Isolation of a new flavonoid from Prasium majus L. with evaluation of its potential biological activities

References

• Alhamzani AG, Al-Smadi ZM, Al-Jaber HI, Tashtoush HI, Abu Orabi ST, Al-Qudah MA. 2023. A new flavonoid isolated from the aerial parts of Ajuga orientalis from Jordan. Phytochem Lett. 54:133–136. doi:10.1016/j.phytol.2023.02.004.
   Web of Science ®Google Scholar
• Al-Jaber HI, Abrouni KK, Al-Qudah MA, Abu Zarga MH. 2012. New terpenes from Salvia palaestina Benth. and Salvia syriaca L. growing wild in Jordan. J Asian Nat Prod Res. 14(7):618–625. doi:10.1080/10286020.2012.682151.
   PubMed Web of Science ®Google Scholar
• Al-Jaber HI, Abu Zarga MH, Al-Qudah MA, Shawaqfeh AT. 2023. Ceratoluteolin: a new flavonoid from Salvia ceratophylla from Jordan. Arab J Chem. 16(3):104511. doi:10.1016/j.arabjc.2022.104511.
   Web of Science ®Google Scholar
• Al-Qaralleh OS, Al-Zereini WA, Al-Mustafa AH. 2021. Antibacterial, antioxidant and neuroprotective activities of crude extract from the endophytic fungus Fusarium sp. isolate OQ-Fus-2-F from Euphorbia sp. plant. J Pharm Pharmacogn Res. 9(6):755–765. doi:10.56499/jppres21.1077_9.6.755.
   Web of Science ®Google Scholar
• Al-Qudah MA, Abu Zarga MH. 2010. Chemical constituents of Sisymbrium irio L. from Jordan. Nat Prod Res. 24(5):448–456. doi:10.1080/14786410903388025.
   PubMed Web of Science ®Google Scholar
• Al-Qudah MA, Al-Jaber HI, Abu Zarga MH, Orabi STA. 2014. Flavonoid and phenolic compounds from Salvia palaestina L. growing wild in Jordan and their antioxidant activities. Phytochemistry. 99:115–120. doi:10.1016/j.phytochem.2014.01.001.
   PubMed Web of Science ®Google Scholar
• Al-Qudah MA, Migdadi RS, Mayyas AS, Al-Zereini WA, Al-Dalahmeh Y, Abu Orabi FM, Bataineh TT, Abu-Orabi ST. 2022. Chemical composition, cytotoxicity and antioxidant activity of the essential oil from flower buds and leaves of the Pulicaria incisa (Lam.) DC and Pulicaria crispa (Forskel) Oliver. J Essent Oil-Bear Plants. 25(4):758–772. doi:10.1080/0972060X.2022.2121618.
   Web of Science ®Google Scholar
• Al-Qudah MA, Otoom NK, Al-Jaber HI, Saleh AM, Abu Zarga MH, Afifi FU, Abu Orabi ST. 2017. New flavonol glycoside from Scabiosa prolifera L. aerial parts with in vitro antioxidant and cytotoxic activities. Nat Prod Res. 31(24):2865–2874. doi:10.1080/14786419.2017.1305377.
   PubMed Web of Science ®Google Scholar
• Al-Qudah MA, Tashtoush HI, Khlaifat EF, Ibrahim SO, Saleh AM, Al-Jaber HI, Abu Zarga MH, Abu Orabi ST. 2020. Chemical constituents of the aerial parts of Salvia judaica Boiss. from Jordan. Nat Prod Res. 34(20):2981–2985. doi:10.1080/14786419.2019.1597349.
   PubMed Web of Science ®Google Scholar
• Al-Zereini WA, Al-Rimawi F, Abu-Lafi S, ALAkHRAS F, Al-Mazaideh GM, Salman HJA, Jamhour M. 2018. Identification and antibacterial evaluation of selected Jordanian medicinal plants. Orient J Chem. 34(5):2456–2463. doi:10.13005/ojc/340530.
   Google Scholar
• Al-Zereini WA, Al-Trawneh IN, Al-Qudah MA, TumAllah HM, Abudayeh ZH, Hijazin T. 2023. Antibacterial, antioxidant, and cytotoxic activities of Syzygium aromaticum (L.) Merr. & Perry essential oil with identification of its chemical constituents. Z Naturforsch C J Biosci. 78(3-4):105–112. doi:10.1515/znc-2022-0056.
   PubMed Web of Science ®Google Scholar
• Al-Zereini WA, Al-Trawneh IN, Al-Qudah MA, TumAllah HM, Al Rawashdeh HA, Abudayeh ZH. 2022. Essential oils from Elettaria cardamomum (L.) Maton grains and Cinnamomum verum J. Presl barks: chemical examination and bioactivity studies. J Pharm Pharmacogn Res. 10(1):173–185. doi:10.56499/jppres21.1162_10.1.173.
