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Biflavonoids from the leaves and stem bark of Garcinia griffithii and their biological activities

Yıl 2017, Cilt: 21 Sayı: 4, 889 - 897, 01.12.2017

Öz

The phytochemical and biological activity of the leaves and stem
barks of Garcinia griffithii have been investigated. Extraction and
chromatographic purification of the leaves and stem barks extracts
have successfully afforded five biflavonoids namely amento-
4’’-methylether (1), 3,8’’-binaringenin (2), morelloflavone (3),
3,8’’-binaringenin-7’’-O-glucoside (4) and morelloflavone-7’’-Oglucoside
(5), together with squalene (6), canophyllol (7), friedelin
(8) and β-amyrin (9) which were characterized spectroscopically.
All extracts and phytochemicals were tested for antioxidant,
antityrosinase and antibacterial activities. The antioxidant assay
on DPPH radical scavenging showed that the n-hexane extract
of the stem barks had the highest radical scavenging activity
with IC50 value of 96.4 μg/mL, while compound (3) was found
to be the strongest antioxidant compound with IC50 value of 57.6
μg/mL. The methanol extract of the leaves showed the highest
total phenolic content with 444.1 mg/g of gallic acid equivalent
(GAE/L) and 423.1 mg/g of cathechin equivalent (CE/L). The
extracts and all compounds were found to have weak antityrosinase
activity. The antimicrobial assays of all the extracts
were carried out by minimum inhibition concentration (MIC)
and minimum bactericidal concentration (MBC). The methanol
extract of the leaves showed the most significant antimicrobial
activity towards E. faecalis and K. pneumoniae with MIC and
MBC value ranged between 225-450 μg/mL compared to the
other extracts.

