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Type :thesis
Subject :QD Chemistry
Main Author :M. Nur Sidik
Title :Isolation of chemical constituents from Alphonsea sp and their in silico xanthine oxidase inhibitory activities
Place of Production :Tanjong Malim
Publisher :Fakulti Sains dan Matematik
Year of Publication :2022
Corporate Name :Universiti Pendidikan Sultan Idris
PDF Guest :Click to view PDF file

Abstract : Universiti Pendidikan Sultan Idris
The aim of this study was to identify the chemical constituents from two species of Alphonsea sp., which were Alphonsea cylindrica and Alphonsea elliptica and their in silico xanthine oxidase inhibitory activities. The samples were dried, then extracted sequentially using hexane, dichloromethane, and methanol. Chemical constituents were isolated and purified through chromatographic techniques. The structure of the compounds were elucidated through spectroscopic data and comparison with literature. In silico based on molecular docking using YASARA program was carried out to study the inhibition mechanism and interactions of compounds against xanthine oxidase. Six chemical constituents were isolated; stigmasterol, atherospermidine, kinabaline, muniranine, methyl 4-hydroxy-3,5- dimethoxybenzoate and 3- hydroxy-4-methoxy-benzoic acid. Both methyl 4- hydroxy-3,5-dimethoxybenzoate and 3- hydroxy-4-methoxy-benzoic acid were firstly reported from Alphonsea sp. The results of the molecular docking study revealed that atherospermidine bind to active sites located in the FAD domain of xanthine oxidase which suggest it is a competitive inhibitor. Meanwhile, other compounds isolated are non-competitive inhibitors. In conclusion, six chemical compounds were isolated from Alphonsea sp and all interactions of the compounds with xanthine oxidase in silico were investigated. The findings of this study reveal the potential of Alphonsea sp. as remedy for gout.

References

Abdul Hafiz, F., Mohammed, A., Kayat, F., Bhaskar, M., Hamzah, Z., Podapati, S. K. & Reddy, L.V. (2020). Xanthine oxidase inhibitory activity, chemical composition, antioxidant properties and GC-MS analysis of keladi cantik (Alocasia longiloba Miq). Molecules, 25, 2658. 

Abdul Latieff Mohamad (2015). The country's biodiversity policy is a highlight.Journal of Salam Lestari. Institute for Environment and Development. 35, 1-9. 

Abdul Rauf & Noor Jehan. (2017). Natural products as a potential enzyme inhibitors from medicinal plants. Book IntechOpen. 165-177. 

Afroz, M., Zihad, S. M. N. K., Uddin, S. J., Rouf, R., Rahman, M. S., Islam, M. T. & Sarker, S. D. (2019). A systematic review on antioxidant and antiinflammatory activity of Sesame (Sesamum indicum L.) oil and further confirmation of antiinflammatory activity by chemical profiling and molecular docking. Journal of Phytotherapy Research, 1-25. 

Ahmed, K. O., Kareem, M. M., Aowda, S. A. & Raju, A. K. (2016). Synthesis and characterization of new prodrug polymers and study of their biological activity. International Journal of Chemistry, Technology, and Research, 9(8), 398-413. 

Aldulaimi, A. K. O., Azziz, S. S. S. A., Bakri, Y. M., Nafiah, M. A., Aowda, S. A., Awang, K., and Litaudon, M. (2019). Two new isoquinoline alkaloids from the bark of Alphonsea cylindrica King and their antioxidant activity. Journal of Phytochemistry Letter. 29 (1), 110-114. 

Alirezaei, A., Argani, H., Asgharpour, M., Bahadorimonfared, A. & Bakhtiar .M., (2017). An update on allopurinol and kidney failure; new trend for an old drug. Journal of Renal Injury Prevention, 6(4), 297-302. 

Almeida, J. R. G., da S., Lúcio, A. S. S. C., da-Cunha, E. V. L., Tavares, J. F. & Barbosa Filho, J. M. (2015). Alkaloids of the Annonaceae: Occurrence and a compilation of their biological activities. The Alkaloids: Chemistry and Biology, 233–409. 

Arango, G. J., Cortes, D., Cassels, B. K., Mérienne, C. & Cavé, A. (1987). Azafluorenones from Oxandra cf. major and biogenetic considerations. Journal of Phytochemistry, 26(7), 2093–2098. 

Arumugam. G., Swamy M. K. & Sinniah U. R. (2016). Plectranthus amboinicus (Lour.) Spreng: botanical, phytochemical, pharmacological and nutritional significance. Molecules, 21(4), 1-26. 

Asyraf, M. & Mashhor, M. (2001). Weedy Plants of Ayer Hitam Forest Reserve, Selangor. Pertanika Journal of Tropical Agricultural Science. 24 (1), 1-5 

Atta-ur-rahman. (2013). Studies in natural products chemistry. Vol 39, 1st Ed. Elsevier, 393. 

Atta-ur-rahman., Ahmed, D. M., Asif, E. & Ahmad, S. (1991). Chemical constituents of Buxus Sempervirens. Journal of Natural Product, 54(1), 79-82. 

Attiq. A., Jalil. J. & Husain. K. (2017). Anti-inflammatory activity of Annonaceae species. Journal of Frountiers in Pharmacology. 8, 1-24. 

Attiq. A., Jalil. J., Husain. K. Hazni. F. M. & Abrar. A. (2021). Luteolin and apigenin derived glycosides from Alphonsea elliptica abrogate LPS-induced inflammatory responses in human plasma. Journal of Etnopharmacology. 275 (0), 114-120. 

