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Total polyphenolic content, antioxidant, cytotoxic, antidiabetic activities, and polyphenolic compounds of Sophora japonica grown in Egypt

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Abstract

The genus Sophora belongs to Fabaceae family, contains about 52 species that are widely distributed in Asia. Several phytochemical, in vivo and in vitro, experiments in addition to clinical practices have demonstrated that Sophora has many phyto-constituents and possesses valuable pharmacological and therapeutic properties. The total polyphenolic’s content, antioxidant, cytotoxic, and antidiabetic activities of Sophora japonica leaves were investigated along with their bio-guided chromatographic isolated polyphenolic constituents. Tested fractions from chromatographic separation of 80 % MeOH extract of S. japonica leaves revealed remarkable antioxidant(s) activity accompanied with some cytotoxic and antidiabetic activities. Moreover, six known polyphenolic constituents isolated from these fractions were identified: tamarixetin, ellagic acid 4-O-α-l-arabinofuranoside, sissotrin, rutin, gallic acid, and quercetin.

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References

  • Agrawal PK, Bansal MC (1989) Flavonoid glycosides. In: Agrawal PK (ed) Studies in organic chemistry 39, 13C-NMR of flavonoids. Elsevier, New York, pp 283–364

    Google Scholar 

  • Ahmed R (2005) The physiological and biochemical effects of diabetes on the balance between oxidative stress and antioxidant defense system. Med J Islamic World Acad Sci 15(1):31–42

    Google Scholar 

  • Ahmed F, Chandra J, Timmaiah NV (2012) An in vitro study on the inhibitory activities of Eugenia jambolana seeds against carbohydrate hydrolyzing enzymes. J Young Pharmacists 1:317–321

    Article  Google Scholar 

  • Ali M, El H, Mi Hwa C, Hossam MA, Tsutomu N, Masao H (2010) Estrogenic activity of a naringinase-treated extract of Sophora japonica cultivated in Egypt. Pharma Biol 48(2):177–181

    Article  Google Scholar 

  • Aslan M, Orhan N, Orhan DD, Ergun F (2010) Hypoglycemic activity and antioxidant potential of some medicinal plants traditionally used in Turkey for diabetes. J Ethnopharmacol 128(2):384–389

    Article  PubMed  Google Scholar 

  • Bach MK, Brashler JR (1975) Inhibition of IgE and compound 48/80-induced histamine release by lectins. Immunol 29:371–386

    CAS  Google Scholar 

  • Bailey CJ (2003) Textbook of diabetes 2. 3rd edn. Blackwell Science Ltd, London, p 73.1–73.21

  • Bandeira PN, Fairas SS, Lemos TLG, Braz-Filho R, Santos HS, Albuquerque MRJR, Costa SMO (2011) New derivatives of isoflavone and other flavonoids from the resin Amburana cearensis. J Braz Chem Soc 22:372–375

    Article  CAS  Google Scholar 

  • Barakat HH, Nawwar MA, Buddrus J, Linscheid M (1987) A phenolic glyceride and two phenolic aldehydes from roots of Tamarix nilotia. Phytochem 26:1837–1838

    Article  CAS  Google Scholar 

  • Baron AD (1998) Postprandial hyperglycemia and á-glucosidase inhibitors. Diabetes Res Clin Pract 40:51–55

    Article  Google Scholar 

  • Bendini A, Cerretani L, Pizzolante L, Gallina-Toschi T, Guzzo F, Ceoldo S, Marconi AM, Andreetta F, Levi M (2006) Phenol content related to antioxidant and an-timicrobial activity of passiflora spp Extracts. Eur Food Res Technol 223(1):102–109

    Article  CAS  Google Scholar 

  • Blickle JF, Andres E, Brogard JM (2008) Current status of the treatment of type 2 diabetes mellitus: alpha-glucosidase inhibitors. Food Chem 106:247–252

