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Published February 29, 2020 | Version v1
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Ent-abietane and ent-pimarane diterpenoids from Croton mubango (Euphorbiaceae)

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  • 1. , Moses K. Langat & , Eduard Mas-Claret & , Blaise M. Mbala & ∗ & Natural Products Research Group, Department of Chemistry, Faculty of Engineering and Physical Sciences, University of Surrey, Guildford, GU2 7XH, UK

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Isyaka, Sani M., Langat, Moses K., Mas-Claret, Eduard, Mbala, Blaise M., Mvingu, Bienvenu K., Mulholland, Dulcie A. (2020): Ent-abietane and ent-pimarane diterpenoids from Croton mubango (Euphorbiaceae). Phytochemistry (112217) 170: 112217, DOI: 10.1016/j.phytochem.2019.112217, URL: http://dx.doi.org/10.1016/j.phytochem.2019.112217

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urn:lsid:plazi.org:pub:FFEFFFDBD075FFC0FFE2C3538A12FFF4

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Figure: 10.5281/zenodo.8160327 (DOI)
Dataset: http://table.plazi.org/id/DF00663DD077FFC2FF80C2BE8B62FDE8 (URL)
Dataset: http://table.plazi.org/id/DF00663DD076FFC3FF86C3F28B92FF39 (URL)
Figure: 10.5281/zenodo.8160329 (DOI)
Figure: 10.5281/zenodo.8160331 (DOI)
Figure: 10.5281/zenodo.8160333 (DOI)
Figure: 10.5281/zenodo.8160335 (DOI)
Dataset: http://table.plazi.org/id/DF00663DD070FFC5FF86C6688B6AFA9C (URL)
Dataset: http://table.plazi.org/id/DF00663DD073FFC6FF86C3F28B6AFF39 (URL)
Dataset: http://table.plazi.org/id/DF00663DD073FFC6FF86C6FB8FC3FA26 (URL)
Figure: 10.5281/zenodo.8160337 (DOI)
Figure: 10.5281/zenodo.8160339 (DOI)

