Sains Malaysiana 47(1)(2018): 117–122
http://dx.doi.org/10.17576/jsm-2018-4701-14
Chemical Constituents of
Malaysian Apis mellifera Propolis
(Juzuk Kimia Propolis Apis melliferaMalaysia)
TUAN NADRAH NAIM TUAN ISMAIL1, SITI AMRAH SULAIMAN2, KANNAN THIRUMULU PONNURAJ1,3, CHE NIN MAN4 & NORUL BADRIAH HASSAN2*
1School
of Dental Sciences, Universiti Sains Malaysia, 16150 Kubang Kerian,
Kelantan Darul Naim, Malaysia
2Department
of Pharmacology, School of Medical Sciences, Universiti Sains Malaysia, 16150 Kubang Kerian, Kelantan Darul Naim,
Malaysia
3Human
Genome Centre, School of Medical Sciences, Universiti Sains Malaysia, 16150 Kubang Kerian, Kelantan Darul Naim,
Malaysia
4National
Poison Centre, Universiti Sains Malaysia, 11800 Penang, Pulau Pinang, Malaysia
Received:
27 March 2015/Accepted: 7 June 2017
ABSTRACT
Propolis is
a resinous material collected by honey bees from various plant sources. The
chemical constituents differ depending on the source of vegetation area. To
date, no study of the chemical constituents of Apis mellifera propolis from
Malaysia has been reported. Thus, the aim of this study was to determine the
chemical constituents of Malaysian Apis mellifera propolis. Raw propolis samples were collected from Acacia mangium apiary from northern and southern regions of
Peninsular Malaysia and were extracted using 70% ethanol. Then, the ethanolic extracts were evaporated and were lyophilized to
dryness. The silylated compounds were identified by
gas chromatography with mass spectrometry analysis (GC-MS).
The compounds were characterised by comparison with NIST02
and Wiley275 libraries. Twenty-six individual compounds were identified and
β-panasinsene was identified for the first time
in propolis. The main compounds identified from both
southern and northern regions of Peninsular Malaysia were terpenoids. Terpenoids belong to an important class in the propolis compounds due to its valuable biological
properties. The amount of terpenoids ranged from 7.19
to 11.46% indicating that although the main plant source for both regions was Acacia mangium, other shrubs and fruit orchards
surrounding the two apiaries may differ which may contribute to the variations.
Keywords: Ethanolic extract; GC-MS; Malaysian propolis
ABSTRAK
Propolis adalah bahan resin yang dipungut oleh lebah madu daripada pelbagai sumber tumbuh-tumbuhan. Juzuk kimia berbeza bergantung kepada sumber kawasan tumbuh-tumbuhan. Sehingga kini, tiada kajian juzuk kimia propolis Apis melliferadari Malaysia dilaporkan. Justeru, tujuan kajian ini adalah untuk mengenal pasti kandungan kimia propolis Apis melliferaMalaysia. Sampel propolis mentah telah dikumpul dari tempat ternakan lebah Acacia mangiumdari kawasan utara dan selatan Semenanjung Malaysia dan telah diekstrak menggunakan 70% etanol. Kemudian, ekstrak etanol telah disejat dan dibeku keringkan. Sebatian sililasi telah dikenal pasti menggunakan analisis kromatografi gas dan jisim spektrometri (GC-MS). Sebatian dicirikan melalui perbandingan dengan perpustakaan NIST02 and Wiley275. Dua puluh enam sebatian individu telah dikenal pasti dan β-panasinsene telah dikenal pasti buat kali pertama daripada propolis. Sebatian utama yang dikenal pasti daripada kedua-dua kawasan selatan dan utara Semenanjung Malaysia adalah terpenoid. Jumlah terpenoid antara 7.19-11.46% menunjukkan bahawa walaupun sumber tumbuhan utama untuk kedua-dua kawasan adalahAcacia mangium, tetapi pokok renek lain dan kebun buah-buahan di sekitar dua apiari mungkin berbeza dan menyumbang kepada perbezaan.
