Biodiversity Literature Repository

Submit to community
Liberated Data
Published August 31, 2020 | Version v1
Journal article Restricted

Alkane-, alkene-, alkyne-γ-lactones and ryanodane diterpenes from aeroponically grown Persea indica roots

Authors/Creators

  • 1. ∗ & Instituto de Productos Naturales y Agrobiología, C.S.I.C., Avda. Astrofísico F. Sánchez 3, 38206, La Laguna, Tenerife, Canary Islands, Spain

Description

Fraga, Braulio M., Díaz, Carmen E., Bolaños, Patricia, Bailén, María, Andrés, María Fe, González-Coloma, Azucena (2020): Alkane-, alkene-, alkyne-γ-lactones and ryanodane diterpenes from aeroponically grown Persea indica roots. Phytochemistry (112398) 176: 1-9, DOI: 10.1016/j.phytochem.2020.112398, URL: http://dx.doi.org/10.1016/j.phytochem.2020.112398

Files

Restricted

The record is publicly accessible, but files are restricted to users with access.

Linked records

Additional details

Identifiers

LSID
urn:lsid:plazi.org:pub:FFABFFD2ED74FFEDA31EFF8C1373FF96

References

  • Alves, H.M., Coxon, D.T., Falshaw, C.P., Godtfredsen, W.O., Olis, W.D., 1970. Avocatins. New class of natural products. An. Acad. Bras. Cienc. 42 (Suppl. l.), 45-48.
  • Alves-Reis, I.M., Souza-Conceicao, R., Ferreira, R.S., dos Santos, C.C., da Silva, G.R., de Mattos-Oliveira, L., Almeida-Cassiano, D.S., dos Santos-Junior, M.C., Borges-Botura, M., Amaral da Silva, V.D., Lima-Costa, S., Sarmento da Silva, T.M., Curcino-Vieira, I.J., Braz-Filho, R., Branco, A., 2019. Alkene lactones from Persea fulva (Lauraceae): evaluation of their effects on tumor cell growth in vitro and molecular docking studies. Bioorg. Chem. 86, 665-673.
  • Anderson, J.E., Ma, W., Smith, D.L., Chang, C., Mclaughlin, J.L., 1992. Biologically active γ-lactones and methylketoalkenes from Lindera benzoin. J. Nat. Prod. 55, 71-83.
  • Andres, M.F., Gonzalez-Coloma, A., Sanz, J., Burillo, J., Sainz, P., 2012. Nematicidal activity of essential oils: a review. Phytochemistry Rev. 11, 371-390.
  • Barbier, P., Benezra, C., 1982. Allergenic α-methylene-γ-butyrolactones. Stereospecific syntheses of (+)- and (-)-γ-methyl-α-methylene-γ-butyrolactones. A study of the specificity of (+)- and (-)-enantiomers in inducing allergic contact dermatitis. J. Med. Chem. 25, 943-946.
  • Barreiros, M.L., David, J.P., David, J.M., Lopes, L.M.X., Sa de, M.S., Costa, J.F.O., Almeida, M.Z., Queiroz, L.P. de, Sant'Ana, A.E.G., 2007. Ryanodanre diterpenes from two Erythroxylum species. Phytochemistry 68, 1735-1739.
  • Beecham, A.F., 1972. The CD of αβ-unsaturated lactones. Tetrahedron 28, 5543-5554.
  • Bowers, W.S., Bodenstein, W.G., 1971. Sex pheromone mimics of the American cockroach. Nature 232, 259-261.
  • Bramwell, D., 1976. In: Kunkel, G. (Ed.), Biogeography and Ecology of the Canary Islands. D.R.W. Junk, The Hague, pp. 207.
  • Chai, X.Y., Bai, C.C., Shi, H.M., Xu, Z.R., Ren, H.Y., Li, F.F., Lu, Y.N., Song, Y.L., Tu, P.F., 2008. Six insecticidal isoryanodane diterpenoids from the bark and twigs of Itoa orientalis. Tetrahedron 64, 5743-5747.
  • Chang, S.Y., Cheng, M.J., Peng, C.F., Chang, H.S., Chen, I.S., 2008. Antimicobacterial butanolides from the root of Lindera akoensis. Chem. Biodivers. 5, 2690-2698.
  • Coll, C.J., Borden, F.D., 1986. The application of vacuum liquid chromatography to the separation of terpene mixtures. J. Nat. Prod. 49, 934-936.
  • Fraga, B.M., Terrero, D., 1996. Alkene-γ-lactones and avocadofurans from Persea indica: a revision of the structure of majorenolide and related lactones. Phytochemistry 41, 229-232.
  • Fraga, B.M., Gonzalez-Coloma, A., Gutierrez, C., Terrero, D., 1997. Insect antifeedant isoryanodane diterpenes from Persea indica. J. Nat. Prod. 60, 880-883.
