Sains Malaysiana 50(11)(2021): 3231-3239
http://doi.org/10.17576/jsm-2021-5011-07
Phytochemicals and Bioactivities of Syzygium filiforme var. filiforme
(Fitokimia dan Bioaktiviti Syzygium filiforme var. filiforme)
MOHD HAFIZ AHMAD1,3*, NORHAZANA NOR IZAN2,
NOR HADIANI ISMAIL3 & HUMERA NAZ4
1Nanotechnology & Catalysis Research Centre (NANOCAT),
University of Malaya, Block 3A, Inst. of Graduate Studies Building, 50603 Kuala
Lumpur, Federal Territory, Malaysia
2Faculty of Applied Sciences, Universiti Teknologi MARA,
40450 Shah Alam, Selangor Darul Ehsan, Malaysia
3Atta-ur-Rahman Institute for Natural Produtcs Discovery
(AuRIns), Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak
Alam, Selangor Darul Ehsan, Malaysia
4Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam
Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia
Received: 3 May 2020/Accepted: 17 March 2021
ABSTRACT
Syzygium filiforme var. filiforme is a plant variety from dicotyledonous plant family (Myrtaceae).
Phytochemical studies on S. filiforme var. filiforme stem bark have successfully
isolated and characterized arjunolic acid (1),
alphitolic acid (2), betulinic acid
(3), ursolic acid (4), ursolic acid 3-methyl ester (5), β-sitosterol (6) and
stigmasterol (7). The inhibitory
activities against free radical, starch, and bacteria for major compounds were
tested by using DPPH, α-glucosidase and minimum inhibitory and bacterial
concentration assays, respectively. No promising antioxidant activity was shown
on tested samples except methanolic crude extract. For antidiabetic activity,
methanolic and dichloromethane crude extracts displayed potent activity
compared to 1-deoxynojirimycin. Minimum inhibitory concentration (MIC) and
minimum bacterial concentration (MBC) assays for antibacterial activity were
evaluated on Escherichia coli, Staphylococcus aureus, and Bacillus subtilis. All
crude extracts and major compounds displayed weak and no promising activities
for MIC method, respectively. Meanwhile, for MBC method, hexane crude extract
and compound 1 showed inhibition
against B. subtilis.
Keywords: Antibacterial; antidiabetic; antioxidant;
Myrtaceae; Syzygium
filiforme var. filiforme
ABSTRAK
Syzygium filiforme var. filiforme adalah varieti tumbuhan daripada keluarga tumbuhan dicotyledonous
(Myrtaceae). Kajian fitokimia pada kulit batang S. filiforme var. filiforme berjaya mengasingkan dan mencirikan asid arjunolik (1), asid alfitolik (2), asid betulinik (3), asid ursolik (4), asid ursolik 3-metil ester (5), β-sitosterol (6) dan stigmasterol (7). Aktiviti penghambatan terhadap
radikal bebas, kanji dan bakteria untuk sebatian utama diuji dengan menggunakan
DPPH, α-glukosidase dan uji kepekatan minimum dan kepekatan bakteria,
masing-masing. Tiada aktiviti antioksidan yang menjanjikan pada sampel yang
diuji kecuali ekstrak mentah metanolik. Untuk aktiviti antidiabetik, ekstrak
mentah metanol dan diklorometana menunjukkan aktiviti yang kuat berbanding
dengan 1-deoxynojirimycin. Kaedah kepekatan perencatan minimum (MIC) dan
kepekatan bakteria minimum (MBC) untuk aktiviti antibakteria dinilai pada Escherichia
coli, Staphylococcus aureus dan Bacillus
subtilis. Semua ekstrak mentah dan
sebatian utama masing-masing menunjukkan aktiviti lemah dan tidak menjanjikan
untuk kaedah MIC. Sementara itu, untuk kaedah MBC, ekstrak mentah heksana dan
sebatian 1 menunjukkan perencatan
terhadap B. subtilis.
Kata kunci: Antibakteria; antidiabetik; antioksidan;
Myrtaceae; Syzygium
filiforme var. filiforme
REFERENCES
Ajiboye, B.O., Ojo,
O.A., Oyinloye, B.E., Akuboh, O., Okesola, M.A., Idowu, O. & Kappo, A.P.
2020. In vitro antioxidant and
inhibitory activities of polyphenolic-rich extracts of Syzygium cumini (Linn) Skeels leaf on two important enzymes relevant to type II diabetes mellitus. Pakistan Journal of Pharmaceutical Sciences 33(2): 523-529.
Babu, T.M.C., Rajesh,
S.S., Bhaskar, B.V., Devi, S., Rammohan, A., Sivaraman, T. & Rajendra, W.
2017. Molecular docking, molecular dynamics simulation, biological evaluation
and 2D QSAR analysis of flavonoids from Syzygium
alternifolium as potent anti-Helicobacter
pylori agents. The Royal Society of
Chemistry Advances 7(30): 18277-18292.