Kata kunci: Ekstrak etanol; GC-MS; propolis Malaysia
REFERENCES
Agüero,
M.B., Svetaz, L., Baroni,
V., Lima, B., Luna, L., Zacchino, S., Saavedra, P., Wunderlin, D., Feresin, G.E.
& Tapia, A. 2014. Urban propolis from San Juan province
(Argentina): Ethnopharmacological uses and antifungal
activity against Candida and dermatophytes. Industrial Crops and Products 57:
166-173.
Ahn, M-R., Kumazawa, S., Usui, Y., Nakamura,
J., Matsuka, M., Zhu, F. & Nakayama, T. 2007. Antioxidant activity and constituents of propolis collected in various areas of China. Food Chemistry 101(4): 1383-1392.
Ahn, M-R., Kumazawa, S., Hamasaka, T., Bang, K-S. & Nakayama, T. 2004.
Antioxidant activity and constituents of propolis collected in various areas of Korea. Journal of Agricultural and Food
Chemistry 52(24): 7286-7292.
Bankova, V.
2005. Chemical diversity of propolis and the problem of standardization. Journal of Ethnopharmacology 100(1): 114-117.
Bankova,
V.S., de Castro, S.L. & Marcucci, M.C. 2000. Propolis: Recent advances in chemistry and plant origin. Apidologie 31(1): 3-16.
Banskota, A.H., Tezuka,
Y., Adnyana, I.K., Ishii, E., Midorikawa,
K., Matsushige, K. & Kadota,
S. 2001. Hepatoprotective and anti-helicobacter pylori activities of constituents from
Brazilian propolis. Phytomedicine 8(1): 16-23.
Boonsai, Pattaraporn, Preecha Phuwapraisirisan & Chanpen Chanchao. 2014. Antibacterial
activity of a cardanol from Thai Apis melliferapropolis. International
Journal of Medical Sciences 11(4): 327-336.
Chen, J., Long, Y., Han, M., Wang, T., Chen, Q. & Wang, R.
2008. Water-soluble derivative of propolis mitigates scopolamine-induced learning and memory impairment in mice. Pharmacology
Biochemistry and Behavior 90(3): 441-446.
Roumen Christov, Boryana Trusheva, Milena Popova, Vassya Bankova & Michel Bertrand. 2006. Chemical composition of propolis from Canada,
its antiradical activity and plant origin. Natural Product Research 20(06):
531-536.
Cole, N., Sou, P.W., Ngo, A., Tsang,
K.H., Severino, J.A.J., Arun,
S.J., Duke, C.C. & Reeve, V.E. 2010. Topical 'Sydney'propolis protects against UV-radiation-induced inflammation,
lipid peroxidation and immune suppression in mouse skin. International
Archives of Allergy and Immunology 152(2): 87-97.
de Barros, M.P., Lemos, M., Maistro, E.L., Leite, M.F.,
Sousa, J.P.B., Bastos, J.K. & de Andrade, S.F. 2008. Evaluation
of antiulcer activity of the main phenolic acids found in Brazilian green propolis. Journal of Ethnopharmacology 120(3): 372- 377.
Garcia-Viguera, C., Ferreres,
F. & Tomas-Barberan, F.A. 1993. Study of Canadian propolis by GC-MS and
HPLC. Zeitschrift für Naturforschung C 48(9-10):
731-735.
Ghisalberti, E.L. 1979. Propolis:
A review. Bee World 60(2): 59-84.
Gregoris, E., Fabris,
S., Bertelle, M., Grassato,
L. & Stevanato, R. 2011. Propolis as potential cosmeceutical
sunscreen agent for its combined photoprotective and
antioxidant properties. International Journal of Pharmaceutics 405(1):
97-101.
