Cytotoxicity of triterpenes from the leaves of Garcinia prainiana King (Guttiferae)

Abstract

Phytochemical investigation of the leaves of Garcinia prainiana resulted in the isolation of five triterpenes identified as squalene 1, friedelin 2, lupeol 3, 3β-hydroxyeupha-5,22-diene 4, and 3β-acetoxyeupha-5,22-diene 5. The structures of these compounds were established by analysis of their spectroscopic data, as compared to that of reported compounds. All compounds were screen for cytotoxicity against H1299 and A549 lung cancer cell lines using MTT assay. Compound 5 exhibited the most significant activity against H1299 and A549 cell lines with IC₅₀ values 18.0 µg/ml and 36.3 µg/ml, respectively.  

Keywords

• Triterpene,Garcinia prainiana,Cytotoxicity

Garcinia prainiana King (Guttiferae) Yapraklarından Elde Edilen Triterpenlerin Sitotoksik Özellikleri

Abstract

Garcinia prainiana yapraklarını konu alan fitokimyasal  araştırmalar sonucunda triterpen yapısında beş bileşik izole  edilmiştir; skualen 1, friedelin 2, lupeol 3, 3β-hidroksiöfa-  5,22-dien 4, and 3β-asetoksiöfa-5,22-dien 5. İzole edilen  bileşiklerin yapıları spektroskopik yöntemler kullanılarak  aydınlatılmış ve elde edilen sonuçlar yukarıda belirtilen  bileşiklere ait spektroskopik verilerle karşılaştırılmıştır. Tüm  bileşiklerin, H1299 ve A549 akciğer kanseri hücre hatları  üzerindeki sitotoksik etkileri MTT yöntemiyle çalışılmıştır.  3β-Asetoksiöfa-5,22-dien 5, H1299 ve A549 hücre hatlarına  karşı sırasıyla IC50 = 18.0 μg/ml ve IC50= 36.3 μg/ml derişimde  etki göstererek serisindeki en etkili bileşik olarak öne çıkmıştır.  

Keywords

• Triterpen,Garcinia prainiana,Sitotoksisite

References

1. Rhourri-Frih B, Renimel I, Chaimbault P, André P, Herbette G, Lafosse M. Pentacyclic triterpenes from Manilkara bidentata resin. Isolation, identification and biological properties. Fitoterapia 2013; 88: 101-108.
2. Silchenko AS, Kalinovsky AI, Avilov SA, Andryjaschenko PV, Dmitrenok PS, Martyyas EA, Kalinin VI. Triterpene glycosides from the sea cucumber Eupentacta fraudatrix. Structure and biological action of cucumariosides I1, I3, I4, three new minor disulfated pentaosides. Nat Prod Commun 2013; 8: 1053-1058.
3. Kim KH, Moon E, Choi SU, Kim SY, Lee KR. Lanostane triterpenoids from the mushroom Naematoloma fasciculare. J Nat Prod 2013; 76: 845-851.
4. McMurry J, Chemia Organiczna, 3rd ed., Wydawnictwo Naukowe PWN: Warszawa, Poland, 2005.
5. Breitmaier E. Terpenes: Flavors, Fragrances, Pharmaca, Pheromones, 1st ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2006.
6. Fulda S. Betulinic acid: A natural product with anticancer activity. Mol Nutr Food Res 2009; 53: 140-146.
7. Liaw CC, Chen YC, Huang GJ, Tsai YC, Chien SC, Wu JH, Wang SY, Chao LK, Sung PJ, Huang HC, Kuo YH. Anti-inflammatory lanostanoids and lactone derivatives from Antrodia camphorata. J Nat Prod 2013; 76: 489-494.
8. De Silva ML, David JP, Silva LC, Santos RA, David JM, Lima LS, Reis PS, Fontana R. Bioactive oleanane, lupane and ursane triterpene acid derivatives. Molecules 2012; 17: 12197-12205.

