Identification of Active Chemical Compounds of Honey from Some Regions in Indonesia
Abstract
Bees produce honey from plant nectar, plant secretions, and excretions of plant-sucking insects. Indonesian local honey contains active compounds that have the potential effect as antioxidant and anticancer. The composition and biological effects of honey vary depending on the flower sources; seasonal and environmental factors can also influence the composition and the physical products. This research was conducted to identify the chemical compounds found in several honey samples produced by beekeepers in Indonesia with LCMS/MS method and to determine the profiles of the honey from Indonesia with the Chemspider and MassBank Database. Honey samples were collected from several regions in Indonesia. The results of the analysis showed that the honey’s diastase number vary from region to region and showed that the HMF contents are relatively low. The compounds that were allegedly found through LCMS/MS analysis include and have been traced based on literature studies had bioactive activity and beneficial to health, include: millefin (potential for treating heart disease and cancer), mangiferin (anti-inflammatory, anti-diabetes, immunomodulators, anti-tumor, antioxidants), rhamnetin (anti-inflammatory), tricin (antioxidant-like), acacetin (inhibit tumor angiogenesis agents), aurantiamide acetate (antiviral or anti-inflammatory, therapeutic agent for the treatment of influenza), salvigenin (controlling inflammation, acute and chronic pain), brucine (modulates anti-inflammatory and analgesic properties), dehydrocostus lactone (anti-inflammatory), santonin (anthelmintic activity), dimethylesculetin (bilirubin clearance), imidazole 4- acetic acid (neuropharmacological properties), propafenone (antiarrhythmic), yohimbine (affected sexual performance), Velutin (anti-inflammatory), narigenin (linked to cardiovascular disease protection). Eventually, honey is is such a natural product with a number of salient therapeutic properties. However, there are still components that were found but their roles cannot be described in detail. Therefore, it is recommended that further meticulous studies should bring to light the other hidden properties of the honey compounds.
References
Alimentarius, C. (1998). Codex Alimentarius standard for honey Ref. Technical report, CL 1998/12-S. FAO and WHO. Rome
Alvarez-Suarez, J., F. Giampieri, and M. Battino (2013). Honey as a Source of Dietary Antioxidants: Structures, Bioavailability and Evidence of Protective Effects Against Human Chronic Diseases. Current Medicinal Chemistry, 20(5); 621–638
Alvarez-Suarez, J. M., S. Tulipani, D. Díaz, Y. Estevez, S. Romandini, F. Giampieri, E. Damiani, P. Astolfi, S. Bompadre, and M. Battino (2010). Antioxidant and antimicrobial capacity of several monoflo- ral Cuban honeys and their correlation with color, polyphenol con- tent and other chemical compounds. Food and Chemical Toxicology, 48(8-9); 2490–2499
Barreto, J. C., M. T. S. Trevisan, W. E. Hull, G. Erben, E. S. de Brito, B. Pfundstein, G. Wurtele, B. Spiegelhalder, and R. W. Owen (2008). Characterization and Quantitation of Polyphenolic Com- pounds in Bark, Kernel, Leaves, and Peel of Mango (MangiferaindicaL.). Journal of Agricultural and Food Chemistry, 56(14); 5599–
5610
Bastos, D. M., É. Monaro, É. Siguemoto, and M. Séfora (2012).