Awodiran, M. O., Adepiti, A. O. & Akinwunmi, K. F. (2018). Assessment of the cytotoxicity and genotoxicity properties of Uvaria chamae P. Beauv (Annonaceae) and Morinda lucida Benth ( Rubiaceae ) in mice. Journal of Drug and Chemical Toxicology, 41(2), 232-237. 

Ayyappan, P. & Nampoothiri, S. V. (2020). Bioactive natural products as potent inhibitors of xanthine oxidase. Studies in Natural Products Chemistry, 391–416. Azmi, S. M. N., Jamal, P. & Amid, A. (2012). Xanthine oxidase inhibitory activity from potential Malaysian medicinal plant as remedies for gout. International Food Research Journal, 19(1), 159-165. 

Azziz, S. S. S. A. A., Aldulaimi, A. K. O., Bakri, Y. M., Nafiah, M. A., Awang K., Abdulla, A. S., Litaudon, M., Hassan, N. M., Naz, H., Abbas, P., Has-Yun Hashim, Y. Z. & Majhool, A. A. (2018). Alkaloids from Alphonsea elliptica barks and their biological activities. Journal of Global Pharma Technology. 10(8), 270- 275. 

Bakri, Y. M., Aldulaimi, A. K. O., Azziz, S. S. S. A., Nafiah, M. A., Abdulla, S. A., Hazim, M., Awang, K., Has-Yun Hashim, Y. Z. & Abbas, P. (2019). Cytotoxic and xanthine oxidase inhibitory activities of chemical constituents of Alphonsea cylindrica King. Research Journal of Pharmacology and Technology, 12(9), 4129-4134. 

Batugal, P. A., Kanniah, J., Lee, S.Y. & Oliver, J. T. (2004). Medicinal plant research in Asia. Project Work Plan and Framework. International Plant Genetic Resources Institute - Regional Office for Asia, Pacific and Oceania (IPGRI- APO), Serdang, Selangor DE, Malaysia. 

Berg, J. M., Tymoczko, J. L. & Stryer, L. (2002). Biochemistry, 5th Ed. W. H. Freeman and Company, San Francisco. 

Bingtao. L. & Gilbert. M.G., (2011). Annonaceae. Journal of Flora of China. 19(1), 672-713. 

Borges, F., Fernandes, E. & Roleira, F. (2003). Progress towards the discovery of xanthine oxidase inhibitors. Journal of Current Medicinal Chemistry. 9(1): 195- 217. 

Bou-Abdallah, E., Jossay, A., Tadic, D., Lebceuf, M. & Cave, A. (1989). Alcaloides des annonacees, 9 1. L'oncodine, nouvel Alcaloide a squelette azafluori~noniseo le de Oncodostzgma monosperma. Journal of Natural Product. 52(2), 273.278. 

Burkill, I. H. (1966). A Dictionary of Economic Products of the Malay Peninsular. Vol.1. Reprint. Kuala Lumpur: Ministry of Agriculture & Cooperatives. 

Bustanji, Y., Hudaib, M., Tawaha, K., Mohammad, M. K., Almasri, I., Hamed S. & Oran S. (2011). In vitro xanthine oxidase inhibition by selected Jordanian medicinal plants. Jordan Journal of Pharmaceutical Sciences, 4(1), 49-55 

Carnevale N. F., Guaratini. T., Costa-Latufo. L., Colepicolo, P., Gates, P. J. & Lopes, N. P. (2016). Re-investigation of fragmentation of prononated carotenoids by electrospray ionization and nanospray tandem mass spectrometry. Journal of WILEY: Rapid communications Mass Spectrometry. 30(13). 1540-1548 

Chakravarthi, P. V. Murugesan, S., Arivuchelvan, A., Sukumar, K., Arulmozhi, A. & Jagadeeswaran, A. (2018). In vitro xanthine oxidase inhibitory activity of Piper betle and Phyllanthus niruri. Journal of Pharmacognosy and Phytochemistry. 7(5), 959-961. 

Chandrasekar, R., Jayanth, P. C. & Ninrajan Babu, M. (2019). Protective effect of ethanolic leaf extract of Alphonsea sclerocarpa against ethylene glycol induced urolithiasis in rats. Indian Journal of Natural Product., 10(4), 252-258 

Chatrou, L. W., Erkens, R. H. J., Richardson, J. E., Saunders, R. M. K. & Fay, M. F. (2012). The natural history of Annonaceae. Botanical Journal of the Linnean Society. 169, 1-4. 

Chen, B., Feng, C., Li, B. G., & Zhang, G. L. (2003). Two new alkaloids from Miliusa cuneata. Journal of Natural Product Research, 17(6), 397–402. 

Chen, C. Y., Wang, Y. D. & Wang, H. M. (2010). Chemical constituents from the roots of Synsepalum dulcificum. Chemistry of Natural Compounds, 46(3), 448-449 

Chen, H. C., Kao, C. L., Chen, C. T., Li, H. T. & Chen, C. Y. (2018). Chemical constituents of the leaves of Michelia figo. Journal Chemistry of Natural Compounds, 54(2), 407–410. 

Ching-Kuo L., Ping-Hung, L. & Yueh-Hsiung, K. (2001). The chemical constituents from the aril of Cassia fistula L. Journal of the Chinese Chemical Society, 48, 1053-1058 

Chung-Yi, C., Fang-Rong, C., Chc-Ming, T. & Yang-Chang, W. (1999). Cheritamine, a new N-fatty acyl tryptamine and other constituents from the stems of Annona cherimola. Journal of the Chinese Chemical Society, 1999, 46, 77-86. 

