Published February 28, 2023
| Version v1
Journal article
Restricted
Labdane diterpenoids from the heartwood of Leucosceptrum canum that impact on root growth and seed germination of Arabidopsis thaliana
Authors/Creators
- 1. * & State Key Laboratory of Southwestern Chinese Medicine Resources, and Innovative Institute of Chinese Medicine and Pharmacy, Chengdu University of Traditional
Description
Liu, Yan, Zhou, Yan-Ying, Luo, Shi-Hong, Guo, Kai, Zhang, Man-Wen, Jing, Shu-Xi, Li, Chun-Huan, Hua, Juan, Li, Sheng-Hong (2023): Labdane diterpenoids from the heartwood of Leucosceptrum canum that impact on root growth and seed germination of Arabidopsis thaliana. Phytochemistry (113531) 206: 1-10, DOI: 10.1016/j.phytochem.2022.113531, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113531
Files
Restricted
The record is publicly accessible, but files are restricted. <a href="https://zenodo.org/account/settings/login?next=https://zenodo.org/records/8230418">Log in</a> to check if you have access.
Linked records
Additional details
Identifiers
- LSID
- urn:lsid:plazi.org:pub:FD24111CAB113E007668FF9CFFE9FF8E
References
- Blilou, I., Xu, J., Wildwater, M., Willemsen, V., Paponov, I., Friml, J., Heidstra, R., Aida, M., Palme, K., Scheres, B., 2005. The PIN auxin efflux facilitator network controls growth and patterning in Arabidopsis roots. Nature 433, 39-44. https://doi. org/10.1038/nature03184.
- Bj¨orklund, S., Antti, H., Uddestrand, I., Moritz, T., Sundberg, B., 2007. Cross-talk between gibberellin and auxin in development of Populus wood: gibberellin stimulates polar auxin transport and has a common transcriptome with auxin. Plant J. 52, 499-511. https://doi.org/10.1111/j.1365-313X.2007.03250.x.
- Chen, Y.G., Li, D.S., Ling, Y., Liu, Y.C., Zuo, Z.L., Gan, L.S., Luo, S.H., Hua, J., Chen, D.Y., Xu, F., Li, M., Guo, K., Liu, Y., Gershenzon, J., Li, S.H., 2021. A cryptic plant terpene cyclase producing unconventional 18- and 14-membered macrocyclic C25 and C20 terpenoids with immunosuppressive activity. Angew. Chem. Int. Ed. 60, 25468-25476. https://doi.org/10.1002/anie.202110842.
- Fang, J.M., Chen, Y.C., Wang, B.W., Cheng, Y.S., 1996. Terpenes from heartwood of Juniperus chinensis. Phytochemistry 41, 1361-1365. https://doi.org/10.1016/0031- 9422(95)00795-4.
- Grieneisen, V.A., Xu, J., Maree, A.F., Hogeweg, P., Scheres, B., 2007. Auxin transport is sufficient to generate a maximum and gradient guiding root growth. Nature 449, 1008-1013. https://doi.org/10.1038/nature06215.
- Guo, K., Liu, Y.C., Liu, Y., Luo, S.H., Li, W.Y., Li, X.N., Li, S.H., 2019. Diversified abietane family diterpenoids from the leaves of Leucosceptrum canum and their cytotoxic activity. Phytochemistry 157, 43-52. https://doi.org/10.1016/j. phytochem.2018.10.010.
- Hansen, D.M., Olesen, J.M., Mione, T., Johnson, S.D., Muller, C.B., 2007. Coloured nectar: distribution, ecology, and evolution of an enigmatic floral trait. Biol. Rev. 82, 83-111. https://doi.org/10.1111/j.1469-185X.2006.00005.x.
- Jefferson, R.A., Kavanagh, T.A., Bevan, M.W., 1987. Gus fusions: beta-glucuronidase as a sensitive and versatile gene fusion marker in higher plants. EMBO J. 6, 3901-3907. https://doi.org/10.1002/j.1460-2075.1987.tb02730.x.
- Liu, Y., Luo, S.H., Schmidt, A., Wang, G.D., Sun, G.L., Grant, M., Kuang, C., Yang, M.J., Jing, S.X., Li, C.H., Schneider, B., Gershenzon, J., Li, S.H., 2016. A geranylfarnesyl diphosphate synthase provides the precursor for sesterterpenoid (C25) formation in the glandular trichomes of the mint species Leucosceptrum canum. Plant Cell 28, 804-822. https://doi.org/10.1105/tpc.15.00715.
- Luo, S.H., Hua, J., Li, C.H., Jing, S.X., Liu, Y., Li, X.N., Zhao, X., Li, S.H., 2012a. New antifeedant C20 terpenoids from Leucosceptrum canum. Org. Lett. 14, 5768-5771. https://doi.org/10.1021/ol302787c.
- Luo, S.H., Hua, J., Li, C.H., Liu, Y., Li, X.N., Zhao, X., Li, S.H., 2013a. Unusual antifeedant spiro-sesterterpenoid from the flowers of Leucosceptrum canum. Tetrahedron Lett. 54, 235-237. https://doi.org/10.1016/j.tetlet.2012.11.010.
