Abstract
This study was undertaken to isolate and characterize saponins from seeds of Camellia sinensis. Four triterpene saponins S 1 , S 2 , S 3 , and S 4 were isolated by chromatography on silica (60–120 mesh), followed by purification on Sep-Pak C-18 columns. The chemical structures (S 1 –S 4 ) were elucidated on the basis of 1-D and 2-D NMR. All the saponins show broad-spectrum antifungal activity against Candida albicans, Issatchenkia orientalis, Aspergillus flavus, A. niger, A. ochraceous, A. parasiticus, A. sydowii, and Trichophyton rubrum. The most susceptible test fungus was T. rubrum inhibited at a minimum inhibitory concentration of 31.25 μg/ml by all the four saponins. Cytotoxicity of these saponins was evaluated by methyl thiazole tetrazolium and sulfo-rhodamine B assays. The saponins when tested against five human cancer cells lines, viz., OVCAR-5 (ovarian carcinoma cells), MCF-7 (human breast adenocarcinoma cells), PC-3 (human prostate cancer cells), Colo-205 (colorectal adenocarcinoma cells), and HL-60 (human promyelocytic leukemia cells) showed high cytotoxicity activity (99 %) by S 1 and S 2 on PC-3 cells at concentration of 100 μg/ml. Similarly, when these saponins were tested against human PBMCs by lymphocytes proliferation assay, none showed significant activity. S 3 (IC50 = 1.72 mg/ml) showed high metal-chelating activity at a concentration of 20 mg/ml.
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References
Akagi M, Fukuishi Kan NT, Sagesaka YM, Akagi R (1997) Anti-allergic effect of tea-leaf saponin (TLS) from tea leaves (Camellia sinensis var. sinensis). Biol Pharm Bull 20:565–567
Carmichael J, DeGraff WG, Gazdar AF, Minna JD (1987) Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of chemosensitivity testing. Cancer Res 47:936–942
Ceyhun Sezgin AE, Artik N (2010) Determination of saponin content in Turkish tahini halvah by using HPLC. Adv J Food Sci Technol 2:109–115
Cos P, Vlietinck AJ, Berghe BV, Maes L (2006) Anti-infective potential of natural products: how to develop a stronger in vitro concept. J Ethanopharmacol 106:290–302
Dinis TCP, Madeira VMC, Almeida MLM (1994) Action of phenolic derivates (acetoaminophen, salycilate and 5-aminosalycilate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Arch Biochem Biophys 315:161–169
Estrada AG, Katselis S, Laarveld B, Barl B (2000) Isolation and evaluation of immunological adjuvant activities of saponins from Polygala senega L. Comparative immunology. Comp Immunol Microbiol Infect Dis 23:27–43
Favel A, Steinmetz MD, Regli P, Vidal-Ollivier E, Elias R, Balansard G (1994) In vitro antifungal activity of triterpenoid saponins. Planta Med 60:50–53
Francis G, Kerem Z, Harinder P, Makkar S, Becker K (2002) The biological action of saponins in animal system: a review. Brit J Nutr 88:587–605
Gaidi G, Miyamoto T, Rustaiyan A, Laurens V, Marie-Aleth LD (2000) Two new biologically active triterpene saponins from Acanthophyllum squarrosum. J Nat Prod 63:1497–1502
Gulcin I, Mshvildadze V, Gepdiremen A, Elias R (2006) Antioxidant activity of a triterpenoid glycoside isolated from the berries of Hedera colchica: 3-O-(β-d-glucopyranosyl)-hederagenin. Phytother Res 20:130–134
Huang D, Qi DF (2005) Dammarane sapogenins, their use as anti-cancer agents, and a process producing same. US patent 6,888,014
Ibanoglu E, Ibanoglu S (2000) Foaming behavior of liquorice (Glycyrrhiza glabra) extract. Food Chem 70:333–336
Lacaille-Dubois MA, Wagner HA (1996) A review of the biological and pharmacological activities of saponins. Phytomedicine 2:363–386
Lim YY, Lim TTLim, Tee JJ (2007) Antioxidant properties of several tropical fruits: a comparative study. Food Chem 103:1003–1008