Maillard reaction products in processed food: pros and cons. INTECH
Open Access Publisher
Belchor, M. N., H. H. Gaeta, C. F. B. Rodrigues, C. R. da Cruz Costa,
D. de Oliveira Toyama, L. D. Passero, M. D. Laurenti, and M. H. Toyama (2017). Evaluation of Rhamnetin as an Inhibitor of the Pharmacological Effect of Secretory Phospholipase A2. Molecules, 22(9); 1441
Bertoncelj, J., T. Polak, U. Kropf, M. Korošec, and T. Golob (2011). LC-DAD-ESI/MS analysis of flavonoids and abscisic acid with chemometric approach for the classification of Slovenian honey. Food Chemistry, 127(1); 296–302
Bhat, T. A., D. Nambiar, D. Tailor, A. Pal, R. Agarwal, and R. P. Singh (2013). Acacetin Inhibits In Vitro and In Vivo Angiogenesis and Downregulates Stat Signaling and VEGF Expression. Cancer Prevention Research, 6(10); 1128–1139
Bogdanov, S., K. Ruoff, and L. P. Oddo (2004). Physico-chemical methods for the characterisation of unifloral honeys: a review. Api- dologie, 35(1); 4–17
Boussaid, A., M. Chouaibi, L. Rezig, R. Hellal, F. Donsì, G. Ferrari, and S. Hamdi (2018). Physicochemical and bioactive properties of six honey samples from various floral origins from Tunisia. Arabian Journal of Chemistry, 11(2); 265–274
Carvalho, R. R., C. H. Pellizzon, L. Justulin, S. L. Felisbino, W. Vile- gas, F. Bruni, M. Lopes-Ferreira, and C. A. Hiruma-Lima (2009). Effect of mangiferin on the development of periodontal disease: Involvement of lipoxin A4, anti-chemotaxic action in leukocyte rolling. Chemico-Biological Interactions, 179(2-3); 344–350
Cha, J.-D., S.-M. Choi, and J. H. Park (2014). Combination of Acacetin with Antibiotics against Methicillin Resistant Staphylo- coccus aureus Isolated from Clinical SpecimensCombination of Acacetin with Antibiotics against Methicillin Resistant Staphylococ- cus aureus Isolated from Clinical Specimens. Advances in Bioscience and Biotechnology, 5(4); 398–408
Chadwick, M., H. Trewin, F. Gawthrop, and C. Wagstaff (2013). Sesquiterpenoids Lactones: Benefits to Plants and People. Interna- tional Journal of Molecular Sciences, 14(6); 12780–12805
Cheftel, J.-C., J.-L. Cuq, and D. Lorient (1989). Proteínas alimentarias: bioquímica, propiedades funcionales, valor nutricional, modificaciones químicas. Universidad de la Republica. Zaragoza, Spain., xvii edition
Chirife, J., M. C. Zamora, and A. Motto (2006). The correlation be- tween water activity and % moisture in honey: Fundamental aspects and application to Argentine honeys. Journal of Food Engineering, 72(3); 287–292
Dananjaya, A., S. Winarsih, and B. Prijadi (2013). Pengaruh Ekstrak Metanol Fraksi Etil Asetat Madu Terhadap Pertumbuhan Escherichia coli Secara In Vitro. Ph.D. thesis, Universitas Brawijaya
Dar, A., S. Faizi, S. Naqvi, T. Roome, S. Z. ur Rehman, M. Ali, S. Firdous, and S. T. Moin (2005). Analgesic and Antioxidant Activity of Mangiferin and Its Derivatives: the Structure Activity Relationship. Biological & Pharmaceutical Bulletin, 28(4); 596–600
Daud, M. H., A. S. Ramli, S. Abdul-Razak, M. R. Isa, F. H. Yusoff, N. Baharudin, M. S. Mohamed-Yassin, S. F. Badlishah-Sham, A. W. Nikmat, N. Jamil, and H. Mohd-Nawawi (2020). The EMPOWER-SUSTAIN e-Health Intervention to improve patient activation and self-management behaviours among individuals with Metabolic Syndrome in primary care: study protocol for a pilot randomised controlled trial. Trials, 21(1)
de Oliveira, R. G. et al. (2018). Nutritional Composition and Medical Properties of Honey from Stingless Bees. Nutrition & Food Science International Journal, 7(2); 42–43
