Hyperascyrones A-H, polyprenylated spirocyclic acylphloroglucinol derivatives from Hypericum ascyron Linn.

Phytochemistry

Volumn 115, Issue 1, 2015, Pages 222-230

  Zhu, Hucheng ^a   Chen, Chunmei ^a   Liu, Junjun ^a   Sun, Bin ^a   Wei, Guangzheng ^a   Li, Yan ^b   Zhang, Jinwen ^a   Yao, Guangmin ^a   Luo, Zengwei ^a   Xue, Yongbo ^a   Zhang, Yonghui ^a  

^a HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b KUNMING INSTITUTE OF BOTANY   (China)

Author keywords

Acylphloroglucinol derivatives; Acylphloroglucinols; Anti HIV 1 activities; Cytotoxic activities; Hypericaceae; Hypericum ascyron Linn.; Polycyclic polyprenylated; Polyprenylated spirocyclic

Indexed keywords

CLUSIACEAE; HUMAN IMMUNODEFICIENCY VIRUS 1; HYPERICUM ASCYRON;

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ANTINEOPLASTIC AGENT; HERBACEOUS AGENT; PHLOROGLUCINOL; SPIRO COMPOUND;

ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; DRUG SCREENING; HL 60 CELL LINE; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; HYPERICUM; IC50; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE;

ANTI-HIV AGENTS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; DRUG SCREENING ASSAYS, ANTITUMOR; DRUGS, CHINESE HERBAL; HIV-1; HL-60 CELLS; HUMANS; HYPERICUM; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PHLOROGLUCINOL; SPIRO COMPOUNDS;

EID: 84934950337     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2015.02.009     Document Type: Article

References (23)

1. Abe, S., Tanaka, N., Kobayashi, J., 2011. Prenylated acylphloroglucinols, chipericumins A-D, from Hypericum chinense. J. Nat. Prod. 75, 484-488.
2. Chen, X. Q., Li, Y., Li, K. Z., Peng, L. Y., He, J., Wang, K., Pan, Z. H., Cheng, X., Li, M. M., Zhao, Q. S., 2011. Spirocyclic acylphloroglucinol derivatives from Hypericum beanii. Chem. Pharm. Bull. 59, 1250-1253.
3. Ciochina, R., Grossman, R. B., 2006. Polycyclic polyprenylated acylphloroglucinols. Chem. Rev. 106, 3963-3986.
4. Force, R., Chen, S. L., Fortier, E., Rowlands, E., Heneks, J., Rovnyak, D., 2014. Spirocyclic acylphloroglucinol derivatives from Hypericum pyramidatum. Nat. Prod. Commun. 9, 961-964.
5. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J. A., Peralta, J. E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, K. N., Staroverov, V. N., Keith, T., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, J. M., Klene, M., Knox, J. E., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Martin, R. L., Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J. J., Dapprich, S., Daniels, A. D., Farkas, O., Foresman, J. B., Ortiz, J. V., Cioslowski, J., Fox, D. J., 2010. Gaussian 09, Revision C.01. Gaussian Inc., Wallingford, CT.
6. Hashida, W., Tanaka, N., Takaishi, Y., 2007. Prenylated xanthones from Hypericum ascyron. J. Nat. Med. 61, 371-374.
7. Hashida, W., Tanaka, N., Kashiwada, Y., Sekiya, M., Ikeshiro, Y., Takaishi, Y., 2008. Tomoeones A-H, cytotoxic phloroglucinol derivatives from Hypericum ascyron. Phytochemistry 69, 2225-2230.
8. Hu, L. H., Yip, S. C., Sim, K. Y., 1999. Xanthones from Hypericum ascyron. Phytochemistry 52, 1371-1373.
9. Jiang Su New Medical College, 1977. Dictionary of Chinese Crude Drugs. Scientific, Technological Publishers, Shanghai (p. 1002).
10. Li, D., Xue, Y., Zhu, H., Li, Y., Sun, B., Liu, J., Yao, G., Zhang, J., Du, G., Zhang, Y., 2015. Hyperattenins A-I, bioactive polyprenylated acylphloroglucinols from Hypericum attenuatum Choisy. RSC Adv. 5, 5277-5287.
11. Nör, C., Albring, D., Ferraz, A. B. F., Schripsema, J., Pires, V., Sonnet, P., Guillaume, D., Poser, G. L. V., 2004. Phloroglucinol derivatives from four Hypericum species belonging to the Trigynobrathys section. Biochem. Syst. Ecol. 32, 517-519.
12. O'Boyle, N. M., Vandermeersch, T., Flynn, C. J., Maguire, A. R., Hutchison, G. R., 2011. Confab-systematic generation of diverse low-energy conformers. J. Cheminformat. 3, 1-9.
13. Park, H. J., Kwon, S. H., Yun, S. Y., Lee, K. T., 2000. Isolation of steroids and flavonoids from the herbs of Hypericum ascyron L. Saengyak Hakhoechi 31, 39-44.
14. Richard, J. A., Pouwer, R. H., Chen, D. Y. K., 2012. The chemistry of the polycyclic polyprenylated acylphloroglucinols. Angew. Chem. Int. Ed. 51, 4536-4561.
15. Shu, P., Wei, X., Xue, Y., Li, W., Zhang, J., Xiang, M., Zhang, M., Luo, Z., Li, Y., Yao, G., 2013. Wilsonols A-L, megastigmane sesquiterpenoids from the Leaves of Cinnamomum wilsonii. J. Nat. Prod. 76, 1303-1312.
16. Singh, I. P., Bharate, S. B., 2006. Phloroglucinol compounds of natural origin. Nat. Prod. Rep. 23, 558-591.
17. Tomasi, J., Mennucci, B., Cammi, R., 2005. Quantum mechanical continuum solvation models. Chem. Rev. 105, 2999-3094.
18. Vainio, M. J., Johnson, M. S., 2007. Generating conformer ensembles using a multiobjective genetic algorithm. J. Chem. Inf. Model. 47, 2462-2474.
19. Verma, V., Smelcerovic, A., Zuehike, S., Hussain, M. A., Mudasir, S., Thorsten, A., Ziebach, T., Qazi, G. N., Spiteller, M., 2008. Phenolic constituents and genetic profile of Hypericum perforatum L.from India. Biochem. Syst. Ecol. 36, 201-206.
20. Wan, Z., Lu, Y., Liao, Q., Wu, Y., Chen, X., 2012. Fangchinoline inhibits human immunodeficiency virus type 1 replication by interfering with gp160 proteolytic processing. PLoS ONE 7, e39225.
21. Wu, C. C., Yen, M. H., Yang, S. C., Lin, C. N., 2008. Phloroglucinols with antioxidant activity and xanthonolignoids from the heartwood of Hypericum geminiflorum. J. Nat. Prod. 71, 1027-1031.
22. Yin, S., Chen, X., Su, Z. S., Yang, S. P., Fan, C. Q., Ding, J., Yue, J. M., 2009. Harrisotones A-E, five novel prenylated polyketides with a rare spirocyclic skeleton from Harrisonia perforata. Tetrahedron 65, 1147-1152.
23. Zhu, H., Chen, C., Yang, J., Li, X. N., Liu, J., Sun, B., Huang, S. X., Li, D., Yao, G., Luo, Z., Li, Y., Zhang, J., Xue, Y., Zhang, Y., 2014. Bioactive acylphloroglucinols with adamantyl skeleton from Hypericum sampsonii. Org. Lett. 16, 6322-6325.