Hegazi, A.G., El-Hady, F.K.A. & Abd Allah, F.A.M. 2000. Chemical composition and antimicrobial activity of European propolis. Zeitschrift fur Naturforschung C 55(1/2): 70-75.
Huang, M., Lu, J-J., Huang, M-Q., Bao,
J-L., Chen, X-P. & Wang, Y-T. 2012. Terpenoids:
Natural products for cancer therapy. Expert Opinion on Investigational Drugs 21(12): 1801-1818.
Huang, S., Zhang, C-P., Wang, K., Li, G.Q. & Hu, F-L. 2014. Recent advances in the chemical composition of propolis. Molecules 19(12): 19610-19632.
Hübschmann,
H-J. 2015. Handbook of GC-MS: Fundamentals and Applications. New
York: John Wiley & Sons.
Nurhamizah Ibrahim, Nurul Farah Shakila Mohd Niza,
Muhammad Muslim Mohd Rodi, Abdul Jamil Zakaria, Zhari Ismail & Khamsah Suryati Mohd. 2016. Chemical and biological analyses of
Malaysian stingless bee propolis extracts. Malaysian
Journal of Analytical Sciences 20(2): 413-422.
Jacob, A., Parolia, A., Pau, A. & Amalraj, F.D. 2015. The
effects of Malaysian propolis and Brazilian red propolis on connective tissue fibroblasts in the wound
healing process. BMC Complementary and Alternative Medicine 15(1):
294.
Murat Kartal, Serdar Kaya & Semra Kurucu. 2002. GC-MS analysis of propolis samples from two
different regions of Turkey. Zeitschrift fur Naturforschung C-Journal of Biosciences 57(9-10):
905-909.
Krell, R. 1996. Value-added Products from Beekeeping: Food &
Agriculture Org. http://www.fao.org/docrep/w0076e/ w0076e00.htm.
Li,
F., Awale, S., Zhang, H., Tezuka,
Y., Esumi, H. & Kadota,
S. 2009. Chemical constituents of propolis from
Myanmar and their preferential cytotoxicity against a human pancreatic cancer
cell line. Journal of Natural Products 72(7): 1283-1287.
Machado,
J.L., Martins Assunçao, A.K., Pinto da Silva, M.C.,
dos Reis, A.S., Costa, G.C., de Sousa Arruda, D.,
Rocha, B.A., de Oliveira Lima Leite Vaz, M.M., de Andrade Paes, A.M.,
Guerra, R.N.M., Berretta, A.A. & do Nascimento,
F.R.F. 2012. Brazilian green propolis:
Anti-inflammatory property by an immunomodulatory activity. Evidence-Based
Complementary and Alternative Medicine 2012: Article ID. 157652.
Maciejewicz, W., Daniewski,
M., Bal, K. & Markowski,
W. 2001. GC-MS identification of the flavonoid aglycones isolated from propolis. Chromatographia 53(5-6): 343-346.
Marcucci, M.C. 1995. Propolis:
Chemical composition, biological properties and therapeutic activity. Apidologie 26(2): 83-99.
Marquez
Hernandez, I., Osmany, C-R., Fernandez, M.C., Perez,
A.R., de Oca Porto, R.M., Piccinelli,
A.L. & Rastrelli, L. 2010. Studies on the
constituents of yellow Cuban propolis: GC-MS
determination of triterpenoids and flavonoids. Journal of Agricultural and
Food Chemistry 58(8): 4725-4730.
McNair, H.M. & Miller, J.M. 2011. Basic Gas Chromatography. New York: John Wiley
& Sons.
Medana,
C., Carbone, F., Aigotti, R., Appendino,
G. & Baiocchi, C. 2008. Selective analysis of phenolic compounds in propolis by HPLC-MS/MS. Phytochemical Analysis 19(1): 32-39.
Melliou,
E., Stratis, E. & Chinou,
I. 2007. Volatile constituents of propolis from various regions of Greece-Antimicrobial activity. Food Chemistry 103(2): 375-380.
