Volume 6 Issue 4
Oct.  2021
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James T. Carrillo, Dulal Borthakur. Do Uncommon Plant Phenolic Compounds Have Uncommon Properties? A Mini Review on Novel Flavonoids[J]. Journal of Bioresources and Bioproducts, 2021, 6(4): 279-291. doi: 10.1016/j.jobab.2021.09.001
Citation: James T. Carrillo, Dulal Borthakur. Do Uncommon Plant Phenolic Compounds Have Uncommon Properties? A Mini Review on Novel Flavonoids[J]. Journal of Bioresources and Bioproducts, 2021, 6(4): 279-291. doi: 10.1016/j.jobab.2021.09.001

Do Uncommon Plant Phenolic Compounds Have Uncommon Properties? A Mini Review on Novel Flavonoids

doi: 10.1016/j.jobab.2021.09.001
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  • Corresponding author: E-mail address: dulal@hawaii.edu (Dulal Borthakur)
  • Received Date: 2021-06-20
  • Accepted Date: 2021-07-18
  • Rev Recd Date: 2021-07-13
  • Publish Date: 2021-10-01
  • Unique plants and their properties, once considered synonymous to medicine, remain a potent source for new compounds in modern science. Plant polyphenols and natural products continue to be investigated for effective treatments for the most persistent of human ailments. In this review, fifty novel plant phenolic compounds have been compiled and briefly described from the previous five years. Select compounds and notable plant species from genus Morinda and Sophora are further expanded on. Traditional medicine plants often contain rich and diverse mixtures of flavonoids, from which rare compounds should receive attention. The bioactivity of crude plant extracts, purified compounds and mixtures can differ greatly, requiring that these interactions and mechanisms of action be investigated in greater detail. Novel applications of uncommon natural products, namely mimosine and juglone, are explored within this review. The 2019 coronavirus pandemic has resulted in abrupt spike of related scientific publications: speculation is made regarding plant natural products and future of antiviral drug discovery.

     

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  • Abdel Bar, F.M., Abbas, G.M., Gohar, A.A., Lahloub, M.F.I., 2020. Antiproliferative activity of stilbene derivatives and other constituents from the stem bark of Morus nigra L. Nat. Prod. Res. 34, 3506-3513 doi: 10.1080/14786419.2019.1573236
    Ahn, J., Kim, Y.M., Chae, H.S., Choi, Y.H., Ahn, H.C., Yoo, H., Kang, M., Kim, J., Chin, Y.W., 2019. Prenylated flavonoids from the roots and rhizomes of Sophora tonkinensis and their effects on the expression of inflammatory mediators and proprotein convertase subtilisin/kexin type 9. J. Nat. Prod. 82, 309-317 doi: 10.1021/acs.jnatprod.8b00748
    Akhtar, M.N., Zareen, S., Yeap, S.K., Ho, W.Y., Lo, K.M., Hasan, A., Alitheen, N.B., 2013. Total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues. Mol. Basel Switz. 18, 10042-10055 doi: 10.3390/molecules180810042
    Al Musayeib, N.M., Ibrahim, S.R.M., Amina, M., Al Hamoud, G.A., Mohamed, G.A., 2017. Curviflorside and curviflorin, new naphthalene glycoside and flavanol from Plicosepalus curviflorus. Zeitschrift Fur Naturforschung C J. Biosci. 72, 197-201 doi: 10.1515/znc-2016-0180
    Aly, S.H., Elissawy, A.M., Eldahshan, O.A., Elshanawany, M.A., Efferth, T., Singab, A.N.B., 2019. The pharmacology of the genus Sophora (Fabaceae): an updated review. Phytomedicine 64, 153070
    Aoyama, H., Sakagami, H., Hatano, T., 2018. Three new flavonoids, proanthocyanidin, and accompanying phenolic constituents from Feijoa sellowiana. Biosci. Biotechnol. Biochem. 82, 31-41 doi: 10.1080/09168451.2017.1412246
    Aziz, M., Abu, N., Yeap, S., Ho, W., Omar, A., Ismail, N., Ahmad, S., Pirozyan, M., Akhtar, N., Alitheen, N., 2016. Combinatorial cytotoxic effects of damnacanthal and doxorubicin against human breast cancer MCF-7 cells in vitro. Molecules 21, 1228 doi: 10.3390/molecules21091228