Duarte-Almeida, J. M., A. V. Novoa, A. F. Linares, F. M. Lajolo, and M. I. Genovese (2006). Antioxidant Activity of Phenolics Compounds From Sugar Cane (Saccharum officinarum L.) Juice. Plant Foods for Human Nutrition, 61(4); 187–192
Evahelda, F. Pratama, N. Malahayati, and B. Santoso (2015). Uji Aktivitas Enzim Diastase, Kadar Gula Pereduksi dan Kadar Air pada Madu Bangka dan Madu Kemasan yang Dipasarkan di Kota Palembang. In Prosiding Seminar Nasional Lahan Suboptimal; 1–6
Fallico, B., M. Zappalà, E. Arena, and A. Verzera (2004). Effects of conditioning on HMF content in unifloral honeys. Food Chemistry, 85(2); 305–313
Feás, X., J. Pires, A. Iglesias, and M. L. Estevinho (2010). Characteri- zation of artisanal honey produced on the Northwest of Portugal by melissopalynological and physico-chemical data. Food and Chemical Toxicology, 48(12); 3462–3470
Gabor, L. and M. Goian (2006). Methods of finding counterfeit honeybees. Scientifical papers Faculty of Agriculture XXXVIII. 4th session, Soil Sciences; 301–305
Gu, J.-Q., Y. Wang, S. G. Franzblau, G. Montenegro, D. Yang, and B. N. Timmermann (2004). Antitubercular Constituents ofValeri- ana laxiflora. Planta Medica, 70(6); 509–514
Guha, S., S. Ghosal, and U. Chattopadhyay (1996). Antitumor, Im- munomodulatory and Anti-HIV Effect of Mangiferin, a Naturally Occurring Glucosylxanthone. Chemotherapy, 42(6); 443–451
Gündoğdu, E., S. Çakmakçı, and İ. G. Şat (2019). An Overview of Honey: Its Composition, Nutritional and Functional Properties. Journal of Food Science and Engineering, 9(1)
Hasegawa, T., A. Tanaka, A. Hosoda, F. Takano, and T. Ohta (2008). Antioxidant C-glycosyl flavones from the leaves of Sasa kurilensis var. gigantea. Phytochemistry, 69(6); 1419–1424
Houghton, R. A., P. J. (1998). Laboratory Handbook for Fractionation of Natural Extracts. Technical report, London: Chapman and Hall Huang, W., J. Zhang, and D. D. Moore (2004). A traditional herbal medicine enhances bilirubin clearance by activating the nuclear
receptor CAR. Journal of Clinical Investigation, 113(1); 137–143 Islam, M. N., M. I. Khalil, M. A. Islam, and S. H. Gan (2013). Toxic compounds in honey. Journal of Applied Toxicology, 34(7); 733–742 Jadeja, R. N. and R. V. Devkar (2014). Polyphenols and Flavonoids in Controlling Non-Alcoholic Steatohepatitis. In Polyphenols in Human
Health and Disease. Elsevier, pages 615–623
Kesić, A., I. Zaimović, N. Ibrišimović-Mehmedinović, and A. Šestan
(2017). The Influence of Thermal Treatment on the Concentration of HMF in Honey. International Journal of Environmental Chemistry, 2(1); 1–5
Khalil, M., S. Sulaiman, and S. Gan (2010). High 5- hydroxymethylfurfural concentrations are found in Malaysian honey samples stored for more than one year. Food and Chem- ical Toxicology, 48(8-9); 2388–2392
Konz, K.-H., P. A. Berg, and L. Seipel (2008). Cholestase nach antiarrhythmischer Therapie mit Propafenon. DMW - Deutsche Medizinische Wochenschrift, 109(40); 1525–1527
Kowalski, S., M. Lukasiewicz, S. Bednarz, and M. Panuś (2012). Diastase number changes during thermaland microwave processing of honey. Czech Journal of Food Sciences, 30(No. 1); 21–26
Kuwabara, H., K. Mouri, H. Otsuka, R. Kasai, and K. Yamasaki (2003). Tricin from a Malagasy Connaraceous Plant with Potent Antihis- taminic Activity. Journal of Natural Products, 66(9); 1273–1275
© 2021 The Authors.
Page 82 of 84
Sumarlin et. al.
