Determination of phytochemical contents by LC/QTOF/MS and evaluation of <i>in-vitro </i> biological activities of 2 <i>Peltigera</i> lichens from Bursa

TÜZÜN, BURCU S.; KARADAĞ, BAŞAK T.; ORAN, SEYHAN; ÖZTÜRK, ŞULE; YILMAZ, FETHİYE F.; FAFAL, TUĞÇE; KIVÇAK, BİJEN

doi:10.1590/0001-3765202420230657

Acessibilidade / Reportar erro

Brasil

Anais da Academia Brasileira de Ciências

Español English

Brasil

Español English

sumário « anterior atual seguinte »

Sumário

CHEMICAL SCIENCES • An. Acad. Bras. Ciênc. 96 (2) • 2024 • https://doi.org/10.1590/0001-3765202420230657 copy

Determination of phytochemical contents by LC/QTOF/MS and evaluation of in-vitro biological activities of 2 Peltigera lichens from Bursa

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

Lichens are symbiotic associations of algae and fungi. They are edible as food and have been used in traditional medicine for years. It is aimed to screen Peltigera praetextata (Flörke ex Sommerf.) Zopfand and Peltigera elisabethae Gyeln. phytochemically by LC/QTOF/MS and according to the constituents to evaluate the antioxidant, tyrosinase inhibitory, and antibacterial activities. In total 54 of metabolites detected by LC/QTOF/MS were common in both species. According to LC/QTOF/MS scanning results, alkaloids, iridoid glycosides, phenolics, cyanogenetic glycosides, and terpenic structures were detected. DPPH, ABTS, superoxide radical scavenging activities, and metal chelating capacity IC₅₀ values were 84.55, 9.349; 51.27, 9.127; 95.01, 58.65 and 20.57, 70.08 µg/mL., respectively. The CUPRAC reducing power was determined as 4.69 and 9.57 TEAC_CUPRAC, respectively. Tyrosinase inhibitor activity were found to be 86.95 and 196.7 µg/mL. Both lichens did not show antimicrobial effects. As a result of the antioxidant and tyrosinase inhibitor activities it was seen that their activities were significant and further in vivo studies could be carried out on this lichens.

Key words
Antioxidant; LC/QTOF/MS; Lichen phenolics; Peltigera elisabethae Gyeln; Peltigera praetextata (Flörke ex Sommerf.); Tyrosinase inhibitor

Activity	Sum of Squares	df	Mean Square	F	Sig.
Between Groups	10344.257	3	3448.086	11966.634	.000
Within Groups	2.305	8	.288
Total	10346.562	11