    Bageel, A., Honda, M.D.H., Carrillo, J.T., Borthakur, D., 2020. Giant Leucaena (Leucaena leucocephala subsp. glabrata): a versatile tree-legume for sustainable agroforestry. Agrofor. Syst. 94, 251-268 doi: 10.1007/s10457-019-00392-6
    Bai, W.X., Wang, C., Wang, Y.J., Zheng, W.J., Wang, W., Wan, X.C., Bao, G.H., 2017. Novel acylated flavonol tetraglycoside with inhibitory effect on lipid accumulation in 3T3-L1 cells from Lu'an GuaPian tea and quantification of flavonoid glycosides in six major processing types of tea. J. Agric. Food Chem. 65, 2999-3005 doi: 10.1021/acs.jafc.7b00239
    Bajwa, D.S., Pourhashem, G., Ullah, A.H., Bajwa, S.G., 2019. A concise review of current lignin production, applications, products and their environmental impact. Ind. Crops Prod. 139, 111526
    Basic, M., Elgner, F., Bender, D., Sabino, C., Herrlein, M.L., Roth, H., Glitscher, M., Fath, A., Kerl, T., Schmalz, H.G., Hildt, E., 2019. A synthetic derivative of houttuynoid B prevents cell entry of Zika virus. Antivir. Res. 172, 104644
    Boozari, M., Nejad Ebrahimi, S., Soltani, S., Tayarani-Najaran, Z., Emami, S.A., Asili, J., Iranshahi, M., 2019. Absolute configuration and anti-cancer effect of prenylated flavonoids and flavonostilbenes from Sophora pachycarpa: possible involvement of Wnt signaling pathway. Bioorg. Chem. 85, 498-504
    Bose, M., Kamra, M., Mullick, R., Bhattacharya, S., Das, S., Karande, A.A., 2017. Identification of a flavonoid isolated from plum (Prunus domestica) as a potent inhibitor of Hepatitis C virus entry. Sci. Rep. 7, 3965
    Cao, Y.G., Zheng, X.K., Yang, F.F., Li, F., Qi, M., Zhang, Y.L., Zhao, X., Kuang, H.X., Feng, W.S., 2018. Two new phenolic constituents from the root bark of Morus alba L. and their cardioprotective activity. Nat. Prod. Res. 32, 391-398 doi: 10.1080/14786419.2017.1309535
    Chatham, L., West, L., Berhow, M.A., Vermillion, K.E., Juvik, J.A., 2018. Unique flavanol-anthocyanin condensed forms in Apache red purple corn. J. Agric. Food Chem. 66, 10844-10854 doi: 10.1021/acs.jafc.8b04723
    Chen, H., Yang, J., Hao, J., Lv, Y., Chen, L., Lin, Q.X., Yuan, J.Q., Yang, X.Z., 2019. A novel flavonoid kushenol Z from Sophora flavescens mediates mTOR pathway by inhibiting phosphodiesterase and Akt activity to induce apoptosis in non-small-cell lung cancer cells. Molecules 24, 4425 doi: 10.3390/molecules24244425
    Chen, L.L., Dou, J., Su, Z.Z., Zhou, H.M., Wang, H., Zhou, W.D., Guo, Q.L., Zhou, C.L., 2011. Synergistic activity of baicalein with ribavirin against influenza A (H1N1) virus infections in cell culture and in mice. Antivir. Res. 91, 314-320
    Chen, Y., Li, P., Su, S.J., Chen, M., He, J., Liu, L.W., He, M., Wang, H., Xue, W., 2019. Synthesis and antibacterial and antiviral activities of myricetin derivatives containing a 1, 2, 4-triazole Schiff base. RSC Adv. 9, 23045-23052 doi: 10.1039/c9ra05139b
    Chiow, K.H., Phoon, M.C., Putti, T., Tan, B.K.H., Chow, V.T., 2016. Evaluation of antiviral activities of Houttuynia cordata Thunb. extract, quercetin, quercetrin and cinanserin on murine coronavirus and dengue virus infection. Asian Pac. J. Trop. Med. 9, 1-7 doi: 10.1016/j.apjtm.2015.12.002
    Chobot, V., 2010. Simultaneous detection of pro- and antioxidative effects in the variants of the deoxyribose degradation assay. J. Agric. Food Chem. 58, 2088-2094 doi: 10.1021/jf902395k
    Chobot, V., Hadacek, F., 2011. Exploration of pro-oxidant and antioxidant activities of the flavonoid myricetin. Redox Rep. 16, 242-247 doi: 10.1179/1351000211Y.0000000015
    Chobot, V., Hadacek, F., Bachmann, G., Weckwerth, W., Kubicova, L., Pro- and antioxidant activity of three selected flavan type flavonoids: catechin, eriodictyol and taxifolin. Int. J. Mol. Sci.
