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Phytochemical and biological studies on rare and endangered plants endemic to China. Part XXII. Structurally diverse diterpenoids from the leaves and twigs of the endangered conifer Torreya jackii and their bioactivities
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- 1. *** & * & Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou & ** & * & School of Pharmacy, Fudan University, Shanghai, 201203, PR China
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Li, Hao, Tang, Yu, Liang, Kai-Yuan, Zang, Yi, Osman, Ezzat E.A., Jin, Ze-Xin, Li, Jia, Xiong, Juan, Li, Junmin, Hu, Jin-Feng (2022): Phytochemical and biological studies on rare and endangered plants endemic to China. Part XXII. Structurally diverse diterpenoids from the leaves and twigs of the endangered conifer Torreya jackii and their bioactivities. Phytochemistry (113161) 198: 1-9, DOI: 10.1016/j.phytochem.2022.113161, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113161
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- urn:lsid:plazi.org:pub:FF80FFFFFFA1570DE36FD8365457FFEF
References
- Abdelkafi, H., Nay, B., 2012. Natural products from Cephalotaxus sp.: chemical diversity and synthetic aspects. Nat. Prod. Rep. 29, 845-869. https://doi.org/10.1039/ c2np20037f.
- Ayer, W.A., Macaulay, J.B., 1987. Metabolites of the honey mushroom, Armillaria mellea. Can. J. Chem. 65, 7-14. https://doi.org/10.1139/v87-002.
- Bai, M., Zheng, C.-J., Huang, G.-L., Mei, R.-Q., Wang, B., Luo, Y.-P., Zheng, C., Niu, Z.-G., Chen, G.-Y., 2019. Bioactive meroterpenoids and isocoumarins from the mangrove derived fungus Penicillium sp. TGM112. J. Nat. Prod. 82, 1155-1164. https://doi.
- Butchart, S.H.M., Walpole, M., Collen, B., van Strien, A., Scharlemann, J.P.W., Almond, R.E.A., Baillie, J.E.M., Bomhard, B., Brown, C., Bruno, J., Carpenter, K.E., Carr, G.M., Chanson, J., Chenery, A.M., Csirke, J., Davidson, N.C., Dentener, F., Foster, M., Galli, A., Galloway, J.N., Genovesi, P., Gregory, R.D., Hockings, M., Kapos, V., Lamarque, J.-F., Leverington, F., Loh, J., McGeoch, M.A., McRae, L., Minasyan, A., Morcillo, M.H., Oldfield, T.E.E., Pauly, D., Quader, S., Revenga, C., Sauer, J.R., Skolnik, B., Spear, D., Stanwell-Smith, D., Stuart, S.N., Symes, A., Tierney, M., Tyrrell, T.D., Vi´e, J.-C., Watson, R., 2010. Global biodiversity: indicators of recent declines. Science 328, 1164-1168. https://doi.org/10.1126/ science.1187512.
- Chen, S.-P., Dong, M., Kita, K., Shi, Q.-W., Cong, B., Guo, W.-Z., Sugaya, S., Sugita, K., Suzuki, N., 2010. Anti-proliferative and apoptosis-inducible activity of labdane and abietane diterpenoids from the pulp of Torreya nucifera in HeLa cells. Mol. Med. Rep. 3, 673-678. https://doi.org/10.3892/mmr_00000312.
- Chen, X.W., 2020. Historical radial growth of Chinese Torreya trees and adaptation to climate change. Atmosphere 11, 691. https://doi: 10.3390/atmos11070691.
- Chiang, Y.-M., Liu, H.-K., Lo, J.-M., Chien, S.-C., Chan, Y.-F., Lee, T.-H., Su, J.-K., Kuo, Y.- H., 2003. Cytotoxic constituents of the leaves of Calocedrus formosana. J. Chin.
- Doken ¨, V.M., Nimsch, H., Rudall, P.J., 2019. Origin of the Taxaceae aril: evolutionary implications of seed-cone teratologies in Pseudotaxus chienii. Ann. Bot. 123, 133-143. https://doi.org/10.1093/aob/mcy150.
- Dreaden, T.J., Quesada, T., Smith, J.A., 2020. Detection method for Fusarium torreyae the canker pathogen of the critically endangered Florida torreya, Torreya taxifolia. For. Pathol. 50, e12597. https://doi: 10.1111/efp.12597.
- Du, J., Wang, M.-L., Chen, R.-Y., Yu, D.-Q., 2001. Two new bislabdane-type diterpenoids and three new diterpenoids from the roots of Cunninghamia lanceolata. Planta Med. 67, 542-547. https://doi.org/10.1055/s-2001-16491.
