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Macluracochinones A-E, antimicrobial flavonoids from Maclura cochinchinensis (Lour.) Corner
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- 1. * & Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand & ** & School of Chemistry and Molecular Bioscience, University of Wollongong, Wollongong, New South Wales, 2522, Australia
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Polbuppha, Isaraporn, Suthiphasilp, Virayu, Maneerat, Tharakorn, Charoensup, Rawiwan, Limtharakul, Thunwadee, Cheenpracha, Sarot, Pyne, Stephen G., Laphookhieo, Surat (2021): Macluracochinones A-E, antimicrobial flavonoids from Maclura cochinchinensis (Lour.) Corner. Phytochemistry (112773) 187: 1-7, DOI: 10.1016/j.phytochem.2021.112773, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112773
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- urn:lsid:plazi.org:pub:FFD4FF98FA4D7876FF849237FFD50114
References
- Al-Maharik, N., Botting, N.P., 2003. Synthesis of lupiwighteone via a para -Claisen-Cope rearrangement. Tetrahedron 59, 4177-4181. https://doi.org/10.1016/S0040-4020 (03)00579-9.
- Bayma, J.C., Arruda, M.S., Neto, M.S., 1998. A prenylated xanthone from the bark of Symphonia globulifera. Phytochemistry 49, 1159-1160. https://doi.org/10.1016/ S0031-9422(98)00085-5.
- Bohlmann, F., Abraham, W.R., King, R.M., Robinson, H., 1981. Thiophene acetylenes and flavanols from Pterocaulon virgatum. Phytochemistry 20, 825-827. https://doi.org/ 10.1016/0031-9422(81)85187-4.
- Botta, B., Delle Monache, G., Delle Monache, F., Bettolo, G.M., Menichini, F., 1986. Vismione H and prenylated xanthones from Vismia guineensis. Phytochemistry 25, 1217-1219. https://doi.org/10.1016/S0031-9422(00)81583-6.
- Bourdy, G., de Michel, L.C., Roca-Coulthard, A., 2004. Pharmacopoeia in a shamanistic society: the Izoceno-Guarani (Bolivian Chaco). J. Ethnopharmacol. 91, 189-208. https://doi.org/10.1016/j.jep.2003.09.013.
- Bueno, N.R., Castilho, R.O., Costa, R.B.D., Pott, A., Pott, V.J., Scheidt, G.N., Batista, M.D. S., 2005. Medicinal plants used by the Kaiowa´and Guarani indigenous populations in the Caarapo´Reserve, Mato Grosso do Sul, Brazil. Acta Bot. Bras. 19, 39-44. https://doi.org/10.1590/S0102-33062005000100005.
- Bunyapraphatsara, N., Dechsree, S., Yoosook, C., Herunsalee, A., Panpisutchai, Y., 2000. Anti-herpes simplex virus component isolated from Maclura cochinchinensis. Phytomedicine 6, 421-424. https://doi.org/10.1016/S0944-7113(00)80069-0.
- Chien, T.V., Anh, N.T., Thanh, N.T., Thao, T.T.P., Loc, T.V., Sung, T.V., 2019. Two new prenylated isoflavones from Maclura cochinchinensis collected in Hoa Binh province Vietnam. Nat. Prod. Res. 33, 212-218. https://doi.org/10.1080/ 14786419.2018.1443096.
- Cioffi, G., Escobar, L.M., Braca, A., De Tommasi, N., 2003. Antioxidant chalcone glycosides and flavanones from Maclura (Chlorophora) tinctoria. J. Nat. Prod. 66, 1061-1064. https://doi.org/10.1021/np030127c.
- Deachathai, S., Mahabusarakam, W., Phongpaichit, S., Taylor, W.C., 2005. Phenolic compounds from the fruit of Garcinia dulcis. Phytochemisty 66, 2368-2375. https:// doi.org/10.1016/j.phytochem.2005.06.025.
- El-Sohly, H.N., Joshi, A., Li, X.C., Ross, S.A., 1999. Flavonoids from Maclura tinctoria. Phytochemistry 52, 141-145. https://doi.org/10.1016/S0031-9422(99)00126-0.