    Chokchaisiri, S., Siriwattanasathien, Y., Thongbamrer, C., Suksamrarn, A., Rukachaisirikul, T., 2019. Morindaquinone, a new bianthraquinone from Morinda coreia roots. Nat. Prod. Res. 1-7
    Cinatl, J., Morgenstern, B., Bauer, G., Chandra, P., Rabenau, H., Doerr, H., 2003. Glycyrrhizin, an active component of liquorice roots, and replication of SARS-associated coronavirus. Lancet 361, 2045-2046
    Dai, Y., Gold, B., Vishwanatha, J.K., Rhode, S.L., 1994. Mimosine inhibits viral DNA synthesis through ribonucleotide reductase. Virology 205, 210-216
    Dang, T., Tawata, S., Dang, T., 2013. Herbicidal activity of mimosine and its derivatives. Herbicides-Advances in Research. Intech, Rijeka, Croatia, pp. 299–312.
    de la Cruz-Sánchez, N.G., Gómez-Rivera, A., Alvarez-Fitz, P., Ventura-Zapata, E., Pérez-García, M.D., Avilés-Flores, M., Gutiérrez-Román, A.S., González-Cortazar, M., 2019. Antibacterial activity of Morinda citrifolia Linneo seeds against Methicillin-Resistant Staphylococcus spp. Microb. Pathog. 128, 347-353
    Devi, A., Namsa, N.D., Doley, R., 2020. In silico and in vitro neutralization of PLA2 activity of Daboxin P by butein, mimosine and bakuchiol. Int. J. Biol. Macromol. 165, 1066-1078
    Duarte, J., Francisco, V., Perez-Vizcaino, F., 2014. Modulation of nitric oxide by flavonoids. Food Funct 5, 1653-1668
    Eley, K.L., Halo, L.M., Song, Z., Powles, H., Cox, R.J., Bailey, A.M., Lazarus, C.M., Simpson, T.J., 2007. Biosynthesis of the 2-pyridone tenellin in the insect pathogenic fungus Beauveria bassiana. ChemBioChem 8, 289-297 doi: 10.1002/cbic.200600398
    Evidente, A., Fiore, M., Bruno, G., Sparapano, L., Motta, A., 2006. Chemical and biological characterisation of sapinopyridione, a phytotoxic 3, 3, 6-trisubstituted-2, 4-pyridione produced by Sphaeropsis sapinea, a toxigenic pathogen of native and exotic conifers, and its derivatives. Phytochemistry 67, 1019-1028
    Fei, Y., Wang, J., Peng, B., Peng, J.N., Hu, J.H., Zeng, Z.P., Chen, J., Li, Q.E., Gao, Z.P., Yan, X.L., 2017. Phenolic constituents from Rheum nobile and their antioxidant activity. Nat. Prod. Res. 31, 2842-2849 doi: 10.1080/14786419.2017.1303691
    Fiorito, S., Genovese, S., Taddeo, V.A., Mathieu, V., Kiss, R., Epifano, F., 2016. Novel juglone and plumbagin 5-O derivatives and their in vitro growth inhibitory activity against apoptosis-resistant cancer cells. Bioorg. Med. Chem. Lett. 26, 334-337
    Fu, Y.H., Sun, X.Y., Chen, S.Q., Duan, Y.Z., Han, Y., 2021. Chemical constituents of the antiulcer purified fractions of Lindera reflexa Hemsl. and its quantitative analysis. Fitoterapia 148, 104795
    Gao, L., Li, Y.D., Zhu, B.K., Li, Z.Y., Huang, L.B., Li, X.Y., Wang, F., Ren, F.C., Liao, T.G., 2018. Two new prenylflavonoids from Morus alba. J. Asian Nat. Prod. Res. 20, 117-121 doi: 10.1080/10286020.2017.1343303
    García-Vilas, J.A., Pino-Ángeles, A., Martínez-Poveda, B., Quesada, A.R., Medina, M. Á., 2017. The noni anthraquinone damnacanthal is a multi-kinase inhibitor with potent anti-angiogenic effects. Cancer letters 385, 1-11
    Gilbert, D.M., Neilson, A., Miyazawa, H., DePamphilis, M.L., Burhans, W.C., 1995. Mimosine arrests DNA synthesis at replication forks by inhibiting deoxyribonucleotide metabolism. J. Biol. Chem. 270, 9597-9606
    Gonzales, G.F., Valerio, L.G., 2006. Medicinal plants from Peru: a review of plants as potential agents against cancer. Anti Cancer Agents Med. Chem. 6, 429-444 doi: 10.2174/187152006778226486