    Article  Google Scholar 

  • Boyd MR (1997) The NCI in vitro anticancer drug discovery screen: Concept, implementation and operation (1985–1995). In: Teicher BA (ed) Anticancer drug development guide, preclinical screening, clinical trials and approval. Humana Press, Totowa, pp 23–42

    Chapter  Google Scholar 

  • Brattain MG, Fine WD, Khaled FM, Thompson J, Brattain DE (1981) Heterogeneity of malignant cells from a human colonic carcinoma. Cancer Res 41:1751–1756

  • Cai Y, Luo Q, Sun M, Corke H (2004) Antioxidant activity and phenolic compounds of 112 traditional Chinese medicinal plants associated with anticancer. Life Sci 74:2157–2184

    Article  CAS  PubMed  Google Scholar 

  • Campbell RA, Bhat-Nakshatri P, Patel NM, Constantinidou D, Ali S, Nakshatri H (2001) Phosphatidylinositol/3-kinase/Akt-mediated activation of estrogen receptor a: a new model for anti-estrogen receptor resistance. J Biol Chem 276:9817–9824

    Article  CAS  PubMed  Google Scholar 

  • Ceriello A (1998) The emerging role of post-prandial hyperglycemic spikes in the pathogenesis of diabetic complications. Diabetic Med 15:188–193

    Article  CAS  PubMed  Google Scholar 

  • Ceriello A (2003) New insights on oxidative stress and diabetic complications may lead to a “causal” antioxidant therapy. Diabetes Care 26(5):1589–1596

    Article  CAS  PubMed  Google Scholar 

  • Chen H-N, Hsieh C-L (2010) Effects of Sophora japonica flowers (Huaihua) on cerebral infarction. Chin Med 5(34):1–4

    CAS  Google Scholar 

  • Chung WY, Jung YJ, Surh YJ, Lee SS, Park KK (2001) Antioxidative and tumor promoting effects of [6]-paradol and its homologs. Mutat Res 496:199–206

    Article  CAS  PubMed  Google Scholar 

  • Chunga IM, Kima EH, Yeoa MA, Kima SJ, Seob MC, Moonc HI (2011) Antidiabetic effects of three Korean sorghum phenolic extracts in normal and streptozotocin-induced diabetic rats. Food Res Int 44(1):127–132

    Article  Google Scholar 

  • Dahlqvist A (1964) Method for assay of intestinal disaccharides. Anal Biochem 7:18–25

    Article  CAS  PubMed  Google Scholar 

  • Ding PL, Liao ZX, Huang H, Zhou P, Chena DF (2006) (+)-12a-Hydroxysophocarpine, a new quinolizidine alkaloid and related anti-HBV alkaloids from Sophora flavescens. Bioorg Med Chem Lett 16:1231–1235

    Article  CAS  PubMed  Google Scholar 

  • Dlugosz A, Lembas-Bogaczy KJ, Lamer-Zaraw- ska E (2006) Antoxid increases ferric reducing antioxidant power (FRAP) even stronger than Vitamin C. Acta Pol Pharm 63:446–448

    CAS  PubMed  Google Scholar 

  • Fathiazada F, Delazara A, Amiria R, Sarker SD (2006) Extraction of flavonoids and quantification of rutin from waste tobacco leaves. Iran J Pharmaceut Res 3:222–227

  • Fresco P, Borges F, Diniz C, Marques MP (2006) New insights on the anticancer properties of dietary polyphenols. Med Res Rev 26:747–766.