Liu J, Henkel T (2002) Traditional Chinese medicine (TCM): are polyphenols and saponins the key ingredients triggering biological activities? Curr Med Chem 9:1483–1485
Mahato SB, Nandy AK (1991) Triterpenoid saponins discovered between 1987 and 1989. Phytochemistry 30:1357
Masayuki Y, Toshio M, Ning L, Akifumi N, Xian L, Hisashi M (2005) Triterpene Saponins with Gastroprotective effect from the seeds of Camellia sinensis-theasaponins E3, E4, E5, E6, and E7. Chem Pharm Bull 53:1559–1564
Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55–63
Nozzolillo C, Arnason JT, Campos F, Donskov N, Jurzysta M (1997) Alfalfa leaf saponins and insects resistance. J Chem Ecol 23:995–1002
Okubo S, Toda M, Hara Y, Shimamura T (1991) Antifungal and fungicidal activities of tea extract and catechin against Trichophyton. Jpn J Bacteriol 46:509–514
Oleszek W, Price KR, Colquhoun IJ, Jurzysta M, Pzoszy NM, Fenwick GR (1990) Isolation and identification of alfalfa (Medicago sativa L.) root saponins: their activity in relation to a fungal bioassay. J Agric Food Chem 38:1810–1817
Palazon J, Moyano E, Bonfill M, Osuna LT, Cusido RM, Pinol MT (2006) Effect of organogenesis on steroidal saponin biosynthesis in calli cultures of Ruscus aculeatus. Fitoterapia 77(3):216–220
Patel S, Gheewala N, Suthar A, Shah A (2009) In vitro cytotoxicity activity of Solanum nigrum extract agonist HELA cell line and VERO cell line. J Pharm Pharma Sci 1:38–46
Prasad A, Prasad KN, Yadav A, Gupta RK, Pradhan S, Jha S, Tripathi M, Husain M (2008) Lymphocyte transformation test: a new method for diagnosis of neurocysticerosis. Diagn Micr Infec Dis 61:198–202
Sagesaka-Mitane Y, Sugiura T, Miwa Y, Yamaguchi K, Kyuki K (1996) Effect of tea-leaf saponin on blood pressure of spontaneously hypertensive rats. Yakugaku Zasshi 116:388–395
Timbekova AE, Isaev MI, Abubakirov NK (1996) Chemistry and biological activity of triterpenoid glycosides from Medicago sativa. Adv Exp Med Biol 405:171–182
Treyvaud V, Marston A, Dyatmiko W, Hostettmann K (2000) Molluscicidal saponins from Phytolacca icosandra. Phytochemistry 55:603–609
Walia M, Mann TS, Kumar D, Agnihotri VK, Singh B (2012) Chemical composition and in vitro cytotoxicity of essential oil of leaves of Malus domestica growing in western Himalaya (India). Evid-Based Compl Alt 2012:649727
Wang ZW, Gu MY, Li GZ (2005) Surface properties of gleditsia saponin and synergisms of its binary system. J Disper Sci Technol 26:341–347
Xiao K, Yi YH, Wang ZZ, Tang HF, Li YQ, Lin HW (1999) A cytotoxic triterpene saponin from the root bark of Aralia dasyphylla. J Nat Prod 62:1030–1032
Yoshiki Y, Kudou S, Okubo K (1998) Relationship between chemical structures and biological activities of triterpenoid saponins from soybean. Biosci Biotechnol Biochem 62:2291–2299
Zhan Y (1999) Animal feed compositions and uses of triterpenoid saponin obtained from Camellia L. plants. US Patent 6,007,822
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Authors are grateful to the Director, IHBT, Palampur, for providing necessary facilities. Authors acknowledge financial assistance received from CSIR under the project “High value products from agro-forestry resources from Himalayan region and quality product development including facility for evaluation of nutraceutical/value added products.”
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Joshi, R., Sood, S., Dogra, P. et al. In vitro cytotoxicity, antimicrobial, and metal-chelating activity of triterpene saponins from tea seed grown in Kangra valley, India. Med Chem Res 22, 4030–4038 (2013). https://doi.org/10.1007/s00044-012-0404-4
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DOI: https://doi.org/10.1007/s00044-012-0404-4