GC-MS analysis of three Diospyros species and evaluation of its in vitro rat intestinal a-glucosidase and FRAP activity

##plugins.themes.bootstrap3.article.main##

NOVA ALFIAN HARIYANTO
RICO RAMADHAN
https://orcid.org/0000-0002-2565-7944
YANUARDI RAHARJO
YAZDANIYAR FAJRI HALIMI FIRDAUS
IRMAYANTI TRI KURNIA
DINDA AYU LESTARI
SUHARTINI SUWANDARI
NUR FARIHA MAHMUDA
JOURDHAM NATHANAEL
KIETTIPUM PHONTREE
PREECHA PHUWAPRAISIRISAN
LUKMAN RIYADI
ARRIZAL RAHMAN
NURLITA ABDULGANI

Abstract

Abstract. Hariyanto NA, Ramadhan R, Raharjo Y, Firdaus YFH, Kurnia IT, Lestari DA, Suwandari S, Mahmuda NF, Nathanael J, Phontree K, Phuwapraisirisan P, Riyadi L, Rahman A, Abdulgani N. 2024. GC-MS analysis of three Diospyros species and evaluation of its in vitro rat intestinal a-glucosidase and FRAP activity. Biodiversitas 25: 2442-2453. The vast diversity of natural products has long been recognized as a potentially valuable source of bioactive compounds derived from nature. The Diospyros species, belonging to the Ebenaceae family, thrive in tropical forest regions and have been traditionally used for treating various disorders such as ischemic stroke, hypertension, and infectious diseases. This research aims to assess the phytochemical constituents, rat intestinal a-glucosidase, and Ferric-Reducing Antioxidant Power (FRAP) of non-polar (n-hexane) and semi-polar (dichloromethane) extracts from three Diospyros species, i.e., Diospyros buxifolia (Blume) Hiern; Diospyros celebica Bakh.; Diospyros confertiflora (Hiern) Bakh). Gas Chromatography-Mass Spectrometry (GC-MS) analysis identified numerous bioactive secondary metabolites in the extracts. The study revealed that the semi-polar extracts of D. buxifolia exhibited potent rat intestinal a-glucosidase inhibitory activities, with an IC50 value of 33.31±3.23 ug/mL. The IC50 of acarbose as a positive control was 6.31±0.31 ug/mL. The FRAP test demonstrated that the non-polar and semi-polar leaf extracts of the three Diospyros species from East Kalimantan are potential sources of natural antioxidants, with the IC50 in the range of 6.48±0.38 umol Fe/g - 11.35±0.16 umol Fe/g. The results of this study confirm the therapeutic properties of leaf extracts derived from 3 Diospyros species, which align with their traditional medicinal use.