    Article  CAS  PubMed  Google Scholar 

  • Fu M-Q, Deng D, Feng S-X, Huang R-M, Tian S, Qiu S-X (2012) Chemical constituents from roots of Flemingia philippinensis. Chin Herb Med 4(1):8–11

    CAS  Google Scholar 

  • Giugliano D, Ceriello A, Paolisso G (1996) Oxidative stress and diabetic vascular complications. Diabetes Care 19(3):257–267

    Article  CAS  PubMed  Google Scholar 

  • Gupta RK, Al-Shafi SM, Layden K, Haslam E (1982) The metabolism of gallic acid and hexahydroxydiphenic acid in plants. Part 2. Esters of (S)-hexahydroxydiphenic acid with D-glucopyranose (4C1). Biochem Soc Trans 1:2525–2534

    Google Scholar 

  • Haddock EA, Gupta RK, Al-Shafi SMK, Haslam E (1982) The metabolism of gallic acid and hexahydroxy diphenolic acid in plants Part I, introduction naturally occurring galloyl esters. J Chem Soc Perkin Trans 1:2515

    Article  Google Scholar 

  • Harborne JB (1984) Phytochemical methods: a guide to modern technique of plant analysis, 2nd edn. Champan and Hall Ltd, London, pp 37–99

    Book  Google Scholar 

  • Harborne JB, Mabry TJ, Mabry H (1975) The flavonoids, chapman and hall, London. Phytochemistry 12:3963–3968

    Google Scholar 

  • Harish R, Shivanandappa T (2006) Antioxidant activity and hepatoprotective potential of Phyllanthus niruri. Food Chem 95(2):180–185

    Article  CAS  Google Scholar 

  • Hassimotto N, Genovese M, Lajolo F (2005) Antioxidant activity of dietary fruits, vegetables, and commercial frozen fruit pulps. J Agr Food Chem 53(8):2928–2935

    Article  CAS  Google Scholar 

  • Hauri HP, Wacker H, Rickli EE, Bigler-Meier B, Quaroni A, Semenza G (1982) Biosynthesis of sucrase-isomaltase: purification and NH2-terminal amino acid sequence of the rat sucrase-isomaltase precursor (pro-sucrase-isomaltase) from fetal intestinal transplants. J Biol Chem 257:4522–4528

    CAS  PubMed  Google Scholar 

  • Hiermann A (1983) Die untersuchung potentieller wirkstoffe in epilobium-arten. Sci Pharm 51:158–167

    Google Scholar 

  • Honda M, Hara Y (1993) Inhibition of rat small intestinal sucrase and á-glucosidase activities by tea polyphenols. Biosci Biotechnol Biochem 57:123–124

    Article  CAS  Google Scholar 

  • Hu ZL, Zhang JP, Qian DH, Lin W, Xie WF, Zhang XR, Chen WZ (1996a) Effects of matrine on mouse splenocyte proliferation and release of interleukin- 1 and -6 from peritoneal macrophages in vitro. Zhongguo Yao Li Xue Bao 17:259–261

    CAS  PubMed  Google Scholar 

  • Hu ZL, Zhang JP, Wan MB, Yu XB, Lin W, Qian DH (1996b) Effect of matrine on mouse hepatitis and tumour necrosis factor production induced by Propionibacterium acnes/lipopolysaccharides. Zhongguo Yao Li Xue Bao 31:662–665

    CAS  Google Scholar 

  • Hu ZL, Zhang JP, Yu XB, Lin W, Qian DH, Wan MB (1996c) Effect of matrine on lipopolysaccharides/Dgalactosamine-induced hepatitis and tumor necrosis factor release from macrophages in vitro. Zhongguo Yao Li Xue Bao 17:351–353

    CAS  PubMed  Google Scholar 

  • Ishida H, Umino T, Tsuji K, Kosuge T (1989) Studies on the antihemostatic substances in herbs classified as hemostatics in traditional Chinese medicine. I. On the antihemostatic principles in Sophora japonica L. Chem Pharm Bull 37:1616–1618

    Article  CAS  PubMed  Google Scholar 

  • Kamalakkannan N, Prince PS (2006) Antihyperglycaemic and antioxidant effect of rutin, a polyphenolic flavonoid, in streptozotocin-induced diabetic wistar rats. Basic Clin Pharmacol Toxicol 98(1):97–103

    Article  CAS  PubMed  Google Scholar 

  • Kikuzaki H, Hisamoto M, Hirose K, Akiyama K, Taniguchi H (2002) Antioxidant properties of ferulic acid and its related compounds. J Agric Food Chem 50:2161–2168