	Compound name	Chemical structure	Detected Lichens	Retention time	Mass	Ion mode	Biological activity	Ref.for activity
1	Feruloylagmatine	Cinnamamides	PE	1.149	306.1702	Positive	Antioxidant and Antibacterial	Wang et al. 2020WANG W, SNOOKS HD & SANG S. 2020. The Chemistry and Health Benefits of Dietary Phenolamides. J Agric Food Biochem 68: 6248-6267. https://dx.doi.org/10.1021/acs.jafc.0c02605. https://doi.org/10.1021/acs.jafc.0c02605... , Zeiss et al. 2021ZEISS DR, PIATER LA & DUBERY IA. 2021. Hydroxycinnamate amides: Intriguing conjugates of plant protective metabolites. Trends in Plant Sci 26(2): 184-195. https://doi.org/10.1016/j.tplants.2020.09.011. https://doi.org/10.1016/j.tplants.2020.0...
2	Neolinustatin	cyanogenic glycoside	PE	1.372	423.1744	Positive	Antioxidant	Li et al. 2012a
3	Chavicol glycoside	Phenyl propanoid	PE	1.383	296.1267	Positive	Antioxidant and tyrosinase inhibitor	Oliveira et al 2021, Avetisyan et al 2017
4	Dehydrofalcarinone	ynone	PE	1.697	240.1515	Positive	Antioxidant	Khalil et al. 2022KHALIL N, ELHADY SS, DIRI RM, FEKRY MI, BISHR M, SALAMA O & EL-ZALABANI SM. 2022. Salicylic Acid Spraying Affects Secondary Metabolites and Radical Scavenging Capacity of Drought- Stressed Eriocephalus africanus L. Agronomy 12: 2278. https://doi.org/10.3390/agronomy12102278. https://doi.org/10.3390/agronomy12102278...
5	Tetramethylquercetin 3- rutinoside	Flavonoid glycoside	PE	2.223	666.2150	Negative	Antioxidant	Olgun et al. 2018OLGUN FAO, UZER A, OZTURK BD & APAK R. 2018. A novel cerium oxide nanoparticles-based colorimetric sensor using tetramethyl benzidine reagent for antioxidant activity assay. Talanta 182: 55- 61. https://doi.org/10.1016/j.talanta.2018.01.047. https://doi.org/10.1016/j.talanta.2018.0... , Si et al. 2012SI Y-X, YIN S-J, OH S, WANG Z-J, YE S, YAN L, YANG J-M, PARK Y-D, LEE J & QIAN GY. 2012. An Integrated Study of Tyrosinase Inhibition by Rutin: Progress using a Computational Simulation. J Biomol Struct Dyn 29(5): 999-1002. https://doi.org/10.1080/073911012010525028. https://doi.org/10.1080/0739110120105250...
6	Atraric Acid	Phenolic	PE	2.725	196.0743	Positive	Antioxidant and tyrosinase inhibitor	Mitrovic et al. 2014MITROVIC T ET AL. 2014. Platismatia glauca and Pseudovernia furfuracea lichens as sources of antioxidant, antimicrobial and antibiofilm agents. EXCLI J 13 938-953., Lie et al. 2022
7	Levosimendan	Pyridazinone	PE	3.173	280.1068	Positive	Antioxidant	Abeer et al. 2017ABEER MR, ALZOUBİ KH & ATMEH A. 2017. Levosimendan enhances memory through antioxidant effect in rat model: behavioral and molecular study. Behav Pharmacol 29(4): 344-350. http://dx.doi.org/10.1097/FBP.0000000000000362. https://doi.org/10.1097/FBP.000000000000...
8	Pyridyl nicotine and derivates	Alkoloid	PE	3.218	239.1419	Positive	Antioxidant and tyrosinase inhibitor	Lin et al. 2012LIN Y-S, CHEN S-H, HUANG W-J, CHIEN M-Y, LIN S-Y & HOU W-C. 2012. Effects of nicotinic acid derivatives on tyrosinase inhibitory and antioxidant activities. Food Chem 132: 2074-2080. https://doi.org/10.1016/j.foodchem.2011.12.052. https://doi.org/10.1016/j.foodchem.2011....
9	Donepezil	Piperidine derivate	PE	3.274	379.2130	Positive	Antioxidant	Umukoro et al. 2014UMUKORO S, ADEWOLE FA, EDUVIERE AT, ADERIBIGBE AO & ONWUCHEKWA C. 2014. Free Radical Scavenging Eff ect of Donepezil as the Possible Contribution to its Memory Enhancing Activity in Mice. Drus Res 64(5): 236-239. https://doi.org/10.1055/s-0033-1357126. https://doi.org/10.1055/s-0033-1357126...
10	Nitrendipine	Pyridine derivate	PE	3.441	360.1328	Positive	Antioxidant	Unuvar et al. 2021UNUVAR S, GÜRSOY Ş, BERK A, KAYMAZ B, İLHAN N & AKTAY G. 2021. Antioxidant Effect of a Dihydropyridine Calcium Antagonist Nitrendipine in Streptozotocin_Induced Diabetes. Experiment Papers 57(1): 126-133.
11	Austin	Terpene	PE	3.508	500.2031	Positive	Antioxidant and tyrosinase inhibitor	Burgos & Serranilos 2012BURGOS EG & SERRANILOS MPG. 2012. Terpene Compounds in Nature: A Review of Their Potential Antioxidant Activity. Curr Med Chem 19: 5319-5341. https://doi.org/10.2174/092986712803833335. https://doi.org/10.2174/0929867128038333... , Kootheat et al. 2023KOOTHEAT T, TEDASEN A, YAMASAKI K & CHATATIKUN M. 2023. Melanogenesis Inhibitory Activity, Chemical Components and Molecular Docking Studies of Prunus cerasoides Buch.-Ham. D. Don. Flowers. J Evid Based Immig Med 28: 1-20. https://doi.org/10.1177/2515690x231152928. https://doi.org/10.1177/2515690x23115292...