Kaynakça

  • 1. Gautam B. Natural product: Chemistry, Biochemistry and Pharmocology. Alpha Science International Ltd. (Oxford, UK), 2009. 2. Bennett GJ, Lee HJ. Xanthones from Guttiferae. Phytochemistry 1989; 28: 967-998. 3. Waterman PG, Hussain RA. Systematic significance of xanthones, benzophenones and biflavonoids in Garcinia. Biochem Syst Ecol 1983; 11: 21-28. 4. Whitemore TC. Malayan Forest Records No. 26: Tree of Malaya: A Manual for Foresters. Longman (Kuala Lumpur), 1972. 5. Parveen M, Khan NU, Acchari B, Dutta PK. A triterpene from Garcinia mangostana. Phytochemistry 1991; 30: 361-2. 6. Corner EJH. Wayside Trees of Malaya, Government Printing Office, 1940. 7. Nilar LH, Nguyen D, Ganpathi V, Sim K-Y, Harrison LJ. Xanthones and benzophenones from Garcinia griffthii and Garcinia mangostana. Phytochemistry 2005; 66: 1718-23. 8. Xu YJ, Cao SG, Wu XH, Lai YH, Tan BHK, Pereira JT, Goh SH, Venkatraman G, Harrison LJ, Sim KY. Griffipavixanthone, a novel cytotoxic bixanthone from Garcinia griffithii and G. parvifolia. Tetrahedron Lett 1998; 39: 9103-6. 9. Elfita E, Muharni M, Madyawati L, Darwati D, Ari W, Supriyatna S, Husein HB, Dachriyanus D, Paul C, Louis M, Kenne F, Sandra A, Luc P. Antiplasmodial and other constituents from four Indonesian Garcinia spp. Phytochemistry 2009; 70: 907- 12. 10. Anu Aravind AP, Asha KRT, Rameshkumar KB. Phytochemical analysis and antioxidant potential of the leaves of Garcinia travancorica Bedd. Nat Prod Res 2016; 30: 232-6. 11. Permanaa D, Abas F, Maulidiani, Shaari K, Stanslas J, Ali AM, Lajis N. Atrovirisidone B, a new prenylated depsidone with cytotoxic property from the roots of Garcinia atroviridis. Z Naturforsch 2005; 60: 523-6. 12. Panthong K, Hutadilok-Towatana N, Panthong A. Cowaxanthone F, a new tetraoxygenated xanthone, and other anti-inflammatory and antioxidant compounds from Garcinia cowa. Canadian J Chem 2009; 87: 1636-40. 13. Jamila N, Khairuddean M, Khan SN, Khan N. Complete NMR assignments of bioactive rotameric (3→8) biflavonoids from the bark of Garcinia hombroniana. Magn Reson Chem 2014; 52: 345-52. 14. Al-Shaghdari A, Bello Alarcón A, Cuesta-Rubio O. Determination of biflavonoids in different parts of Garcinia bakeriana (Urb) borhidi. Rev Cuba Farm 2014; 48: 307-15. 15. Ito T, Yokota R, Watarai T, Mori K, Oyama M, Nagasawa H, Matsuda H, Iinuma M. Isolation of six isoprenylated biflavonoids from the leaves of Garcinia subelliptica. Chem Pharm Bull 2013; 61: 551-8. 16. Gontijo VS, Judice WAS, Codonho B, Pereira IO, Assis DM, Januário JP, Caroselli EE, Juliano MA, De Carvalho Dosatti A, Marques MJ, Junior CV, Santos MHD. Leishmanicidal, antiproteolytic and antioxidant evaluation of natural biflavonoids isolated from Garcinia brasiliensis and their semisynthetic derivatives. Eur J Med Chem 2012; 58: 613-23. 17. Kaikabo AA, Eloff JN. Antibacterial activity of two biflavonoids from Garcinia livingstonei leaves against Mycobacterium smegmatis. J Ethnopharmacol 2011; 138: 253-5. 18. Castardo JC, Prudente AS, Ferreira J, Guimarães CL, Monache FD, Filho VC, Otuki MF, Cabrini DA. Anti-inflammatory effects of hydroalcoholic extract and two biflavonoids from Garcinia gardneriana leaves in mouse paw oedema. J Ethnopharmacol 2008; 118: 405-11. 