    Gupta, H.K., Atreja, P.P., 1998. Influence of ferric chloride treated Leucaena leucocephala on metabolism of mimosine and 3-hydroxy 4(1H)-pyridone in growing rabbits. Animal Feed. Sci. Technol. 74, 45-55
    Haidari, M., Ali, M., Ward Casscells, S., Madjid, M., 2009. Pomegranate (Punica granatum) purified polyphenol extract inhibits influenza virus and has a synergistic effect with oseltamivir. Phytomedicine 16, 1127-1136
    He, Q.F., Wu, Z.L., Huang, X.J., Zhong, Y.L., Li, M.M., Jiang, R.W., Li, Y.L., Ye, W.C., Wang, Y., 2018. Cajanusflavanols A-C, three pairs of flavonostilbene enantiomers from Cajanus cajan. Org. Lett. 20, 876-879 doi: 10.1021/acs.orglett.8b00010
    Huang, X.B., Yuan, L.W., Shao, J., Yang, Y., Liu, Y., Lu, J.J., Chen, L., 2020. Cytotoxic effects of flavonoids from root of Sophora flavescens in cancer cells. Nat. Prod. Res. 1-6 doi: 10.1080/14786419.2020.1712382
    Issarachot, P., Sangkaew, W., Sianglum, W., Saeloh, D., Limsuwan, S., Voravuthikunchai, S.P., Joycharat, N., 2019. Α-Glucosidase inhibitory, antibacterial, and antioxidant activities of natural substances from the wood of Derris reticulata Craib. Nat. Prod. Res. 1-8
    Janibekov, A.A., Youssef, F.S., Ashour, M.L., Mamadalieva, N.Z., 2018. New flavonoid glycosides from two Astragalus species (Fabaceae) and validation of their antihyperglycaemic activity using molecular modelling and in vitro studies. Ind. Crops Prod. 118, 142-148
    Karim, N., Khan, I., Abdelhalim, A., Khan, A., Halim, S.A., 2018. Antidepressant potential of novel flavonoids derivatives from sweet violet (Viola odorata L): pharmacological, biochemical and computational evidences for possible involvement of serotonergic mechanism. Fitoterapia 128, 148-161
    Kim, J.H., Cho, C.W., Kim, H.Y., Kim, K.T., Choi, G.S., Kim, H.H., Cho, I.S., Kwon, S.J., Choi, S.K., Yoon, J.Y., Yang, S.Y., Kang, J.S., Kim, Y.H., 2017. Α-Glucosidase inhibition by prenylated and lavandulyl compounds from Sophora flavescens roots and in silico analysis. Int. J. Biol. Macromol. 102, 960-969
    Kouamé, B.K.F.P., Kablan, L., N'dri Marcelline Adiko, O.A., Akoubet, G.G.D., Diomandé, S.J.A., Bedi, G., Tea, I., Robins, R., Adjou, A., Tonzibo, F.Z., 2019. A novel anthraquinone from Morinda lucida Benth (Rubiaceae). J. Pharmacognosy Phytochem. 8, 11-14
    Krishna, P.M., Knv, R., Sandhya, S., Banji, D., 2012. A review on phytochemical, ethnomedical and pharmacological studies on genus Sophora. Fabaceae. Rev. Bras. Farmacogn. 22, 1145-1154
    Lachowicz, J.I., Dalla Torre, G., Cappai, R., Randaccio, E., Nurchi, V.M., Bachor, R., Szewczuk, Z., Jaremko, L., Jaremko, M., Pisano, M.B., Cosentino, S., Orrù, G., Ibba, A., Mujika, J., Lopez, X., 2020. Metal self-assembly mimosine peptides with enhanced antimicrobial activity: towards a new generation of multitasking chelating agents. Dalton Trans. 49, 2862-2879 doi: 10.1039/c9dt04545g
    Latifah, S.Y., Gopalsamy, B., Abdul Rahim, R., Manaf Ali, A., Haji Lajis, N., 2021. Anticancer potential of damnacanthal and nordamnacanthal from Morinda elliptica roots on T-lymphoblastic leukemia cells. Molecules 26, 1554 doi: 10.3390/molecules26061554
    Lau, K.M., Lee, K.M., Koon, C.M., Cheung, C.S.F., Lau, C.P., Ho, H.M., Lee, M.Y.H., Au, S.W.N., Cheng, C.H.K., Lau, C.B.S., Tsui, S.K.W., Wan, D.C.C., Waye, M.M.Y., Wong, K.B., Wong, C.K., Lam, C.W.K., Leung, P.C., Fung, K.P., 2008. Immunomodulatory and anti-SARS activities of Houttuynia cordata. J. Ethnopharmacol. 118, 79-85
