Antihyperglycemic activities of cryptolepine analogues: An ethnobotanical lead structure isolated from Cryptolepis sanguinolenta

Journal of Medicinal Chemistry

Volumn 41, Issue 15, 1998, Pages 2754-2764

  Bierer, Donald E ^a,b   Dubenko, Larisa G ^a   Zhang, Pingsheng ^a   Lu, Qing ^a   Imbach, Patricia A ^a   Garofalo, Albert W ^a   Phuan, Puay Wah ^a   Fort, Diana M ^a   Litvak, Joane ^a   Gerber, R Eric ^a   Sloan, Barbara ^a   Luo, Jian ^a   Cooper, Raymond ^a   Reaven, Gerald M ^a  

^a Shaman Pharmaceuticals Inc   (United States)

^b Shaman Pharmaceuticals

Author keywords

[No Author keywords available]

Indexed keywords

4 METHOXY 5 METHYLQUINDOLINIUM; ANTIDIABETIC AGENT; CRYPTOLEPINE; CRYPTOLEPINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG ISOLATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; GLUCOSE BLOOD LEVEL; MOUSE; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; ORAL DRUG ADMINISTRATION; STRUCTURE ACTIVITY RELATION;

3T3 CELLS; ADIPOSE TISSUE; ALKALOIDS; ANIMALS; BIOLOGICAL TRANSPORT; BLOOD GLUCOSE; DIABETES MELLITUS, EXPERIMENTAL; GLUCOSE; HYPOGLYCEMIC AGENTS; INDOLES; MICE; MICE, OBESE; PLANTS, MEDICINAL; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 14444274095     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970735n     Document Type: Article

References (26)