   Web of Science ®Google Scholar
• Barhoumi LM, Al-Jaber HI, Abu Zarga MH, Al-Qudah MA. 2023. A study of the chemical constituents of Nepeta curviflora from Jordan. Arab J Chem. 16(4):104534. doi:10.1016/j.arabjc.2022.104534.
   Web of Science ®Google Scholar
• Boukamcha H, Jannet HB, Bouazizi Y, Mighri Z. 2003. Isolation and structure determination of a novel furanic ester from the aerial part of Prasium Majus. Nat Prod Res. 17(1):63–66. doi:10.1080/1478641031000062214.
   PubMed Web of Science ®Google Scholar
• Correia AS, Vale N. 2021. Antidepressants in alzheimer’s disease: a focus on the role of mirtazapine. Pharmaceuticals (Basel). 14(9):930. doi:10.3390/ph14090930.
   PubMedGoogle Scholar
• Cuong NM, Khanh PN, Nhung TH, Ha NX, Huong TT, Bauerov K, Kim YH, Tung DD, Thuy TT, Anh NTH. 2023. Acetylcholinesterase inhibitory activities of some flavonoids from the root bark of Pinus krempfii Lecomte: in vitro and in silico study. J Biomol Struct Dyn. 42(9):4888–4901. doi:10.1080/07391102.2023.2223664.
   PubMedGoogle Scholar
• Ettcheto M, Olloquequi J, Sánchez-López E, Busquets O, Cano A, Manzine PR, Beas-Zarate C, Castro-Torres RD, García ML, Bulló M, et al. 2019. Benzodiazepines and related drugs as a risk factor in Alzheimer’s disease dementia. Front Aging Neurosci. 11:344. doi:10.3389/fnagi.2019.00344.
   PubMed Web of Science ®Google Scholar
• Fernandes R. 1972. Prasium L. In: Tutin TG, Heywood VH, Burges NA, editors. Flora Europaea, vol 3. Cambridge: Cambridge University Press. p. 137.
   Google Scholar
• Frota LS, Alves DR, Freitas LS, Lopes FF, Marinho MM, Marinho ES, Morais SMD. 2022. In vitro antioxidant and anticholinesterase activities of Ouratea fieldingiana (Gardner) Eng. leaf extract and correlation with its phenolics profile with an in silico study in relation to Alzheimer’s disease. J Braz Chem Soc. 33:446–455. doi:10.21577/0103-5053.20210163.
   Web of Science ®Google Scholar
• Gade IS, Chadeneau C, Tagne Simo R, Atchade ADT, Talla E, Seite P, Vannier B, Guillard J, Laurent S, Henoumont C, et al. 2022. A new flavonoid glycoside from Tapinanthus sp.(Loranthaceae) and evaluation of anticancer activity of extract and some isolated compounds. Nat Prod Res. 36(16):4085–4093. doi:10.1080/14786419.2021.1963243.
   PubMed Web of Science ®Google Scholar
• Górniak I, Bartoszewski R, Króliczewski J. 2019. Comprehensive review of antimicrobial activities of plant flavonoids. Phytochem Rev. 18(1):241–272. doi:10.1007/s11101-018-9591-z.
   Web of Science ®Google Scholar
• Greuter W, Long G. 1986. Med‐Checklist. Vol. 3. (Convolvulaceae‐ Labiatae).
   Google Scholar
• Hallahan DL. 2000. Monoterpenoid biosynthesis in glandular trichomes of Labiate plants. Adv Botan Res 31:77–120. doi:10.1016/S0065-2296(00)31007-2.
   Google Scholar
• Hammami S, Jannet HB, Ciavatta ML, Cimino G, Mighri Z. 2007. A novel iridoid glycoside from the aerial parts of the Tunisian Prasium majus. Nat Prod Res. 21(8):692–697. doi:10.1080/14786410500480761.
   PubMed Web of Science ®Google Scholar
• Hammami S, Jannet HB, Mighri Z, Nuzillard JM. 2003. Iridoid and flavonoid glycosides from the aerial part of Prasium majus growing in Tunisia. J Soc Chimique De Tun. 5(1):17–24.
   Google Scholar
• Hasan MR, Al-Jaber HI, Al-Qudah MA, Abu Zarga MH. 2016. New sesterterpenoids and other constituents from Salvia dominica growing wild in Jordan. Phytochem Lett. 16:12–17. doi:10.1016/j.phytol.2016.02.009.
   Web of Science ®Google Scholar
• Jung M, Park M. 2007. Acetylcholinesterase inhibition by flavonoids from Agrimonia pilosa. Molecules. 12(9):2130–2139. doi:10.3390/12092130.