Naito, Yukiko, Misao Yasumuro,
Keiichiro Kondou & Naoki Ohara. 2007. Antiinflammatory effect of topically applied propolis extract in carrageenan-induced rat hind paw edema. Phytotherapy Research 21(5): 452-456.
Nakajima, Yoshimi, Masamitsu Shimazawa, Satoshi Mishima &
Hideaki Hara. 2007. Water extract of propolis and its
main constituents, caffeoylquinic acid derivatives,
exert neuroprotective effects via antioxidant actions. Life Sciences 80(4):
370-377.
Nik Yusliyana Nik Yusoff, Suharni Mohamad, Haswati@ Nurhayati Abdullah, Nurhayu Ab Rahman, Kumitaa Theva Das, Khoirulzariah Ismail, Dasmawati Mohamad, Siti Noor Fazliah Mohd Noor, Siti Razila Abdul Razak & Muggundha Raaov Ramachandran. 2016. Antifungal activity of
Malaysian honey and propolis extracts against
pathogens implicated in denture stomatitis. Paper read at AIP Conference
Proceedings.
Nur Liyana Rosli, Husniyati Roslan, Eshaifol Azam Omar, Norehan Mokhtar, Nor Hussaini Abdul Hapit, Nornaimah Asem, Kumitaa Theva Das, Khoirulzariah Ismail, Dasmawati Mohamad & Siti Noor Fazliah Mohd Noor. 2016.
Phytochemical analysis and antioxidant activities of Trigona apicalispropolis extract. Paper read at AIP Conference Proceedings.
Osmany,
C-R., Piccinelli, A.L., Fernandez, M.C., Hernandez,
I.M., Rosado, A. & Rastrelli, L. 2007. Chemical characterization of Cuban propolis by
HPLC− PDA, HPLC− MS, and NMR: The brown, red, and yellow Cuban
varieties of propolis. Journal of Agricultural and
Food Chemistry 55(18): 7502-7509.
Paintz, M.
& Metzner, J. 1979. On the local anaesthetic action of propolis and some of its constituents. Die Pharmazie34(12): 839-841.
Park, Y.K., Alencar, S.M. & Aguiar, C.L. 2002. Botanical origin and chemical composition of Brazilian propolis. Journal of Agricultural and Food
Chemistry 50(9): 2502-2506.
Park,
Y.K., Paredes-Guzman, J.F., Aguiar, C.L., Alencar, S.M. & Fujiwara, F.Y.
2004. Chemical constituents in Baccharis dracunculifoliaas the main botanical origin of
southeastern Brazilian propolis. Journal of
Agricultural and Food Chemistry 52(5): 1100-1103.
Paulino,
N., Barbosa, A.P., Paulino, A.S. & Marcucci, M.C. 2014. Hepatoprotective effect of green propolis is related with antioxidant
action in vivo and in vitro. Oxidants and Antioxidants in
Medical Science 3(1): 43-50.
Popova, M., Trusheva, B., Cutajar, S., Antonova, D.,
Mifsud, D., Farrugia, C. & Bankova,
V. 2012. Identification of the plant origin of the
botanical biomarkers of Mediterranean type propolis. Natural Product Communications 7(5): 569-570.
Popova, M., Trusheva, B., Antonova, D., Cutajar, S.,
Mifsud, D., Farrugia, C., Tsvetkova,
I., Najdenski, H. & Bankova,
V. 2011. The specific chemical profile of Mediterranean propolis from Malta. Food Chemistry 126(3):
1431-1435.
Popova, M.P., Graikou, K., Chinou, I. & Bankova, V.S.
2010. GC-MS profiling of diterpene compounds
in Mediterranean propolis from Greece. Journal of
Agricultural and Food Chemistry 58(5): 3167-3176.
