Published January 31, 2023
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Monoterpenoid acylphloroglucinols from Hypericum hengshanense W. T. Wang with antiproliferative activities
Authors/Creators
- 1. * & Key Laboratory of Ecology and Environment in Minority Areas (Minzu University of China), National Ethnic Affairs Commission, Beijing, 100081, People's Republic of China & * & College of Life and Environmental Sciences, Minzu University of China, Beijing, 100081, People's Republic of China
Description
Zhang, Ruifei, Cheng, Zhuo, Fang, Qiong, Kennelly, Edward J., Long, Chunlin (2023): Monoterpenoid acylphloroglucinols from Hypericum hengshanense W. T. Wang with antiproliferative activities. Phytochemistry (113500) 205: 1-8, DOI: 10.1016/j.phytochem.2022.113500, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113500
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- LSID
- urn:lsid:plazi.org:pub:631CFFE83D3B0563FFC2FFF4035CFFD0
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- http://publication.plazi.org/id/631CFFE83D3B0563FFC2FFF4035CFFD0
References
- Athanasas, K., Magiatis, P., Fokialakis, N., Skaltsounis, A.L., Pratsinis, H., Kletsas, D., 2004. Hyperjovinols A and B: two new phloroglucinol derivatives from Hypericum jovis with antioxidant activity in cell cultures. J. Nat. Prod. (Lloydia) 67 (6), 973-977. https://doi.org/10.1021/np034051w.
- Bridi, H., de Carvalho Meirelles, G., von Poser, G.L., 2018. Structural diversity and biological activities of phloroglucinol derivatives from Hypericum species. Phytochemistry 155, 203-232. https://doi.org/10.1016/j.phytochem.2018.08.002.
- Bruhn, T., Schaumloffel ¨, A., Hemberger, Y., Bringmann, G., 2013. SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality 25 (4), 243-249. https://doi.org/10.1002/chir.22138.
- Fobofou, S.A.T., Franke, K., Sanna, G., Porzel, A., Bullita, E., La Colla, P., Wessjohann, L. A., 2015. Isolation and anticancer, anthelminthic, and antiviral (HIV) activity of acylphloroglucinols, and regioselective synthesis of empetrifranzinans from Hypericum roeperianum. Bioorg. Med. Chem. 23 (19), 6327-6334. https://doi.org/ 10.1016/j.bmc.2015.08.028.
- Fuentes, R.G., Pearce, K.C., Du, Y., Rakotondrafara, A., Valenciano, A.L., Cassera, M.B., Rasamison, V.E., Crawford, T.D., Kingston, D.G., 2018. Phloroglucinols from the roots of Garcinia dauphinensis and their antiproliferative and antiplasmodial activities. J. Nat. Prod. (Lloydia) 82 (3), 431-439. https://doi.org/10.1021/acs. jnatprod.8b00379.
- Han, Q., Shu, G., Cheng, H., Wang, S., Zhou, T., Zhou, X., Sefidkon, F., Hossseini, M.M.Z., Yang, X., 2022. New aclyphloroglucinols and geranyl-α- pyrones from Hypericum hengshanense. Fitoterapia 105253. https://doi.org/10.1016/j.fitote.2022.105253.
- Jefford, C.W., Jaggi, D., Bernardinelli, G., Boukouvalas, J., 1987. The synthesis of (± )-cavernosine. Tetrahedron Lett. 28 (35), 4041-4044. https://doi.org/10.1016/ S0040-4039(01)83856-9.
- Li, Q.J., Tang, P.F., Zhou, X., Lu, W.J., Xu, W.J., Luo, J., Kong, L.Y., 2020. Dimethylated acylphloroglucinol meroterpenoids with anti-oral-bacterial and anti-inflammatory activities from Hypericum elodeoides. Bioorg. Chem. 104, 104275 https://doi.org/ 10.1016/j.bioorg.2020.104275.
- Liu, X.Z., Zhou, M., Du, C.C., Zhu, H.H., Lu, X., He, S.L., Chen, H.F., 2021. Unprecedented monoterpenoid polyprenylated acylphloroglucinols with a rare 6/6/5/4 tetracyclic core, enhanced MCF-7 cells' sensitivity to camptothecin by inhibiting the DNA damage response. Biomedicines 9 (10), 1473. https://doi.org/10.3390/ biomedicines9101473.