- Luo, S.H., Hua, J., Niu, X.M., Liu, Y., Li, C.H., Zhou, Y.Y., Jing, S.X., Zhao, X., Li, S.H., 2013b. Defense sesterterpenoid lactones from Leucosceptrum canum. Phytochemistry 86, 29-35. https://doi.org/10.1016/j.phytochem.2012.11.008.
- Luo, S.H., Hugelshofer, C.L., Hua, J., Jing, S.X., Li, C.H., Liu, Y., Li, X.N., Zhao, X., Magauer, T., Li, S.H., 2014. Unraveling the metabolic pathway in Leucosceptrum canum by isolation of new defensive leucosceptroid degradation products and biomimetic model synthesis. Org. Lett. 16, 6416-6419. https://doi.org/10.1021/ ol503230s.
- Luo, S.H., Liu, Y., Hua, J., Niu, X.M., Jing, S.X., Zhao, X., Schneider, B., Gershenzon, J., Li, S.H., 2012b. Unique proline-benzoquinone pigment from the colored nectar of "bird' s Coca cola tree" functions in bird attractions. Org. Lett. 14, 4146-4149. https://doi.org/10.1021/ol3017879.
- Luo, S.H., Luo, Q., Niu, X.M., Xie, M.J., Zhao, X., Schneider, B., Gershenzon, J., Li, S.H., 2010. Glandular trichomes of Leucosceptrum canum harbor defensive sesterterpenoids. Angew. Chem. Int. Ed. 49, 4471-4475. https://doi.org/10.1002/ anie.201000449.
- Luo, S.H., Weng, L.H., Xie, M.J., Li, X.N., Hua, J., Zhao, X., Li, S.H., 2011. Defensive sesterterpenoids with unusual antipodal cyclopentenones from the leaves of Leucosceptrum canum. Org. Lett. 13, 1864-1867. https://doi.org/10.1021/ ol200380v.
- Ma, S.Z., Mandalapu, D., Wang, S., Zhang, Q., 2022. Biosynthesis of cyclopropane in natural products. Nat. Prod. Rep. 39, 926-945. https://doi.org/10.1039/ d1np00065a.
- Malamy, J.E., Benfey, P.N., 1997. Organization and cell differentiation in lateral roots of Arabidopsis thaliana. Development 124, 33-44. https://doi.org/10.1242/ dev.124.1.33.
- Muchlinski, A., Jia, M.R., Tiedge, K., Fell, J.S., Pelot, K.A., Chew, L., Davisson, D., Chen, Y.X., Siegel, J., Lovell, J.T., Zerbe, P., 2021. Cytochrome P450-catalyzed biosynthesis of furanoditerpenoids in the bioenergy crop switchgrass (Panicum virgatum L.). Plant J. 108, 1053-1068. https://doi.org/10.1111/tpj.15492.
- Nilsson, J., Karlberg, A., Antti, H., Lopez-Vernaza, M., Mellerowicz, E., Perrot- Rechenmann, C., Sandberg, G., Bhalerao, R.P., 2008. Dissecting the molecular basis of the regulation of wood formation by auxin in hybrid aspen. Plant Cell 20, 843-855. https://doi.org/10.1105/tpc.107.055798.
- Peng, H., Wu, Z.Y., 2001. The floristic characteristics and its significance in conservation of semi-humid evergreen broad-leaved forests in Mt Wuliangshan. Acta Bot. Yunnanica 23, 278-286.
- Pu, X.Y., Zhou, J., 1989. Studies on the chemical components from Leucosceptrum canum. Acta Bot. Yunnanica 11, 263-266.
- Savidge, R.A., 1988. Auxin and ethylene regulation of diameter growth in trees. Tree Physiol. 4, 401-414. https://doi.org/10.1093/treephys/4.4.401.
- Tuominen, H., Puech, L., Fink, S., Sundberg, B., 1997. A radial concentration gradient of indole-3-acetic acid is related to secondary xylem development in hybrid aspen. Plant Physiol. 115, 577-585. https://doi.org/10.1104/pp.115.2.577.
- Ulmasov, T., Murfett, J., Hagen, G., Guilfoyle, T.J., 1997. Aux/IAA proteins repress expression of reporter genes containing natural and highly active synthetic auxin response elements. Plant Cell 9, 1963-1971. https://doi.org/10.1105/ tpc.9.11.1963.
- Zhang, M.W., Guo, K., Zhang, Y., Teng, L.L., Huang, Q.P., Liu, L., Li, S.H., 2021. Leucoabietenes A and B, rearranged abietane and ent -abietane diterpene hydrocarbons against resistant infectious fungus and bacterium from the leaves of Leucosceptrum canum. Tetrahedron Lett. 81, 153356 https://doi.org/10.1016/j. tetlet.2021.153356.
- Zhao, Y.X., Zhou, L., Guo, L., Luo, X.D., Zhou, J., 2005. A new diterpenoid and active stilbenes from Pinus armandii heartwood. J. Asian Nat. Prod. Res. 7, 259-264. https://doi.org/10.1080/10286020410001690163.
- Zhu, D.Q., Seo, M.J., Ikeda, H., Cane, D.E., 2011. Genome mining in streptomyces. Discovery of an unprecedented P450-catalyzed oxidative rearrangement that is the final step in the biosynthesis of pentalenolactone. J. Am. Chem. Soc. 133, 2128-2131. https://doi.org/10.1021/ja111279h.