    LeCher, J.C., Diep, N., Krug, P.W., Hilliard, J.K., 2019. Genistein has antiviral activity against Herpes B virus and acts synergistically with antiviral treatments to reduce effective dose. Viruses 11, 499 doi: 10.3390/v11060499
    Li, J.Q., Xiao, C.J., Li, Y.M., Tian, X.Y., Dong, X., Jiang, B., 2020. Astrernestin, a novel aurone-phenylpropanoid adduct from the roots of Astragalus ernestii. Nat. Prod. Res. 34, 2894-2899 doi: 10.1080/14786419.2019.1596101
    Li, X.L., Zhou, A.G., 2012. Evaluation of the immunity activity of glycyrrhizin in AR mice. Mol. Basel Switz. 17, 716-727 doi: 10.3390/molecules17010716
    Liu, Y.P., Guo, J.M., Yan, G., Zhang, M.M., Zhang, W.H., Qiang, L., Fu, Y.H., 2019. Anti-inflammatory and antiproliferative prenylated isoflavone derivatives from the fruits of Ficus carica. J. Agric. Food Chem. 67, 4817-4823
    Long, G.Q., Wang, D.D., Wang, J., Jia, J.M., Wang, A.H., 2020. Chemical constituents of Sophora flavescens Ait. and cytotoxic activities of two new compounds. Nat. Prod. Res. 1-6 doi: 10.1080/14786419.2020.1765340
    Longue Ekon, J.P., Zra, T., Lobe Songue, J., Wondja Ngoko, M.L., Ngassoum, M.B., Talla, E., Kamdem Waffo, A.F., Sewald, N., Wansi, J.D., 2020. New anthraquinone derivatives from the stem barks of Morinda lucida Benth. Phytochem. Lett. 39, 94-98
    Luo, H., Wang, Y., Qin, Q.Y., Wang, Y.H., Xu, J.W., He, X.J., 2021. Anti-inflammatory naphthoates and anthraquinones from the roots of Morinda officinalis. Bioorg. Chem. 110, 104800
    Luo, R.L., Li, F.Q., Zhuang, H.D., Wang, L.Q., 2021. (±) Erysectin A, a new isoprenylated isoflavone with a rare acetonyl group from Erythrina secundiflora Hassk. Nat. Prod. Res. 1-6 doi: 10.1080/14786419.2021.1908280
    Luo, Y., Shen, H.Y., Shen, Q.X., Cao, Z.H., Zhang, M., Long, S.Y., Wang, Z.B., Tan, J.W., 2017. A new anthraquinone and a new naphthoquinone from the whole plant of Spermacoce latifolia. J. Asian Nat. Prod. Res. 19, 869-876 doi: 10.1080/10286020.2017.1279609
    Ma, Y.R., Zhou, T.X., Zhao, P., Choi, H.Y., Hao, J., Huang, H.Q., Wu, C.Q., Yang, X.Z., Pang, K.J., 2021. New flavonoids from the roots of Sophora davidii (Franch. ) Skeels and their glucose transporter 4 translocation activities. Bioorg. Chem. 106, 104500
    Macé, S., Truelstrup Hansen, L., Rupasinghe, H.P.V., 2017. Anti-bacterial activity of phenolic compounds against Streptococcus pyogenes. Medicines 4, 25 doi: 10.3390/medicines4020025
    Mai, H.D.T., Toan, T.P., Huu, G.T., Le, T.N., Oanh, V.T.K., Hang, N.T.M., Thu, H.T., Chau, V.M., Litaudon, M., Pham, V.C., 2020. New flavonoid and stilbene derivatives from the fruits of Macaranga balansae. Nat. Prod. Res. 34, 2772-2778 doi: 10.1080/14786419.2019.1587425
    Mfonku, N.A., Tadjong, A.T., Kamsu, G.T., Kodjio, N., Ren, J., Mbah, J.A., Gatsing, D., Zhan, J.X., 2021. Isolation and characterization of antisalmonellal anthraquinones and coumarins from Morinda lucida Benth. (Rubiaceae). Chem. Pap. 75, 2067-2073 doi: 10.1007/s11696-020-01460-3
    Mottaghipisheh, J., Iriti, M., 2020. Sephadex® LH-20, isolation, and purification of flavonoids from plant species: a comprehensive review. Molecules 25, 4146 doi: 10.3390/molecules25184146