- Elpe, C., Knopf, P., Stutzel, T., Schulz, C., 2018. Diversity and evolution of leaf anatomical characters in Taxaceae s.l.-fluorescence microscopy reveals new delimitating characters. J. Plant Res. 131, 125-141. https://doi.org/10.1007/ s10265-017-0973-x.
- Forster, P.G., Ghisalberti, E.L., Jefferies, P.R., 1985. Labdane diterpenes from an Acacia species. Phytochemistry 24, 2991-2993. https://doi.org/10.1016/0031-9422(85) 80042-X.
- Fox, J.L., 1984. Endangered U.S. plants to be collected, conserved. Science 226, 150. https://doi.org/10.1126/science.226.4671.150.
- Fraga, B.M., Diaz, C.E., Guadanot, A., Gonzalez-Coloma ´, A., 2005. Diterpenes from Salvia broussonetii Transformed roots and their insecticidal activity. J. Agric. Food Chem. 53, 5200-5206. https://doi.org/10.1021/jf058045c.
- Fu, L.K., Jin, J.-M., 1992. China Plant Red Data Book: Rare and Endangered Plants I.
- Galli, B., Gasparrini, F., Lanzotti, V., Misiti, D., Riccio, R., Villani, C., He, G.-F., Ma, Z.- W., Yin, W.-F., 1999. Grandione, a new heptacyclic dimeric diterpene from Torreya grandis Fort. Tetrahedron 55, 11385-11394. https://doi.org/10.1016/S0040-4020 (99)00634-1.
- Ge, Z.-P., Fan, Y.-Y., Deng, W.-D., Zheng, C.-Y., Li, T., Yue, J.-M., 2021. Cephalodiones A- D: compound characterization and semisynthesis by [6+6] cycloaddition. Angew.
- Glatzel, D.K., Koeberle, A., Pein, H., L¨oser, K., Stark, A., Keksel, N., Werz, O., Muller, R., Bischoff, I., Furst, R., 2018. Acetyl-CoA carboxylase 1 regulates endothelial cell migration by shifting the phospholipid composition. J. Lipid Res. 59, 298-311. https://doi.org/10.1194/jlr.M080101.
- Godfrey, R.K., Kurz, H., 1963. The Florida torreya destined for extinction. Science 136, 900-902. https://pubmed.ncbi.nlm.nih.gov/17754185.
- Harriman, G., Greenwood, J., Bhat, S., Huang, X.Y., Wang, R.Y., Paul, D., Tong, L., Saha, A.K., Westlin, W.F., Kapeller, R., Harwood Jr., H.J., 2016. Acetyl-CoA carboxylase inhibiton by ND-630 reduces hepatic steatosis, improves insulin sensitivity, and modulates dyslipidemia in rats. Proc. Natl. Acad. Sci. Unit. States Am. 113, E1796-E1805. https://doi.org/10.1073/pnas.1520686113.
- Hirata, A., Kim, S.-Y., Kobayakawa, N., Tanaka, N., Kashiwada, Y., 2015. Miltiorins A-D, diterpenes from radix Salviae miltiorrhizae. Fitoterapia 102, 49-55. https://doi.org/ 10.1016/j.fitote.2015.01.013.
- Hu, Z.-Y., Li, Y.-Y., Huang, Y.-J., Su, W.-J., Shen, Y.-M., 2008. Three new sesquiterpenoids from Xylaria sp. NCY2. Helv. Chim. Acta 91, 46-52. https://doi.
- Hu, Z.-Y., Li, Y.-Y., Lu, C.-H., Lin, T., Hu, P., Shen, Y.-M., 2010. Seven novel linear polyketides from Xylaria sp. NCY2. Helv. Chim. Acta 93, 925-933. https://doi.org/ 10.1002/hlca.200900323.
- Huang, T., Ying, S.-H., Li, J.-Y., Chen, H.-W., Zang, Y., Wang, W.-X., Li, J., Xiong, J., Hu, J.-F., 2020. Phytochemical and biological studies on rare and endangered plants endemic to China. Part XV. Structurally diverse diterpenoids and sesquiterpenoids from the vulnerable conifer Pseudotsuga sinensis. Phytochemistry 169, 112184. https://doi.org/10.1016/j.phytochem.2019.112184.
