The need for the discovery and development of new pharmaceuticals for the treatment of cancer demands that all approaches to drug discovery should be exploited. Among the possible approaches, the one from natural products has made many unique and vital contributions to drug discovery. This mini review focuses on researches made in our laboratory on cycloartanes isolated from Parthenium argentatum, as well as some of its derivatives, in order to obtain potential anti-inflammatory and anti-cancer agents.
VerpoorteR. (1998) Exploration of nature's chemodiversity: the role of secondary metabolites as leads in drug developmentDrug Discovery Today, 3, 232–238.
2.
WilliamsDH, StoneMJ, HauckPR, RahmanSK. (1989) Why are secondary metabolites (natural products) biosynthesized?Journal of Natural Products, 5, 1189–1208.
3.
NewmanDJ, CraggGM, KingstonDGI. (2003) Natural products as pharmaceuticals and sources for lead structures. In The Practice of Medicinal Chemistry, WermuthCG. (Ed), Elsevier, 91–109.
4.
CraggGM, NewmanDJ. (2005) Plants as a source of anti-cancer agents. Journal of Ethnopharmacology, 100, 72–79.
5.
Argumedo-DeliraR, Parra-DelgadoHRamírez-ApanT, Nieto-CamachoA, Martínez-VázquezM. (2003) Isolation and chemical transformations of some anti-inflammatory triterpenes from Salvia mexicana L. var. minor Benth. Revista de la Sociedad Química de México, 47, 167–172.
6.
CichewitzRH, KouziSA. (2004) Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infections. Medicinal Research Reviews, 24, 90–114.
7.
ChoiCY, YouHJ, JeongHG. (2001) Nitric oxide and tumor necrosis factor-a production by oleanolic acid via nuclear factor-kB activation in macrophages. Biochemistry Biophysics Research Communications, 288, 49–55.
8.
SubbaramaiahK, MichaluartP, SpornMB, DannenbergAJ. (2000) Ursolic acid inhibits cyclooxygenase-2. Transcription in human mammary epithelial cells. Cancer Research, 60, 2399–2404.
9.
HondaT, GribbleGW, SuhN, FinlayHJ, RoundsBV, BoreL, FavaloroFG, WangY, SpornMB. (2000) Novel synthetic oleanane and ursane triterpenoids with various enone functionalities in ring A as inhibitors of nitric oxide production in mouse macrophages. Journal of Medicinal Chemistry, 43, 1866–1877;
10.
HondaT, RoundsBV, BoreL, FinlayHJ, FavaloroFG, SuhN, WangY, SpornMB, GribbleGW. (2000) Novel synthetic oleanane and ursane triterpenoids with modified rings A and C: A series of highly active inhibitors of nitric oxide production in mouse macrophages. Journal of Medicinal Chemistry, 43, 4233–4246.
DvorakHF. (1986) Tumors: wounds that not heal. Similarities between tumor stroma generation and wound healing. New England Journal of Medicine, 315, 1650–1659.
13.
MaedaH, AkaikeT. (1998) Nitric oxide and oxygen radicals in infection, inflammation and cancer. Biochemistry, 63, 854–865.
García-ArgaezAN, Ramírez-ApanT, Parra-DelgadoH, VelásquezG, Martínez-VázquezM. (2000) Anti-inflammatory activity of coumarins from Decatropis bicolor on TPA ear mice model. Planta Medica, 66, 279–281.
16.
Martínez-VázquezM, de la CuevaLDG, Estrada-ReyesR, González LugoNM, Ramírez-ApanT, HeinzeG. (2005) Bio-guided isolation of the cytotoxic corytenchine and isocoreximine from roots of Annona cherimolia. Fitoterapia, 76, 733–736.
17.
Oviedo ChávezI, Ramírez ApanT, Martínez-VázquezM. (2005) Cytotoxic activity and effect on nitric oxide production of tirucallane-type triterpenes. Journal of Pharmacy and Pharmacology, 57, 1087–1091.