References

  • Aldhaher, A., Langat, M., Ndunda, B., Chirchir, D., Midiwo, J.O., Njue, A., Schwikkard, S., Carew, M., Mulholland, D., 2017. Diterpenoids from the roots of Croton dichogamus pax. Phytochemistry 144, 1-8.
  • Alqahtani, A.M., 2015. Phytochemical Investigation of Members of the Asparagaceae and Euphorbiaceae Families. PhD Thesis. University of Surrey.
  • Ansell, S.M., Pegel, K.H., Taylor, D.A.H., 1993. Diterpenes from the timber of 20 Erythroxylum species. Phytochemistry 32, 953-959.
  • Anthonse, T., Bergland, G., 1973. Constituents of Solidago species 3. The constitution and sterochemistry of diterpenoids from Solidago missouriensis nutt. Acta Chem. Scand. 27, 1073-1082.
  • Ayafor, J.F., Tchuendem, M.H.K., Nyasse, B., Tillequin, F., Anke, H., 1994. Aframodial and other bioactive diterpenoids from Aframomum species. Pure Appl. Chem. 66, 2327-2330.
  • Brown, G.D., 1994. Phytene-1,2-diol from Artemisia annua. Phytochemistry 36, 1553-1554.
  • Campos, A.R., Albuquerque, F.A.A., Rao, V.S.N., Maciel, M.A.M., Pinto, A.C., 2002. Investigations on the antinociceptive activity of crude extracts from Croton cajucara leaves in mice. Fitoterapia 73, 116-120.
  • Chawla, A.S., Sharma, A.K., Handa, S.S., Dhar, K.L., 1991. Chemical investigation and antiinflammatory activity of Vitex negundo seeds: Part I. Indian J. Chem., Sect. B 30, 773-776.
  • Clemans, G.B., Alemayehu, M., 1993. The gamma gauche substituent effect in 13C NMR. Tetrahedron Lett. 34, 1563-1566.
  • Conner, A.H., Nagasampagi, B.A., Rowe, J.W., 1980. Terpenoid and other extractives of western white-pine bark. Phytochemistry 19, 1121-1131.
  • Craveiro, A.A., Andrade, C.H.S., Matos, F.J.A., Alencar, J.W., Dantas, T.N.C., 1980. Fixed and volatile constituents of Croton aff. nepetifolius. J. Nat. Prod. 43, 756-757.
  • Delcorral, J.M.M., Gordaliza, M., Salinero, M.A., Sanfeliciano, A., 1994. 13C NMR data for abieta-8,11,13-triene diterpenoids. Magn. Reson. Chem. 32, 774-781.
  • Feliciano, A.S., Delcorral, J.M.M., Gordaliza, M., Salinero, M.A., 1993a. 13C NMR data for abieta-7,13-diene diterpenoids. Magn. Reson. Chem. 31, 841-844.
  • Feliciano, A.S., Gordaliza, M., Delcorral, J.M.M., Castro, M.A., Garciagravalos, M.D., Ruizlazaro, P., 1993b. Antineoplastic and antiviral activities of some cyclolignans. Planta Med. 59, 246-249.
  • Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., Nakatsuji, H., Li, X., Caricato, M., Marenich, A.V., Bloino, J., Janesko, B.G., Gomperts, R., Mennucci, B., Hratchian, H.P., Ortiz, J.V., Izmaylov, A.F., Sonnenberg, J.L., Williams, Ding, F., Lipparini, F., Egidi, F., Goings, J., Peng, B., Petrone, A., Henderson, T., Ranasinghe, D., Zakrzewski, V.G., Gao, J., Rega, N., Zheng, G., Liang, W., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Throssell, K., Montgomery Jr., J.A., Peralta, J.E., Ogliaro, F., Bearpark, M.J., Heyd, J.J., Brothers, E.N., Kudin, K.N., Staroverov, V.N., Keith, T.A., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A.P., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Millam, J.M., Klene, M., Adamo, C., Cammi, R., Ochterski, J.W., Martin, R.L., Morokuma, K., Farkas, O., Foresman, J.B., Fox, D.J., 2016. Gaussian 09. Rev. A.02, Wallingford, CT.
  • Grimblat, N., Zanardi, M.M., Sarotti, A.M., 2015. Beyond DP4: an improved probability for the stereochemical assignment of isomeric compounds using quantum chemical calculations of NMR shifts. J. Org. Chem. 80, 12526-12534.
  • Langat, M.K., Crouch, N.R., Pohjala, L., Tammela, P., Smith, P.J., Mulholland, D.A., 2012. Ent-kauren-19-oic acid derivatives from the stem bark of Croton pseudopulchellus Pax. Phytochem. Lett. 5, 414-418.
  • Langat, M.K., Crouch, N.R., Smith, P.J., Mulholland, D.A., 2011. Cembranolides from the leaves of Croton gratissimus. J. Nat. Prod. 74, 2349-2355.
  • Langat, M.K., Helfenstein, A., Horner, C., Tammela, P., Hokkanen, H., Izotov, D., Mulholland, D.A., 2018. Pumilol, a diterpenoid with a rare strobane skeleton from Pinus pumila (pinaceae). Chem. Biodivers. 15.
  • Lima, S.G.D., Cito, A.M.G.L., Lopes, J.A.D., Neto, J.M.M., Chaves, M.H., Silveira, E.R., 2010. Fixed and volatile constituents of genus Croton plants: C. adenocalyx baill - Euphorbiaceae. Rev. Latinoam. Quim. 38, 133-144.