   PubMed Web of Science ®Google Scholar
• Karmakar A, Ambure P, Mallick T, Das S, Roy K, Begum NA. 2019. Exploration of synthetic antioxidant flavonoid analogs as acetylcholinesterase inhibitors: an approach towards finding their quantitative structure–activity relationship. Med Chem Res. 28(5):723–741. doi:10.1007/s00044-019-02330-8.
   Web of Science ®Google Scholar
• Kauffmann AC, Castro VS. 2023. Phenolic compounds in bacterial inactivation: a perspective from Brazil. Antibiotics. 12(4):645. doi:10.3390/antibiotics12040645.
   Google Scholar
• Khan, Haroon, Amin, Surriya, Kamal, Mohammad Amjad, Patel, Seema, Marya,. 2018. Flavonoids as acetylcholinesterase inhibitors: current therapeutic standing and future prospects.Biomed Pharmacother. 101:860–870. doi:10.1016/j.biopha.2018.03.007.
   PubMed Web of Science ®Google Scholar
• Khemiss F, Saidane D, Moshtaghie AA. 2005. Effect of aqueous extract of Prasium majus’s L. leaves on water and electrolytes transport in rat intestine. Pak J Biol Sci. 8(10):1424–1429. doi:10.3923/pjbs.2005.1424.1429.
   Google Scholar
• Lee CJ, Chen LG, Chang TL, Ke WM, Lo YF, Wang CC. 2011. The correlation between skin-care effects and phytochemical contents in Lamiaceae plants. Food Chem. 124(3):833–841. doi:10.1016/j.foodchem.2010.07.003.
   Web of Science ®Google Scholar
• Mandalari G, Bennett RN, Bisignano G, Trombetta D, Saija A, Faulds CB, Gasson MJ, Narbad A. 2007. Antimicrobial activity of flavonoids extracted from bergamot (Citrus bergamia Risso) peel, a byproduct of the essential oil industry. J Appl Microbiol. 103(6):2056–2064. doi:10.1111/j.1365-2672.2007.03456.x.
   PubMed Web of Science ®Google Scholar
• Mendez MF. 2021. The relationship between anxiety and Alzheimer’s disease. ADR. 5(1):171–177. doi:10.3233/ADR-210294.
   Google Scholar
• Remya C, Dileep KV, Tintu I, Variyar EJ, Sadasivan C. 2014. Flavanone glycosides as acetylcholinesterase inhibitors: computational and experimental evidence. Indian J Pharm Sci. 76(6):567–570.
   PubMed Web of Science ®Google Scholar
• Roseiro LB, Rauter AP, Serralheiro MLM. 2012. Polyphenols as acetylcholinesterase inhibitors: structural specificity and impact on human disease. Nutrition and Aging. 1(2):99–111. doi:10.3233/NUA-2012-0006.
   Google Scholar
• Shamsudin NF, Ahmed QU, Mahmood S, Ali Shah SA, Khatib A, Mukhtar S, Alsharif MA, Parveen H, Zakaria ZA. 2022. Antibacterial effects of flavonoids and their structure-activity relationship study: a comparative interpretation. Molecules. 27(4):1149. doi:10.3390/molecules27041149.
   PubMed Web of Science ®Google Scholar
• Ullah A, Munir S, Badshah SL, Khan N, Ghani L, Poulson BG, Emwas A, Jaremko M. 2020. Important flavonoids and their role as a therapeutic agent. Molecules. 25(22):5243. doi:10.3390/molecules25225243.
   PubMed Web of Science ®Google Scholar
• Uriarte-Pueyo I, Calvo M. 2011. Flavonoids as acetylcholinesterase inhibitors. Curr Med Chem. 18(34):5289–5302. doi:10.2174/092986711798184325.
   PubMed Web of Science ®Google Scholar
• Wang J, Fang X, Ge L, Cao F, Zha L, Wang Z, Xiao W. 2018. Antitumor, antioxidant and anti-inflammatory activities of kaempferol and its corresponding glycosides and the enzymatic preparation of kaempferol. PLoS One. 13(5):e0197563. doi:10.1371/journal.pone.0197563.
   PubMed Web of Science ®Google Scholar
• Werker E. 1993. Function of essential oil‐secreting glandular hairs in aromatic plans of Lamiacea—a review. Flavour & Fragrance J. 8(5):249–255. doi:10.1002/ffj.2730080503.
   Web of Science ®Google Scholar
• Xie Y, Yang W, Chen X, Xiao J. 2014. Inhibition of flavonoids on acetylcholine esterase: binding and structure–activity relationship. Food Funct. 5(10):2582–2589. doi:10.1039/c4fo00287c.
   PubMed Web of Science ®Google Scholar
• Zhou P, Hua F. 2020. Exploration of acetylcholinesterase inhibitors from flavonoids and flavonoid glycosides. Neurochem J. 14:251–256. doi:10.1134/S1819712420030137.
   Google Scholar