18.
Rodríguez-HannL, Romo de VivarA, OrtegaA, AguilarM, RomoJ. (1970) Determinación de las estructuras de las argentatinas A, B y C del guayule. Revista Latinoamericana de Química, 1, 24–38.
19.
Romo de VivarA, MatsubaraC. (1986) Los terpenoides de Parthenium incanum. Estudio cristalográfico por rayos X de incalina y argentatina B. Revista Latinoamericana de Química, 17, 7–9.
20.
KomoroskiAA, GressEC, ShockorJP, GeckleJM. (1986) Identification of guayule triterpenes by two dimensional and multipulse NMR techniques. Magnetic Resonance in Chemistry, 24, 534–543.
21.
Romo de VivarA, Martínez-VázquezM, MatsubaraC, PérezG, Joseph-NathanP. (1990) Triterpenes in Parthenium argentatum Phytochemistry, 29, 915–918.
22.
SchlomanWW, HivelyRA, KrishenA, AndrewMA. (1983) Guayule by product evaluation: extract characterization. Journal of Agricultural Food Chemistry, 31, 873–876;
CéspedesCL, Martínez-VázquezM, CalderónJS, SalazarJR, ArandaA. (2001) Insect growth regulatory activity of some extracts and compounds from Parthenium argentatum. Zeitschritt für Naturforschung, 56c, 95–105.
26.
Hernández-OrtegaS, Parra DelgadoH, MartínezM. (2005) Incaline (isoargentatin A) from Parthenium argentatum. Acta Crystallographica, E61, 1921–1923.
27.
MartínezR, Martínez-VázquezM, Zamorano-MaciasO. (1990) Electron impact mass spectrometry of triterpenoids from guayule. Organic Mass Spectrometry, 25, 237–238.
28.
Martínez-VázquezM, MartínezR, ToscanoRA. (1995) Preparation, spectral studies and X-ray crystal structures of (16S, 17R, 20S)-3-oxo-16-hydroxy-25-nor-lanostan-24-oic lactone (II) and (16S, 17R, 20S)-4,16-dihydroxy-25-nor-3,4-seco-lanostan-3,24-dioic acid dilactone (III). Journal of Chemical Crystallography, 25, 331–337.
29.
MartínezR, Arellano-GarcíaMA, Martínez-VázquezM, GallegosJ. (1993) Synthesis of carbenoxolone analogs from argentatin B. Organic Preparations and Procedures International, 25, 698–792.
30.
MartínezR, LimónE, ArellanoMR, MartínezM, BritoM. (1995) Synthesis of pyrazole from argentatin B. Collection of Czechoslovak Chemical Communications, 60, 612–618.
31.
TangW, EisenbrandG. (1992) Chinese drugs of plant origin: Chemistry, Pharmacology, and use in Traditional and Modern Medicine, Springer-Verlag.
32.
AkihisaT, YasukawaK, OiumaH, KasaharaY, YamanouchiS, TakidoM, KumakiK, TamuraT. (1996) Triterpene alcohols from the flowers of Compositae and their anti-inflammatory effects. Phytochemistry, 43, 1255–1260.
33.
AkihisaT, YasukawaK. (2001) Anti-tumor-promoting and anti-inflammatory activities of triterpenoids and sterols from plants and fungi. In Studies of Natural Products Chemistry. Atta-ur-Rahman (Ed.), 25, 43–87.
34.
CalzadaL, SalazarEL, TéllezJ, MartínezM, MartínezR. (1995) Effect of tetracyclic triterpenes (argentatins A, B and D) on the stradiol receptor of hormone-dependent tumours of human breast. Medicine Science Research, 23, 815–816.
35.
ÖksüzS, ShiehHL, PezzutoJM, ÖzhatayN, CordellGA. (1993) Biologically active compounds from the Euphorbiaceae, Part 1. Triterpenoids of Euphorbia nicaeensis subsp. glareosa. Planta Medica, 59, 472–473.