Costa, V. E., Maria, L. B. P., Afonso, D. L. S., Anderson, B., Francinete, R.C., Rodrigo, H. V., Tania, U. N., Benedito, P. D. F. & Celso, V.N. (2011). Trypanocidal activity of oxoaporphine and pyrimidine-ß carboline alkaloids from the branches of Annona foetida Mart. (Annonaceae). Journal of Molecules, 16, 9714-9720 

Dantas, E. P., Jackson, M., de Medeiros, L. S., Romanelli, M. M., Amaral, M., Tempone, A. G., Lago, J. H. G., Soares, M. G. & Sartorelli, P. (2020). Dereplication of aporphine alkaloids by UHPLC-HR-ESI-MS/MS and NMR from Duguetia lanceolata St.-Hil (Annonaceae) and antiparasitic activity evaluation. Journal of the Brazilian Chemical Society. 31(9), 1908-1916. 

Dar, R.A., Shahnawaz, M. & Qazi, P.H. (2017). Natural product medicines: A literature update. The Journal of Phytopharmacology, 6(6), 349-351. 

De. S. Araújo, C., de Oliveira, A. P., de Oliveira-Junior, R. G., de Siqueira-Filho, J. A., Braz-Filho, R., Tavares, J. F., et al. (2017). Chemical constituents isolated from extracts of Annona vepretorum Mart. (Annonaceae) leaves. Journal of Medicinal Plants Research, 11(28), 439-444 

Diantari, E & Candra, A. (2013). The effect of purine and fluid intake on uric acid levels in women aged 50-60 years in Gajah Mungkur subdistrict, Semarang. Journal of College Nutrition, 2 (1), 44-49. 

Enroth, C., Eger, B. T., Okamoto, K., Nishino, T. & Pai, E. F. (2000). Crystal structures of bovine milk xanthine dehydrogenase and xanthine oxidase: structure-based mechanism of conversion. Proceedings of the National Academy of Sciences USA, 97(20), 10723-10728 

Fauziah, A., Nor, H. I., Fadzureena, J. & Siti, N.A.M.H. (2013). Xanthine oxidase inhibitory activity of Tetracera indica. The Open Conference Proceedings Journal, 2013, 4, 93-94. 

Fazilatun, N., Zhari, I. & Nornisah, M. (2010). Xanthine oxidase inhibitory activities of extracts and flavonoids of the leaves of Blumea balsamifera, Journal of Pharmaceutical Biology, 48:12, 1405-1412 

Fazleen, A. B., Mohd, F., A. B., Asmah, R., Norazlin, A., Siti F, S. & Susi, E. (2018). Anti-gout potential of Malaysian medicinal plants. Frontiers in Pharmacology, 9, 1-14. 

Fitria, L., Widyananda, M. H. & Sakti, P. S. (2019). Analysis of allopurinol, cucurbitacin B, morindine, and piperine as xanthine oxidase by molecular docking. Journal of Smart Bioprospecting and Technology, 1(1), 6-11. 

Goncalves, G. L. P., Domingues, V. C., Ribeiro, L. P., Fernandes, J. B., Fernandes, M. F. G., Forim, M. R. & Vendramim, J. D. (2017). Compounds from Duguetia lanceolata St.- Hil. (Annonaceae) bioactive against Zabrotes subfasciatus (Boheman) (Coleoptera: Chrysomelidae: Bruchinae). Journal of Industrial Crops and Products, 97, 360–367. 

Grouleff, J., Irudayam, S. J., Skeby, K. K. & Schiott, B. (2015). The influence of cholesterol on membrane protein structure, function, and dynamics studied by molecular dynamics simulations. Journal of Biochimica et Biophysica Acta (BBA) - Biomembranes, 1848(9), 1783–1795. 

Handayani. T. (2018). Diversity, potential and conservation of Annonaceae in Bogor Botanic Gardens, Indonesia. Journal of Biodiversity. 19(2), 591-603. 

Havva, O. & Türkmen, N. (2019). Investigation of plants with ethnobotanical use in Gaziantep province (Turkey). GSC Biological and Pharmaceutical Sciences, 7(2), 71-78. 

Horgen, F. D., Edrada, R. A., de los Reyes, G., Agcaoili, F., Madulid, D. A., Wongpanich, V. & Farnsworth, N. R. (2001). Biological screening of rain forest plot trees from Palawan Island (Philippines). Journal of Phytomedicine, 8(1), 71– 81. 

Hufford, C. D., Liu, S., Clark, A. M. & Oguntimein, B. O. (1987). Anticandidal activity of eupolauridine and onychine, alkaloids from Cleistopholis patens. Journal of Natural Products, 50(5), 961–964. 

Ibrahim, M., Azziz, S. S. S. A., Wong, C. F., Bakri, Y. M. & Abdullah. F. (2019). Interactions of flavone and steroid from A. subintegra as potential inhibitors for porcine pancreatic lipase. Journal of Current Computer-Aided Drug Design. 16 (6), 698-706. 

Indrani, V., Madhuri, T., Lakshmi, K. B. & Suvarnalatha, D. P. (2015). Invitro comparative antifungal studies of Alphonsea sclerocarpa with local herbal shampoo against clinically isolated Aspergillus flavus. International Journal of Science Research Management Study, 3(2): 2103-2105. 