- Fukai, T., Wang, Q.H., Takayama, M., Nomura, T., 1990. Structures of five new prenylated flavonoids, gancaonins L, M, N, O, and P from aerial parts of Glycyrrhiza uralensis. Heterocycles (Sendai) 31, 373-382. https://doi.org/10.3987/COM-89- 5260.
- Ganapaty, S., Nair, V., Devi, D.R., Pannakal, S.T., Laatsch, H., Dittrich, B., 2014. Rare prenylated isoflavones from Tephrosia calophylla. Nat. Prod. Commun. 9, 937-940. https://doi.org/10.1177/1934578X1400900713.
- Govindachari, T.R., Kalyanaraman, P.S., Muthukumaraswamy, N., Pai, B.R., 1971. Xanthones of Garcinia mangostana Linn. Tetrahedron 27, 3919-3926. https://doi. org/10.1016/S0040-4020(01)98253-5.
- Hajdu, Z., Hohmann, J., 2012. An ethnopharmacological survey of the traditional medicine utilized in the community of Porvenir, Bajo Paragua ´Indian Reservation, Bolivia. J. Ethnopharmacol. 139, 838-857. https://doi.org/10.1016/j. jep.2011.12.029.
- Han, X.H., Hong, S.S., Jin, Q., Li, D., Kim, H.K., Lee, J., Kwon, S.H., Lee, D., Lee, C.K., Lee, M.K., Hwang, B.Y., 2009. Prenylated and benzylated flavonoids from the fruits of Cudrania tricuspidata. J. Nat. Prod. 72, 164-167. https://doi.org/10.1021/ np800418j.
- Horowitz, R.M., Jurd, L., 1961. Spectral studies on flavonoid compounds. II. Isoflavones and flavanones. J. Org. Chem. 26, 2446-2449. https://doi.org/10.1021/ jo01351a070.
- Jain, A.C., Sharma, B.N., 1974. Synthesis of alpinum isoflavone, osajin, and warangalone. J. Org. Chem. 39, 2215-2217. https://doi.org/10.1021/jo00929a016.
- Joo, T., Sowndhararajan, K., Hong, S., Lee, J., Park, S.Y., Kim, S., Jhoo, J.W., 2014. Inhibition of nitric oxide production in LPS-stimulated RAW 264.7 cells by stem bark of Ulmus pumila L. Saudi J. Biol. Sci. 21, 427-435. https://doi.org/10.1016/j. sjbs.2014.04.003.
- Jung, H.A., Woo, J.J., Jung, M.J., Hwang, G.S., Choi, J.S., 2009. Kaempferol glycosides with antioxidant activity from Brassica juncea. Arch Pharm. Res. (Seoul) 32, 1379-1384. https://doi.org/10.1007/s12272-009-2006-3.
- Kobayashi, M., Mahmud, T., Yoshioka, N., Shibuya, H., Kitagawa, I., 1997. Indonesian medicinal plants. XXI. Inhibitors of Na+/H+ exchanger from the bark of Erythrina variegata and the roots of Maclura cochinchinensis. Chem. Pharm. Bull. 45, 1615-1619. https://doi.org/10.1248/cpb.45.1615.
- Tunsirikongkon, A., Pandith, H., 2016. Determination of morin in Maclura cochinchinensis heartwood by HPLC. J. Chromatogr. Sci. 1-5. https://doi.org/ 10.1093/chromsci/bmw191.
- Kwon, J., Hiep, N.T., Kim, D.W., Hong, S., Guo, Y., Hwang, B.Y., Lee, H.J., Mar, W., Lee, D., 2016. Chemical constituents isolated from the root bark of Cudrania tricuspidata and their potential neuroprotective effects. J. Nat. Prod. 79, 1938-1951. https://doi.org/10.1021/acs.jnatprod.6b00204.
- Lane, G.A., Newman, R.H., 1986. Isoflavones from Lupinus angustifolius root. Phytochemistry 26, 295-300. https://doi.org/10.1016/S0031-9422(00)81531-9.
- Lee, S.J., Wood, A.R., Maier, C.G.A., Dixon, R.A., Mabry, T.J., 1998. Prenylated flavonoids from Maclura pomifera. Phytochemistry 49, 2573-2577. https://doi.org/ 10.1016/S0031-9422(98)00380-X.
