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 mellifera Malaysia)
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
Diserahkan: 27 Mac 2015/Diterima: 7 Jun 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 mellifera dari Malaysia dilaporkan.
Justeru, tujuan kajian ini adalah untuk mengenal pasti kandungan kimia propolis Apis mellifera Malaysia. Sampel propolis mentah telah dikumpul dari
tempat ternakan lebah Acacia mangium dari 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
adalah Acacia 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
RUJUKAN
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
mellifera propolis. 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
apicalis propolis 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 Pharmazie 34(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
dracunculifolia as 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, Ž., Štroser, M., Žarković,
K., Žarković, 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.
*Pengarang untuk surat-menyurat; email: norul@usm.my
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