9. Baltina LA, Flekhter OB, Nigmatullina LR, Boreko EI, Pavlova NI, Nikolaeva SN, Savinova OV, Tolstikov GA. Lupane triterpenes and derivatives with antiviral activity. Bioorg Med Chem Lett 2003; 13: 3549-3552.
10. Ahmed Y, Sohrab MH, Al-Reza SM, Tareq FS, Hasan CM, Sattar MA. Antimicrobial and cytotoxic constituents from leaves of Sapium baccatum. Food Chem Toxicol 2010; 48: 549-552.
11. Mokoka TA, McGaw LJ, Mdee LK, Bagla VP, Iwalewa EO, Eloff JN. Antimicrobial activity and cytotoxicity of triterpenes isolated from leaves of Maytenus undata (Celastraceae). BMC Complement Altern Med 2013; 13: doi:10.1186/1472-6882-13-111.
12. Chudzik M, Korzonek-Szlacheta I, Król W. Triterpenes as potentially cytotoxic compounds. Molecules 2015; 20: 1610-1625;
13. Ampofo SA, Waterman PG. Xanthones from three Garcinia species. Phytochemistry 1986; 25: 2351-2355.
14. Whitmore TC. Tree Flora of Malaya 2: A Manual for Foresters. Kuala Lumpur: Longman Malaysia, 1973.
15. Peres V, Nagem TJ, Faustino de Oliveira F. Tetraoxygenated naturally occuring xanthones. Phytochemistry 2000; 55: 683-710.
16. Panthong K, Pongcharoen W, Phongphaichit S, Taylor WC. Tetaroxygenated xanthones from the fruits of Garcinia cowa. Phytochemistry 2006; 67: 999-1004.
17. Tian Z, Shen J, Moseman AP, Yang Q, Yang J, Xiao P, Wu E, Kohane IS. Dulxanthone A induces cell cycle arrest and apoptosis via up-regulation of p53 through mitochondrial pathway in HepG2 cells. Int J Cancer 2008; 122: 31-38.
18. Jayaprakasha GK, Negi PN, Jena BS. Antioxidative and antimutagenic activities of the extracts from the rinds of Garcinia penduculala. Innov. Food Sci Emerg Technol 2006; 7: 246-250.
19. Burkill IH. A dictionary of the economic products of the Malay Peninsula. Ministry of Agriculture and Co-operatives, Kuala Lumpur, 1966.
20. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immun Methods 1983; 65: 55-63.
21. Nottola SA, Makabe S, Stallone T, Familiari G, Correr S, Macchiarelli G. Surface morphology af the zona pellucida surrounding human blastocysts obtained after in vitro fertilization Arch Histol Cytol 2005; 68: 133-141.
22. Taher M, Susanti D, Rezali MF, Zohri FS, Ichwan SJ, Alkhamaiseh SI, Ahmad F. Apoptosis, antimicrobial and antioxidant activities of phytochemicals from Garcinia malaccensis Hk.f. Asian Pacific J Trop Med 2012; 5: 136-141.
23. Mawa S, Said MI. Chemical constituents of Garcinia prainiana. Sains Malay 2012; 41: 585-590.
24. Susanti D, Ali MZ, Amiroudine M, Rezali MF, Taher M. Friedelin and lanosterol from Garcinia prainiana stimulated glucose uptake and adipocytes differentiation in 3T3-L1 adipocytes. Nat Prod Res 2013; 27: 417-424.
25. Jabit ML, Wahyuni FS, Khalid R, Israf DA, Shaari K, Lajis NH, Stanslas J. Cytotoxic and nitric oxide inhibitory activities of methanol extracts of Garcinia species. Pharm Biol 2009; 47: 1019-1026.
26. Klaiklay S, Sukpondma Y, Rukachaisirikul V, Hutadilok-Towatana N, Chareonrat K. Flavanone glucuronides from the leaves of Garcinia prainiana. Canadian J Chem 2011; 89: 461-464.
27. D. Susanti, M. Taher, N. Attoumani, F. Ahmad, “Free radical scavenging and antibacterial activities of Malaysian guttiferae plants,” Journal of Medicinal Plant Research, vol. 5, pp. 6714-6718, 2011.
28. Reddy LH, Renoir JM, Marsaud V, Lepetre-Mouelhi S, Desmaele D, Couvreur P. Anticancer efficacy of squalenoyl gemcitabine nanomedicine on 60 human tumor cell panel and on experimental tumor. Mol Pharm 2009; 6: 1526-1535.
29. Chudzik M, Korzonek-Szlacheta I, Krol W. Triterpenes as potentially cytotoxic compounds. Molecules 2015; 20: 1610-1625.