Shimazawa,
M., Chikamatsu, S., Morimoto, N., Mishima,
S., Nagai, H. & Hara, H. 2005. Neuroprotection
by Brazilian green propolis against in vitro and in vivo ischemic neuronal damage. Evidence-Based Complementary
and Alternative Medicine 2(2): 201-207.
Shiva Mohammadzadeh, Mohammad Shariatpanahi, Manoochehr Hamedi, Reza Ahmadkhaniha, Nasrin Samadi & Seyed Nasser Ostad. 2007. Chemical composition, oral toxicity and
antimicrobial activity of Iranian propolis. Food
Chemistry 103(4): 1097-1103.
Sobočanec, S., Balog,
T., Šariċ, A., Mačak-Šafranko, ˇ., Štroser, M., ˇarković, K., ˇarković,
N., Stojković, R., Ivanković,
S. & Marotti, T. 2011. Antitumor
effect of Croatian propolis as a consequence of
diverse sex-related dihydropyrimidine dehydrogenase
(DPD) protein expression. Phytomedicine 18(10): 852-858.
Syamsudin, Sudjaswadi Wiryowidagdo, Partomuan Simanjuntak &
Wan Lelly Heffen. 2009.
Chemical composition of propolis from
different regions in Java and their cytotoxic activity. American Journal of Biochemistry & Biotechnology 5(4): 180-183.
Toreti, V.C.,
Sato, H.H., Pastore, G.M. & Park,
Y.K. 2013. Recent progress of propolis
for its biological and chemical compositions and its botanical origin.
Evidence-Based Complementary and Alternative Medicine 2013:
Article ID. 697390.
Trusheva, B.,
Popova, M., Koendhori, E.B., Tsvetkova,
I., Naydenski, C. & Bankova,
V. 2011. Indonesian propolis: Chemical composition,
biological activity and botanical origin. Natural Product Research
25(6): 606-613.
Volpi, N.
& Bergonzini, G. 2006. Analysis of flavonoids from propolis
by on-line HPLC-electrospray mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis 42(3): 354-361.
Xuan,
H., Li, Z., Yan, H., Sang, Q., Wang, K., He, Q., Wang, Y. & Hu, F. 2014. Antitumor activity of Chinese propolis in
human breast cancer MCF-7 and MDA-MB-231 cells. Evidence- Based Complementary and Alternative Medicine 2014:
Article ID. 280120.
Yildirim,
A., Duran, G.G., Duran, N., Jenedi, K., Bolgul, B.S., Miraloglu, M. & Muz, M. 2016. Antiviral
activity of Hatay propolis against
replication of herpes simplex virus type 1 and type 2. Medical Science Monitor: International
Medical Journal of Experimental and Clinical Research 22: 422-430.
Zayyanu Usman
Umar, Abu Bakar Ainul Bahiyah
& Mohamed Mahaneem. 2016a.
Phytochemical screening and comparison of antioxidant activity of
water and ethanol extract propolis from
Malaysia. International Journal of Pharmacy and Pharmaceutical
Sciences 8(5): 413-415.
Zayyanu Usman
Umar, Ainul Bahiyah
Abu Bakar & Mahaneem Mohamed. 2016b.
Phytochemical composition and activity against hyperglycaemia
of Malaysian propolis in diabetic rats.
Biomedical Research 27(1).
Zayyanu Usman
Umar & Mahaneem Mohamed. 2015.
Analysis of phytochemical compounds in water and ethanol extracts
of Malaysian propolis. International Journal of Pharma and Bio Sciences 6(2): P374-P380.
Zhu, W., Chen, M., Shou, Q., Li, Y. &
Hu, F. 2011. Biological activities of Chinese propolis and Brazilian propolis
on streptozotocin-induced type 1 diabetes
mellitus in rats. Evidence-Based
Complementary and Alternative Medicine 2011: Article ID. 468529.
*Corresponding author;
email: norul@usm.my
|