Science and Technology Indonesia, 6 (2021) 74-84
Kwon, Y. S. and C. M. Kim (2003). Antioxidant constituents from the stem ofSorghum bicolor. Archives of Pharmacal Research, 26(7); 535–539
Kwon, Y. S., E. Y. Kim, W. J. Kim, W. K. Kim, and C. M. Kim (2002). Antioxidant constituents fromSetaria viridis. Archives of Pharmacal Research, 25(3); 300–305
Li, H., C. Zhou, Y. Pan, X. Gao, X. Wu, H. Bai, L. Zhou, Z. Chen, S. Zhang, S. Shi, J. Luo, J. Xu, L. Chen, X. Zheng, and Y. Zhao (2005). Evaluation of Antiviral Activity of Compounds Isolated fromRanunculus sieboldiiandRanunculus sceleratus. Planta Medica, 71(12); 1128–1133
Liang, H.-R., P. Vuorela, H. Vuorela, and R. Hiltunen (1997). Isolation and Immunomodulating Effect of Flavonol Glycosides fromEpimedium hunanense. Planta Medica, 63(04); 316–319
Lou, Z., H. Wang, S. Rao, J. Sun, C. Ma, and J. Li (2012). p-Coumaric acid kills bacteria through dual damage mechanisms. Food Control, 25(2); 550–554
Lu, B., X. Wu, J. Shi, Y. Dong, and Y. Zhang (2006). Toxicology and safety of antioxidant of bamboo leaves. Part 2: Developmental toxicity test in rats with antioxidant of bamboo leaves. Food and Chemical Toxicology, 44(10); 1739–1743
Maharani, T., D. Sukandar, and S. Hermanto (2016). Karakter- isasi Senyawa Hasil Isolasi dari Ekstrak Etil Asetat Daun Namnam (Cynometra Cauliflora L.) yang Memiliki Aktivitas Antibakteri. Jurnal Kimia VALENSI, 2(1); 55–62
Mansourabadi, A. H., H. M. Sadeghi, N. Razavi, and E. Rezvani (2016). Anti-inflammatory and analgesic properties of salvigenin, Salvia officinalis flavonoid extracted. Advanced Herbal Medicine, 2(1); 31–41
Masuyama, H., T. Mitsui, J. Maki, K. Tani, K. Nakamura, and Y. Hi- ramatsu (2016). Dimethylesculetin ameliorates maternal glucose intolerance and fetal overgrowth in high-fat diet-fed pregnant mice via constitutive androstane receptor. Molecular and cellular biochem- istry, 419(1); 185–192
Mbaveng, A. T., Q. Zhao, and V. Kuete (2014). Harmful and Protec- tive Effects of Phenolic Compounds from African Medicinal Plants. Toxicological Survey of African Medicinal Plants; 577–609
Meda, A., C. E. Lamien, M. Romito, J. Millogo, and O. G. Nacoulma (2005). Determination of the total phenolic, flavonoid and proline contents in Burkina Fasan honey, as well as their radical scavenging activity. Food Chemistry, 91(3); 571–577
Morales, A. (2000). Yohimbine in erectile dysfunction: the facts. International Journal of Impotence Research, 12(1); 70–74
Moreira, R. F., C. A. D. Maria, M. Pietroluongo, and L. C. Trugo (2010). Chemical changes in the volatile fractions of Brazilian honeys during storage under tropical conditions. Food Chemistry, 121(3); 697–704
Mu, L., J. Kou, D. Zhu, and B. Yu (2008). Antioxidant activities of the chemical constituents isolated from the leaves of Ginkgo biloba. Chinese Journal of Natural Medicines, 6; 26–29
Muruganandan, S., K. Srinivasan, S. Gupta, P. Gupta, and J. Lal (2005). Effect of mangiferin on hyperglycemia and atherogenicity in streptozotocin diabetic rats. Journal of Ethnopharmacology, 97(3); 497–501
Noratto, G. D., M. C. Bertoldi, K. Krenek, S. T. Talcott, P. C. Stringheta, and S. U. Mertens-Talcott (2010). Anticarcinogenic Effects of Polyphenolics from Mango (Mangifera indica) Varieties. Journal of Agricultural and Food Chemistry, 58(7); 4104–4112
Ouchemoukh, S., H. Louaileche, and P. Schweitzer (2007). Physic- ochemical characteristics and pollen spectrum of some Algerian
honeys. Food Control, 18(1); 52–58