    Article  CAS  PubMed  Google Scholar 

  • Kim JM, Yun-Choi HS (2008) Anti-platelet effects of flavonoids and flavonoid glycosides from Sophora japonica. Arch Pharm Res 31(7):886–890

    Article  CAS  PubMed  Google Scholar 

  • Kinghorn AD, Balandrin MF, Pelletier SW (1984) Alkaloids: chemical and biological perspectives, vol 2. Wiley, New York, pp 105–106

    Google Scholar 

  • Kumar KS, Ganesan K, Rao PV (2008) Antioxidant potential of solvent extracts of Kappaphycus alverezii (Doty). Food Chem 107:289–295

    Article  CAS  Google Scholar 

  • Kumar PS, Sandhya S, Rao KNV, Banji D, Krishna PM, Rajeshwar T (2011) Pharmacognostical studies and preliminary phytochemical investigations on roots of Sophora interrupta Bedd Fabaceae. J Phytol 3(9):42–47

  • Levenson AS, Jordan CV (1997) MCF-7: the first hormone responsive breast cancer cell line. Cancer Res 57:3071–3078

    CAS  PubMed  Google Scholar 

  • Lin W, Zhang JP, Hu ZL, Qian DH (1997) Inhibitory effect of matrine on lipopolysacchride induced tumor necrosis factor and interleukin-6 production from rat Kupffer cells. Acta pharm Sin 32:93–96

    CAS  Google Scholar 

  • Liu M, Liu XY, Cheng JF (2003) Advance in the pharmacological research on matrine. Zhongguo Zhong Yao Za Zhi 28:801–804

    CAS  PubMed  Google Scholar 

  • Mabry TJ, Markham KR, Thomas MB (1970) The systematic identification of flavonoids. Springer, New York, pp 4–35

    Book  Google Scholar 

  • Mahmoud II, Marzouk MSA, Moharram FA, El-Gindi MR, Hassan AMK (2001) Acylated flavonol glycosides from Eugenia jambolana leaves. Phytochemistry 58:1239–1244

    Article  CAS  PubMed  Google Scholar 

  • Maritim AC, Sanders RA, Watkins JB 3rd (2003) Performing your original search, relation between antioxidant and diabetes, in PubMed will retrieve 635. J Biochem Mol Toxicol 17(1):24–38

    Article  CAS  PubMed  Google Scholar 

  • Markham KR (1982) Techniques of flavonoids identification. Academic Press, London

    Google Scholar 

  • Matthew S, Kao K-C, Chang Y-S, Abreu P (2007) Ellagic acid glycosides from Turpinia ternate. Nat Prod Res 21(1):83–88

    Article  CAS  PubMed  Google Scholar 

  • Mavundza EJ, Tshikalange TE, Lall N, Hussein AA, Mudau FN, Meyer JJM (2010) Antioxidant activity and cytotoxicity effect of flavonoids isolated from Athrixia phylicoides. J Med Plant Res 4:2584–2587

    Google Scholar 

  • Mcdonald S, Prenzler PD, Autolovich M, Ro-bards K (2001) Phenolic content and antioxidant activity of olive oil extracts. Food Chem 73(1):73–84

    Article  CAS  Google Scholar 

  • Mensor LL, Menezes FS, Leitão GG, Reis AS, dos Santos TC, Coube CS, Leitão SG (2001) Screening of Brazilian plant extracts for antioxidant activity by the use of DPPH free radical method. Phytother Res 15(2):127–130

    Article  CAS  PubMed  Google Scholar 

  • Minhaj N, Khan H, Zeman A (1976) Unanisoflavan, a new isoflavan from Sophora secondiflora DC. Tetrahedron Lett 27:2391–2394

    Article  Google Scholar 

  • Minhaj N, Khan H, Zaman A (1977) Secondifloran, a novel isoflavanone from Sophora secondiflora DC. Tetrahedron Lett 13:1145–1148