- Ibrahim, M.A., Na, M., Oh, J., Schinazi, R.F., McBrayer, T.R., Whitaker, T., Doerksen, R. J., Newman, D.J., Zachos, L.G., Hamann, M.T., 2013. Significance of endangered and threatened plant natural products in the control of human disease. Proc. Natl. Acad. Sci. U.S.A. 110, 16832-16837. https://doi.org/10.1073/pnas.1311528110.
- Jiang, H.-L., Wang, X.-Z., Xiao, J., Luo, X.-H., Yao, X.-J., Zhao, Y.-Y., Chen, Y.-J., Crews, P., Wu, Q.-X., 2013. New abietane diterpenoids from the roots of Salvia przewalskii. Tetrahedron 69, 6687-6692. https://doi.org/10.1016/j.
- Johnson, T.O., Ermolieff, J., Jirousek, M.R., 2002. Protein tyrosine phosphatase 1B inhibitors for diabetes. Nat. Rev. Drug Discov. 1, 696-709. https://doi.org/10.1038/ nrd895.
- Kantarjian, H.M., O' Brien, S., Cortes, J., 2013. Homoharringtonine/omacetaxine mepesuccinate: the long and winding road to food and drug administration approval. Clin. Lymphoma, Myeloma & Leukemia 13, 530-533. https://doi.org/10.1016/j. clml.2013.03.017.
- Katoh, T., Tanaka, R., Takeo, M., Nishide, K., Node, M., 2002. A new synthesis of a potent cancer chemopreventive agent, 13-oxo-15,16-dinorlabda-8(17),11E -dien-19-oic acid from trans -communic acid. Chem. Pharm. Bull. 50, 1625-1629. https://doi.org/ 10.1248/cpb.50.1625.
- Kim, D.H., Paudel, P., Yu, T., Ngo, T.M., Kim, J.A., Jung, H.A., Yokozawa, T., Choi, J.S., 2017. Characterization of the inhibitory activity of natural tanshinones from Salvia miltiorrhiza roots on protein tyrosine phosphatase 1B. Chem. Biol. Interact. 278, 65-73. https://doi.org/10.1016/j.cbi.2017.10.013.
- Kou, Y.-X., Xiao, K., Lai, X.-R., Wang, Y.-J., Zhang, Z.-Y., 2017. Natural hybridization between Torreya jackii and T. grandis (Taxaceae) in southeast China. J. Systemat. Evol. 55, 25-33. https://doi.org/10.1111/jse.12217.
- Lange, B.M., Conner, C.F., 2021. Taxanes and taxoids of the genus Taxus-A comprehensive inventory of chemical diversity. Phytochemistry 190, 112829. https://doi.org/10.1016/j.phytochem.2021.112829.
- Lee, J.C., Yang, X.S., Schwartz, M., Strobel, G., Clardy, J., 1995. The relationship between an endangered North American tree and an endophytic fungus. Chem. Biol. 2, 721-727. https://pubmed.ncbi.nlm.nih.gov/9383479.
- Lee, W.S., Kim, J.-R., Han, J.-M., Jang, K.C., Sok, D.-E., Jeong, T.-S., 2006. Antioxidant activities of abietane diterpenoids isolated from Torreya nucifera leaves. J. Agric. Food Chem. 54, 5369-5374. https://doi.org/10.1021/jf060896c.
- Li, H., Liang, Y.-R., Chen, S.-X., Wang, W.-X., Zou, Y., Nuryyeva, S., Houk, K.N., Xiong, J., Hu, J.-F., 2020. Amentotaxins C-V, structurally diverse diterpenoids from the leaves and twigs of the vulnerable conifer Amentotaxus argotaenia and their cytotoxic effects. J. Nat. Prod. 83, 2129-2144. https://doi.org/10.1021/acs. jnatprod.0c00064.
- Li, J.-H., Cheng, H.-X., Liu, L.-L., Wang, X.-Y., Pan, T., Hong, X., 2018. The complete chloroplast genome sequence of an endangered plant Torreya jackii (Pinales, Taxaceae). Conserv. Genet. Resour. 10, 487-489. https://10.1007/s12686-017-0 855-5.
- Li, J.H., Davis, C.C., Donoghue, M.J., Kelley, S., Del Tredici, P., 2001. Phylogenetic relationships of Torreya (Taxaceae) inferred from sequences of nuclear ribosomal DNA ITS region. Harv. Pap. Bot. 6, 275-281.
- Li, J.-H., Jin, Z.-X., Li, J.-M., 2007. Genetic diversity of endangered plant Torreya jackii: a study with RAPD markers. Chin. J. Appl. Ecol. 18, 2661-2667.