19. Nworu CS, Akah PA, Esimone CO, Okoli CO, Okoye FBC. Immunomodulatory activities of kolaviron, a mixture of three related biflavonoids of Garcinia kola Heckel. Immunopharmacol Immunotoxicol 2008; 30: 317-32. 20. Lin YM, Anderson H, Flavin MT, Pai YHS, Mata-Greenwood E, Pengsuparp T, Pezzuto JM, Schinazi RF, Hughes SH, Chen FC. In vitro anti-HIV activity of biflavonoids isolated from Rhus succedanea and Garcinia multiflora. J Nat Prod 1997; 60: 884-8. 21. Gunatilaka AAL, Sriyani HTB, Sotheeswaran S, Waight ES. 2,5-dihydroxy-1,6-dimethoxyxanthone and biflavonoids of Garcinia thwaitesii. Phytochemistry 1983; 22: 233-5. 22. Waterman PG, Crichton EG. Xanthones and biflavonoids from Garcinia densivenia stem bark. Phytochemistry 1980; 19: 2723-6. 23. Bandaranayake WM, Selliah SS, Sultanbawa MUS, Davii OW. Biflavonoids and xanthones of Garcinia terpnophylla and G. echinocarpa. Phytochemistry 1975; 14:, 1878-80. 24. Rice-Evans CA, Miller NJ, Paganga G. Antioxidant properties of phenolic compounds. Trends Pl Sci Rev 1997; 2: 152-9. 25. Te-Sheng C. Review: An updated review of tyrosinase inhibitors. Int J Mol Sci 2009; 10: 2440-75. 26. Chen FC, Lin YM, Hung JC. Phenolic compounds from the heartwood of Garcinia multiflora. Phytochemistry 1975; 14: 300-3. 27. Ryu YB, Jeong HJ, Kim JH, Kim YM, Park JH, Kim D, Naguyen TTH, Park SJ, Chang JS, Park KH, Rho MC, Lee WS. Biflavonoids from Torreya nucifera displaying SARS-CoV 3CLpro inhibition. Bioorg Med Chem 2010; 18: 7940-7. 28. Ragasa CY, Levida RM, Don MJ, Shen CC. Cytotoxic isothiocyanates from Moringa oleifera Lam seeds. Philippine Sci Lett 2012; 5: 46-52. 29. Nozaki H, Suzuki H, Hirayama T, Kasai R, Wu RY, Lee KH. Antitumor triterpenes of Maytenus diversifolia. Phytochemistry 1986; 25: 479-85. 30. Hui WH, Ko PDS, Lee YK, Li MM, Arthur HR. Triterpenoids from the ten Lithocarpus species of Hong Kong. Phytochemistry 1975; 14: 1063-6. 31. Tahany MAAR, Hegazy AK, Sayed AM, Kabiel HF, El-Alfy T, El-Komy SM. Study on combined antimicrobial activity of some biologically active constituents from wild Moringa peregrine Forssk. J Yeast Fungal Res 2010; 1: 15-24. 32. Salleh WMNHW, Ahmad F. Antioxidant and antiinflammatory activities of essential oils of Actinodaphne macrophylla and A. pruinosa (Lauraceae). Nat Prod Commun.2016; 11: 853-5. 33. Salleh WMNHW, Ahmad F, Khong HY, Zulkifli RM. Chemical constituents and bioactivities from the leaves of Beilschmiedia glabra Kosterm (Lauraceae). Marmara Pharm J 2016: 20: 400- 6. 34. Salleh WMNHW, Ahmad F, Khong HY, Zulkifli RM. Comparative biological activities of extracts from three Malaysian Beilschmiedia species. Marmara Pharm J 2016; 20: 224-31. 35. Zavala MA, Perez GS, Perez GRM. Antimicrobial screening of some medicinal plants. Phytother Res 1997; 11: 368-71. 36. Petrus EM, Tinakumari S, Chai LC, Ubong A, Tunung R, Elexson N, Chai LF, Son R. A study on the minimum inhibitory concentration and minimum bactericidal concentration of nano colloidal silver on food-borne pathogens. Int Food Res J 2011; 18: 55-66.
Yıl 2017, Cilt: 21 Sayı: 4, 889 - 897, 01.12.2017