12	Anabsin	Sesquiterpenoid	PE	3.777	512.2750	Positive	Antioxidant	Brunet et al. 2005BRUNET JM, DJILAS SM, CETKOVIC CS & TUMBAS VT. 2005. Free-radical scavenging activity of wormwood (Artemisia absinthium L) extracts. J Sci Food Agric 85: 265-272. https://doi.org/10.1002/jsfa.1950. https://doi.org/10.1002/jsfa.1950...
13	Avenanthramide	Phenolic alkoloid	PE	3.788	361.1167	Positive	Antioxidant and tyrosinase inhibitor	Dimberg et al. 1993DİMBERG LH, THEANDER O & LİNGNERT H. 1993. Avenanthramides: A group of phenolic antioxidants in oats. AACCI 70(6): 637-641., Park et al 2021
14	Tocopheronic Acid	Sesquiterpenoid	PE	3.889	294.1471	Positive	Antioxidant	Al-Fatlawi & Al-Fatlawi 2020AL-FATLAWI AAY & AL-FATLAWI AAY. 2020. Tocopheronic acid attenuates chlorpromazine induced liver injury in rats, targeting oxidative stress and same biochemical markers. Int J Pharm Res 12(4): 2001-2011. http://dx.doi.org/10.31838/ijpr/2020.12.04.285. https://doi.org/10.31838/ijpr/2020.12.04...
15	3- methoxy chalcones	Chalcone	PE	3.934	448.1729	Positive	Antioxidant	Bandgar et al. 2010, Akhtar et al. 2015AKHTAR MN, SAKEH NM, ZAREEN S, GUL S, LO KM, UL-HAQ Z, SHAH SAA & AHMAD S. 2015. Design and synthesis of chalcone derivatives as potent tyrosinase inhibitors and their structural activity relationship. J Mol Struct 1085: 97-103. https://doi.org/10.1016/j.molstruc.2014.12.073. https://doi.org/10.1016/j.molstruc.2014....
16	Jasmonic acid glucoside	Jasmonate	PP	4.034	388.1729	Negative	Antioxidant	Sirhindi et al. 2016SIRHINDI G, MIR MA, ABD-ALLAH EH, AHMAD P & GUCEL S. 2016. Jasmonic Acid Modulates the Physio-Biochemical Attributes, Antioxidant Enzyme Activity, and Gene Expression in Glycine max under Nickel Toxicity. Front in Plant Sci 7: 591-603. https://doi.org/10.3389/fpls.2016.00591. https://doi.org/10.3389/fpls.2016.00591...
17	Hordatine B	heterodimer of feruloylagmatine	PE	4.213	580.3141	Positive	Antioxidant	Wang et al. 2020WANG W, SNOOKS HD & SANG S. 2020. The Chemistry and Health Benefits of Dietary Phenolamides. J Agric Food Biochem 68: 6248-6267. https://dx.doi.org/10.1021/acs.jafc.0c02605. https://doi.org/10.1021/acs.jafc.0c02605...
18	5,6,7- Trimethoxycoumarin	Coumarin	PE	4.437	236.0692	Positive	Antioxidant and tyrosinase inhibitor	Matos et al. 2017MATOS JM, SALETA V-R ANDRE F, EUGENIA U, LAURDES S & FERNANDO B. 2017. Heterocyclic antioxidants in nature: Coumarins. Curr Org Chem 21(4): 311-324. http://dx.doi.org/10.2174/1385272820666161017170652. https://doi.org/10.2174/1385272820666161... , Menezes & Diederich 2019MENEZES JCJMDS & DIEDERICH MF. 2019. Natural dimers of coumarin, chalcones, and resveratrol and the link between structure and pharmacology. Europ J Med Chem 182: 111637. https://doi.org/10.1016/j.ejmech.2019.111637. https://doi.org/10.1016/j.ejmech.2019.11...
19	Mycophenolate mofetil	Carboxylic ester	PE	4.549	433.2096	Positive	Antioxidant	Dalmarco et al. 2009DALMARCO EM, BUDNİ P, PARİSOTT EB, FİLHO DW & FRÖDE TS. 2009. Antioxidant effects of mycophenolate mofetil in a murine pleurisy model. Transpl Immunol 22: 12-17. https://doi.org/10.1016/j.trim.2009.09.005. https://doi.org/10.1016/j.trim.2009.09.0...
20	Marmin	Coumarin	PP	4.779	360.1561	Positive	Antioxidant	Chian et al. 2018CHIAN R, KASSIM NK, YEAP YS, LIAN GC, YAZAN SL & MUSA KH. 2018. Isolation of Carbazole Alkaloids and Coumarins from Aegle marmelos and Murraya koenigii and Their Antioxidant Properties. Sains Malays 47(8): 1749-1756. http://dx.doi.org/10.17576/jsm-2018-4708-14. https://doi.org/10.17576/jsm-2018-4708-1...
21	Xanthosine	purine nucleoside	PP/PE	5.048	284.0753	Negative	Antibrowning agent	Tao et al. 2021TAO N, WANG R, XU X, DONG T, ZHANG S, LIANG M &WANG Q. 2021. Xanthosine is a novel anti-browning compound in potato identified by widely targeted metabolomic analysis and in vitro test. Postharvest Biol Technol 171: 111367. https://doi.org/10.1016/j.postharvbio.2020.111367. https://doi.org/10.1016/j.postharvbio.20...