- Li, B., Ni, Y., Zhu, L.J., Wu, F.B., Yan, F., Zhang, X., Yao, X.S., 2015. Flavonoids from Matteuccia struthiopteris and their anti-influenza virus (H1N1) activity. J. Nat. Prod. 78, 987-995. https://doi.org/10.1021/np500879t.
- Mabry, T., Markham, K.R., Thomas, M.B., 2012. The Systematic Identification of Flavonoids, first ed. Springer Science & Business Media, Berlin, Germany,
- Mahabusarakam, W., Nuangnaowarat, W., Taylor, W.C., 2006. Xanthone derivatives from Cratoxylum cochinchinense roots. Phytochemistry 67, 470-474. https://doi.org/ 10.1016/j.phytochem.2005.10.008.
- M´aximo, P., Lourenco, A., Feio, S.S., Roseiro, J.C., 2000. Flavonoids from Ulex species. Z. Naturforsch. 55, 506-510. https://doi.org/10.1515/znc-2000-7-804.
- Mizuno, M., Matsuura, N., Iinuma, M., Tanaka, T., Phengklai, C., 1990. Isoflavones from stems of Euchresta horsfieldii. Phytochemistry 29, 2675-2677. https://doi.org/ 10.1016/0031-9422(90)85211-W.
- Mohan Rao, K.S.R., Iyer, C.R., Iyer, P.R., 1987. Synthesis of alpinum isoflavone, derrone and related pyranoisoflavones. Tetrahedron 43, 3015-3019. https://doi.org/ 10.1016/S0040-4020(01)86841-1.
- Nakashima, K., Ogiwara, T., Hirai, T., Tanaka, T., Murata, H., Kaburagi, K., Fujii- Kuriyama, Y., Hayashi, H., Inoue, M., 2017. Gerontoxanthone B from Maclura cochinchinensis var. gerontogea exhibits anti-inflammatory potential as an aryl hydrocarbon receptor agonist. Bioorg. Med. Chem. 25, 4253-4258. https://doi.org/ 10.1016/j.bmc.2017.05.047.
- Nakashima, K., Tanaka, T., Murata, H., Kaburagi, K., Inoue, M., 2015. Xanthones from the roots of Maclura cochinchinensis var. gerontogea and their retinoic acid receptor- α agonistic activity. Bioorg. Med. Chem. Lett 25, 1998-2001. https://doi.org/ 10.1016/j.bmcl.2015.02.075.
- Oh, W.K., Lee, H.S., Ahn, S.C., Ahn, J.S., Mbafor, J.T., Wandji, J., Fomum, Z.T., Chang, H. K., Kim, Y.H., 1999. Prenylated isoflavonoids from Erythrina senegalensis. Phytochemistry 51, 1147-1150. https://doi.org/10.1016/S0031-9422(99)00171-5.
- Orhan, I., Senol, F.S., Kartal, M., Dvorska, M., ˇZemliˇcka, M., Smejkal ˇ, K., Mokry, P., 2009. Cholinesterase inhibitory effects of the extracts and compounds of Maclura pomifera (Rafin.) Schneider. Food Chem. Toxicol. 47, 1747-1751. https://doi.org/10.1016/j. fct.2009.04.023.
- Osawa, K., Yasuda, H., Maruyama, T., Morita, H., Takeya, K., Itokawa, H., 1992. Isoflavanones from the heartwood of Swartzia polyphylla and their antibacterial activity against cariogenic bacteria. Chem. Pharm. Bull. 40, 2970-2974. https://doi. org/10.1248/cpb.40.2970.
- Oyama, S.D.O., Souza, L.A.D., Baldoqui, D.C., Sarragiotto, M.H., Silva, A.A., 2013. Prenylated flavonoids from Maclura tinctoria fruits. Quim. Nova 36, 800-802. https://doi.org/10.1590/S0100-40422013000600010.
- Pistelli, L., Spera, K., Flamini, G., Mele, S., Morelli, I., 1996. Isoflavonoids and chalcones from Anthyllis hermanniae. Phytochemistry 42, 1455-1458. https://doi.org/ 10.1016/0031-9422(96)00128-8.
- Polbuppha, I., Maneerat, W., Sripisut, T., Limtharakul, T., Cheenpracha, S., Pyne, S.G., Muanprasat, C., Seemakhan, S., Borwornpinyo, S., Laphookhieo, S., 2017. Antioxidant, cytotoxic and α -glucosidase inhibitory activities of compounds isolated from the twig extracts of Maclura fruticosa. Nat. Prod. Commun. 12, 1073-1076. https://doi.org/10.1177/1934578X1701200718.
