Drug discovery based on classic natural products

Yaoxue Xuebao

Volumn 44, Issue 1, 2009, Pages 11-18

  Hu, Li Hong ^a   Xu, Ji Qing ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Classic natural product; Drug discovery; Molecular mechanism of action; Resource study; Structure activity relationship study

Indexed keywords

10 DEACTYLBACCATIN; 4 (8 BETULINOYLAMINOOCTANOYLAMINO) 3 HYDROXY 6 METHYLHEPTANOIC ACID; BETULIC ACID; CAMPTOTHECIN; CATHARANTHINE; COSITECAN; DOCETAXEL; GIMATECAN; IRINOTECAN; NATURAL PRODUCT; NAVELBINE; NEW DRUG; UNCLASSIFIED DRUG; VINBLASTINE; VINCA ALKALOID; VINCRISTINE; VINDESINE; VINDOLINE; VINFLUNINE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ANTIDIABETIC AGENT; ANTINEOPLASTIC AGENT; BERBERINE; BIOLOGICAL PRODUCT; OLEANOLIC ACID; TRITERPENE;

BIOASSAY; CAMPTOTHECA; DRUG MECHANISM; DRUG SCREENING; REVIEW; STRUCTURE ACTIVITY RELATION; TAXUS; ANALOGS AND DERIVATIVES; ANIMAL; CHEMISTRY; DRUG DEVELOPMENT; HUMAN; SYNTHESIS;

ANIMALS; ANTI-HIV AGENTS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BERBERINE; BIOLOGICAL PRODUCTS; CAMPTOTHECIN; DRUG DISCOVERY; HUMANS; HYPOGLYCEMIC AGENTS; OLEANOLIC ACID; TRITERPENES; VINBLASTINE;

EID: 62749192574     PISSN: 05134870     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (45)