    Nascimento, A.C., Valente, L.M.M., Gomes, M., Barboza, R.S., Wolff, T., Neris, R.L.S., Figueiredo, C.M., Assunção-Miranda, I., 2017. Antiviral activity of Faramea bahiensis leaves on dengue virus type-2 and characterization of a new antiviral flavanone glycoside. Phytochem. Lett. 19, 220-225
    Nguyen, B.C.Q., Tawata, S., 2015. Mimosine dipeptide enantiomsers: improved inhibitors against melanogenesis and cyclooxygenase. Mol. Basel Switz. 20, 14334-14347 doi: 10.3390/molecules200814334
    Park, S., Kim, N., Nhiem, N.X., Kwak, H.J., Yang, H.W., Kim, S.H., 2020. Neuraminidase inhibitors from the roots of Caragana sinica. Chem. Biodivers. 17, e2000470
    Pel, P., Chae, H.S., Nhoek, P., Kim, Y.M., Khiev, P., Kim, G.J., Nam, J.W., Choi, H., Choi, Y.H., Chin, Y.W., 2020. A stilbene dimer and flavonoids from the aerial parts of Chromolaena odorata with proprotein convertase subtilisin/kexin type 9 expression inhibitory activity. Bioorg. Chem. 99, 103869
    Peng, F., Zhu, H., Meng, C.W., Ren, Y.R., Dai, O., Xiong, L., 2019. New isoflavanes from Spatholobus suberectus and their cytotoxicity against human breast cancer cell lines. Molecules 24, 3218 doi: 10.3390/molecules24183218
    Pollo, L.A.E., Martin, E.F., Machado, V.R., Cantillon, D., Wildner, L.M., Bazzo, M.L., Waddell, S.J., Biavatti, M.W., Sandjo, L.P., 2021. Search for antimicrobial activity among fifty-two natural and synthetic compounds identifies anthraquinone and polyacetylene classes that inhibit Mycobacterium tuberculosis. Front. Microbiol. 11, 622629
    Ponkratova, A.O., Whaley, A.K., Orlova, A.A., Smirnov, S.N., Serebryakov, E.B., Proksch, P., Luzhanin, V.G., 2021. A new dimethoxy dihydrochalcone isolated from the shoots of Empetrum nigrum L. Nat. Prod. Res. 1-6 doi: 10.1080/14786419.2021.1920584
    Posri, P., Suthiwong, J., Thongsri, Y., Yenjai, C., 2019. Antifungal activity of compounds from the stems of Dalbergia stipulacea against Pythium insidiosum. Nat. Prod. Res. 1-8
    Rebensburg, S., Helfer, M., Schneider, M., Koppensteiner, H., Eberle, J., Schindler, M., Gürtler, L., Brack-Werner, R., 2016. Potent in vitro antiviral activity of Cistus incanus extract against HIV and Filoviruses targets viral envelope proteins. Sci. Rep. 6, 20394
    Renault, H., Alber, A., Horst, N.A., Basilio Lopes, A., Fich, E.A., Kriegshauser, L., Wiedemann, G., Ullmann, P., Herrgott, L., Erhardt, M., Pineau, E., Ehlting, J., Schmitt, M., Rose, J.K.C., Reski, R., Werck-Reichhart, D., 2017. A phenol-enriched cuticle is ancestral to lignin evolution in land plants. Nat. Commun. 8, 14713
    Sánchez-Calvo, J.M., Barbero, G.R., Guerrero-Vásquez, G., Durán, A.G., Macías, M., Rodríguez-Iglesias, M.A., Molinillo, J.M.G., Macías, F.A., 2016. Synthesis, antibacterial and antifungal activities of naphthoquinone derivatives: a structure-activity relationship study. Med. Chem. Res. 25, 1274-1285 doi: 10.1007/s00044-016-1550-x
    Saputri, R.D., Tjahjandarie, T.S., Tanjung, M., 2021. Two novel coumarins bearing an acetophenone derivative from the leaves of Melicope Quercifolia. Nat. Prod. Res. 35, 1256-1261 doi: 10.1080/14786419.2019.1644634
    Sassa, T., Uchie, K., Kato, H., Onuma, Y., 1987. Decomposition of fruit rot toxin A, a host-selective phytotoxin from Botryosphaeria berengeriana. Agric. Biol. Chem. 51, 271-272 doi: 10.1080/00021369.1987.10867985
    Saura, M., Zaragoza, C., McMillan, A., Quick, R.A., Hohenadl, C., Lowenstein, J.M., Lowenstein, C.J., 1999. An antiviral mechanism of nitric oxide: inhibition of a viral protease. Immunity 10, 21-28