  • Matsumoto, T., Endo, Y., Okimoto, M., 1983. The synthesis of (+)-Pisiferol and (+)-Pisiferal. Bull. Chem. Soc. Jpn. 56, 2018-2022.
  • Matsuo, A., Ono, K., Hamasaki, K., Nozaki, H., 1996. Phaeophytins from a cell suspension culture of the liverwort Plagiochila ovalifolia. Phytochemistry 42, 427-430.
  • Motta, L.B., Furlan, C.M., Santos, D., Salatino, M.L.F., Negri, G., de Carvalho, J.E., Monteiro, P.A., Ruiz, A., Caruzo, M.B., Salatino, A., 2013. Antiproliferative activity and constituents of leaf extracts of Croton sphaerogynus Baill. (Euphorbiaceae). Ind. Crops Prod. 50, 661-665.
  • Mulholland, D.A., Langat, M.K., Crouch, N.R., Coley, H.M., Mutambi, E.M., Nuzillard, J.M., 2010. Cembranolides from the stem bark of the southern African medicinal plant, Croton gratissimus (Euphorbiaceae). Phytochemistry 71, 1381-1386.
  • Nardi, G.M., Felippi, R., DalBo, S., Siqueira-Junior, J.M., Arruda, D.C., Delle Monache, F., Timbola, A.K., Pizzolatti, M.G., Ckless, K., Ribeiro-do-Valle, R.M., 2003. Anti-inflammatory and antioxidant effects of Croton celtidifolius bark. Phytomedicine 10, 176-184.
  • National Cancer Institute, 2019. NCI DTP Developmental Therapeutics Program. https:// dtp.cancer.gov/discovery_development/nci-60/methodology.htm, Accessed date: 10 January 2019.
  • Ndunda, B., Langat, M.K., Mulholland, D.A., Eastman, H., Jacob, M.R., Khan, S.I., Walker, L.A., Muhammad, I., Kerubo, L.O., Midiwo, J.O., 2016. New ent-clerodane and abietane diterpenoids from the roots of Kenyan Croton megalocarpoides friis. & M. G. Gilbert. Planta Med. 82, 1079-1086.
  • Nugroho, A.E., Morita, H., 2014. Circular dichroism calculation for natural products. J. Nat. Med. 68, 1-10.
  • Orihara, Y., Saiki, K., Furuya, T., 1994. Biotransformation of caryophyllene oxide by cultured cells of Eucalyptus perriniana. Phytochemistry 35, 635-639.
  • Pieters, L., de Bruyne, T., Claeys, M., Vlietinck, A., Calomme, M., vanden Berghe, D., 1993. Isolation of a dihydrobenzofuran lignan from south American dragon's blood (Croton spp.) as an inhibitor of cell proliferation. J. Nat. Prod. 56, 899-906.
  • Rao, V.S., Gurgel, L.A., Lima-Junior, R.C.P., Martins, D.T.O., Cechinel-Filho, V., Santos, F.A., 2007. Dragon's blood from Croton urucurana (Baill.) attenuates visceral nociception in mice. J. Ethnopharmacol. 113, 357-360.
  • Righi, A.A., Motta, L.B., Klafke, G.M., Pohl, P.C., Furlan, C.M., Santos, D.Y.A.C., Salatino, M.L.F., Negri, G., Labruna, M.B., Salatino, A., 2013. Chemical composition and efficacy of dichloromethane extract of Croton sphaerogynus Baill. (Euphorbiaceae) against the cattle tick Rhipicephalus microplus (Acari: ixodidae). Vet. Parasitol. 192, 292-295.
  • Salatino, A., Salatino, M.L.F., Negri, G., 2007. Traditional uses, chemistry and pharmacology of Croton species (Euphorbiaceae). J. Braz. Chem. Soc. 18, 11-33.
  • Shoemaker, R.H., 2006. The NCI60 human tumour cell line anticancer drug screen. Nat. Rev. Cancer 6, 813-823.
  • Tabekoueng, G.B., Akak, C.M., Langat, M.K., Azebaze, A.G.B., Waffo, A.F.K., Mulholland, D.A., Vardamides, J.C., 2019. The chemical constituents of Penianthus longifolius Miers. Phytochem. Lett. 30, 103-106.
  • Tembu, V.J., Langat, M.K., Crouch, N.R., Mulholland, D.A., 2014. Use of circular dichroism to determine the absolute configuration of a pimarane diterpenoid from the southern african Sclerocroton integerrimus (euphorbiaceae). Nat. Prod. Commun. 9, 1131-1133.
  • Thuong, P.T., Pham, T.H.M., Le, T.V.T., Dao, T.T., Dang, T.T., Nguyen, Q.T., Oh, W.K., 2012. Symmetric dimers of ent-kaurane diterpenoids with cytotoxic activity from Croton tonkinensis. Bioorg. Med. Chem. Lett 22, 1122-1124.
  • Topcu, G., Ulubelen, A., 1990. Diterpenoids from Salvia wiedemannii. 29, 2346-2348.
  • Urones, J.G., Marcos, I.S., Ferreras, J.F., Barcala, P.B., 1988. Terpenoids from Nepeta tuberosa subsp reticulata (II). Phytochemistry 27, 523-526.
  • Zhou, B.N., 1991. Some progress on the chemistry of natural bioactive terpenoids from Chinese medicinal plants. Mem. Inst. Oswaldo Cruz 86, 219-226.