Jayaraj, P., Mathew, B., Parimaladevi, B., Ramani, V. A. & Govindarajan, R. (2014). Isolation of a bioactive flavonoid from Spilanthes calva D.C. in vitro xanthine oxidase assay and in silico study. Journal of Biomedicine & Preventive Nutrition, 4(4), 481–484. 

Jermnak, U., Yoshinari, T., Sugiyama, Y., Tsuyuki, R., Nagasawa, H. & Sakuda, S. (2012). Isolation of methyl syringate as a specific aflatoxin production inhibitor from the essential oil of Betula alba and aflatoxin production inhibitory activities of its related compounds. International Journal of Food Microbiology, 153(3), 339–344. 

Johnson, T. A., Sohn, J., Ward, A. E., Cohen, T. L., Lorig-Roach, N. D., Chen, H. & Bjeldanes, L. F. (2013). (+)-Altholactone exhibits broad spectrum immune modulating activity by inhibiting the activation of pro-inflammatory cytokines in RAW 264.7 cell lines. Journal of Bioorganic & Medicinal Chemistry, 21(14), 4358–4364 

Joshi, S. D. S. D., Chander, A., Surya, N. S., Padmavathi, C. H., Madhavi, J. & Krishna, S. A. (2018). Antioxidant and anticancer activities of an aporphine alkaloid isolated from Alphonsea sclerocarpa. The Journal of Phytopharmacology, 7(1), 51-55. 

Joshi, S. D. S. D., Venkata, R. G., Satya, P.M., Kishore, B. M., Surya, N. S. & Krishna, S. A. (2017). Phytochemical screening and evaluation of antioxidant, antibacterial and antifungal activity of medicinal plant Alphonsea sclerocarpa Thaw. Journal of Pharmacognosy and Phytochemistry, 6(4), 1280-1286. 

Kabera, J. N., Semana, E., Mussa, A.R. & He, X. (2014). Plant secondary metabolites: biosynthesis, classificatiopn, function and pharmacological properties. Journal of Pharmacy and Pharmacology, 2, 377-392. 

Kar, A., Bora, D., Borthakur, S. K., Goswami, N. K. & Saharia, D. (2013). Wild edible plant resources used by the mizos of Mizoram, India. Kathmandu University Journal Science, Engineering and Technology, 9(1), 106-126. 

Kisker, C., Schindelin, H., Baas, D., Rétey, J., Meckenstock, R. U., & Kroneck, P. M. H. (1998). A structural comparison of molybdenum cofactor-containing enzymes. FEMS Microbiology Reviews, 22(5), 503–521. 

Koyama, J., Morita, I., Kobayashi, N., Osakai, T., Usuki, Y., & Taniguchi, M. (2005). Structure–activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds. Journal of Bioorganic & Medicinal Chemistry Letters, 15(4), 1079–1082. 

Koyama, J., Okatani, T. & Tagahara, K. (1989). Synthesis of alkaloids,cleistopholine, oxylopine (isoursuline), and ursuline. Journal of Heterocycles , 29(9), 1649 – 1654. 

Kraus, G.A & Kempema, A. (2010). Synthesis of azafluorenone antimicrobial agents. Journal of Natural Product. 73, 1967-1968. 

Krenitsky, T. A., Spector, T. & Hall, W. W. (1986). Xanthine oxidase from human liver: purification and characterization. Archives of biochemistry and biophysics. 247(1), 108-119. 

Krieger, E., Koraimann, G. & Vriend, G. (2002). Increasing the precision of comparative models with YASARA NOVA-a self-parameterizing force field. Proteins: Structure, Function, and Bioinformatics, 47(3), 393–402. 

Kumalo, H., Bhakat, S. & Soliman, M. (2015). Theory and applications of covalent docking in drug discovery: merits and pitfalls. Journal of Molecules, 20(2), 1984– 2000. 

Kuppusamy. P., Yusoff. M. M., Parine N. R. & Govindan. N. (2015). Evaluation of in- vitro antioxidant and antibacterial properties of Commelina nudiflora L. extracts prepared by different polar solvents. Saudi Journal of Biological Sciences, 22(3),293–301. 

Laskowski, R. A. & Swindells, M. B. (2011). LigPlot+: Multiple ligand–protein interaction diagrams for drug discovery. Journal of Chemical Information and Modeling, 51(10), 2778–2786. 

Latiff, A. (2013). On the Annonaceae of Taman Negara, Peninsular Malaysia. Malayan Nature Journal, 65(4), 247-273. 

Latiff, A., Hanum, I. F., Ibrahim, A. Z., Goh, M. W. K., Loo, A. H. B., & Tan, H. T. W. (1999). On the vegetation and flora of Pulau Tioman, Peninsular Malaysia. Raffles Bulletin of Zoology, 47(6), 11–72. 

Lekphrom, R., Kanokmedhakul, K., Schevenels, F. & Kanokmedhakul, S. (2018). Antimalarial polyoxygenated cyclohexene derivatives from the roots of Uvaria cherrevensis. Fitoterapia, 127(11), 420–424. 

Lopes, J. C., Chatrou, L. W., Mello-Silva, R., Rudall, P. J. & Sajo, M. G. (2018). Phylogenomics and evolution of floral traits in the Neotropical tribe 

Malmeeae (Annonaceae). Molecular Phylogenetics and Evolution, 118(8), 379–391.Lumintang, R.F., Wuisan. J. & Wowor.P. M. (2015). Uji efek analgesik ekstrak kulit batang pohon matoa (Pometia pinnata) pada mencit (Mus musculus). Jurnal e- Biomedik (eBm), 3(2), 634-639. 