1. Mayaux JF, Bousseau A, Pauwels R, et al. Triterpene derivatives that block entry of human immunodeficiency virus type 1 into cells [J]. Proc Natl Acad Sci USA, 1994, 91: 3564-3568.
2. Labrosse B, Pleskoff O, Sol N, et al. Resistance to a drug blocking human immunodeficiency virus type 1 entry (RPR103611) is conferred by mutations in gp41 [J]. J Virol, 1997, 71: 8230-8236.
3. Labrosse B, Treboute C, Alizon M. Sensitivity to a nonpeptidic compound (RPR103611) blocking human immunodeficiency virus type 1 env-mediated fusion depends on sequence and accessibility of the gp41 loop region [J]. J Virol, 2000, 74: 2142-2150.
4. Fujioka T, Kashiwada Y, Kilkuskie R, et al. Anti-AIDS agents, 11. Betulinic acid and platanic acid as anti-HIV principles from syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids [J]. J Nat Prod, 1994, 57: 243-247.
5. Kashiwada Y, Hashimoto F, Cosentino M, et al. Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents [J]. J Med Chem, 1996, 39: 1016-1017.
6. Kanamoto T, Kashiwada Y, Kanbara K, et al. Anti-human immunodeficiency virus activity of YK-FH312 (a betulinic acid derivative), a novel compound blocking viral maturation [J]. Antimicrob Agents Chemother, 45: 1225-1230.
7. Li F, Goila-Gaur R, Salzwedel K, et al. PA-457: a potent HIV inhibitor that disrupts core condensation by targeting a late step in Gag processing [J]. Proc Natl Acad Sci USA, 2003, 100: 13555-13560.
8. Zhou J, Yuan X, Dismuke D, et al. Small-molecule inhibition of human immunodeficiency virus type 1 replication by specific targeting of the final step of virion maturation [J]. J Virol, 2004, 78: 922-929.
9. Huang L, Yuan X, Aiken C, et al. Bifunctional anti-human immunodeficiency virus type 1 small molecules with two novel mechanisms of action [J]. Antimicrob Agents Chemother, 2004, 48: 663-665.
10. Wall ME, Wani MC, Cook CE, et al. Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminate [J]. J Am Chem Soc, 1966, 88: 3888-3890.
11. Hsiang YH, Hertzberg R, Hecht S, et al. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I [J]. J Biol Chem, 1985, 260: 14873-14878.
12. Hsiang YH, Lihou MG Liu LF. Arrest of replication forks by drug-stabilized topoisomerase I-DNA cleavable complexes as a mechanism of cell killing by camptothecin [J]. Cancer Res, 1989, 49: 5077-5082.
13. Takimoto CH, Wright J, Arbuck SG Clinical applications of the camptothecins [J]. Biochim Biophys Acta, 1998, 1400: 107-109.
14. Schiff PB, Fant J, Horwitz SB. Promotion of microtubule assembly in vitro by taxol [J]. Nature, 1979, 277: 665-667.
15. Gan FY, Shen YM, Hao XJ. Recent advance on taxol biosynthesis [J]. Prog Biotechnol, 2000, 20: 52-56.
16. Holton RA, Somoza C, Kim HB, et al. First total synthesis of taxol 1: functionalization of the B ring [J]. J Am Chem Soc, 1994, 116: 1597-1598.
17. Holton RA, Somoza C, Kim HB, et al. First total synthesis of taxol 2: completion of the C and D ring [J]. J Am Chem Soc, 1994, 116: 1599-1600.
18. Nicolaou KC, Yang Z, Liu JJ, et al. Total synthesis of taxol [J]. Nature, 1994, 367: 630-634.
19. Danishefsky SJ, Masters JJ, Link JJ, et al. Total synthesis of baccatin III and taxol [J]. J Am Chem Soc, 1996, 118: 2843-2859.
20. Wender PA, Badham NF, Conway SP, et al. The pinene path to taxanes. 6. a concise stereocontrolled synthesis of taxol [J]. J Am Chem Soc, 1997, 119: 2757-2758.
21. Riou JF, Naudin A, Lavelle F. Effects of taxotere on murine and human tumor cell lines [J]. Biochem Biophys Res Commun, 1992, 187: 164-170.
22. Hanauske AR, Degen D, Hilsenbeck SG, et al. Effects of taxotere and taxol on in vitro colony formation of freshly explanted human tumor cells [J]. Anti-Cancer Drug, 1992, 3: 121-124.
23. Vogel M, Hilsenbeck SG, Depenbrock H, et al. Preclinical activity of taxotere (RP 56976, NSC 628503) against freshly explanted clonogenic human tumor cells: comparison with taxol and conventional antineoplastic agents [J]. Eur J Cancer, 1993, 29A: 2009-2014.
24. Eisenhauer EA, Trudeau M. An overview of phase II studies of docetaxel in patients with metastatic breast cancer [J]. Eur J Cancer, 1995, 31A: S11-S13.