  • Fraga, B.M., Terrero, D., Gutierrez, C., Gonzalez-Coloma, A., 2001. Minor diterpenes from Persea indica: their antifeedant activity. Phytochemistry 56, 315-320.
  • Fraga, B.M., Terrero, D., Bolanos, P., Diaz, C.E., 2017. Diterpenes with new isoryanodane derived skeletons from Persea indica. Tetrahedron Lett. 58, 2261-2263.
  • Gawronski, J.K., van Oeveren, A., van der Deen, H., Leun, C.W., Feringa, B.L., 1996. Simple circular dichroic method for the determination of absolute configuration of 5- substituted 2(5H)-furanones. J. Org. Chem. 61, 1513-1515.
  • Gonzalez-Coloma, A., Hernandez, M.G., Perales, A., Fraga, B.M., 1990. Chemical ecology of Canarian laurel forest: toxic diterpenes from Persea indica (Lauraceae). Chem. Ecol. 16, 2723-2733.
  • Gonzalez-Coloma, A., Cabrera, R., Castanera, P., Gutierrez, C., Fraga, B.M., 1992. Insecticidal activity and diterpene content of Persea indica. Phytochemistry 31, 1549-1552.
  • Gonzalez-Coloma, A., Cabrera, R., Socorro, A.R., Fraga, B.M., 1993. Persea indica as a natural source of the insecticide ryanodol. Phytochemistry 34, 397-400.
  • Gonzalez-Coloma, A., Terrero, D., Perales, A., Escoubas, P., Fraga, B.M., 1996. Insect antifeedant ryanodane diterpenes from Persea indica. J. Agric. Food Chem. 44, 296-300.
  • Gonzalez-Coloma, A., Gutierrez, C., Hubner, H., Achenbach, H., Terrero, D., Fraga, B.M., 1999. Selective insect antifeedant and toxic action of ryanodoid diterpenes. J. Agric. Food Chem. 47, 4419-4424.
  • Gonzalez-Coloma, A., Guadano, A., de Ines, C., Martinez-Diaz, R., Cortes, D., 2002. Selective action of acetogenin mitochondrial complex I inhibitors. Z. Naturforsch. 57c, 1028-1034.
  • Gutierrez, C., Fereres, A., Reina, M., Cabrera, R., Gonzalez-Coloma, A., 1997. Behavioural, sub-lethal effects of structurally-related lower terpenes on Myzus persicae. J. Chem. Ecol. 23, 1641-1650.
  • Han, G.Q., Huang, Q.L., 1993. Two new cinnamic acid derivatives from Magnolia biondii Pamp. Chin. Chem. Lett. 4, 33-34.
  • Isogai, A., Suzuki, A., Tamura, S., Murakoshi, S., Ohashi, Y., Sasada, S., 1976. Structures of cinnzeylanine and cinnzeylanol, polyhydroxylated pentacyclic diterpenes from Cinnamomum zeylanicum Nees. Agric. Biol. Chem. 40, 2305-2306.
  • Kashman, Y., Neeman, I., Lifshitz, A., 1969. New compounds from avocado pear. Tetrahedron 25, 4617-4631.
  • Kelly, R.B., Whittingham, D.J., Wiesner, K., 1951. The structure of ryanodine I. Can. J. Chem. 29, 905-910.
  • Koga, K., Taniguchi, M., Yamada, S., 1971. A new synthesis of D-ribose from L-glutamic acid. Tetrahedron Lett. 12, 263-266.
  • Koshimizu, M., Nagatomo, M., Inoue, M., 2016. Unified total synthesis of 3-epi -ryanodol, cinnzeylanol, cinncassiols A and B, and structural revision of natural ryanodol and cinnacasol. Angew. Chem. Int. Ed. 55, 2493-2497.
  • Ma, W.W., Anderson, J.E., Chang, C.J., Smith, D.L., McLaughlin, J.L., 1989. Majorenolide and majorynolide: a new pair of cytotoxic and pesticidal alkene-alkyne δ-lactones from Persea major. J. Nat. Prod. 52, 1263-1266.
  • Ma, W.W., Anderson, J.E., Chang, C.J., Smith, D.L., McLaughlin, J.L., 1990. Majoranolide: a δ-lactones from Persea major. Phytochemistry 29, 2698-2699.
  • Manabe, S., Nishino, C., 1983. Sex pheromonal activity of (+)-bornyl acetate and related compounds to the American cockroach. J. Chem. Ecol. 9, 433-448.
  • Michel, A.G., Drouin, M., 1993. Structure of 3-epiryanodol: a heptahydro diterpene. Acta Crystallogr. C49, 1685-1688.
  • Morais, T.R., Costa-Silva, T.A., Ferreira, D.D., Novais, B.J., Torrecilhas, A.C.T., Tempone, A.G., Lago, J.H.G., 2019. Antitrypanosomal activity and effect in plasma membrane permeability of (-)-bornyl p -coumarate isolated from Piper cernuum (Piperaceae). Biorg. Chem. 89, 103001.
  • Mossman, T., 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65, 55-63.