Pietta, P.-G. (2000). Flavonoids as Antioxidants. Journal of Natural
Products, 63(7); 1035–1042
Rajendran, P., G. Ekambaram, and D. Sakthisekaran (2008). Pro-
tective Role of Mangiferin against Benzo(a)pyrene Induced Lung Carcinogenesis in Experimental Animals. Biological & Pharmaceuti- cal Bulletin, 31(6); 1053–1058
Rice-Evans, C., N. Miller, and G. Paganga (1997). Antioxidant proper- ties of phenolic compounds. Trends in Plant Science, 2(4); 152–159 Sadeghi, H., A. Mansourabadi, M. Rezvani, M. Ghobadi, N. Razavi, and M. Bagheri (2016). Salvigenin has Potential to Ameliorate
Streptozotocin-induced Diabetes Mellitus and Heart Complica- tions in Rats. British Journal of Medicine and Medical Research, 15(2); 1–12
Sakai, A., K. Watanabe, M. Koketsu, K. Akuzawa, R. Yamada, Z. Li, H. Sadanari, K. Matsubara, and T. Murayama (2008). Anti- Human Cytomegalovirus Activity of Constituents from Sasa Albo- Marginata (Kumazasa in Japan). Antiviral Chemistry and Chemother- apy, 19(3); 125–132
Sakipova, Z., N. S. H. Wong, T. Bekezhanova, Sadykova, A. Shukir- bekova, and F. Boylan (2017). Quantification of santonin in eight species of Artemisia from Kazakhstan by means of HPLC- UV: Method development and validation. PLOS ONE, 12(3); e0173714
Salehi, B., P. Fokou, M. Sharifi-Rad, P. Zucca, R. Pezzani, N. Martins, and J. Sharifi-Rad (2019). The Therapeutic Potential of Narin- genin: A Review of Clinical Trials. Pharmaceuticals, 12(1); 11
Sanna, G., M. I. Pilo, P. C. Piu, A. Tapparo, and R. Seeber (2000). Determination of heavy metals in honey by anodic stripping voltam- metry at microelectrodes. Analytica Chimica Acta, 415(1-2); 165– 173
Schlepper, M. (1987). Propafenone, a review of its profile. European heart journal, 8(suppl_A); 27–32
Schuff-Werner, P., D. Kaiser, C. Lueders, and P. Berg (1981). Propafenon-induced cholestatic liver injury–a further example for allergic drug hepatitis (author’s transl). Zeitschrift fur Gastroenterolo- gie, 19(10); 673–679
Shalini, V., A. Jayalekshmi, and A. Helen (2015). Mechanism of anti-inflammatory effect of tricin, a flavonoid isolated from Njavara rice bran in LPS induced hPBMCs and carrageenan induced rats. Molecular Immunology, 66(2); 229–239
Shapla, U. M., M. Solayman, N. Alam, M. I. Khalil, and S. H. Gan (2018). 5-Hydroxymethylfurfural (HMF) levels in honey and other food products: effects on bees and human health. Chemistry Central Journal, 12(1); 1–18
Siddoway, L. A., D. M. Roden, and R. L. Woosley (1984). Clinical pharmacology of propafenone: Pharmacokinetics, metabolism and concentration-response relations. The American Journal of Cardiology, 54(9); 9D–12D
Soltana, H., M. D. Rosso, H. Lazreg, A. D. Vedova, M. Ham- mami, and R. Flamini (2018). LC-QTOF characterization of non-anthocyanic flavonoids in four Tunisian fig varieties. Journal of Mass Spectrometry, 53(9); 817–823
Stolzenbach, S., D. V. Byrne, and W. L. Bredie (2011). Sensory local uniqueness of Danish honeys. Food Research International, 44(9); 2766–2774
Sumarlin, H. B. I. A. F. A., L.O. (2019b). Anticancer Activity Of Honey Extract From Indonesia By A549 Cell Inhibition In Vitro. Ecology, Environment and Conservation Journal, 25(3); 1196–1202
Sumarlin, L. O., A. Muawanah, F. R. Afandi, and A. Adawiah (2019). Inhibitory Activity of HEp-2 Cells by Honey from Indonesia. Jur-
nal Kimia Sains dan Aplikasi, 22(6); 317–325
Terrab, A., M. J. Di’ez, and F. J. Heredia (2002). Characterisation of
Moroccan unifloral honeys by their physicochemical characteristics.