    Seephonkai, P., Ishikawa, R., Arai, M.A., Kowithayakorn, T., Koyano, T., Ishibashi, M., 2018. New flavanol dimers from the bark of Celtis tetrandra and their TRAIL resistance-overcoming activity. Nat. Prod. Commun. 13, 427-430
    Shaghayegh, G., Alabsi, A.M., Ali-Saeed, R., Ali, A.M., Vincent-Chong, V.K., Ismail, N.H., Choon, Y.F., Zain, R.B., 2017. Effects of damnacanthal and nordamnacanthal on proliferation, apoptosis, and migration of oral squamous cell carcinoma cells. Asian Pac. J. Cancer Prev. 18, 3333-3341
    Sharma, K., Pachauri, S.D., Khandelwal, K., Ahmad, H., Arya, A., Biala, P., Agrawal, S., Pandey, R.R., Srivastava, A., Srivastav, A., Saxena, J.K., Dwivedi, A.K., 2016. Anticancer effects of extracts from the fruit of Morinda citrifolia (noni) in breast cancer cell lines. Drug Res 66, 141-147 doi: 10.5958/0976-4615.2016.00027.2
    Singh, B., Sharma, R.A., 2020. Indian Morinda species: a review. Phytother. Res. 34, 924-1007 doi: 10.1002/ptr.6579
    Sunder, J., Singh, D.R., Jeyakumar, S., Kundu, A., De, A.K., 2011. Antibacterial activity in solvent extract of different parts of Morinda citrifolia plant. Journal of Pharmaceutical Sciences and Research 3, 1404
    Thabti, I., Albert, Q., Philippot, S., Dupire, F., Westerhuis, B., Fontanay, S., Risler, A., Kassab, T., Elfalleh, W., Aferchichi, A., Varbanov, M., 2020. Advances on antiviral activity of Morus spp. plant extracts: human coronavirus and virus-related respiratory tract infections in the spotlight. Molecules 25, 1876 doi: 10.3390/molecules25081876
    Thanasansurapong, S., Tuchinda, P., Reutrakul, V., Pohmakotr, M., Piyachaturawat, P., Chairoungdua, A., Suksen, K., Akkarawongsapat, R., Limthongkul, J., Napaswad, C., Nuntasaen, N., 2020. Cytotoxic and anti-HIV-1 activities of triterpenoids and flavonoids isolated from leaves and twigs of Gardenia sessiliflora. Phytochem. Lett. 35, 46-52
    Tharayil, N., Bhowmik, P., Alpert, P., Walker, E., Amarasiriwardena, D., Xing, B.S., 2009. Dual purpose secondary compounds: phytotoxin of Centaurea diffusa also facilitates nutrient uptake. New Phytol 181, 424-434 doi: 10.1111/j.1469-8137.2008.02647.x
    Upadhyay, A., Chompoo, J., Taira, N., Fukuta, M., Gima, S., Tawata, S., 2011. Solid-phase synthesis of mimosine tetrapeptides and their inhibitory activities on neuraminidase and tyrosinase. J. Agric. Food Chem. 59, 12858-12863 doi: 10.1021/jf203494t
    Vu, L.T.N., Anh, L.T., Cuc, N.T., Nhiem, N.X., Tai, B.H., Van Kiem, P., Litaudon, M., Thach, T.D., Van Minh, C., Mai, H.D.T., Van Cuong, P., 2021. Prenylated flavonoids and other constituents from Macaranga indica. Nat. Prod. Res. 35, 2123-2130 doi: 10.1080/14786419.2019.1662007
    Wang, D.W., Xiao, C.J., Qiu, L., Tian, X.Y., Dong, X., Jiang, B., 2021. Two new 8-isopentenyl isoflavane derivatives from Astragalus dolichochaete Diels. Nat. Prod. Res. 35, 1323-1330 doi: 10.1080/14786419.2019.1647426
    Wang, M.M., Yang, W.J., Liu, X.Q., Liu, Q.Y., Zheng, H., Wang, X.N., Shen, T., Wang, S.Q., Ren, D. M, 2020. Two new compounds with Nrf2 inducing activity from Glycyrrhiza uralensis. Nat. Prod. Res. 1-8 doi: 10.1007/978-981-10-6739-6_35-2
    Wang, Y.F., Xu, L.J., Gao, W., Niu, L.X., Huang, C.Y., Yang, P.M., Hu, X., 2018. Isoprenylated phenolic compounds from Morus macroura as potent tyrosinase inhibitors. Planta Med 84, 336-343