- Li, J.M., Jin, Z.-X., 2007. Genetic variation and differentiation in Torreya jackii Chun, an endangered plant endemic to China. Plant Sci. 172, 1048-1053. https://doi.org/ 10.1016/j.plantsci.2007.02.009.
- Li, W.-S., McChesne, J.D., 1992. Preparation of potential anti-inflammatory agents from dehydroabietic acid. J. Pharm. Sci-US. 81, 646-651. https://pubmed.ncbi.nlm.nih. gov/1403697.
- Lin, S.-J., Short, R.E., Ford, S.P., Grings, E.E., Rosazza, J.P.N., 1998. In vitro biotransformations of isocupressic acid by cow rumen preparations: formation of agathic and dihydroagathic acids. J. Nat. Prod. 61, 51-56. https://doi.org/10.1021/ NP970372U.
- Liu, M.X., Veryser, C., Lu, J.-G., Wenseleers, T., De Borggraeve, W.M., Jiang, Z.-H., Luyten, W., 2018. Bioassay-guided isolation of active substances from Semen Torreyae identifies two new anthelmintic compounds with novel mechanism of action. J. Ethnopharmacol. 224, 421-428. https://doi.org/10.1016/j. jep.2018.06.026.
- Ma, G.-L., Guo, N., Wang, X.-L., Li, J.M., Jin, Z.-X., Han, Y.Q., Dong, S.-Z., Xiong, J., Hu, J.-F., 2020. Cytotoxic secondary metabolites from the vulnerable conifer Cephalotaxus oliveri and its associated endophytic fungus Alternaria alternate Y-4-2. Bioorg. Chem. 105, 104445. https://doi.org/10.1016/j.bioorg.2020.104445.
- McLachlan, J.S., Hellmann, J.J., Schwartz, M.W., 2007. A framework for debate of assisted migration in an era of climate change. Conserv. Biol. 21, 297-302. https://pubmed.ncbi.nlm.nih.gov/17391179.
- Ohmoto, T., Kanatani, K., Yamaguchi, K., 1987a. Constituent of pollen. XIII. Constituents of Cedrus deodara loud. (2). Chem. Pharm. Bull. 35, 229-234. https://doi.org/ 10.1248/cpb.35.229.
- Ohmoto, T., Saito, M., Yamaguchi, K., 1987b. Constituents of pollen. XIV. Constituents of Cedrus deodara loud. (3). Chem. Pharm. Bull. 35, 2443-2447. https://doi.org/ 10.1248/cpb.35.2443.
- Orihara, Y., Yang, J.-W., Komiya, N., Koge, K., Yoshikawa, T., 2002. Abietane diterpenoids from suspension cultured cells of Torreya nucifera var. radicans. Phytochemistry 59, 385-389. https://doi.org/10.1016/S0031-9422(01)00390-9.
- Pascual Teresa, J. de, Barrero, A.F., Muriel, L., San Feliciano, A., Grande, M., 1980. New natural diterpene acids from Juniperus communis. Phytochemistry 19, 1153-1156. https://doi.org/10.1016/0031-9422(80)83074-3.
- Shin, S., Kim, S.-C., Hong, K.N., Kang, H., Lee, J.-W., 2019. The complete chloroplast genome of Torreya nucifera (Taxaceae) and phylogenetic analysis. Mitochondrial DNA B 4, 2537-2538. https://pubmed.ncbi.nlm.nih.gov/33365615.
- Tanaka, R., Ohtsu, H., Matsunaga, S., 1997. Abietane diterpene acids and other constituents from the leaves of Larix kaempferi. Phytochemistry 46, 1051-1057. https://doi.org/10.1016/S0031-9422(97)84396-8.
- Tian, X.-D., Min, Z.-D., Xie, N., Lei, Y., Tian, Z.-Y., Zheng, Q.-T., Xu, R.-N., Tanaka, T., Iinuma, M., Mizuno, M., 1993. Abietane diterpenes from Clerodendron cyrtophyllum. Chem. Pharm. Bull. 41, 1415-1417. https://doi.org/10.1248/cpb.41.1415.
- Tong, X., Li, J.H., Jiang, K., Li, Y.Y., Liu, C.N., Biswas, S., Wang, R., Chen, X.Y., 2021. Back to the brink: phylogeography and demographic history of the endangered Torreya jackii. J. Systemat. Evol. https://doi:10.1111/jse.12728.