22	Cyproterone acetate	Steroidal	PE	5.242	416.1751	Positive	Tyrosinase inhibitor	Tadokoro et al. 2003TADOKORO T, ROUZAUD F, ITAMI S, HEARING WJ & YOSHIKAWA K. 2003. The Inhibitory Effect of Androgen and Sex-Hormone-Binding Globulin on the Intracellular cAMP Level and Tyrosinase Activity of Normal Human Melanocytes. Pigment Cell Res 16: 190-197. https://doi.org/10.1034/j.1600- 0749.2003.00019.x. https://doi.org/10.1034/j.1600- 0749.200...
23	Hexyl glucoside	alkyl polyglycosides	PP	5.622	264.1584	Positive	Antioxidant	Adem et al. 2014ADEM YT, MOLİNA P, LİU H, PATAPOF TW, SREEDHARA A & ESUE O. 2014. Hexyl Glucoside and Hexyl Maltoside Inhibit Light-Induced Oxidation of Tryptophan. J Pharm Sci 103: 409-416. http://dx.doi.org/10.1002/jps.23809. https://doi.org/10.1002/jps.23809...
24	Apigenin	Flavonoid	PE	5.857	270.0539	Positive	Antioxidant and tyrosinase inhibitor	Sadasivam & Kumeresan 2011SADASIVAM K & KUMERESAN R. 2011. A comperative DFT study on the antioxidant activity of apigenin and scutellarein flavonoid compounds. Mol Phys 109(6): 839-852. http://dx.doi.org/10.1080/00268976.2011.556576. https://doi.org/10.1080/00268976.2011.55... , Karaoglan &Koca 2020ARECHE C, PARRA JV, SEPULVEDA B, GALCIA-BELTRAN O & SIMIRGIOTIS MJ 2022. UHPLC-MS Metabolomic Fingerprinting, Antioxidant, and Enzyme Inhibition Activities of Himantormia lugubris from Antarctica. Metabolites 12: 560-581. https://doi.org/10.3390/metabo12060560. https://doi.org/10.3390/metabo12060560...
25	Dihydroartemisinin	Sesquiterpenoid	PE	5.969	284.1629	Positive	Antioxidant	Ittarat et al. 2003ITTARAT W, SREEPIAN A, SRISARIN A & PATHEPCHOTIVANG K. 2003. Effect of dihidroartemisinin on the antioxidant capacity of P. falciparum infected erythrocytes. Southeast Asian J Trop Med Public Health 34(4): 744- 749.
26	C16 Sphinganine	Amino alcohol	PP/PE	6.115	273.2672	Positive	Antioxidant and antibacterial	Tamsir et al. 2020TAMSIR NM, ESA NM, OMAR SNC & SHAFIE NH. 2020. Manilkara zapota (L.) P. Royen: Potential Source of Natural Antioxidants. Malaysian J Med Health Sci 16: 193- 201., Barreto-Bergter et al. 2006BARRETO-BERGTER E, PINTO MR & RODRIGUES ML. 2006. Structural and Functional Aspects of Fungal Glycosphingolipids. Stud Nat ProdChem 33: 1025-1055.
27	Cappariloside A	Alkoloid	PE	6.193	334.1170	Positive	Antioxidant and tyrosinase inhibitor	Aliyazicioglu et al 2013ALIYAZICIOGLU R, EYUPOGLU OE, SAHİN H, YILDIZ O & BALTOS N. 2013. Phenolic components, antioxidatn activity and mineral analysis of Capparis spinosa L. Afr J Biotechnol 12(47): 6643-6649. https://doi.org/10.5897/AJB2013.13241. https://doi.org/10.5897/AJB2013.13241... , Kirkan et al. 2021KIRKAN B, CEYLAN O, SARIKURKCU C & TEPE B. 2021. Phenolic profile, antioxidant and enzyme inhibitory activity of ethyl acetate, methanol and water extracts of Capparis spinosa L. Int J Second Metab 8(4): 337-351. https://doi.org/10.21448/ijsm.981149. https://doi.org/10.21448/ijsm.981149...
28	Tortuosamine	Alkoloid	PP/PE	6.233	326.1978	Negative	Antioxidant and Antimalarial	Olatunji et al. 2021OLATUNJI TL, SIEBERT F, ADETUNJI AE, HARVEY BH, GERICLE J, HAMMAN JH & VANDER KOOY F. 2021. Sceletium tortuosum: Areview on its phytochemistry, pharmacokinetics, biological and clinical activities. J Ethnopharmacol, 280: 114176. https://doi.org/10.1016/j.jep.2021.114711. https://doi.org/10.1016/j.jep.2021.11471...
29	Erythronolide B	Macrolide	PP/PE	6.278	402.2605	Negative	Antibacterial effect inducer	Saito & Mitsuhashi 1971SAITO T & MITSUHASHI S. 1971. Antibacterial activity of megolamicin and its inducer activity for macrolid resistance in Staphylococci. The Antibiot 23(12): 850-854. https://doi.org/10.7164/antibiotics.24.850. https://doi.org/10.7164/antibiotics.24.8...
30	Prosopinine	Alkoloid	PP/PE	6.345	287.2465	Positive	Tyrosinase inhibitor	Saleem et al. 2021SALEEM H, ZENGIN G, LOCATELLI M, ABIDIN SAZ & AHEMAD N. 2021. Investigation of phytochemical composition and enzyme inhibitory potential of Anagallis arvensis L. Nat Prod Res 36 (14): 3750-3755. https://doi.org/10.1080/14786419.2021.1880404. https://doi.org/10.1080/14786419.2021.18...