Bai, L.Y., Chiu, C.F.,
Chiu, S.J., Chen, Y.W., Hu, J.L., Wu, C.Y. & Weng, J.R. 2015. Alphitolic
acid, an anti-inflammatory triterpene, induces apoptosis and autophagy in oral
squamous cell carcinoma cells, in part, through a p53-dependent pathway. Journal of Functional Foods 18: 368-378.
Banerjee, A., Dasgupta,
N. & De, B. 2005. In vitro study
of antioxidant activity of Syzygium
cumini fruit. Food Chemistry 90(4): 727-733.
Chagas, V.T., França,
L.M., Malik, S. & Paes, A.M.d.A. 2015. Syzygium
cumini (L.) skeels: A prominent source of bioactive molecules against
cardiometabolic diseases. Frontiers in
Pharmacology 6: 259-259.
Chandramu, C., Manohar,
R.D., Krupadanam, D.G. & Dashavantha, R.V. 2003. Isolation,
characterization and biological activity of betulinic acid and ursolic acid
from Vitex negundo L. Phytotherapy Research: An International
Journal Devoted to Pharmacological and Toxicological Evaluation of Natural
Product Derivatives 17(2): 129-134.
Cock, I.E. &
Cheesman, M. 2018. Plants of the genus Syzygium (Myrtaceae): A review on ethnobotany, medicinal properties and phytochemistry.
In Bioactive Compounds of Medicinal
Plants: Properties and Potential for Human Health, edited by Goyal, M.R.
& Ayeleso, A. Florida: Apple Academic Press. pp. 35-84.
De Jesus Soares, J., da
Silva Rosa, A., Motta, P.R., Cibin, F.W.S., Roehrs, R. & Denardin, E.L.G.
2019. Protective role of Syzygium cumini leaf extracts against paraquat-induced oxidative stress in
superoxide-dismutase-deficient Saccharomyces
cerevisiae strains. Acta Scientiarum
Biological Sciences 41: e47139-e47139.
De-Eknamkul, W. &
Potduang, B. 2003. Biosynthesis of β-sitosterol and stigmasterol in Croton sublyratus proceeds via a mixed
origin of isoprene units. Phytochemistry 62(3): 389-398.
Djoukeng, J.D.,
Abou-Mansour, E., Tabacchi, R., Tapondjou, A.L., Bouda, H. & Lontsi, D.
2005. Antibacterial triterpenes from Syzygium
guineense (Myrtaceae). Journal of
Ethnopharmacology 101(1-3): 283-286.
Farag, F., Sasse, F.,
Hendrarto, B. & Izzati, M. 2009. Tree species composition and distribution
in Sungai Lalang Forest Reserve, Selangor, Malaysia. The 10th International Seminar on Environment and Architecture 12(1): 29-34.
Faria, A.F., Marques,
M.C. & Mercadante, A.Z. 2011. Identification of bioactive compounds from
jambolao (Syzygium cumini) and
antioxidant capacity evaluation in different pH conditions. Food Chemistry 126(4): 1571-1578.
Gaspar, R.S., da Silva,
S.A., Stapleton, J., Fontelles, J.L.d.L., Sousa, H.R., Chagas, V.T., Alsufyani,
S., Trostchansky, A., Gibbins, J.M. & Paes, A.M.d.A. 2020. Myricetin, the
main flavonoid in Syzygium cumini leaf, is a novel inhibitor of platelet thiol isomerases PDI and ERp5. Frontiers in Pharmacology 10: 1678.
Güvenalp, Z., Kilic, N.,
Kazaz, C., Kaya, Y. & Demi̇rezer, L.Ö. 2006. Chemical constituents of Galium tortumense. Turkish Journal of Chemistry 30(4): 515-523.
Heng, R.K.J., Majid, N.,
Gandaseca, S. & Ahmed, O. 2013. Assessment of floristic composition in a
rehabilitated forest, Sarawak, Malaysia. Borneo
Journal of Resource Science and Technology 2: 60-66.
Hu, Y.K., Wang, L., Li,
Y.Y., Li, M.J., Xu, W., Zhao, Y., Li, F. & Zhao, Y. 2018. Five new
triterpenoids from Syzygium samarangense (Bl.) Merr. et Perry. Phytochemistry
Letters 25: 147-151.
Ismail, I.S., Ismail, N.
& Lajis, N. 2010. Ichthyotoxic properties and essential oils of Syzygium malaccense (Myrtaceae). Pertanika Journal of Science &
Technology 18(1): 1-6.
Ito, H., Iwamori, H.,
Kasajima, N., Kaneda, M. & Yoshida, T. 2004. Kunzeanones A, B, and C: novel
alkylated phloroglucinol metabolites from Kunzea
ambigua. Tetrahedron 60(44):
9971-9976.
Kabra, S. & Patel,
S. 2018. Total phenolics & flavonoid content of the leaves of Carica papaya & Syzygium cumini. World
Journal of Pharmaceutical Research 7(14): 734-741.
Kim, D.H., Han, K.M.,
Chung, I.S., Kim, D.K., Kim, S.H., Kwon, B.M., Jeong, T.S., Park, M.H., Ahn,
E.M. & Baek, N.I. 2005. Triterpenoids from the flower of Campsis grandiflora K. Schum. as human
acyl-CoA: Cholesterol acyltransferase inhibitors. Archives of Pharmacal Research 28(5): 550-556.
