Hasnah Mohd SİRAT, Muhammad TAHER, Shamsul ON, Wan Mohd Nuzul Hakimi Wan SALLEH, Farediah AHMAD

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

Garcinia prainiana yapraklarını konu alan fitokimyasal araştırmalar sonucunda triterpen yapısında beş bileşik izole edilmiştir; skualen 1, friedelin 2, lupeol 3, 3β-hidroksiöfa5,22-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.

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

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 tested for cytotoxicity against H1299 and A549 lung cancer cell lines using MTT assay. 3β-Acetoxyeupha-5,22diene 5 exhibited the most significant activity against human non-small cell lung carcinoma cell lines, H1299 and A549 with IC50 values 18.0 µg/mL and 36.3 µg/mL, respectively.

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Chudzik M, Korzonek-Szlacheta I, Krol W. Triterpenes as potentially cytotoxic compounds. Molecules 2015; 20: 161025.
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: 1526-35.
Susanti D, Taher M, Attoumani N, Ahmad F. Free radical scavenging and antibacterial activities of Malaysian guttiferae plants. J Med Pl Res 2011; 5: 6714-8.
Klaiklay S, Sukpondma Y, Rukachaisirikul V, HutadilokTowatana N, Chareonrat K. Flavanone glucuronides from the leaves of Garcinia prainiana. Canadian J Chem 2011; 89: 4614.
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: 1019-26.
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: 417-24.
Mawa S, Said MI. Chemical constituents of Garcinia prainiana. Sains Malay 2012; 41: 585-90.
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: 136-41.
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: 133-41.
Mosmann T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J Immun Methods 1983; 65: 55-63.
Burkill IH. A dictionary of the economic products of the Malay Peninsula. Ministry of Agriculture and Co-operatives, Kuala Lumpur. 1966.
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: 246-50.
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: 31-8.
Panthong K, Pongcharoen W, Phongphaichit S, Taylor WC. Tetaroxygenated xanthones from the fruits of Garcinia cowa. Phytochemistry 2006; 67: 999-1004.
Peres V, Nagem TJ, Faustino de Oliveira F. Tetraoxygenated naturally occuring xanthones. Phytochemistry 2000; 55: 683710.
Whitmore TC. Tree Flora of Malaya 2: A Manual for Foresters. Longman Malaysia, Kuala Lumpur. 1973.
Ampofo SA, Waterman PG. Xanthones from three Garcinia species. Phytochemistry 1986; 25: 2351-5.
Chudzik M, Korzonek-Szlacheta I, Król W. Triterpenes as potentially cytotoxic compounds. Molecules 2015; 20: 161025.
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:10.1186/1472-688213-111.
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: 54952.
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: 3549-52.
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: 12197-205.
Liaw CC, Chen YC, Huang GJ, Tsai YC, Chien SC, Wu JH, Wang SY, Chao LK, Sung PJ, Huang HC, Kuo YH. Antiinflammatory lanostanoids and lactone derivatives from Antrodia camphorata. J Nat Prod 2013; 76: 489-94.
Fulda S. Betulinic acid: A natural product with anticancer activity. Mol Nutr Food Res 2009; 53: 140-6.
Breitmaier E. Terpenes: Flavors, Fragrances, Pharmaca, Pheromones, 1st ed. Wiley-VCH Verlag GmbH & Co. KGaA Weinheim, Germany. 2006.
McMurry J. Chemia Organiczna, 3rd ed. Wydawnictwo Naukowe PWN, Warszawa, Poland. 2005.
Kim KH, Moon E, Choi SU, Kim SY, Lee KR. Lanostane triterpenoids from the mushroom Naematoloma fasciculare. J Nat Prod 2013; 76: 845-51.
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: 1053-8.
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: 101-8.