Ma, Q., Wei, R., Wang, Z., Liu, W., Sang, Z., Li, Y. & Huang, H. (2017). Bioactive alkaloids from the aerial parts of Houttuynia cordata. Journal of Ethnopharmacology, 195, 166–172. 

Mahani Majid., Mohd Fadzelly., Abu Bakar & Zakbah Mian. (2018). Determination of xanthine oxidase inhibition in stingless bee honey from different botanical origin. IOP Conference Series: Earth and Environmental Science, 269. 

Manpadi, M., Uglinskii, P. Y., Rastogi, S. K., Cotter, K. M., Wong, Y.-S. C., Anderson, L. A. & Kornienko, A. (2007). Three-component synthesis and anticancer evaluation of polycyclic indenopyridines lead to the discovery of a novel indenoheterocycle with potent apoptosis inducing properties. Journal of Organic & Biomolecular Chemistry, 5(23), 3865-3872. 

Mansour, H. H., Elkady, A. A., Elrefaei, A. H. & Hafez, H. F. (2018). Radioprotective, antioxidant and antitumor efficacy of Annona muricata leaf extract. Indian Journal of Biochemistry & Biophysics, 55(7), 205–214. 

Marsh, J. A., & Teichmann, S. A. (2015). Structure, dynamics, assembly, and evolution of protein complexes. Annual Review of Biochemistry, 84(1), 551–575 

Massotte, D & Kieffer, B. L.(1998). A molecular basis for opiate action. Essays in Biochemistry, 33, 65–77. 

Meng, X. Y., Zhang, H. X., Mezei, M., & Cui, M. (2011). Molecular docking: a powerful approach for structure-based drug discovery. Current Computer Aided- Drug Design, 7(2), 146–157. 

Miškovic-Stankovic, V., Jevremovic, I., Jung, I., & Rhee, K. (2014). Electrochemical study of corrosion behavior of graphene coatings on copper and aluminum in a chloride solution. Journal of Carbon, 75, 335–344. 

Monggoot, S., Pichaitam, T., Tanapichatsakul, C. & Pripdeevech, P. (2018). Antibacterial potential of secondary metabolites produced by Aspergillus sp., an endophyte of Mitrephora wangii. Archives of Microbiology, 200(6), 951–959. 

Mueller, D., Davis, R. A., Duffy, S., Avery, V. M., Camp, D. & Quinn, R. J. (2009). Antimalarial activity of azafluorenone alkaloids from the Australian tree Mitrephora diversifolia. Journal of Natural Products, 72(8), 1538–1540. 

Narayanaswamy, R., Isha, A., Wai, L. K. & Ismail, I. S. (2016). Molecular docking analysis of selected Clinacanthus nutans constituents as xanthine oxidase, nitric oxide synthase, human neutrophil elastase, matrix metalloproteinase 2, matrix metalloproteinase 9 and squalene synthase inhibitors. Pharmacognosy magazine, 12, 21–26. 

Narendra, P. D. (2009). Antioxidant activity of Alphonsea sclerocarpa bark. Journal of Pharmacology and Pharmacodynamics. 1(2), 66-69. 

Neto. F. C., Andreo, M. A., Raftery, D., Lopes, J. L. C., Lopes, N. P., Casto-Gamboa, I., Maia, B. H. L. S., Costa, E. V. & Vessechi, R. (2019). Characterization of aporphine alkaloids by electrospray ionization tandem mass spectrometry and density functional theory calculations. Journal of WILEY: Rapid communications Mass Spectrometry . 34(1), 1-11. 

Newman, D. J. & Cragg, G. M. (2020). Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019. Journal of Natural Products. 83(3), 770-803. 

Nguyen, M., Awale, S., Tezuka, T. Q., Watanabe H. & Kadota, S. (2004). Xanthine oxidase inhibitory activity of Vietnamese medicinal plants. Journal of Biological and Pharmaceutical Bulletin, 27(9), 1414-1421. 

Nguyen. K.V., Ho, D. V., Le, A. T., Heinamaki, J., Raal, A. & Nguyen, H. T. (2021). Secondary metabolites from Alphonsea tonkinensis A.DC. showing inhibition of nitric oxide production and cytotoxic activity. Journal of Pharmacy & Pharmacognosy Research, 9 (1), 24-32. 

Ningtiyas, I. F. & Ramadhian, M. R. (2016). The effectiveness of bay leaf extract to reduce uric acid levels in patients with gouty arthritis. Journal of Majority, 5(3) , 105-110. 

Nishino, T. (1994). The conversion of xanthine dehydrogenase to xanthine oxidase and the role of the enzyme in reperfusion injury. The Journal of Biochemistry, 116(1), 1–6. 

Nor‘Asyikin Mat Hayin. (2018). Pulihara flora, fauna royal belum. Obtained 21 October 2019 from https://www.hmetro.com.my/nuansa/2018/07/361576/ pulihara-flora-fauna-royal-belum. 

Norhayati, I., Getha, K., Haffiz, J. M., Ilham, A. M., Sahira, H. L., Siti Syarifah, M. M. & Syamil, M. (2013). In vitro antitrypanosomal activity of Malaysian Plants. Journal of Tropical Forest Science, 25 (1): 52-59. 