31	14,19- Dihyroaspidospermatine	Alkoloid	PP/PE	6.402	340.2136	Negative	Antibacterial	Tanaka et al. 2006TANAKA JCA, SILVA CC, OLIVEIRA AJB, NOKAMURA CV & DIAS FILHA BF. 2006. Antibacterial activity of indole alkoloids from Aspidormea ramiflorum. Braz J Biol Res 39(3): 387-391. https://doi.org/10.1590/S0100-879X2006000300009. https://doi.org/10.1590/S0100-879X200600...
32	Tetradecylamine	Alkyl amine	PP/PE	6.450	213.2464	Positive	Antibacterial	Borick et al. 1959BORICK PM, BRATH M, WILSON AG, WIENTRAUB L & KURA M. 1959. Microbiological activity of certain saturated and unsaturated fatty acids salts of tetra decylamine and related compounds. Appl Microbiol 7(4): 248-251. https://doi.org/10.1128/am.7.4.248-251.1959. https://doi.org/10.1128/am.7.4.248-251.1...
33	Perilloside C	Terpene glycoside	PP	6.457	316.1893	Positive	Antioxidant	Hou et al. 2022HOU T, NETALA VR, ZHANG H, XING Y, LI H & ZHANG Z. 2022. Perilla frutescens: A Rich Source of Pharmacological Active Compounds. Molecules 27: 3758. https://doi.org/10.3390/molecules27113578. https://doi.org/10.3390/molecules2711357...
34	Fenpiclonil	Pyrrole	PP/PE	6.718	235.9907	Negative	Antibacterial	Leroux et al. 1992LEROUX P, LANEN C & FRITZ R. 1992. Similarities in the antifungal activities of fenpiclonil, iprodione and triclofos-methyl against Bortyris cinerea and Fusarium nivale. Pestic Sci 36: 255-261. https://doi.org/10.1002/PS.2780360312. https://doi.org/10.1002/PS.2780360312...
35	Eudesmin	Lignan	PP/PE	6.726	386.1725	Positive	Tyrosinase inhibitor, Antibacterial	Li et al. 2013LI W-J, LIN Y-C, WU P-F, WEN Z-H, LIU P-L, CHEN C-Y & WANG H-M. 2013. Biofunctional Constituents from Liriodendron tulipifera with Antioxidants and Anti-Melanogenic Properties. Int J Mol Sci 14: 1698-1712. https://doi.org/10.3390%2Fijms14011698. https://doi.org/10.3390%2Fijms14011698... , Patel & Patel 2022PATEL DK & PATEL K. 2022. Potential theuropeutic applications of eudesmin in medicine: An overview on medicinal importance, pharmacological activities and analytical prospects. Pharmacol Res- Modern Sci Med 5: 100-175. https://doi.org/10.1016/j.prmcm.2022.100175. https://doi.org/10.1016/j.prmcm.2022.100...
36	Oleamide	Fatty acid amide	PE	6.808	281.2719	Positive	Antioxidant	Reyes-Soto et al. 2022REYES-SOTO CY ET AL. 2022. Oleamide Reduces Mitochondrial Dysfunction and Toxicity in Rat Cortical Slices Through the Combined Action of Cannabinoid Receptors Activation and Induction of Antioxidant Activity. Neurotox Res 40: 2167-2178. https://doi.org/10.1007/s12640-022-00575-7. https://doi.org/10.1007/s12640-022-00575...
37	Vialinin A	Terpene	PE	6.909	562.1624	Positive	Antioxidant	Sonowal et al. 2018SONOWAL H, SHUKLA K, KOTA S, SAXENA A & RAMANA KV. 2018. Vialinin A, an Edible Mushroom-Derived p-Terphenyl Antioxidant, Prevents VEGF-Induced Neovascularization In Vitro and In Vivo. Oxid Med Cell Longev 2018: 1-10. https://doi.org/10.1155/2018/1052102. https://doi.org/10.1155/2018/1052102...
38	n-Pentadecylamine	Alkyl amine	PP/PE	7.020	227.2619	Positive	Antibacterial	Rammali et al. 2012RAMMALI S, HILALI L, DARI K, BENCHARKI B, RAHIM A, TIMINOUNI M, GOBOUNE F, ADLOUNI ME & KHATTABI A. 2012. Antimicrobial and antioxidant activities of Streptomyces species from soils of three different cold sites in the Fez-Melones region Moracco. Nature 12: 17233. https://doi.org/10.1038%2Fs41598-022-21644-z. https://doi.org/10.1038%2Fs41598-022-216...
39	Sulfaphenazole	Sulfonamide	PP	7.064	314.0848	Negative	Antioxidant	Khan et al. 2007KHAN M, MOHAN VK, KUMBALA D & KUPPUSORY P. 2007. Cardioprotection by sulphaphenazole, a cytochrome p 450 inhibitor: Mitigation of ischemia-reperfusion injury by scavenging of reactive oxygen species. J Pharm Experiment Ther 323(3): 813-821. https://doi.org/10.1124/jpet.107.129486. https://doi.org/10.1124/jpet.107.129486...
40	Triclofos	Monoalkyl phosphate	PP/PE	7.134	227.8907	Negative	Antibacterial	Leroux et al. 1992LEROUX P, LANEN C & FRITZ R. 1992. Similarities in the antifungal activities of fenpiclonil, iprodione and triclofos-methyl against Bortyris cinerea and Fusarium nivale. Pestic Sci 36: 255-261. https://doi.org/10.1002/PS.2780360312. https://doi.org/10.1002/PS.2780360312...