36.
Smith-KiellandI, DornishJM, MalterudKE, HvistendahlG, RommingC, BockmanOC, KolsakerP, StenstromY, NordalA. (1996) Cytotoxic triterpenoids from the leaves of Euphorbia pulcherrima. Planta Médica, 62, 322–325.
Parra-DelgadoH, García-PilladoF, SordoM, Ramírez-ApanT, Martínez-VázquezM, Ostrosky-WegmanP. (2005) Evaluation of the cytotoxic, cytostatic and genotoxicity of argentatins A and B from Parthenium argentatum Gray. Life Sciences, 77, 2855–2865.
39.
HyenBJ, SooLY, MoKC, KimJA, SoolKK, ChulSH, KimK. (1997) Intracellular Ca2+ release mediates ursolic acid induced apoptosis in human leukemic HL-60 cells. International Journal of Cancer, 73, 725–728.
40.
KimD, BaekJH, KangC, KimK. (2000) Apoptotic activity of ursolic acid may correlate with inhibition of initiation of DNA replication. International Journal of Cancer, 87, 629–636.
41.
WickW, GrimmelC, WagenknechtB, DichgansJ, Weller (1999) Betunilic acid-induced apoptosis in glioma cells: a sequential requirement for new protein synthesis, formation of reactive oxygen species, and caspase processing. Journal of Pharmacology Experimental Therapy, 289, 1306–1312.
42.
HuangMT, HoCT, WangZY, FerraroT, LouYR, StauberK, MaW, GeorgiadisC, LaskinJD, ConneyAH. (1994) Inhibition of skin tumorigenesis by rosemary and its constituents carnosol and ursolic acid. Cancer Research, 51, 701–708.
43.
LeeHY, ChungHY, KimKH, LeeJJ, KimKW. (1994) Induction of differentiation in the cultured F9 teratocarcinoma stem cells by triterpene acids. Journal of Cancer Research and Clinical Oncology, 120, 513–518.
44.
SohnKL, LeeHY, ChungHY, YoungHS, KimKW. (1993) Anti-angiogenic activity of triterpene acids. Cancer Letters, 94, 213–218.
45.
ChaHJ, BaeSK, LeeHY, LeeOH, SatoH, SeikiM, ChaePB, KimK. (1996) Anti-invasive activity of ursolic acid correlates with reduced expression of matrix metalloproteinase-9 (MMP-9) in HT1080 human fibrosarcoma cells. Cancer Research, 56, 2281–2284.
46.
MizushinaY, LidaA, SugawaraF, SakaguchiK. (2000) Novel triterpenoids inhibit both DNA polymerase and DNA topoisomerase. Biochemical Journal, 350, 757–763.
47.
Parra-DelgadoH, Ramírez-Apan, Martínez-VázquezM. (2005) Synthesis of argentatin A derivatives as growth inhibitors of human cancer cell lines in vitro. Bioorganic & Medicinal Chemistry Letters, 15, 1005–1008.
48.
FenechM. (2000) The in vitro micronucleus technique. Mutation Research, 455, 81–95.
49.
Kirsch-VoldersM.ElhajoujiA, CundariE, VanHP (1997) The in vitro micronucleus test: a multi-endpoint assay to detect simultaneously mitotic delay apoptosis, chromosome breakage, chromosome loss and non-disjunction. Mutation Research, 392, 19–30.
50.
Parra-DelgadoH, CompadreCM, Ramírez-ApanT, Muñoz-FambuenaMJ, CompadreRL, Ostrosky-Wegman, Martínez-VázquezM. (2006) Synthesis and comparative molecular field analysis (CoMFA) of argentatina B derivatives as growth inhibitors of human cancer cell lines. Bioorganic & Medicinal Chemistry, 14, 1889–1901.