- Raju, K.S., Srimannarayana, G., Ternai, B., Stanley, R., Markham, K.R., 1981. 13C NMR studies of some complex natural oxygen heterocyclics: structure of millettin, a novel isoflavone isolated from Millettia auriculata. Tetrahedron 37, 957-962. https://doi. org/10.1016/S0040-4020(01)97667-7.
- Raksat, A., Maneerat, W., Andersen, R.J., Pyne, S.G., Laphookhieo, S., 2018. Antibacterial prenylated isoflavonoids from the stems of Millettia extensa. J. Nat. Prod. 81, 1835-1840. https://doi.org/10.1021/acs.jnatprod.8b00321.
- Raksat, A., Maneerat, W., Rujanapun, N., Andersen, R.J., Pyne, S.G., Laphookhieo, S., 2019. Antibacterial and Inhibitory activities against nitric oxide production of coumaronochromones and prenylated isoflavones from Millettia extensa. J. Nat. Prod. 82, 2343-2348. https://doi.org/10.1021/acs.jnatprod.9b00216.
- Ribaudo, G., Vendrame, T., Bova, S., 2017. Isoflavones from Maclura pomifera: structural elucidation and in silico evaluation of their interaction with PDE5. Nat. Prod. Res. 31, 1988-1994. https://doi.org/10.1080/14786419.2016.1269101.
- Saloua, F., Eddine, N.I., Hedi, Z., 2009. Chemical composition and profile characteristics of Osage orange Maclura pomifera (Rafin.) Schneider seed and seed oil. Ind. Crop. Prod. 29, 1-8. https://doi.org/10.1016/j.indcrop.2008.04.013.
- Sekine, T., Inagaki, M., Ikegami, F., Fujii, Y., Ruangrungsi, N., 1999. Six diprenylisoflavones, derrisisoflavones A-F, from Derris scandens. Phytochemistry 52, 87-94. https://doi.org/10.1016/S0031-9422(99)00103-X.
- Shabbir, M., Zaman, A., 1970. Structure of isoauriculatin and auriculin, extractives of Milletia auriculata-II. Tetrahedron 26, 5041-5044. https://doi.org/10.1016/S0040- 4020(01)93156-4.
- Tahara, S., Nakahara, S., Mizutani, J., Ingham, J.L., 1985. Fungal metabolites of antifungal isoflavone wighteone. Nippon Nogeikagaku Kaishi 59, 1039-1044.
- Tahara, S., Orihara, S., Ingham, J.L., Mizutani, J., 1989. Seventeen isoflavonoids from Lupinus albus roots. Phytochemistry 28, 901-911. https://doi.org/10.1016/0031- 9422(89)80140-2.
- Tantapakul, C., Maneerat, W., Sripisut, T., Ritthiwigrom, T., Andersen, R.J., Cheng, P., Cheenpracha, S., Raksat, A., Laphookhieo, S., 2016. New benzophenones and xanthones from Cratoxylum sumatranum ssp. neriifolium and their antibacterial and antioxidant activities. J. Agric. Food Chem. 64, 8755-8762. https://doi.org/ 10.1021/acs.jafc.6b03643.
- Tsao, R., Yang, R., Young, J.C., 2003. Antioxidant isoflavones in Osage orange, Maclura pomifera (Raf.) Schneid. J. Agric. Food Chem. 51, 6445-6451. https://doi.org/ 10.1021/jf0342369.
- Wang, J.H., Ji, M.H., Shu, H.M., Chen, G.Y., Song, X.P., Wang, J., 2012. Chemical constituents from the roots of Polyalthia oblique. Chin. J. Nat. Med. 4, 303-306. https://doi.org/10.1016/S1875-5364(12)60062-4.
- Wang, S.S., Zhang, X.J., Que, S., Tu, G.Z., Wan, D., Cheng, W., Liang, H., Ye, J., Zhang, Q. Y., 2012. 3-Hydroxy-3-methylglutaryl flavonol glycosides from Oxytropis falcata. J. Nat. Prod. 75, 1359-1364. https://doi.org/10.1021/np300292f.