Food Chemistry, 79(3); 373–379
Tunnicliff, G. (1998). Pharmacology and Function of Imidazole 4-
Acetic Acid in Brain. General Pharmacology: The Vascular System,
31(4); 503–509
Vanhanen, L. P., A. Emmertz, and G. P. Savage (2011). Mineral anal-
ysis of mono-floral New Zealand honey. Food Chemistry, 128(1);
236–240
Wang, H.-B., H. Yao, G.-H. Bao, H.-P. Zhang, and G.-W. Qin
(2004). Flavone glucosides with immunomodulatory activity from
the leaves of Pleioblastus amarus. Phytochemistry, 65(7); 969–974 Wang, Q., B. Hu, X. Hu, H. Kim, M. Squatrito, L. Scarpace, A. C. deCarvalho, S. Lyu, P. Li, Y. Li, F. Barthel, H. J. Cho, Y.-H. Lin, N. Satani, E. Martinez-Ledesma, S. Zheng, E. Chang, C.- E. G. Sauvé, A. Olar, Z. D. Lan, G. Finocchiaro, J. J. Phillips, M. S. Berger, K. R. Gabrusiewicz, G. Wang, E. Eskilsson, J. Hu, T. Mikkelsen, R. A. DePinho, F. Muller, A. B. Heimberger, E. P. Sulman, D.-H. Nam, and R. G. Verhaak (2017). Tumor Evolution
of Glioma-Intrinsic Gene Expression Subtypes Associates with Immunological Changes in the Microenvironment. Cancer Cell, 32(1); 42–56
Watanabe, M. (1999). Antioxidative Phenolic Compounds from Japanese Barnyard Millet (Echinochloa utilis) Grains. Journal of Agricultural and Food Chemistry, 47(11); 4500–4505
Winarno, F. (1992). Kimia Pangan dan Gizi. PT. Gramedia Pustaka Utama, Jakarta. Journal Teknosains Pangan, 3(1); 2302–0733
Xie, C., J. Kang, Z. Li, A. G. Schauss, T. M. Badger, S. Nagarajan, T. Wu, and X. Wu (2012). The açaí flavonoid velutin is a potent anti-inflammatory agent: blockade of LPS-mediated TNF-α and IL-6 production through inhibiting NF-κB activation and MAPK pathway. The Journal of Nutritional Biochemistry, 23(9); 1184–1191
Yin, W., T.-S. Wang, F.-Z. Yin, and B.-C. Cai (2003). Analgesic and anti-inflammatory properties of brucine and brucine N-oxide extracted from seeds of Strychnos nux-vomica. Journal of Ethnophar- macology, 88(2-3); 205–214
Zhang, W., B. Li, Y. Guo, Y. Bai, T. Wang, K. Fu, and G. Sun (2015). Experimental immunology Rhamnetin attenuates cognitive deficit and inhibits hippocampal inflammatory response and oxidative stress in rats with traumatic brain injury. Central European Journal of Immunology, 40(1); 35–41
Zhou, B., Z. Yang, Q. Feng, X. Liang, J. Li, M. Zanin, Z. Jiang, and N. Zhong (2017). Aurantiamide acetate from baphicacanthus cusia root exhibits anti-inflammatory and anti-viral effects via inhibition of the NF-κB signaling pathway in Influenza A virus-infected cells. Journal of Ethnopharmacology, 199; 60–67
Zobeiri, M., T. Belwal, F. Parvizi, R. Naseri, M. H. Farzaei, S. F. Nabavi, A. Sureda, and S. M. Nabavi (2018). Naringenin and its Nano-formulations for Fatty Liver: Cellular Modes of Action and Clinical Perspective. Current Pharmaceutical Biotechnology, 19(3); 196–205
Authors
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.