Kuiate, J.R., Mouokeu,
S., Wabo, H.K. & Tane, P. 2007. Antidermatophytic triterpenoids from Syzygium jambos (L.) Alston (Myrtaceae). Phytotherapy Research: An International
Journal Devoted to Pharmacological and Toxicological Evaluation of Natural
Product Derivatives 21(2): 149-152.
Lee, S.S., Lin, H.C.
& Chen, C.K. 2008. Acylated flavonol monorhamnosides, α-glucosidase
inhibitors, from Machilus philippinensis. Phytochemistry 69(12): 2347-2353.
Maliehe, T.S., Shandu,
J.S., Basson, A.K., Simelane, M.B., Lazarus, G. & Singh, M. 2017.
Pharmacodynamic and cytotoxicity effects of Syzygium
cordatum {S Ncik, 48 (UZ)} fruit-pulp extract in gastrointestinal tract
infections. Tropical Journal of
Pharmaceutical Research 16(6): 1349-1355.
Manaharan, T., Appleton,
D., Cheng, H.M. & Palanisamy, U.D. 2012. Flavonoids isolated from Syzygium aqueum leaf extract as
potential antihyperglycaemic agents. Food
Chemistry 132(4): 1802-1807.
Minh, N.P., Anh, N.H.,
Pha, P.T.L. & Bach, L.G. 2018. Effect of blanching, drying and preservation
of dried wax apple (Syzygium samarangense)
leaf tea. Research on Crops 19(4):
730-735.
Musabayane, C.T.,
Mahlalela, N., Shode, F.O. & Ojewole, J.A. 2005. Effects of Syzygium cordatum (Hochst.) [Myrtaceae]
leaf extract on plasma glucose and hepatic glycogen in streptozotocin-induced
diabetic rats. Journal of
Ethnopharmacology 97(3): 485-490.
Nguyen, T.L., Rusten,
A., Bugge, M.S., Malterud, K.E., Diallo, D., Paulsen, B.S. & Wangensteen,
H. 2016. Flavonoids, gallotannins and ellagitannins in Syzygium guineense and the traditional use among Malian healers. Journal of Ethnopharmacology 192:
450-458.
Reynertson, K.A., Yang,
H., Jiang, B., Basile, M.J. & Kennelly, E.J. 2008. Quantitative analysis of
antiradical phenolic constituents from fourteen edible Myrtaceae fruits. Food Chemistry 109(4): 883-890.
Saleem, U., Ali, N.
& Ahmad, B. 2016. Does Syzygium
cumini possess significant pharmacological effects an overview. Newsletter 2: 26-29.
Savitha, R.C.,
Padmavathy, S. & Sundhararajan, A. 2011. In vitro antioxidant activities on leaf extracts of Syzygium malaccense (L.) merr and perry. Ancient Science of Life 30(4):
110-113.
Shen, S.C., Chang, W.C.
& Chang, C.L. 2012. Fraction from wax apple [Syzygium samarangense (Blume) Merrill and Perry] fruit extract
ameliorates insulin resistance via modulating insulin signaling and
inflammation pathway in tumor necrosis factor α-treated FL83B mouse
hepatocytes. International Journal of
Molecular Sciences 13(7): 8562-8577.
Shinde, J., Taldone, T.,
Barletta, M., Kunaparaju, N., Hu, B., Kumar, S., Placido, J. & Zito, S.W.
2008. α-Glucosidase inhibitory activity of Syzygium cumini (Linn.) Skeels seed kernel in vitro and in Goto-Kakizaki (GK) rats. Carbohydrate Research 343(7): 1278-1281.
Swadhin, T.H., Islam,
M.M. & Lima, K.A. 2019. Effect of different concentration of (Indole
3-Butyric Acid) on stem cutting of jamrul (Syzygium
samarangense) at Patuakhali District under Dumki Upazila. Asian Journal of Research and Review in
Agriculture 1(1): 36-44.
Teoh, W.Y., Sim, K.S.,
Richardson, M., Stella, J., Abdul Wahab, N. & Hoe, S.Z. 2013. Antioxidant
capacity, cytotoxicity, and acute oral toxicity of Gynura bicolor. Evidence-Based
Complementary and Alternative Medicine 2013: 1-10.
Ugbabe, G., Ezeunala,
M., Edmond, I., Apev, J. & Salawu, O. 2010. Preliminary phytochemical,
antimicrobial and acute toxicity studies of the stem, bark and the leaves of a
cultivated Syzygium cumini Linn.
(Family: Myrtaceae) in Nigeria. African
Journal of Biotechnology 9(41): 6943-6747.
Zakaria, Z., Sufian, A.,
Ramasamy, K., Ahmat, N., Sulaiman, M., Arifah, A., Zuraini, A. & Somchit,
M. 2010. In vitro antimicrobial
activity of Muntingia calabura extracts and fractions. African Journal
of Microbiology Research 4(4): 304-308.
*Corresponding author; email:
hafiz99414@yahoo.com
|