25. Trudeau ME, Eisenhauer E, Lofters W, et al. Phase II study of taxotere as first-line chemotherapy for metastatic breast cancer (MBC). A National Cancer Institute of Canada Clinical Trials Group (NCIC CTG) study [J]. Proc Am Soc Clin Oncol, 1993, 12: 64.
26. Seidman AD, Hudis C, Crown JPA, et al. Phase II evaluation of taxotere (RP 56976, NSC 628503) as initial chemotherapy for metastatic breast cancer [J]. Proc Am Soc Clin Oncol, 1993, 12: 63.
27. Jordan MA, Wilson L. Microtubules as a target for anticancer drugs [J]. Nat Rev Cancer, 2004, 4: 253-265.
28. Kruczynski A, Hill BT. Vinflunine, the latest vinca alkaloid in clinical development: a review of its preclinical anticancer properties [J]. Crit Rev Oncol Hemat, 2001, 40: 159-173.
29. Turner N, Li JY, Hu LH, et al. Berberine and its more biologically available derivative, dihydroberberine, inhibit mitochondrial respiratory complex I: a mechanism for the action of berberine to activate AMP-activated protein kinase and improve insulin action [J]. Diabetes, 2008, 57: 1414-1418.
30. Lee YS, Kim WS, Kim KH, et al. Berberine, a natural plant product, activates AMP-activated protein kinase with beneficial metabolic effects in diabetic and insulin-resistant states [J]. Diabetes, 2006, 55: 2256-2264.
31. Hu LH, Li J, James D, et al. 2007.09.30 13,13a-Dihydroberberine derivatives, their pharmaceutical composition and use: PCT/CN2007/002882 [P]. 2006-09-30.
32. Zhang S, Zhang ZY. PTP1B as a drug target: recent developments in PTP1B inhibitor discovery [J]. Drug Discov Today, 2007, 12: 373-381.
33. Zhang YN, Zhang W, Hong D, et al. Oleanolic acid and its derivatives: new inhibitor of protein tyrosine phosphatase IB with cellular activities [J]. Bioorg Med Chem, 2008, 16: 8697-8705.
34. Lin ZH, Zhang Y, Zhang YN, et al. Oleanolic acid derivative NPLC441 potently stimulates glucose transport in 3T3-L1 adipocytes via a multi-target mechanism [J]. Biochem Pharmacol, 2008, 76: 1251-1262.
35. Shi L, Zhang W, Zhou YY, et al. Corosolic acid stimulates glucose uptake via enhancing insulin receptor phosphorylation [J]. Eur J Pharmacol, 2008, 584: 21-29.
36. Zhang W, Hong D, Zhou YY, et al. Ursolic acid and its derivative inhibit protein tyrosine phosphatase IB, enhancing insulin receptor phosphorylation and stimulating glucose uptake [J]. Biochimie, 2006, 1760: 1505-1512.
37. Chen J, Hu LH, Shen X, et al. 3-(2′-Carboxylbenzoyl)-oleanolic acid, the pharmaceutical compositions comprising the said derivatives, and their use of therapies for diabetes and adiposis: CN 20081003435.3 [P]. 2008-03-06.
38. Hu LH, Li J, Ye QZ, et al. Triterpenes type protein tyrosine phosphatase IB inhibitors and the preparation method and the use: PCT/CN2005/000172 [P]. 2005-02-06.
39. Hu LH, Li J, Wang ZP. Total triterpenic acid of loquat (eriobotrya japonica) leaf, its preparation and application: CN 1315865C [P]. 2007-05-16.
40. An TY, Hong D, Li J, et al. Protein tyrosine phosphatases IB inhibitors from traditional Chinese medicine, in herbs: challenges in chemistry and biology [J]. ACS Symposium Series, American Chemical Society: Washington, DC, 2006: 143-156.
41. Zhang HK, Shao Y, Ding H, et al. Synthesis and structure-activity relationship studies of cytotoxic ester and ether anhydrovinblastine derivatives [J]. J Nat Prod, 2008, 71: 1669-1676.
42. Shao Y, Ding H, Tang WD, et al. Synthesis and structure-activity relationships study of novel anti-tumor carbamate anhydrovinblastine analogues [J], Bioorg Med Chem, 2007, 15:5061-5075.
43. Li WH, Shao Y, Hu LH, et al. BM6, a new semisynthetic Vinca alkaloid, exhibits its potent in vivo antitumor activities via its high binding affinity for tubulin and improved pharmacokinetic profiles [J]. Cancer Biol Ther, 2007, 6: el-e8.
44. Hu LH, Shen X, Jiang HL, et al. Novel vinblastine derivatives, their preparation, use and pharmaceutical compositions comprising the said derivatives: PCT/CN2007/003624 [P]. 2007-12-17.
45. Ni XZ, Hu LH. Method for preparing vindoline and catharanthine: CN 100376577C [P]. 2004-02-24.