##plugins.themes.bootstrap3.article.details##

References
Adu OT, Naidoo Y, Lin J, Adu TS, Sivaram V, Dewir YH, El-Banna AN. 2022. Phytochemical screening and biological activities of Diospyros villosa (L.) De Winter leaf and stem-bark extracts. Horticulturae 8: 945. DOI: 10.3390/horticulturae8100945.
Aissaoui N, Mahjoubi M, Nas F, Mghirbi O, Arab M, Souissi Y, Hoceini A, Masmoudi AS, Mosbah A, Cherif A. Antibacterial potential of 2,4-di-tert-butylphenol and calixarene-based prodrugs from thermophilic Bacillus licheniformis isolated in Algerian hot spring. Geomicrobiology 36: 53-62. DOI: 10.1080/01490451.2018.1503377
Akyuz M, Yabo-Dambagi L, Kilic T, Cakir A. 2022. Antidiabetic, neuroprotective and antioxidant potentials of different parts of Pistacia terebinthus fruits. South African Journal of Botany 147: 443 – 456. DOI: 10.1016/j.sajb.2022.01.040.
Bawazeer S, Rauf A. 2021. In vitro antiglycation and lipoxygenase inhibition of naphthoquinones isolated from Diospyros lotus Linn. South African Journal of Botany 143: 406 – 409. DOI: 10.1016/j.sajb.2021.03.014.
Cardeno A, Aparicio-Soto M, Paz SM, Bermudez B, Muriana FJG, Lastra CA. 2015. Squalene targets pro- and anti-inflammatory mediators and pathways to modulate over-activation of neutrophils, monocytes and macrophages. Journal of Functional Foods 14: 779-790. DOI: 10.1016/j.jff.2015.03.009
Cardoso BK, de Oliveira HLM, Melo UZ, Fernandez CMM, Campo CFAA, Goncalves JE, Laverde Jr A, Romagnolo MB, Linde GA, Gazim ZC. 2020. Antioxidant activity of ? and ?-amyrin isolated from Myrcianthes pungens leaves. Natural Products Research 34: 1777-1781. DOI: 10.1080/14786419.2018.1525715
Chen J, Ni C, Lou J, Peng W. 2018. Molecules and functions of rosewood: Diospyros celebica. Arabian Journal of Chemisty 11: 756 – 762. DOI: 10.1016/j.arabjc.2017.12.033.
Chohra D, Ferchichi L, Cakmak YS, Zengin G, Alsheikh SM. 2020. Phenolic pro?les, antioxidant activities and enzyme inhibitory effects of an Algerian medicinal plant (Clematis cirrhosa L.). South Journal of Botany 132: 164-170. DOI:10.1016/j.sajb.2020.04.026
Choi SJ, Kim JK, Kim HY, Harris K, Kim CJ, Park GG, Park CS, Shin DH. 2013. 2,4-di-tert-butylphenol from sweet potato protects against oxidative stress in PC12 cells and in mice. Journal of Medical Food 16: 977-983. DOI: 10.1089/jmf.2012.2739
Demetillo MT, Nuñeza OM, Uy MM, Senarath WTPSK. 2019. Phytochemical screening, antioxidant, and antidiabetic evaluation of leaf extracts from Diospyros blancoi A.DC. Intl J Pharm Sci Res 10 (8): 3951-3956. DOI: 10.13040/IJPSR.0975-8232.10(8).3951-56
du Preez-Bruwer I, Mumbengegwi DR, Louw S. 2022. In vitro antimalarial properties and chemical composition of Diospyros chamaethamnus extracts. South African Journal of Botany 149: 290 – 296. DOI: 10.1016/j.sajb.2022.06.006.
Eswaraiah G, Peele KA, Krupanidhi S, Indira M, Kumar RB, Venkateswarulu TC. 2020. GC–MS analysis for compound identification in leaf extract of Lumnitzera racemosa and evaluation of its in vitro anticancer effect against MCF7 and HeLa cell lines. Journal of King Saud University – Science 32: 780–783. DOI: 10.1016/j.jksus.2019.01.014
Gidik B. 2021. Antioxidant, Antimicrobial Activities and Fatty Acid Compositions of Wild Berberis spp. by Different Techniques Combined with Chemometrics (PCA and HCA). Molecules 26: 7448. DOI: 10.3390/molecules26247448
Grygorieva O, Vergun O, Klymenko S, Zhurba M, Sedlá?ková VH, Ivanišova E, Brindza J. 2020. Estimation of phenolic compounds content and antioxidant activity of leave extracts of some selected non-traditional plant. Potravinarstvo Slovak Journal of Food Sciences 14: 501-509. DOI: 10.5219/1314
Hetta MH, Owis AI, Haddad PS, Eid HM. 2017. The fatty acid-rich fraction of Eruca sativa (rocket salad) leaf extract exerts antidiabetic effects in cultured skeletal muscle, adipocytes and liver cells. Pharmaceutical Biology 55: 810-818. DOI: 10.1080/13880209.2017.1280687
Hossain A, Shadidi F. 2023. Persimmon leaves: nutritional, pharmaceutical, and industrial potential—a review. Plants 12: 937. DOI: 10.3390/plants12040937.
Huang SW, Qiao JW, Sun X, Gao PY, Li LZ, Liu QB, Sun B, Wu DL, Song SJ. 2016. Secoiridoids and lignans from the leaves of Diospyros kaki Thunb. with antioxidant and neuroprotective activities. Journal of Functional Food 24: 183-195. DOI: 10.1016/j.jff.2016.03.025