Novaes, P., Torres, P. B., Cornu, T. A., Lopes, J. Ferreira, M. J. P. & Santos, D. Y. A. C. (2019).  Comparing antioxidant activities of flavonols from Annona coriacea by four approaches. South African Journal of Botany, 123, 253–258. 

Nurraihana Hamzah. (2015). Ethnomedical studies, phytochemical analysis and biological activities of selected antidiabetic plants used by indigenous communities in Gua Musang, Kelantan. Thesis. Universiti Sains Malaysia, Malaysia. 

Obaid, A. K. (2019). Phytochemical study of Polyalthia lateriflora, Alphonsea cylindrica and Alphonsea elliptica and their biological activities. Thesis. Universiti Pendidikan Sultan Idris, Malaysia. 

Okamoto, K., Kusano, T. & Nishino T. (2013). Chemical nature and reaction mechanisms of the molybdenum cofactor of xanthine oxidoreductase. Current Pharmaceutical Design. 19(14), 2606-2614. 

Okomoto, S., Yoshikawa, T., Ihira, M., Suzuki, K., Shimokata, K., Nishiyama, Y. & Asano, Y. (2004). Rapid detection of Varicella-zoster virus infection by a loop- mediated isothermal amplification method. Journal of Medical Virology. 74, 677- 682. 

Orlowska, E., Roller, A., Wiesinger, H., Pignitter, M., Jirsa, F., Krachler, R. & Keppler, B. K. (2016). Benzoic hydroxamate-based iron complexes as model compounds for humic substances: synthesis, characterization and algal growth experiments. Journal of Royal Society of Chemistry Advances, 6(46), 40238–40249. 

Osman, N. I., Sidik, N. J., Awal, A.,  Adam,  N.  A.  &  Rezali,  N.  I.  (2016). In  vitro xanthine oxidase and albumin denaturation inhibition assay of Barringtonia racemosa L. and total phenolic content analysis for potential anti-inflammatory use in gouty arthritis. Journal of Intercultural Ethnopharmacology, 5(4), 343– 349. 

Pagadala, N. S., Khajamohiddin, S. & Jack, T. (2017). A review: software for molecular docking. Biophysical reviews. 9, 91-102. 

Parks, D. A. & Granger, D. N. (1986). Contributions of ischemia and reperfusion to mucosal lesion formation. American Journal of Physiology, 250(6), 749-753 

Patton, S. & Keenan, T. W. (1975). The milk fat globule membrane. Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes, 415 (3), 273-309. 

Pavia, D. L., Lampmam, G. M. & Kris, G. S. (2001). Introduction to spectroscopy: a guide for students of organic chemistry. 3rd Ed. United States: Thomson Brooks.  

Peglow, S., Alexander, H., Toledo., Roberto, A., Fernando, L., Luis, H. & Toledo .P., (2013). Journal of Hepatobiliary Pancreat Sciences, 18: 137-146. 

Peng, J., Li, Y., Zhou, Y., Zhang, L., Liu, X. & Zuo, Z. (2018). Pharmacophore modeling, molecular docking and molecular dynamics studies on natural products database to discover novel skeleton as non-purine xanthine oxidase inhibitors. Journal of Receptors and Signal Transduction, 38(3), 246–255. 

Pinzi, L. & Rastelli, G. (2019). Molecular docking: shifting paradigms in drug discovery. International Journal of Molecular Sciences. 20, 1-23. 

Prachayasittikul, S., Manam, P., Chinworrungsee, M., Isarankura-Na-Ayudhya, C., Ruchirawat, S. & Prachayasittikul, V. (2009). Bioactive azafluorenone alkaloids from Polyalthia debilis (Pierre) Finet & Gagnep. Journal of Molecules, 14, 4414- 4424. 

Pumsalid, K., Thaisuchat, H., Loetchutinat, C., Nuntasaen, N., Meepowpan, P. & Pompimon, W. (2010). A new azafluorenone from the roots of Polyalthia cerasoides and its biological activity. Journal of Natural Product Communications, 5(12), 1931-1934. 

Puvanendran, S., Wickramasinghe, A. & Karunara, D. N. (2007). Screening of antioxidant activity of some endemic Annonaceae plant extracts. Proceedings of the Peradeniya University Research Sessions, Sri Lanka, Vol.12, Part I, 30th November 2007. 

Ramallo, I. A., Zacchino, S. A. & Furlan, R. L. E. (2006). A rapid TLC autographic method for the detection of xanthine oxidase inhibitors and superoxide scavengers. Phytochemical Analysis, 17(1), 15-19 

Ribeiro, L. P., Goncalves, G. L. P., Bicalho, K. U., Fernandes, J. B. & Vendramim, J. D. (2020). Rolliniastatin-1, a bis-tetrahydrofuran acetogenin: The major compound of Annona mucosa Jacq. (Annonaceae) has potent grain-protective properties. Journal of Stored Products Research, 89. 

Roddy, E. & Doherty, M. (2010). Epidemiology of gout. Journal of Arthritis Research & Therapy. 12(6), 232-242. 

Rotschild, B. M. (2013). Gout and pseudogout. Emedicine Medscape, obtained 21 October 2019 from http://www.emedicine.medscape.com/article /329958- author Sahgal, G., Surash, R., Sasidharan, S., Mohd Nizam, M., Sabariah, I. & Sharif, M. M. (2009). In vitro antioxidant and xanthine oxidase inhibitory activities of methanolic Swietenia mahagoni seed extracts. Molecules, 14, 4476-4485. 