- Mamemura, T., Tanaka, N., Shibazaki, A., Gonoi, T., Kobayashi, J.I., 2011. Yojironins A D, meroterpenoids and prenylated acylphloroglucinols from Hypericum yojiroanum. Tetrahedron Lett. 52 (28), 3575-3578. https://doi.org/10.1016/j. tetlet.2011.04.106.
- Pearce, K.C., Fuentes, R.G., Calderon, S., Marolikar, R., Kingston, D.G., Crawford, T.D., 2021. Structure elucidation and confirmation of phloroglucinols from the roots of Garcinia dauphinensis by comparison of experimental and calculated ECD spectra and specific rotations. J. Nat. Prod. (Lloydia) 84 (4), 1163-1174. https://doi.org/ 10.1021/acs.jnatprod.0c01208.
- Robson, N.K.B., 2016. And then came molecular phylogenetics-reactions to a monographic study of Hypericum (Hypericaceae). Phytotaxa 255 (3), 181-198. https://doi.org/10.11646/PHYTOTAXA.255.3.1.
- Reed, L.J., Muench, H., 1938. A simple method of estimating fifty per cent endpoints. Am. J. Epidemiol. 27 (3), 493-497. https://doi.org/10.1093/oxfordjournals.aje. a118408.
- Robson, N.K.B., 2001. Studies in the genus Hypericum L.(Guttiferae) 4 (1). Sections 7. Roscyna to 9. Hypericum sensu lato (part 1). Bull. Nat. Hist. Mus. Land. (Bot) 31 (2), 37-88.
- Schmidt, S., Jurgenliemk, G., Schmidt, T.J., Skaltsa, H., Heilmann, J.R., 2012a. Bi-, tri-, and polycyclic acylphloroglucinols from Hypericum empetrifolium. J. Nat. Prod. (Lloydia) 75 (10), 1697-1705. https://doi.org/10.1021/np300237n.
- Schmidt, S., Jurgenliemk, G., Skaltsa, H., Heilmann, J., 2012b. Phloroglucinol derivatives from Hypericum empetrifolium with antiproliferative activity on endothelial cells. Phytochemistry 77, 218-225. https://doi.org/10.1016/j. phytochem.2011.11.014.
- Shi, Z., Tan, X., Hu, H., Zhang, N., Duan, Y., Guo, Y., Feng, H., Sun, L., Chen, G., Qi, C., Zhang, Y., 2022. Discovery of undescribed monoterpenoid polyprenylated acylphloroglucinols with immunosuppressive activities from Hypericum longistylum. Phytochemistry 198, 113173. https://doi.org/10.1016/j.phytochem.2022.113173.
- Wang, P., Henning, S.M., Heber, D., 2010. Limitations of MTT and MTS-based assays for measurement of antiproliferative activity of green tea polyphenols. PLoS One 5 (4), e10202. https://doi.org/10.1371/journal.pone.0010202.
- Wang, Q., Xu, F.F., 2013. Chemical constituents of ethyl acetate fraction from Hypericum hengshanense. J. Chin. Med. Mater. 36 (10), 1611-1613. https://doi.org/10.13863/j. issn1001-4454.2013.10.023.
- Yang, X.W., Grossman, R.B., Xu, G., 2018. Research progress of polycyclic polyprenylated acylphloroglucinols. Chem. Rev. 118 (7), 3508-3558. https://doi. org/10.1021/acs.chemrev.7b00551.
- Zhang, R., Ji, Y., Morcol, T., Lin, F., Gu, R., Kennelly, E.J., Long, C., 2021. UPLC-QTof-MS chemical profiling and characterization of antiproliferative and anti-inflammatory compounds from seven Hypericum species in China. Ind. Crop. Prod. 173, 114156 https://doi.org/10.1016/j.indcrop.2021.114156.
- Zhang, R., Ji, Y., Zhang, X., Kennelly, E.J., Long, C., 2020. Ethnopharmacology of Hypericum species in China: a comprehensive review on ethnobotany, phytochemistry and pharmacology. J. Ethnopharmacol. 254, 112686 https://doi. org/10.1016/j.jep.2020.112686.