    Article  Google Scholar 

  • Nenadis N, Zhang HJ, Tsimidou MZ (2003) Structure-antioxidant activity relationship of ferulic acid derivatives: effect of carbon side chain characteristic groups. J Agric Food Chem 51:1874–1879

    Article  CAS  PubMed  Google Scholar 

  • Newman DJ, Gragg GM, Holbeck S, Sausville EA (2002) Natural products as leads to cell cycle pathway targets in cancer chemotherapy. Curr Cancer Drug Target 2:279–308

    Article  CAS  Google Scholar 

  • Ohyama M, Tanaka T, Iinuma M (1994) Two novel resveratrol trimers, Leachianols A and B, from Sophora leachiana. Chem Pharm Bull 42:2117–2120

    Article  CAS  Google Scholar 

  • Ou S, Kwok K, Li Y, Fu L (2001) In vitro study of possible role of dietary fiber in lowering postprandial serum glucose. J Agric Food Chem 49:1026–1029

    Article  CAS  PubMed  Google Scholar 

  • Piarulli F, Sartore G, Ceriello A, Ragazzi E, Reitano R, Nollino L, Cosma C, Fedele D, Lapolla A (2009) Relationship between glyco-oxidation, antioxidant status and microalbuminuria in type 2 diabetic patients. Diabetologia 52(7):1419–1425

    Article  CAS  PubMed  Google Scholar 

  • Rahimi R, Nikfar S, Larijani B, Abdollahi M (2005) A review on the role of antioxidants in the management of diabetes and its complications. Biomed Pharmacother 59(7):365–373

    Article  CAS  PubMed  Google Scholar 

  • Rhabasa-Lhoret R, Chiasson JL (2004) International textbook of diabetes mellitus. vol 1, 3rd edn. Wiley, London, p 901–914

  • Saewan N, Koysomboon S, Chantrapromma K (2011) Anti-tyrosinase and anti-cancer activities of flavonoids from Blumea balsamifera. J Med Plant Res 5(6):1018–1025

    CAS  Google Scholar 

  • Sato M, Tsuchiya H, Takase I, Kureshiro H, Tanigaki S, Iinuma M (1995) Antibacterial activity of flavanone isolated from Sophora exigua against methicillin-resistant Staphylococcus aureus and its combination with antibiotics. Phytother Res 9:509–512

    Article  CAS  Google Scholar 

  • Shim YJ, Doo HK, Ahn SY, Kim YS, Seong JK, Park IS (2003) Inhibitory effect of aqueous extract from the gall of Rhus chinensis on alpha-glucosidase activity and postprandial blood glucose. J Etnhopharmacol 85:283–287

    Article  Google Scholar 

  • Silva GL, Iracema M, Machado L, Matos FJA, Braz-Filho R (1999) A new isoflavone isolated from Harpalyce brasiliana. J Braz Chem Soc 10:429–437

    Google Scholar 

  • Skehen P, Storeng R (1990) New colorimetric cytotoxicity assay for anti-cancer drug screening. J Natl Cancer Inst 82:1107–1112

    Article  Google Scholar 

  • Slowing K, Sollhuber M, Carretero E, Villar A (1994) Flavonoid glycosides from Eugenia Jambolana. Phytochemistry 37:255–258

    Article  CAS  PubMed  Google Scholar 

  • Smith I (1960) Chromatographic and electrophoretic techniques. Heinman, London, pp 1–246

    Google Scholar 

  • Son S, Lewis AB (2002) Free radical scavenging and antioxidant activity of caffeic acid amide and ester analogues: structure-activity relationship. J Agric Food Chem 5:468–472

    Article  Google Scholar 

  • Stahl E (1969) Thin layer chromatography, 2nd edn. Springer, New York

    Book  Google Scholar 

  • Taheri E, Djalali M, Saedisomeolia A, Moghadam AM, Djazayeri A, Qorbani M (2012) The relationship between the activates of antioxidant enzymes in red blood cells and body mass index in Iranian type 2 diabetes and healthy subjects. J Diabetes Metab Dis 11:1–5