Sahu, A., Ghosh, G. & Rath, G. (2020). Identification and molecular docking studies of bioactive principles from Alphonsea madraspatana Bedd. against uropathogens. Journal of Current Pharmaceutical Biotechnology. 21(7), 613- 625. 

Sally, A. R., John, R. & Larry L. L. (2009). NMR database of lignin and cell wall modelcompounds.Obtained20November2019fromhttp://www.glbrc.org/databases_and_software/nmrdatabase/ 

Sangster, A.W. & Stuart, K.L. (1964). Ultraviolet spectra of alkaloids. Journal of Chemical Reviews, 65(1), 69-130 

Sanna, C., Scognamiglio, M., Fiorentino, A., Corona, A., Graziani, V., Caredda, A. & Esposito, F. (2018). Phenoglucinol yang diprenilasi dari Hypericum scruglii, spesies endemik Sardinia (Italia), sebagai inhibitor ganda HIV-1 yang baru yang efektif pada replikasi HIV-1. Journal of PLOS ONE, 13 (3),1-19. 

Santi, M. D., Paulino, M. Z., Vera, B., Bouzidi C., Dumontet, V., Abin-Carriquiry, A., Grougnet, R. & Ortega, M. G. (2018). Xanthine oxidase inhibitory activity of natural and hemisynthetic flavonoids from Gardenia oudiepe (Rubiaceae) in vitro and molecular docking studies. European Journal of Medicinal Chemistry, 143, 577-582. 

Saputra, R. (2018). Effect of ethyl acetate fraction ethanol extract of bay leaf (Syzygium polyanthum Wight.) on the reduction of blood uric acid levels in male white mice of balb-c strain induced by potassium oxonate. Thesis, Muhammadiyah University of Surakarta, Indonesia. 

Sarnesto, A., Linder, N. & Raivio, K. O. (1996). Organ distribution and molecular forms of human xanthine dehydrogenase / xanthine oxidase protein. Laboratory Investigation, 74, 48-56. 

Shamma, M. & Slusarchyk, W. A. (1964). The aporphine alkaloids. Chemical Reviews, 64(1), 59–79. 

Shapiro, R. & Vallee, B. L. (1991). Interaction of human placental ribonuclease with placental ribonuclease inhibitor. Journal of Biochemistry, 30(8), 2246-2255 

Sharma, N. K. & Priyanka, K. K. (2010). Molecular docking: an overview. Journal of Advances in Sciences and Research. 1, 67–72. 

Shiao, M. J., Liu, K. H. & Lin, P. Y. (1993). Syntheses of 2-azafluorenones from 3- substituted 4-arylpyridines. Journal of Heterocycles, 36(3), 507-518 

Shu, T. C., Bingtao, L. & Gilbert, M. G. (2011). Alphonsea J. D. Hooker &Thomson. F1 China, (19) 699-700. 

Silmi Qurrotu Aini. (2018). Detection of baccatin III 3-amino 3-phenylpropanoid gene as taxol producer of Sumatranan Yew (Taxus Sumatrana) stem bark endophytic fungi. Thesis. Indonesian Education University. Indonesia 

Sinclair, J. (1955). A revision of the Malayan Annonaceae. Gardens' Bulletin, Singapore, 14, 149 - 516. 

Siti Sarwani Putri Mohd Isa. (2017). Studies on xanthine oxidase inhibitory activity of Plumeria rubra Linn flower. Thesis. Universiti of Malaya, Malaysia. 

Soriano, C. L., Rothenbacher, D., Choi, H, K. & Rodríguez, L. A. (2011). Contemporary epidemiology of gout in the UK general population. Arthritis Research & Therapy. 13 (2), 1-9. 

Srivastava, G. & Mehrotra, R. C. (2013). First fossil record of Alphonsea Hk f & T. (Annonaceae) from the late oligocene sediments of Assam, India and comments on its phytogeography. PLoS ONE, 8 (1), 1-6. 

Stevigny, C., Bailly, C. & Quetin-Leclercq, J. (2005). Cytotoxic and antitumor potentialities of aporphinoid alkaloids. Journal of Current Medicinal Chemistry- Anti Cancer Agents, 5(2), 173-182. 

Subramanion, L. J., Zakaria, Z. & Sreenivasan, S. (2011). Phytochemicals screening, DPPH free radical scavenging and xanthine oxidase inhibitory activities of Cassia fistula seeds extract. Journal of Medicinal Plant Research, 5(10), 1941- 1947. 

Suttiarporn, P., Chumpolsri, W., Mahatheeranont, S., Luangkamin, S., Teepsawang, 

S., & Leardkamolkarn, V. (2015). Structures of phytosterols and triterpenoids with potential anti-cancer activity in bran of black non-glutinous rice. Journal of Nutrients, 7(3), 1672–1687. 

Sweeney, A. P., Wyllie, S. G., Shalliker, R. A. & Markham, J. L. (2001). Xanthine oxidase inhibitory activity of selected Australian native plants. Journal of Ethnopharmacology, 75(2), 273–277. 

Tadic, D., Cassels, B. K., Leboeuf, M. & Cavé, A. (1987). Kinabaline and the aporphinoid biogenesis-of azaanthracene and azafluorene alkaloids. Journal of Phytochemistry, 26(2), 537–541. 

Talip, M. A., Azziz, S. S. S. A., Wong, C. F., Awang, K., Naz, H., Bakri, Y. M., Litaudon, M. (2017). New azafluorenone derivative and antibacterial activities of Alphonsea cylindrica barks. Journal of Natural Product Sciences, 23(3), 151– 156. 