Hutauruk TR, Lahjie AM, Simarangkir BDAS, Aipassa MI, Ruslim Y. 2018. The prospect of the utilization of non-timber forest products from Setulang village forest based on local knowledge of the uma longh community in Malinau, North Kalimantan, Indonesia. Biodiversitas 19: 421 – 430. DOI: 10.13057/biodiv/d190209.
Ji Y, Liu D, Jin Y, Zhao J, Zhao J, Li H, Li L, Zhang H, Wang H. 2021. In vitro and in vivo inhibitory effect of anthocyanin-rich bilberry extract on ?-glucosidase and ?-amylase. LWT 145: 111484. DOI: 10.1016/j.lwt.2021.111484.
Jozwiak M, Filipowska A, Fiorino F, Struga M. 2020. Anticancer activities of fatty acids and their heterocyclic derivatives. European Journal of Pharmacology 871: 172397. DOI: 10.1016/j.ejphar.2020.172937
Khan MA, Rahman MM, Sardar MN, Arman MSI, Islam MB, Khandakar MJA, Rashid M, Sadik G, Alam AHMK. 2016. Comparative investigation of the free radical scavenging potential and anticancer property of Diospyros blancoi (Ebenaceae). Asian Pasific Journal of Tropical Biomedicine 6: 410 – 417. DOI: 10.1016/j.apjtb.2016.03.004.
Koley TK, Maurya A, Tripathi A, Singh BK, Singh M, Bhutia TL, Tripathi PC, Singh B. 2019. Antioxidant potential of commonly consumed underutilized leguminous vegetables. International Journal of Vegetable Science 25: 362–372. DOI: 10.1080/19315260.2018.1519866
Liu S, Yu Z, Zhu H, Zhang W, Chen Y. 2016. In vitro ?-glucosidase inhibitory activity of isolated fractions from water extract of Qingzhuan dark tea. BMC Complement Altern Med 16 (1): 378. DOI: 10.1186/s12906-016-1361-0.
Martinez AG, Alarcon-aquilar FJ, Huang F, Romero-nava R, Roman-ramos R, Almanza-perez JC. 2021. ?-Amyrin induces GLUT4 translocation mediated by AMPK and PPAR?/? in C2C12 myoblasts. Canadian Journal of Physiology and Pharmacology 99: 1-4. DOI: 10.1139/cjpp-2021-0027
Mazumder K, Sumi TS, Golder M, Biswas B, Maknoon, Kerr PG. 2021. Antidiabetic profiling, cytotoxicity and acute toxicity evaluation of aerial parts of Phragmites karka (Retz.). Journal of Ethnopharmacology 270: 113781. DOI: 10.1016/j.jep.2021.113781.
Mensah-agyei GO, Ayeni KI, Ezeamagu CO. 2020. GC-MS analysis of bioactive compounds and evaluation of antimicrobial activity of the extracts of Daedalea elegans: A Nigerian mushroom. African Journal of Microbiology Research 14: 204-210. DOI: 10.5897/AJMR2019.9120
Moukette BM, Pieme CA, Njimou JR, Biapa CPN, Marco B, Ngogang JY. 2015. In vitro antioxidant properties, free radicals scavenging activities of extracts and polyphenol composition of a non-timber forest product used as spice: Monodora myristica. Biological Research 48: 15. DOI: 10.1186/s40659-015-0003-1.
Murthy HN, Dalawai D, Arer I, Karadakatti P, Hafiz K. 2022. Nutritional Value of Underutilized Fruit: Diospyros chloroxylon Roxb. (Green Ebony Persimmon). International Journal of Fruit Science 22: 249-263. DOI: 10.1080/15538362.2021.2023065
Nazemi M, Motallebi A, Abbasi E, Khaledi M, Zare M. 2022. Antibacterial, antifungal, and cytotoxic activity of the fraction contains squalene in the acetone extract of a sea cucumber, Stichopus hermanni. Iranian Journal of Fisheries Sciences 21: 1495-1507. DOI: 10.22092/ijfs.2023.128416
Naghshi S, Aune D, Beyene J, Mobarak S, Asadi M, Sadeghi O. 2021. Dietary intake and biomarkers of alpha linolenic acid and risk of all cause, cardiovascular, and cancer mortality: systematic review and dose-response meta-analysis of cohort studies. BMJ 375: n2213. DOI: 10.1136/bmj.n2213
Olivia NU, Goodness UC, Obinna OM. 2021. Phytochemical profiling and GC-MS analysis of aqueous methanol fraction of Hibiscus asper leaves. Future Journal of Pharmaceutical Sciences 7: 59. DOI: 10.1186/s43094-021-00208-4
Pejin B, Ciric A, Glamoclija J, Nikolic M, Sokovic M. 2015. In vitro anti-quorum sensing activity of phytol. Natural Products Research 29: 374-377. DOI: 10.1080/14786419.2014.945088
Ramadhan R, Rosyidah N, Firdaus YFH, Kurnia TK, Lestari DA, Phontree K, Phuwapraisirisan P, Riyadi L, Rahman A, Abdulgani N, Maretna SA, Fahdila KN. 2023. Phytochemical analysis in conjunction with in vitro ?-glucosidase inhibitory and antioxidant activities of three Diospyros species from East Kalimantan, Indonesia. Biodiversitas 24: 4783 – 4790. DOI: 10.13057/biodiv/d240919.