    Article  Google Scholar 

  • Tang Y, Lou F, Wang J, Zhuang S (2001) Four new isoflavone triglycosides from Sophora japonica. J Nat Prod 64:1107–1110

    Article  CAS  PubMed  Google Scholar 

  • Teixeira CC, Rava CA, Da Silva PM, Melchior R, Argenta R, Anselmi F (2000) Absence of antihyperglycemic effect of Jambolana in experimental and clinical models. J Ethnopharmacol 71:343–347

    Article  CAS  PubMed  Google Scholar 

  • Timothy KJ, Schatzkin A, Willett WC, Allen NE, Spencer EA, Travis RC (2004) Diet, nutrition and the prevention of cancer. Public Health Nutr 7:187–200

    Google Scholar 

  • Tiwari AK, Rao JM (2002) Diabetes mellitus and multiple therapeutic approaches of phytochemicals: present status and future prospects. Curr Sci 23:30–33

    Google Scholar 

  • Tse WP, Che CT, Liu K, Lin ZX (2006) Evaluation of the anti-proliferative properties of selected psoriasis-treating Chinese medicines on cultured HaCaT cells. J Ethnopharmacol 108:133–141

    Article  PubMed  Google Scholar 

  • Tsoong PC, Ma CY (1981a) A study on the genus Sophora Linn. Acta Phytotax Sinica 19:1–22

    Google Scholar 

  • Tsoong PC, Ma CY (1981b) A study on the genus Sophora Linn (Cont.). Acta Phytotaxon Sin 19:143–167

    Google Scholar 

  • Xiao P, Kubo H, Komiya H, Higasshiyama K, Yan YN, Li JS, Ohmiya S (1999) Lupin alkaloids from seeds of Sophora viccifolia. Phytochemistry 50:189–193

    Article  CAS  Google Scholar 

  • Xing NL, Sha N, Yan HX, Pang XY, Guan SH, Yang M, Wu LJ, Hua HM, Guo DA (2008) Isoprenylated flavonoids from the roots of Sophora tonkinensis. Phytochem Lett 1:163–167

    Article  Google Scholar 

  • Xu YL, Ma YB, Xong Tang YP, Hu J, Wang JH, Lou FC (2002) A new coumaronochromone from Sophora japonica. J Asian Nat Prod Res 4:1–5

    Article  CAS  Google Scholar 

  • Yang LL, Lee CV, Yen KY (2000) Induction of apoptosis by hydrolysable tannins from Eugenia jambos on human leukemia cells. Cancer Lett 57:65–75

    Article  Google Scholar 

  • Yi Y, Cao Z, Yang D, Cao Y, Wu Y, Zhao S (1998) A New Isoflavone from Smilax glabra. Molecules 3:145–147

    Article  CAS  Google Scholar 

  • Zhang YF, Wang SZ, Li YY, Xiao ZY, Hu ZL, Zhang JP (2008) Sophocarpine and matrine inhibit the production of TNF and IL-6 in murine macrophages and prevent cachexia-related symptoms induced by colon 26 adenocarcinoma in mice. Int Immunopharmacol 8:1767–1772

    Article  CAS  PubMed  Google Scholar 

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Acknowledgments

Appreciation is expressed to Dr. Mahmoud Abdelsalam, Division of functional Genome Analysis, German Cancer Research Center (DKFZ), Heidelberg, Germany, for his valuable help with the in vitro antidiabetic tests.

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Correspondence to Mohamed I. S. Abdelhady or Taibi Ben Hadda.

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Abdelhady, M.I.S., Kamal, A.M., Othman, S.M. et al. Total polyphenolic content, antioxidant, cytotoxic, antidiabetic activities, and polyphenolic compounds of Sophora japonica grown in Egypt. Med Chem Res 24, 482–495 (2015). https://doi.org/10.1007/s00044-014-1101-2

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