Tao, X., Huang, Y., Wang, C., Chen, F., Yang, L., Ling, L., Che, Z. & Chen, X. (2019). Review: recent developments in molecular docking technology applied in food science. International Journal of Food Science and Technology. 1-13. 

Thang, T. D., Huong, L. T., Dai, D. N. & Oguwande, I. A. (2013). Essential oil compositions of Alphonsea philastreana (Pierre) Pierre ex Finet and Gagnep and Alphonsea gaudighaudiana (Baill) Finet and Gagnep from Vietnam. Journal of Natural Product Research : Formerly Natural Product letter, 27 (21), 2022-2026.  

Tkatchenko, A., Rossi, M., Blum, V., Ireta, J. & Scheffler, M. 2011. Unraveling the Stability of Polypeptide Helices: Critical Role of van der Waals Interactions. Journal of Physical Review Letters. 106(11), 1-4. 

Torres, P. H. M., Sodero, A. C. R., Jofily, P. & Silva-Jr, F. P. (2019). Key Topics in Molecular Docking for Drug Design. International Journal of Molecular Sciences, 20(18), 1-29. 

Turner I. M. (2009). A new species of Alphonsea (Annonaceae) from Borneo. Garden’s Bulletin Singapore, 61, 185-188. 

Turner, I. M. & Utteridge, T. M. A. (2015). A new species of Monoon (Annonaceae) from Peninsular Malaysia. Journal of Plant Taxonomy and Geography, 70 (1), 99-102. 

Turner, I. M. (2015). A new species of Alphonsea (Annonaceae) from Peninsular Malaysia. Blumea, 59, 206-208. 

Turner, I. M. (2016) Notes on the Annonaceae of the Malay Peninsula. Garden’s Bulletin Singapore, 14, 65-69. 

Umamaheswari, M., Asokkumar, K., Somasundaram, A., Sivashanmugam, T., Subhadradevi, V. & Ravi, T. K. (2007). Xanthine oxidase inhibitory activity of some Indian medical plants. Journal of Ethnopharmacology. 109, 547–551 

Ushasree, M. V. & Lee, E. Y. (2020). Flavonoids, terpenoids, and polyketide antibiotics: role of glycosylation and biocatalytic tactics in engineering glycosylation. Journal of Biotechnology Advances, 41(1), 1-22. 

Wan Rohani Wan Taib, Mahfudzah Adanan, Nazihah Mohd Yunus, Tan H. L., Wan Syamimee Wan Ghazali., Phipps-Green, A. J. & Merriman, T. R. (2018). Association of solute carrier family 2, member 9 (SLC2A9) genetic variant rs3733591 with gout in a Malay sample set. Medical Journal of Malaysia, 73(5), 307-310. 

Wei-Sheng, F., Bo, Z., Xiao-Ke, Z., Yan-Li, Z., Li-Gong, Y. & Yuan-Ling, L. (2011) Chemical constituents of Seleginella stautoniana. Chinese Journal of Natural Medicines. 9(2), 108-111 

Widyanto, F. W. (2014). Artritis gout dan perkembangannya, Saintika Medika: Jurna; Ilmu Kesehatan dan Kedokteran Keluarga, 10(2), 145-152. 

Wink, M. (2003). Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. Journal of Phytochemistry, 64(1), 3–19. 

Yamadaa, Y., Kuzuyama, T., Komatsua, M., Shin-yac, K., Omurad, S., Canee, D. E. & Ikeda, H. (2015). Terpene synthases are widely distributed in bacteria. Proceedings of the National Academy of Sciences, 112(3), 857-862. 

Yang, N. Y., Xie, N., Kong, L. Y. Li, G. (2000). Chemical investigation on Alphonsea monogyma. Journal of China Chemistry Letters, 77 (1), 409. 

Yang, Y., Zhang, W., Xie, Z., Lei, J. & Yu, J. (2017). Constituents of Dianthus superbus and their cytotoxic activity. Chemistry of Natural Compounds, 53(4), 740-741. 

Yeap, S. S., Goh E. M. & Gun S. C. (2009). A survey on the management of gout in Malaysia. International Journal of Rheumatic Diseases, 12(4). 329-335. 

Yoshida, N. C., de Siqueira, J. M., Rodrigues, R. P., Correia, R. P. & Garcez, W. S. (2013). An azafluorenone alkaloid and a megastigmane from Unonopsis lindmanii (Annonaceae). Journal of the Brazilian Chemical Society, 24(4), 529– 533. 

Yusuke, T., Kazuaki, S. & Toshinobu, K. (2018). A short-step synthesis of onychine and the related 4-azafluorenones via hetero Diels-Alder reaction of 5-substituted isotellurazoles. Journal of Heterocycles, 96(3), 440-451 

Zhao, X., Zhu, J. X., Mo, S. F., Pan, Y. & Kong, L. D. (2006). Effects of cassia oil on serum and hepatic uric acid levels in oxonate-induced mice and xanthine dehydrogenase and xanthine oxidase activities in mouse liver. Journal of Ethnopharmacology. 103(3): 357-365 

Zhou, Q., Fu, Y. H., Li, X. B., Chen, G. Y., Wu, S. Y., Song, X. P., Liu, Y. P. & Han,C.R.(2015). Bioactive benzylisoquinoline alkaloids from Artabotrys hexapetalus. Journal of Phytochemistry Letters, 11, 296–300. 

 

 

 

 


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