41	Gemfibrozil M1	Aromatic ether	PP/PE	7.743	266.1522	Positive	Antioxidant	Ashidate et al. 2002ASHİDATE K, KAWAMURA M, TOHDA H, MİYAZAKİ S, HAYASHİ H, TERAMOTO T & HİRATA Y. 2002. Ascorbic acid augments cytotoxicity induced by oxidized low-density lipoprotein. J Atheroscler Thromb 10(1): 7-12. https://doi.org/10.5551/jat.10.7. https://doi.org/10.5551/jat.10.7...
42	Dodecyl Phosphocholine	Ethanol amine	PE	7.747	352.2614	Positive	Antioxidant	Balakrishna et al. 2017BALAKRİSHNA M, KAKİ SS, KARUNA MSL, SARADA S, KUMAR CG & PRASAD RBN. 2017. Synthesis and in vitro antioxidant and antimicrobial studies of novel structured phosphatidylcholines with phenolic acids. Food Chem 221: 664-672. http://dx.doi.org/10.1016/j.foodchem.2016.11.121. https://doi.org/10.1016/j.foodchem.2016....
43	9-nonadecene	Fatty acid	PP/PE	8.027	266.2979	Positive	Antioxidant and Antibacterial	Premathilaka & Silva 2016, Mahamuni 2015MAHAMUNI SV. 2015. Antifungal trait of Burkholderia gladioli strain VIMPO2 (JQ811557). Int J Sci Res 4(8): 2059-2064.
44	Delphinidin glucoside	Anthocyanin	PE	8.128	803.2019	Positive	Antioxidant	Watsona & Schönlau 2015WATSON RR & SCHÖNLAU F. 2015. Nutraceutical and antioxidant effects of a delphinidin-rich maqui berry extract Delphinol: a review. Minerva Cardioangiol 63: 1-12.
45	1-Eicosene	Hydrocarbon	PP/PE	8.240	280.3130	Positive	Antibacterial	Lay-Jing et al. 2012LAY-JING S, HOOI-KHENG B, PAZILAH I, AMIRIN S & MOHDZAINI A. 2012. Antimicrobial activity of Gynura segetum’s leaf extracts and its active fractions. Cellmed 2(2): 20.1-20.5. https://doi.org/10.5667/tang.2012.0010. https://doi.org/10.5667/tang.2012.0010...
46	Spermine derivates	Polyamine	PP/PE	8.302	370.2721	Positive	Tyrosinase inhibitor	Kim et al. 2018KIM SB, LIU Q, AHNJH, JO YH, TURK A, HONG IP, HAN SM, HWANG BY & LEE MK. 2018. Polyamine derivatives from the bee pollen of Quercus mongolica with tyrosinase inhibitory activity. Bioorg Chem 81: 127-133. https://doi.org/10.1016/j.bioorg.2018.08.014. https://doi.org/10.1016/j.bioorg.2018.08...
47	Scytonemin	Alkoloid	PE	8.474	544.1423	Positive	Antioxidant and tyrosinase inhibitor	He et al. 2022HE Y, SUYAMA TL, KİM H, GLUKHOV E & GERWİCK WH. 2022. Discovery of Novel Tyrosinase Inhibitors From Marine Cyanobacteria. Front Microbiol 13: 912621. https://doi.org/10.3389/fmicb.2022.912621. https://doi.org/10.3389/fmicb.2022.91262...
48	Diisobutyl/diisononyl phthalate	Benzene carboxylic acid	PP/PE	8.537	278.1521	Positive	Antibacterial	Huang et al. 2021HUANG L, ZHU X, ZHO S, CHENG Z, SHI K, ZHANG C & SHAO H. 2021. Phthalic acid esters: Natural sources and biological activities. Toxins 13: 495. https://doi.org/10.3390/toxins13070495. https://doi.org/10.3390/toxins13070495...
49	10-Gingerol	Phenol	PE	8.586	350.2457	Positive	Antioxidant	Lee & Ahn 1985LEE I-K & AHN S-Y. 1985. The Antioxidant activity of gingerol. Korean J Food Sci Technol 17(2): 55-59. https://doi.org/10.1002/biof.552210157. https://doi.org/10.1002/biof.552210157...
50	Tianeptine		PE	8.633	436.1233	Negative	Antioxidant	Dello et al. 2012
51	Luteolin derivate	Flavonoid	PP/PE	8.686	710.1720	Negative	Tyrosinase inhibitor and Antibacterial	Zhang et al. 2017ZHANG L, ZHAO X, TAO G-J, CHEN J & ZHENG Z-P. 2017. Investigating the inhibitory activity and mechanism differences between norartocarpetin and luteolin for tyrosinase: A combinatory kinetic study and computational simulation analysis. Food Chem 223: 40-48. https://doi.org/10.1016/j.foodchem.2016.12.017. https://doi.org/10.1016/j.foodchem.2016....
52	Nonoxynol-9	Alkane	PP/PE	8.817	616.4182	Positive	Antibacterial	Hillier et al. 2005HILLIER SL, MOENCH TMP, SHATTACK R, REICHERDELFER P & VERONESE F. 2005. In vitro and in vivo the story of nonoxynol-9. J Acquir Immune Defic Syndr 39(1): 1-8. https://doi.org/10.1097/01.qai.0000159671.25950.74. https://doi.org/10.1097/01.qai.000015967...
53	Annosquamosin B	Diterpenoid	PE	9.268	308.2351	Positive	Antioxidant	Pandey & Barve 2011PANDEY N & BARVE D. 2011. Phytochemical and Pharmacological Review on Annona squamosa Linn. Int J Res in Pharmaceut Biomed Sci 2(4): 1404- 1412.
