 18, Issue 4, 2013, Pages 4389-4402

  Gruza, Mariusz M ^a   Jatczak, Kamil ^a   Zagrodzki, Bogdan ^a   Łaszcz, Marta ^a   Koziak, Katarzyna ^b   Malińska, Maura ^c   Cmoch, Piotr ^a,d   Giller, Tomasz ^a   Zegrocka Stendel, Oliwia ^b   Woźniak, Krzysztof ^c   Grynkiewicz, Grzegorz ^a  

^a INDUSTRIAL CHEMISTRY RESEARCH INSTITUTE   (Poland)

^b MEDICAL UNIVERSITY OF WARSAW   (Poland)

^c UNIVERSITY OF WARSAW   (Poland)

^d INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

Escin; Polymorphism; Protoescigenin diacetonide; Protoescigenin hydrates; X ray crystallography

Indexed keywords

ESCIN; SAPOGENIN;

ARTICLE; CHEMISTRY; ISOLATION AND PURIFICATION; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; ESCIN; SAPOGENINS;

EID: 84876755989     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18044389     Document Type: Article

References (22)

1. Pittler, M.H.; Ernst, E. Horse chesnut seed extract for chronic venous insufficiency. Cochrane Db. Syst. Rev. 2012, CD003230.
2. Sirtori, C.R. Aescin: Pharmacology, Pharmacokinetics and therapeutic profile. Pharmacol. Res. 2001, 44, 183-193.
3. Zhang, Z.; Li, S.; Lian, X.-Y. An overview of genus Aesculus. L.: ethnobotany, phytochemistry, and pharmacological activities. Pharmac. Crops 2010, 1, 24-51.
4. Persson, I.A.L.; Persson, K. Horse chesnut (Aesculus. hippocastanum L.). Recent Prog. Med. Plants 2010, 28, 159-171.
5. Zhou, X.Y.; Fu, F.H.; Li, Z.; Dong, Q.J.; He, J.; Wang, C.H. Escin, a natural mixture of triterpene saponins, exhibits antitumor activity against hepatocellular carcinoma. Planta. Med. 2009, 75, 1580-1585.
6. Dinda, B.; Debnath, S.; Mohanta, B.C.; Harigaya, Y. Naturally occurring triterpenoid saponins. Chem. Biodivers. 2010, 7, 2327-2579.
7. Jäger, S.; Trojan, H.; Kopp, T.; Laszczyk, M.N.; Scheffler, A. Pentacyclic triterpene distribution in various plants-rich sources for a new group of multi-potent plant extracts. Molecules 2009, 14, 2016-2031.
8. Newman, D.J.; Cragg, G.M. Natural products as sources of new drugs over the 30 years from 1981 to 2010. J. Nat. Prod. 2012, 75, 311-335.
9. Beutler, J.A. Natural products as a foundation for drug discovery. Curr. Protoc. Pharmacol. 2009, 46, 9.11.1-9.11.21.
10. Sporn, M.B.; Liby, K.T.; Yore, M.M.; Fu, L.; Lopchuk, J.M.; Gribble, G.W. New synthetic triterpenoids: potent agents for prevention and treatment of tissue injury caused by inflammatory and oxidative stress. J. Nat. Prod. 2011, 74, 537-545.
11. Sheng, H.; Sun, H. Synthesis, Biology and clinical significance of pentacyclic triterpenes: A multi-target approach to prevention and treatment of metabolic and vascular diseases. Nat. Prod. Rep. 2011, 28, 543-593.
12. Kuhn, R.; Löw, I. Über die protoäscigeninester aus Äscin. Tetrahedron 1966, 22, 1899-1906.
13. Wulff, G.; Tschesche, R. Über triterpene-XXVI: Über die struktur der rosskastaniensaponnie (Äscin) und die aglykone verwandter glykoside. Tetrahedron 1969, 25, 415-436.
14. Agrawal, P.K.; Thakur, R.S.; Shoolery, J.N. Application of 2D NMR spectroscopy to the structural establishment of the major hydrolysis product of escin. J. Nat. Prod. 1991, 54, 1394-1396.
15. Gruza, M.M.; Zegrocka-Stendel, O.; Giller, T.; Grynkiewicz, G.; Giller, T.; Łaszcz, M.; Jatczak, K. Preparation of protoescigenin from escin. PCT/PL2012/000102, filed 10 October 2012.
16. Wagner, J.; Hoffmann, H.; Löw, I. Über Inhaltsstoffe des Roβkastaniensamens, VII. O-Isopropyliden-Derivate von Protoäscigenin, Barringtogenol C und von deren 21-bzw. 28-Angelika(Tiglin)-säureestern. Liebigs Ann. Chem. 1969, 729, 205-212.
17. Gruza, M.M.; Jatczak, K.; Łaszcz, M.; Grynkiewicz, G.; Giller, T.; Witkowska, A.B. Sposób wytwarzania 3,24;16,22-O,O;O,O-diizopropylideno- protoescygeniny oraz jej postacie krystaliczne. PL/P-402306, filed 30 December 2012.
18. Tsuda, Y.; Kiuchi, F.; Liu, H.-M. Establishment of the structure of gymnemagenin by x-ray analysis and the structure of deacylgymnemic acid. Tetrahedron Lett. 1989, 30, 361-362.
19. Stöcklin, W. Gymnemagenin, vermutliche struktur Glykoside und Aglykone, 289. Mitteilung. Helv. Chim. Acta 1967, 50, 491-503.
20. Kuhn, R.; Löw, I. Über Protoäscigenin, die Stammsubstanz der Äscine. Liebigs. Ann. Chem. 1963, 669, 183-188.
21. Spek, A. Structure validation in chemical crystallography. Acta Crystallogr. D 2009, 65, 148-155.
22. Van der Sluis; P.; Spek, A.L. BYPASS: an effective method for the refinement of crystal structures containing disordered solvent regions. Acta Crystallogr. A 1990, 46, 194-201.