  • Ogungbe, I.V., Crouch, R.A., Haber, W.A., Setzer, W.N., 2010. Phytochemical investigation of Verbesina turbacensis Kunth: trypanosome cysteine protease inhibition by (-)-bornyl esters. Nat. Prod. Commun. 5, 1161-1166.
  • Pessah, I.N., 1989. In: In: Crombie, L. (Ed.), Recent Advances in the Chemistry of Insect Control II, vol. 79. Royal Soc. Chem, Cambridge, pp. 278-296.
  • Pino, J.A., Fernandes, P., Marbot, R., Rosado, A., Fontinha, S.S., 2004. Leaf oils of Helichrysum melaleucum rchb. ex holl., Oenanthe divaricata (R. Br.) mabb. And Persea indica (L.) Spreng. From madeira. J. Essent. Oil Res. 16, 487-489.
  • Reina, M., Gonzalez-Coloma, A., Gutierrez, C., Cabrera, R., Rodriguez, M.L., Fajardo, V., Villarroel, L., 2001. Defensive chemistry of Senecio miser hook. J. Nat. Prod. 64, 6-11.
  • Ruest, L., Deslongchamps, P., 1993. Ryanoids and related compounds. A total synthesis of 3-epiryanodine. Can. J. Chem. 71, 634-638.
  • Sattelle, D.B., Cordova, D., Cheek, T.R., 2008. Insect ryanodine receptors: molecular targets for novel pest control chemicals. Invertebr. Neurosci. 8, 107-119.
  • Setzer, W.N., Setzer, M.C., Bates, R.B., Nakkiew, P., Jackes, B.R., Chen, L., McFerrin, M.B., Meehan, E.J., 1999. Antibacterial hydroxycinnamic esters from Piper caninum from Paluma, North Queensland, Australia. The crystal and molecular structure of (+)-bornyl coumarate. Planta Med. 65, 747-749.
  • Spagnuolo, P.A., Schimmer, A.D., Lee, E.A., 2017. Avocado-derived lipids for use in treating leukemia. US Patent App 15/517, 914.
  • Srivastava, C.P., Przybylska, M., 1968. The molecular structure of ryanodol- p -bromo benzyl ether. Can. J. Chem. 46, 795-797.
  • Sun, Z., Xu, H., 2019. Ryanodine receptors for drugs and insecticides: an overview. Mini Rev. Med. Chem. 19, 22-33.
  • Takeda, K., Sakurawi, K., Ishhi, H., 1972. Components of the Lauraceae family, 1. New lactonic compounds from Litsea japonica. Tetrahedron 28, 3757-3766.
  • Tang, W., Wei, X., Xu, H., Zeng, D., Long, L., 2009. 13-Deoxyitol A, a nerw insectocidal isoryanodane diterpene from the seeds of Itoa orientalis. Fitoterapia 80, 286-289.
  • Teixeira-Maciel e Silva, A., Viana-Pereira, V., Takahashi, J.A., Rodriguez-Silva, R., Pains- Duarte, L., 2018. Microwave-assisted synthesis of borneol esters and their antimicrobial activity. Nat. Prod. Res. 32, 1714-1720.
  • Toyota, M., Saito, T., Maysunami, J., Asakawa, Y., 1997. A comparative study of three chemo-types of the liverwort Conocephalum conicum using volatile constituents. Phytochemistry 44, 1265-1270 1997.
  • Tsai, I.L., Hung, C.H., Duh, C.Y., Chen, J.H., Lin, W.Y., Chen, I.S., 2001. Cytotoxic butanolides from the stem bark of Formosan Lindera communis. Planta Med. 67, 865-867.
  • Uchida, I., Kuriyama, K., 1974. The π-π* circular dichroism of αβ-unsaturated γ-lactones. Tetrahedron Lett. 30, 3761-3764.
  • Venditti, A., Bianco, A., Bruno, M., Ben Jemia, M.B., Nicoletti, M., 2015. Phytochemical study of Cistus libanotis L. Nat. Prod. Res. 29, 189-192.
  • Weyerstahl, P., Marschall, H., Scora, R.W., 1993. Constituents of the leaf essential oil of Persea indica (L.) K. Spreng. Flav. Fragr. J. 8, 201-207.
  • Wiesner, K., Valenta, Z., Findlay, J.A., 1967. The structure of ryanodine. Tetrahedron Lett. 8, 221-225.
  • Xu, Y.M., Gao, S., Bunting, D.P., Gunatilaka, A.A.L., 2011. Unusual withanolides from aeroponically grown Withania somnifera. Phytochemistry 72, 518-522.
  • Yagi, A., Tokubuchi, N., Nohara, T., Onaka, G., Nishioka, I., Koda, A., 1980. The constituents of Cinnamomi cortex. I. Structures of cinncassiol A and its glucoside. Chem. Pharm. Bull. 28, 1433-1436.
  • Zhang, X.F., Li, X., Min, B.S., Bae, K.H., 2008. A new diterpenoid from the stem bark of Populus daviniana. Chin. Chem. Lett. 19, 1080-1082.