- Wakil, S.J., Abu-Elheiga, L.A., 2009. Fatty acid metabolism: target for metabolic syndrome. J. Lipid Res. 50, S138-S143. https://doi.org/10.1194/jlr.R800079- JLR200.
- Wang, B., Ju, J., He, X.-F., Yuan, T., Yue, J.-M., 2010. Three new terpenoids from Pinus yunnanensis. Helv. Chim. Acta 93, 490-496. https://doi.org/10.1002/ hlca.200900238.
- Wang, Q., Rong, Z., Teng, J., Takaishi, Y., Duan, H.Q., 2008. Two new antitumor diterpenes from Pinus Sylvestris. Chin. Chem. Lett. 19, 187-189. https://doi.org/ 10.1016/j.cclet.2007.11.028.
- Wang, Y.-F., Shi, Q.-W., Dong, M., Kiyota, H., Gu, Y.-C., Cong, B., 2011. Natural taxanes: developments since 1828. Chem. Rev. 111, 7652-7709. https://doi.org/10.1021/ cr100147u.
- Wang, Y.-J., Xiao, K., Kou, Y.-X., 2019. Torreya jackii (Taxaceae): a special species that is genetically admixed, morphologically distinct, and geographically sympatric with parent species. Forests 10, 174. https://doi: 10.3390/f10020174.
- Wei, W.-J., Zhou, P.-P., Lin, C.-J., Wang, W.-F., Li, Y., Gao, K., 2017. Diterpenoids from Salvia miltiorrhiza and their immune-modulating activity. J. Agric. Food Chem. 65, 5985-5993. https://doi.org/10.1021/acs.jafc.7b02384.
- Wu, L., Li, Y.-L., Li, S.-M., Yang, X.-W., Xia, J.-H., Zhou, L., Zhang, W.-D., 2010. Systematic phytochemical investigation of Abies spectabilis. Chem. Pharm. Bull. 58, 1646-1649. https://doi.org/10.1248/cpb.58.1646.
- Xiong, J., Hu, C.-L., Wang, P.-P., Gao, D.-D., Huang, F., Li, J., Hu, J.-F., 2020. Spirobiflavonoid stereoisomers from the endangered conifer Glyptostrobus pensilis and their protein tyrosine phosphatase 1B inhibitory activity. Bioorg. Med. Chem. Lett 30, 126943. https://doi.org/10.1016/j.bmcl.2019.126943.
- Xiong, J., Zhou, P.-J., Jiang, H.-W., Huang, T., He, Y.-H., Zhao, Z.-Y., Zang, Y., Choo, Y.- M., Wang, X., Chittiboyina, A.G., Pandey, P., Hamann, M.T., Li, J., Hu, J.-F., 2021. Forrestiacids A and B, pentaterpene inhibitors of ACL and lipogenesis: extending the limits of computational NMR methods in the structure assignment of complex natural products. Angew. Chem. Int. Ed. 60, 22270-22275. https://doi.org/ 10.1002/anie.202109082.
- Zhang, H.-F., Zheng, X.-L., Wang, L., Xu, B.-Y., Yao, G.-D., Guo, R.-X., Shi, Q.-W., 2014. Abietane, labdane, and pimarane diterpenoids from the pulp of Torreya nucifera. Chem. Nat. Compd. 50, 165-168. https://doi.org/10.1007/s10600-014-0902-3.
- Zhang, X., Zhang, H.-J., Landis, J.B., Deng, T., Meng, A.-P., Sun, H., Peng, Y.-S., Wang, H.-C., Sun, Y.-X., 2019. Plastome phylogenomic analysis of torreya (Taxaceae). J. Systemat. Evol. 57, 607-615. https://doi.org/10.1111/jse.12482.
- Zhou, P.-J., Zang, Y., Li, C., Yuan, L., Zeng, H.Q., Li, J., Hu, J.-F., Xiong, J., 2021. Forrestiacids C and D, unprecedented michael adducts from the vulnerable Asian douglas-fir pseudotsuga forrestii. Chin. Chem. Lett. (Ms. CCLET-. https://doi.org/ 10.1016/j.cclet.2021.12.009. D-21-02313R1) (in press).
- Zhu, F., Qin, C., Tao, L., Liu, X., Shi, Z., Ma, X., Jia, J., Tan, Y., Cui, C., Lin, J., Tan, C., Jiang, Y., Chen, Y., 2011. Clustered patterns of species origins of nature-derived drugs and clues for future bioprospecting. Proc. Natl. Acad. Sci. U.S.A. 108, 12943-12948. https://doi.org/10.1073/pnas.1107336108.