54	Aeglin	Fatty acyl glycoside	PE	9.324	510.2095	Positive	Antioxidant	Patel et al. 2020PATEL DK, PATEL K, RAHMAN M & CHAUDHARY S. 2020. Theurapeutic potential of “Aegline”, an important phytochemical of Aegle marmelos: Current health perspectives for the treatment of disease. Chapter Nanomed Bioact: 383- 392.
55	Rubroskyrin	Bis-anthroquinone	PP	9.373	574.1103	Negative	Antioxidant and tyrosinase inhibitor	Bräse et al. 2012BRÄSE S, GLÄSER F, KRAMER CS, LINDNER S, LINSENMEIER AM, MASTERS K-S, MEISER A-C, RUFF BM & ZHANG S. 2012. Skyrins. Progress in the chemistry of organic natural compounds. Chem Mycotox 2012: 139-151.
56	Quercetin-3- glucoside	Flavonoid	PP	9.466	714.1554	Positive	Antioxidant and tyrosinase inhibitor	Chen & Kubo, 2002CHEN Q-X & KUBO I. 2002. Kinetics of Mushroom Tyrosinase Inhibition by Quercetin. J Agric Food Chem 50: 4108-4112. https://doi.org/10.1021/jf011378z. https://doi.org/10.1021/jf011378z... , Heo et al. 2007HEO HJ, KİM YJ, CHUNG D & KİM D-O. 2007.Antioxidant capacities of individual and combined phenolics in a model system. Food Chem 104: 87-92. https://doi.org/10.1016/j.foodchem.2006.11.002 https://doi.org/10.1016/j.foodchem.2006.... , Baghel et al. 2012BAGHEL SS, SHRİVASTAVA S, BAGHEL RS, AGRAWAL P & RAJPUT S. 2012. A review of quercetin:antioxidant and anticancer properties. WJPPS 1(1): 146- 160.
57	Harderoporphyrin	Heterocyclic m crocycle	PP/PE	9.761	608.2627	Positive	Tyrosinase inhibitor	Baldea et al. 2016BALDEA I, OLTEANU DE, BOLFA P, TABARAN F, ION R-M & FILIP GA. 2016. Melanogenesis and DNA damage following photodynamic therapy in melanoma with two meso-substituted porphyrins. J Photochem Photobiol B: Biol 161: 402-410. https://doi.org/10.1016/j.jphotobiol.2016.06.012. https://doi.org/10.1016/j.jphotobiol.201...
58	Pheophorbide A	Heterocyclic compound	PE	10.085	592.2687	Positive	Antioxidant and tyrosinase inhibitor	Lanfer et al. 2005LANFER UM, BARROS RMC & SINNECKER P. 2005. Antioxidant activity of chlorophylls and their derivatives. Food Res Int 38: 885-891. https://doi.org/10.1016/j.foodres.2005.02.012. https://doi.org/10.1016/j.foodres.2005.0... , Li et al. 2012bLI J, JIANG S, HUANG C & YANG X. 2022. Atraric Acid Ameliorates Hyperpigmentation through the Downregulation of the PKA/CREB/MITF Signaling Pathway. Int J Mol Sci 23: 15952. https://doi.org/10.3390/ijms232415952. https://doi.org/10.3390/ijms232415952...
59	Ginsenoside Rh4	Saponin	PE	10.152	620.4282	Positive	Tyrosinase inhibitor	Kim 2015KIM K. 2015. Effect of ginseng and ginsenosides on melanogenesis and their mechanism of action. J Ginseng Res 39: 1-6. https://doi.org/10.1016%2Fj.jgr.2014.10.006. https://doi.org/10.1016%2Fj.jgr.2014.10....
60	Melilotoside A	Hydroxycinnamic acid derivate	PE	10.722	590.4177	Positive	Antioxidant and tyrosinase inhibitor	Yang et al. 2007YANG L, HAN H, NAKAMURA N, HATTORI M, WANG Z & XU WL. 2007. Bio-guided isolation of antioxidants from the stems of Dendrobium aurantiacum var. denneanum. Phytothe Res 21(7): 696-698. https://dx.doi.org/10.1002/ptr.2133. https://doi.org/10.1002/ptr.2133... ; Güven et al. 2023
61	Paradol	Phenol	PE	10.890	334.2504	Positive	Antioxidant and tyrosinase inhibitor	Nile & Park 2015, Viggiano et al. 2023VIGGIANO S, PANZELLA L, REICHENBACH M, HANS J & NAPOLITANO A. 2023. The Effect of Cosmetic Ingredients of Phenol Type on Immediate Pigment Darkening and Their (Photo)Protective Action in Association with Melanin Pigmentation: A Model In Vitro Study. Cosmetics 10: 22-37. https://doi.org/10.3390/cosmetics10010022. https://doi.org/10.3390/cosmetics1001002...
62	Biotin	Heterocyclic compound	PE	11.259	614.4155	Positive	Antioxidant	Al-Quadah & Ismail 2012AL-QUADAH KM & ISMAIL ZB. 2012. The relationship between serum biotin and oxidant/antioxidant activities in bovine lameness. Res Vet Sci 92: 138-141. https://doi.org/10.1016/j.rvsc.2010.10.017. https://doi.org/10.1016/j.rvsc.2010.10.0...
63	Methenamine	Heterocyclic compound	PE	12.791	140.1063	Positive	Antioxidant	Wetchakul et al. 2022WETCHAKUL P, CHANSUT P, PUNSAWAD C & SONPİNİT S. 2022. Characterization, antioxidant activity and in-vitro toxicity of medicinal plants from the Tri-Than-Thip Remedy. Evidence Based Complement Med 2022: 1-10. https://doi.org/10.1155/2022/4477003. https://doi.org/10.1155/2022/4477003...