1. Fichter, F.; Boehringer, R. Ueber Chindolin. (Over Quindoline.) Chem. Ber. 1906, 39, 3932-3942.
2. Clinquart, E. Sur la composition chimique de Cryptolepis triangularis, plante congolaise. (On the Chemical Composition of Cryptolepis triangularis, Plants from the (Belgian) Congo.) Bull. Acad. R. Med. Belg. 1929, 9, 627-635.
3. 2, was first isolated as a purple solid (mp 175-178°C) by Gellért in 1951 from C. sanguinolenta (see ref 6). Gellért assigned the structure of (1) to cryptolepine. The structure of cryptolepine was recently verified by NMR spectroscopy in 1991 by Tackie et al. (see ref 7) and by unambiguous synthesis in 1998 by Bierer et al. (see ref 8).
4. Delvaux, E. Sur la Cryptolepine. (On Cryptolepine.) J. Pharm. Belg. 1931, 13, 955-959.
5. Delvaux, E. Sur la Cryptolépine. (On Cryptolepine.) J. Pharm. Belg. 1931, 13, 973-977.
6. Gellért, E.; Raymond-Hamet; Schlittler, E. Die Konstitution des Alkaloids Cryptolepin. (The Constitution of the Alkaloid Cryptolepine.) Helv. Chim. Acta 1951, 34, 642-651.
7. Tackie, A. N.; Sharaf, M. H. M.; Schiff, P. L., Jr.; Boye, G. L.; Crouch, R. C.; Martin, G. E. Assignment of the Proton and Carbon NMR Spectra of the Indoloquinoline Alkaloid Cryptolepine. J. Heterocycl. Chem. 1991, 28, 1429-1435.
8. Bierer, D. E.; Fort, D. M.; Mendez, C. D.; Luo, J.; Imbach, P. A.; Dubenko, L. G.; Gerber, R. E.; Litvak, J.; Lu, Q. Zhang, P.; Reed, M. J.; Waldeck, N.; Bruening, R. C.; Noamesi, B. K.; Hector. R. F.; Carlson, T. J-; King, S. R. Ethnobotanical-Directed Discovery of the Antihyperglycemic Properties of Cryptolepine: Its Isolation from Cryptolepis sanguinolenta, Synthesis, and In Vitro and In Vivo Activities. J. Med. Chem. 1998, 41, 894-901.
9. Dalziel, J. M. African Leather Dyes. Kew Bull. 1926, 225-238.
10. Dalziel, J. M. The Useful Plants of West Tropical Africa; Crown Agents for Overseas Governments and Administrations; London, 1955; 2nd reprint, p 387.
11. See ref 8 and references therein.
12. Luo, J.; Fort, D. M.; Carlson, T. J.; Noamesi, B.; nii-Amon-Kotei, D.; King, S. R.; Tsai, J.; Quan, J.; Hobensack, C.; Lapresca, P.; Waldeck, N.; Mendez, C. D.; Jolad, S. D.; Bierer, D. E.; Reaven, G. M. Cryptolepine, A Potentially Useful New Antihyperglycaemic Agent Isolated from Cryptolepis sanguinolenta: An Example of the Ethnobotanical Approach to Drug Discovery. Diabetic Med. 1998, 15, 367-374.
13. Bierer, D. E.; Carlson, T. J.; King, S. R. Integrating Indigenous Knowledge, Tropical Medicinal Plants, Medicine, Modern Science and Reciprocity into a Novel Drug Discovery Approach. Network Sci. 1996, 2 (No. 5) (http://www.awod.com/netsci/Issues/ May96/feature2.html).
14. Bierer, D. E.; Dener, J. M.; Dubenko, L. G.; Gerber, R. E.; Litvak, J.; Peterli, S.; Peterli-Roth, P.; Truong, T. V.; Mao, G.; Bauer, B. E. Novel 1,2-Dithiins: Synthesis, Molecular Modeling Studies, and Antifungal Activity. J. Med. Chem. 1995, 38, 2628-2648.
15. Yamato, M.; Takeuchi, Y.; Chang, M.; Hashigaki, K.; Tsuruo, T.; Tashiro. T.; Tsukagoshi, S. Synthesis and Antitumor Activity of Fused Quinoline Derivatives. Chem. Pharm. Bull. 1990, 38, 3048-3052.
16. Yamato, M.; Takeuchi, Y.; Chang, M.; Hashigaki, K. Synthesis and Antitumor Activity of Fused Quinoline Derivatives. II. Novel 4- and 7-Hydroxyindolo-[3,2-b]quinolines. Chem. Pharm. Bull. 1992, 40, 528-530.
17. Görlitzer, K.; Stockmann, R.; Walter, R. D. Gegen Malaria wirksame 10H-Indolo[3,2-b]chinolin-11-yl-amine. Part 1: Phenol-Mannich-Basen vom Amodiaquin-und Cycloquin-Typ. (Antimalarial 10H-Indolo[3,2-b]quinolin-11-ylamines. Part I: Phenol-Mannich Bases of the Amodiaquine and Cycloquine Type.) Pharmazie 1994, 49, 231-235.
18. Görlitzer, K.; Weber, J. Anellierte Chinoline, 6. Mitt. 10H-Indolo-[3,2-b]chinoline (Fused Quinolines VI: 10H-Indolo[3,2-b]quinoline). Arch. Pharm. (Weinheim) 1981, 314, 852-861.
19. Chang, M.; Takeuchi, Y.; Hashigaki, K.; Yamato, M. Synthesis of 7-Substituted Indolo[3,2-b]quinoline Derivatives. Heterocycles 1992, 33, 147-152.
20. Sunder, S.; Peet, N. P. Synthesis of Benzofuro[3,2-b]quinoline-6(11H)one and Derivatives. J. Heterocycl. Chem. 1978, 15, 1379-1382.
21. Görlitzer, K.; Weber, J. Anellierte Chinoline 4. Mitt. 11-Oxo-5, 11-dihydrobenzothieno[3,2-b][1]chinoline, S, S.-Dioxide und Thionierungsprodukte. (Fused Quinolines. Part 4. 5,11-Dihydrobenzothieno[3,2-b][1]quinolin-11-ones, S,S-Dioxides and Thionation Products.) Arch. Pharm. (Weinheim) 1980, 314, 76-84.
22. Görlitzer, K. Untersuchungen an 1,3-Dicarbonylverbindungen, 11 Mitt. Anellierte Chinolone II, N- und O-Alkylierungsprodukte. (Studies on 1,3-Dicarbonyl Compounds, XI: Fused Quinolines II, N- and O-Alkylated Products.) Arch. Pharm. (Weinheim) 1979, 312, 254-261.
23. Kempter, G.; Noack, H.; Russ, G. Heterocyclen aus Aminoketonen; Reaktionen monoalkylierter Amine mit aktiven Halogeniden. (Heterocycles from Amino Ketones: Reaction of Monoalkylated Amines with Active Halides.) Z. Chem. 1963, 3, 352-353.
24. 25 a report appeared which studied the effect that N-5 substitution of quindoline had on renal vasodilation and inhibition of platelet aggregation in a rat model. See: Oyekan, A. O.; Ablordeppy, S. Y. N-5 Alkylation of 3:4 Benz-Δ-carboline is a Requirement for Renal Vasodilation and Inhibition of Platelet Aggregation in the Rat. Med. Chem. Res. 1996, 6, 602-610.
25. Bierer, D. E. Cryptolepine Analogs with Hypoglycemic Activity. U.S. Patent 5,681,958, October 28, 1997, filed June 7, 1995.
26. Moran, K. In Biodiversity and Human Health; Grifo, F., Rosenthal, J., Eds.; Island Press: Washington, D.C., 1997; pp 243-263.