    Wang, Y.F., Yu, M.H., Xu, L.J., Niu, L.X., Huang, C.Y., Xu, H., Yang, P.M., Hu, X., 2018. Diels-Alder type adducts with potent alpha-glucosidase inhibitory activity from Morus macroura. Phytochem. Lett. 26, 149-153
    Wang, Y.N., Liu, M.F., Hou, W.Z., Xu, R.M., Gao, J., Lu, A.Q., Xie, M.P., Li, L., Zhang, J.J., Peng, Y., Ma, L.L., Wang, X.L., Shi, J.G., Wang, S.J., 2017. Bioactive benzofuran derivatives from cortex mori radicis, and their neuroprotective and analgesic activities mediated by mGluR1. Molecules 22, 236 doi: 10.1109/JSEN.2016.2630726
    Wei, H., Zhu, J.J., Liu, X.Q., Feng, W.H., Wang, Z.M., Yan, L.H., 2016. Review of bioactive compounds from root barks of Morus plants (Sang-Bai-Pi) and their pharmacological effects. Cogent Chem 2, 1212320 doi: 10.1080/23312009.2016.1212320
    Wen, L.R., Shi, D.D., Zhou, T., Tu, J.M., He, M.Y., Jiang, Y.M., Yang, B., 2020. Identification of two novel prenylated flavonoids in mulberry leaf and their bioactivities. Food Chem 315, 126236
    Wu, G.Y., Zhang, X., Guo, X.Y., Huo, L.Q., Liu, H.X., Shen, X.L., Qiu, S.X., Hu, Y.J., Tan, H.B., 2019. Prenylated stilbenes and flavonoids from the leaves of Cajanus cajan. Chin. J. Nat. Med. 17, 381-386
    Xu, L., Ying, Z.M., Wei, W.J., Hao, D., Wang, H.B., Zhang, W.J., Li, C.Y., Jiang, M.Y., Ying, X.X., Liu, J., 2017. A novel alkaloid from Portulaca oleracea L. Nat. Prod. Res. 31, 902-908 doi: 10.1080/14786419.2016.1253081
    Xu, L.J., Yu, M.H., Huang, C.Y., Niu, L.X., Wang, Y.F., Wu, C.Z., Yang, P.M., Hu, X., 2018. Isoprenylated flavonoids from Morus nigra and their PPAR γ agonistic activities. Fitoterapia 127, 109-114
    Xu, L.J., Yu, M.H., Niu, L.X., Huang, C.Y., Wang, Y.F., Wu, C.Z., Yang, P.M., Hu, X., 2020. Phenolic compounds isolated from Morus nigra and their α-glucosidase inhibitory activities. Nat. Prod. Res. 34, 605-612 doi: 10.1080/14786419.2018.1491041
    Xu, X., Huang, Y.Y., Xu, J.W., He, X.J., Wang, Y.H., 2020. Anti-neuroinflammatory and antioxidant phenols from mulberry fruit (Morus alba L. ). J. Funct. Foods 68, 103914
    Yao, J.B., He, H.H., Xue, J., Wang, J.F., Jin, H.H., Wu, J., Hu, J.N., Wang, R.W., Kuchta, K., 2019. Mori Ramulus (Chin. Ph. )—the dried twigs of Morus alba L. /Part 1: discovery of two novel coumarin glycosides from the anti-hyperuricemic ethanol extract. Molecules 24, 629 doi: 10.3390/molecules24030629
    Yap, J.K.Y., Tan, S.Y.Y., Tang, S.Q., Thien, V.K., Chan, E.W.L., 2021. Synergistic antibacterial activity between 1, 4-naphthoquinone and β-lactam antibiotics against methicillin-resistant Staphylococcus aureus. Microb. Drug Resist. Larchmo. N Y 27, 234-240 doi: 10.1089/mdr.2020.0178
    Ynag, G., Bao, X., Chen, Y., Wu, Y., Ma, J., 2018. Antibacterial activities of six phenolic compounds and juglone in vitro. Chin. J. Animal Nutrit. 30, 3710-3719
    Zaki, A.A., Ross, S.A., El-Amier, Y.A., Khan, I.A., 2018. New flavans and stilbenes from Cyperus conglomeratus. Phytochem. Lett. 26, 159-163
    Zhai, H.J., Yu, J.H., Zhang, Q.Q., Liu, H.S., Zhang, J.S., Song, X.Q., Zhang, Y.Y., Zhang, H., 2019. Cytotoxic and antibacterial triterpenoids from the roots of Morinda officinalis var. officinalis. Fitoterapia 133, 56-61
    Zmantar, T., Miladi, H., Kouidhi, B., Chaabouni, Y., Ben Slama, R., Bakhrouf, A., Mahdouani, K., Chaieb, K., 2016. Use of juglone as antibacterial and potential efflux pump inhibitors in Staphylococcus aureus isolated from the oral cavity. Microb. Pathog. 101, 44-49
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