Öz

Kaynakça

  • 1. Gautam B. Natural product: Chemistry, Biochemistry and Pharmocology. Alpha Science International Ltd. (Oxford, UK), 2009. 2. Bennett GJ, Lee HJ. Xanthones from Guttiferae. Phytochemistry 1989; 28: 967-998. 3. Waterman PG, Hussain RA. Systematic significance of xanthones, benzophenones and biflavonoids in Garcinia. Biochem Syst Ecol 1983; 11: 21-28. 4. Whitemore TC. Malayan Forest Records No. 26: Tree of Malaya: A Manual for Foresters. Longman (Kuala Lumpur), 1972. 5. Parveen M, Khan NU, Acchari B, Dutta PK. A triterpene from Garcinia mangostana. Phytochemistry 1991; 30: 361-2. 6. Corner EJH. Wayside Trees of Malaya, Government Printing Office, 1940. 7. Nilar LH, Nguyen D, Ganpathi V, Sim K-Y, Harrison LJ. Xanthones and benzophenones from Garcinia griffthii and Garcinia mangostana. Phytochemistry 2005; 66: 1718-23. 8. Xu YJ, Cao SG, Wu XH, Lai YH, Tan BHK, Pereira JT, Goh SH, Venkatraman G, Harrison LJ, Sim KY. Griffipavixanthone, a novel cytotoxic bixanthone from Garcinia griffithii and G. parvifolia. Tetrahedron Lett 1998; 39: 9103-6. 9. Elfita E, Muharni M, Madyawati L, Darwati D, Ari W, Supriyatna S, Husein HB, Dachriyanus D, Paul C, Louis M, Kenne F, Sandra A, Luc P. Antiplasmodial and other constituents from four Indonesian Garcinia spp. Phytochemistry 2009; 70: 907- 12. 10. Anu Aravind AP, Asha KRT, Rameshkumar KB. Phytochemical analysis and antioxidant potential of the leaves of Garcinia travancorica Bedd. Nat Prod Res 2016; 30: 232-6. 11. Permanaa D, Abas F, Maulidiani, Shaari K, Stanslas J, Ali AM, Lajis N. Atrovirisidone B, a new prenylated depsidone with cytotoxic property from the roots of Garcinia atroviridis. Z Naturforsch 2005; 60: 523-6. 12. Panthong K, Hutadilok-Towatana N, Panthong A. Cowaxanthone F, a new tetraoxygenated xanthone, and other anti-inflammatory and antioxidant compounds from Garcinia cowa. Canadian J Chem 2009; 87: 1636-40. 13. Jamila N, Khairuddean M, Khan SN, Khan N. Complete NMR assignments of bioactive rotameric (3→8) biflavonoids from the bark of Garcinia hombroniana. Magn Reson Chem 2014; 52: 345-52. 14. Al-Shaghdari A, Bello Alarcón A, Cuesta-Rubio O. Determination of biflavonoids in different parts of Garcinia bakeriana (Urb) borhidi. Rev Cuba Farm 2014; 48: 307-15. 15. Ito T, Yokota R, Watarai T, Mori K, Oyama M, Nagasawa H, Matsuda H, Iinuma M. Isolation of six isoprenylated biflavonoids from the leaves of Garcinia subelliptica. Chem Pharm Bull 2013; 61: 551-8. 16. Gontijo VS, Judice WAS, Codonho B, Pereira IO, Assis DM, Januário JP, Caroselli EE, Juliano MA, De Carvalho Dosatti A, Marques MJ, Junior CV, Santos MHD. Leishmanicidal, antiproteolytic and antioxidant evaluation of natural biflavonoids isolated from Garcinia brasiliensis and their semisynthetic derivatives. Eur J Med Chem 2012; 58: 613-23. 17. Kaikabo AA, Eloff JN. Antibacterial activity of two biflavonoids from Garcinia livingstonei leaves against Mycobacterium smegmatis. J Ethnopharmacol 2011; 138: 253-5. 18. Castardo JC, Prudente AS, Ferreira J, Guimarães CL, Monache FD, Filho VC, Otuki MF, Cabrini DA. Anti-inflammatory effects of hydroalcoholic extract and two biflavonoids from Garcinia gardneriana leaves in mouse paw oedema. J Ethnopharmacol 2008; 118: 405-11. 19. Nworu CS, Akah PA, Esimone CO, Okoli CO, Okoye FBC. Immunomodulatory activities of kolaviron, a mixture of three related biflavonoids of Garcinia kola Heckel. Immunopharmacol Immunotoxicol 2008; 30: 317-32. 20. Lin YM, Anderson H, Flavin MT, Pai YHS, Mata-Greenwood E, Pengsuparp T, Pezzuto JM, Schinazi RF, Hughes SH, Chen FC. In vitro anti-HIV activity of biflavonoids isolated from Rhus succedanea and Garcinia multiflora. J Nat Prod 1997; 60: 884-8. 21. Gunatilaka AAL, Sriyani HTB, Sotheeswaran S, Waight ES. 2,5-dihydroxy-1,6-dimethoxyxanthone and biflavonoids of Garcinia thwaitesii. Phytochemistry 1983; 22: 233-5. 22. Waterman PG, Crichton EG. Xanthones and biflavonoids from Garcinia densivenia stem bark. Phytochemistry 1980; 19: 2723-6. 23. Bandaranayake WM, Selliah SS, Sultanbawa MUS, Davii OW. Biflavonoids and xanthones of Garcinia terpnophylla and G. echinocarpa. Phytochemistry 1975; 14:, 1878-80. 24. Rice-Evans CA, Miller NJ, Paganga G. Antioxidant properties of phenolic compounds. Trends Pl Sci Rev 1997; 2: 152-9. 25. Te-Sheng C. Review: An updated review of tyrosinase inhibitors. Int J Mol Sci 2009; 10: 2440-75. 26. Chen FC, Lin YM, Hung JC. Phenolic compounds from the heartwood of Garcinia multiflora. Phytochemistry 1975; 14: 300-3. 27. Ryu YB, Jeong HJ, Kim JH, Kim YM, Park JH, Kim D, Naguyen TTH, Park SJ, Chang JS, Park KH, Rho MC, Lee WS. Biflavonoids from Torreya nucifera displaying SARS-CoV 3CLpro inhibition. Bioorg Med Chem 2010; 18: 7940-7. 28. Ragasa CY, Levida RM, Don MJ, Shen CC. Cytotoxic isothiocyanates from Moringa oleifera Lam seeds. Philippine Sci Lett 2012; 5: 46-52. 29. Nozaki H, Suzuki H, Hirayama T, Kasai R, Wu RY, Lee KH. Antitumor triterpenes of Maytenus diversifolia. Phytochemistry 1986; 25: 479-85. 30. Hui WH, Ko PDS, Lee YK, Li MM, Arthur HR. Triterpenoids from the ten Lithocarpus species of Hong Kong. Phytochemistry 1975; 14: 1063-6. 31. Tahany MAAR, Hegazy AK, Sayed AM, Kabiel HF, El-Alfy T, El-Komy SM. Study on combined antimicrobial activity of some biologically active constituents from wild Moringa peregrine Forssk. J Yeast Fungal Res 2010; 1: 15-24. 32. Salleh WMNHW, Ahmad F. Antioxidant and antiinflammatory activities of essential oils of Actinodaphne macrophylla and A. pruinosa (Lauraceae). Nat Prod Commun.2016; 11: 853-5. 33. Salleh WMNHW, Ahmad F, Khong HY, Zulkifli RM. Chemical constituents and bioactivities from the leaves of Beilschmiedia glabra Kosterm (Lauraceae). Marmara Pharm J 2016: 20: 400- 6. 34. Salleh WMNHW, Ahmad F, Khong HY, Zulkifli RM. Comparative biological activities of extracts from three Malaysian Beilschmiedia species. Marmara Pharm J 2016; 20: 224-31. 35. Zavala MA, Perez GS, Perez GRM. Antimicrobial screening of some medicinal plants. Phytother Res 1997; 11: 368-71. 36. Petrus EM, Tinakumari S, Chai LC, Ubong A, Tunung R, Elexson N, Chai LF, Son R. A study on the minimum inhibitory concentration and minimum bactericidal concentration of nano colloidal silver on food-borne pathogens. Int Food Res J 2011; 18: 55-66.
Toplam 1 adet kaynakça vardır.