Rao PV, Krishinasamy E, Reddy IRM, Naidu MD, Gan SH. 2016. Phytochemical analysis and in vitro evaluation of antidiabetic activity of Diospyros buxifolia. Am J Biochem Mol Biol 6 (3): 95-101. DOI: 10.3923/ajbmb.2016.95.101.
Rathore K, Singh VK, Jain P, Rao SP, Ahmed Z, Singh VD. 2014. In-vitro and in-vivo antiadipogenic, hypolipidemic and antidiabetic activity of Diospyros melanoxylon (Roxb). Journal of Ethnopharmacology 155: 1171 – 1176. DOI: 10.1016/j.jep.2014.06.050.
Sakthivel R, Malar DS, Devi KP. 2018. Phytol shows anti-angiogenic activity and induces apoptosis in A549 cells by depolarizing the mitochondrial membrane potential. Biomedicine & Pharmacotherapy 105: 742-752. DOI: 10.1016/j.biopha.2018.06.035
Seenivasan A, Manikkam R, Kaari M, Sahu AK, Said M, Dastager SG. 2022. 2,4-di-tert-butylphenol (2,4-DTBP) puri?ed from Streptomyces sp. KCA1 from Phyllanthus niruri: Isolation, characterization, antibacterial and anticancer properties. Journal of King Saud University – Science 34: 102088. DOI: 10.1016/j.jksus.2022.102088
Silva CT, Araujo ECG, Lins TRS, Reis CA, Sanquetta CR, da Rocha MP. 2020. Non-timber forest products in Brazil: A bibliometric and a state of the art review. Sustainability 12: 7151. DOI: 10.3390/su12177151.
Silva RO, Sousa FBM, Damasceno SRB, Carvalho NS, Silva VG, Oliveira FRMA, Sousa DP, Aragao KS, Barbosa ALR, Freitas RM, Medeiros JVR. Phytol, a diterpene alcohol, inhibits the inflammatory response by reducing cytokine production and oxidative stress. Fundamental & Clinical Pharmacology 28: 455 – 464. DOI: 10.1111/fcp.12049.
Spiegel M, Kapsuta K, Kolodziejczyk W, Saloni J, Zbikowska B, Hill GA, Sroka Z. 2020. Antioxidant activity of selected phenolic acids–ferric reducing antioxidant power assay and QSAR analysis of the structural features. Molecules 25: 3088. DOI: 10.3390/molecules25133088
Viet TD, Xuan TD, Anh LH. 2021. ?-Amyrin and ?-Amyrin isolated from Celastrus hindsii leaves and their antioxidant, anti-xanthine oxidase, and anti-tyrosinase potentials. Molecules 26: 7248. DOI: 10.3390/molecules26237248
Vijayan K, Gopinathan M, Ambikapathy V. 2020. Phytochemical screening and antioxidant activity of Diospyros ebenum J. Koenig Ex Retz leave extract. International Journal of Pharmaceutical Sciences and Research 11: 5163 – 5169. DOI: 10.13040/IJPSR.0975-8232.11(10).5163-69
Wairata J, Fadlan A, Purnomo AS, Taher M, Ersam T. 2022. Total phenolic and flavonoid contents, antioxidant, antidiabetic and antiplasmodial activities of Garcinia forbesii King: A correlation study. Arabian Journal of Chemistry 15: 103541. DOI: 10.1016/j.arabjc.2021.103541
Wang J, Hu X, Ai W, Zhang F, Yang K, Wang L, Zhu X, Gao P, Shu G, Jiang Q, Wang S. Phytol increases adipocyte number and glucose tolerance through activation of PI3K/Akt signaling pathway in mice fed high-fat and high-fructose diet. Biochemical and Biophysical Research Communications 489: 432-438. DOI: 10.1016/j.bbrc.2017.05.160
Widyawati T, Syarifah S, Sumantri IB. 2021. Squalene decreased fasting blood glucose level of type II diabetic rats. IOP Conf. Series: Earth and Environmental Science 912: 012088. DOI: 10.1088/1755-1315/912/1/012088
Worawalai W, Wacharasindhu S, Phuwapraisirisan P. 2015. N-Arylmethylaminoquercitols, a new series of effective antidiabetic agents having ?-glucosidase inhibition and antioxidant activity. Bioorganic & Medicinal Chemistry Letters 25: 2570 – 2573. DOI: 10.1016/j.bmcl.2015.04.033
Yunusa UM, Urek RO. 2023. Determination of phenolic compounds in Diospyros lotus by RP-HPLCDAD and evaluation of antioxidant and cytotoxic properties. Journal of Food Measurement and Characterization 17: 1413 – 1427. DOI: 10.1007/s11694-022-01696-5.
Zhang P, Liu N, Xue M, Zhang M, Xiao Z, Xu C, Fan Y, Qiu J, Zhang Q, Zhou Y. 2023. Anti-inflammatory and antioxidant properties of squalene in copper sulfate-induced inflammation in zebrafish (Danio rerio). International Journal of Molecular Sciences 24: 8518. DOI: 10.3390/ijms24108518
Zreen Z, Hameed A, Kiran S, Farooq T, Zarooq MS. A Comparative study of Diospyros malabarica (Gaub) extracts in various polarity-dependent solvents for evaluation of phytoconstituents and biological activities. Biomed Research International 2022: 4746223. DOI: 10.1155/2022/4746223

Most read articles by the same author(s)