	(mg GAE/ g extract)^a	(mg QE/ g extract)^b	(IC₅₀) (µg/mL)^c	(IC₅₀) (µg/mL)^d	(IC₅₀) (µg/mL)^e	(IC₅₀) (µg/mL)^f	(TEAC_CUPRAC)^g
PP	29,81±4,3	32,87±1,8	84,55±0,34	51,27±0,10	95,01±0,23	20,57±0,19	4,69±0,11
PE	168,47±4,1	34,88±1,5	9,349±0,14	9,127±0,08	58,65±0,26	70,08±0,11	9,57±1,1
α-tocopherol
Trolox				18.87±0.01
Ascorbic Acid			4.474 ± 0.31		5.992± 0.01
EDTA						6,619±0,21

	slope
Trolox	0,052
PP	0,2439
PE	0,4975

	Tyrosinase inhibitory activity(IC₅₀) (µg/mL)
PP	86,95±0,11
PE	196,7±0,22
Kojic acid	37.40 ± 0.42

Academia Brasileira de Ciências Rua Anfilófio de Carvalho, 29, 3º andar, 20030-060 Rio de Janeiro RJ Brasil, Tel: +55 21 3907-8100, CLOCKSS system has permission to ingest, preserve, and serve this Archival Unit - Rio de Janeiro - RJ - Brazil
E-mail: aabc@abc.org.br

Acompanhe os números deste periódico no seu leitor de RSS

[1] Correspondence to: Burcu Sümer Tüzün E-mail: burcusmer@gmail.com / burcu.sumer@ege.edu.tr