Ayrıntılar

Konular Sağlık Kurumları Yönetimi
Bölüm Makaleler
Yazarlar

Wan Mohd Nuzul Hakimi Wan Salleh Bu kişi benim

Nik Shazwani Afifah Nik Sazalı Bu kişi benim

Farediah Ahmad Bu kişi benim

Muhammad Taher Bu kişi benim

Yayımlanma Tarihi 1 Aralık 2017
Yayımlandığı Sayı Yıl 2017 Cilt: 21 Sayı: 4

Kaynak Göster

APA Salleh, W. M. N. H. W., Sazalı, N. S. A. N., Ahmad, F., Taher, M. (2017). Biflavonoids from the leaves and stem bark of Garcinia griffithii and their biological activities. Marmara Pharmaceutical Journal, 21(4), 889-897.
AMA Salleh WMNHW, Sazalı NSAN, Ahmad F, Taher M. Biflavonoids from the leaves and stem bark of Garcinia griffithii and their biological activities. mpj. Aralık 2017;21(4):889-897.
Chicago Salleh, Wan Mohd Nuzul Hakimi Wan, Nik Shazwani Afifah Nik Sazalı, Farediah Ahmad, ve Muhammad Taher. “Biflavonoids from the Leaves and Stem Bark of Garcinia Griffithii and Their Biological Activities”. Marmara Pharmaceutical Journal 21, sy. 4 (Aralık 2017): 889-97.
EndNote Salleh WMNHW, Sazalı NSAN, Ahmad F, Taher M (01 Aralık 2017) Biflavonoids from the leaves and stem bark of Garcinia griffithii and their biological activities. Marmara Pharmaceutical Journal 21 4 889–897.
IEEE W. M. N. H. W. Salleh, N. S. A. N. Sazalı, F. Ahmad, ve M. Taher, “Biflavonoids from the leaves and stem bark of Garcinia griffithii and their biological activities”, mpj, c. 21, sy. 4, ss. 889–897, 2017.
ISNAD Salleh, Wan Mohd Nuzul Hakimi Wan vd. “Biflavonoids from the Leaves and Stem Bark of Garcinia Griffithii and Their Biological Activities”. Marmara Pharmaceutical Journal 21/4 (Aralık 2017), 889-897.
JAMA Salleh WMNHW, Sazalı NSAN, Ahmad F, Taher M. Biflavonoids from the leaves and stem bark of Garcinia griffithii and their biological activities. mpj. 2017;21:889–897.
MLA Salleh, Wan Mohd Nuzul Hakimi Wan vd. “Biflavonoids from the Leaves and Stem Bark of Garcinia Griffithii and Their Biological Activities”. Marmara Pharmaceutical Journal, c. 21, sy. 4, 2017, ss. 889-97.
Vancouver Salleh WMNHW, Sazalı NSAN, Ahmad F, Taher M. Biflavonoids from the leaves and stem bark of Garcinia griffithii and their biological activities. mpj. 2017;21(4):889-97.