Published December 31, 2021
| Version v1
Journal article
Restricted
Prenylated C -C derivatives from the stems and branches of Illicium ternstroemioides A. C. Smith with antiviral activity
Creators
- 1. * & State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union
Description
Zhang, Jian-Pei, Li, Wen-Rui, Wu, Shuo, Wang, Xiao-Jing, Wang, Ru-Bing, Li, Mi, Su, Guo-Zhu, Wang, Hai-Qiang, Yong, Jin-Yao, Yang, Jia, Li, Li, Li, Yu-Huan, Ma, Shuang-Gang (2021): Prenylated C -C derivatives from the stems and branches of Illicium ternstroemioides A. C. Smith with antiviral activity. Phytochemistry (112935) 192: 1-11, DOI: 10.1016/j.phytochem.2021.112935, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112935
Files
Linked records
Additional details
Identifiers
- LSID
- urn:lsid:plazi.org:pub:F76AFFACFFB0CB05FFB1FF8C1242FFD6
References
- Duan, L., Huang, J.M., Yang, C.S., Ma, C.H., 2006. Chemical characteristics of pericarp of Illicium temstroemioides. Chin. Pharmaceut. J. 41, 411-412. https://doi.org/10.3321/ j.issn:1001-2494.2006.06.004.
- Fang, Z.F., Zhang, G.J., Chen, H., Bai, J., Yu, S.S., Liu, Y., Wang, W.J., Ma, S.G., Qu, J., Xu, S., 2013. Diterpenoids and sesquiterpenoids from the twigs and leaves of Illicium majus. Planta Med. 79, 142-149. https://doi.org/10.1055/s-0032-1328056.
- Fukuyama, Y., Shida, N., Hata, Y., Kodama, M., 1994. Prenylated C6-C3 compounds from Illicium tashiroi. Phytochemistry 36, 1497-1503. https://doi.org/10.1016/S0031- 9422(00)89750-2.
- Fukuyama, Y., Shida, N., Kodama, M., Chaki, H., Yugami, T., 1995. Tricycloillicinone, a novel prenylated C6-C3 compounds increasing choline acetyltransferase (ChAT) activity, isolated from Illicium tashiroi. Chem. Pharm. Bull. 43, 2270-2272. https:// doi.org/10.1248/cpb.43.2270.
- Fukuyama, Y., Shida, N., Sakurai, T., Kodama, M., 1992. Prenylated C6-C3 compounds from Illicium tashiroi. Phytochemistry 31, 3975-3979. https://doi.org/10.1016/ s0031-9422(00)97566-6.
- Gawronski, J.K., 1982. Circular dichroism and stereochemistry of chiral conjugated cyclohexenones. Tetrahedron 38, 3-26. https://doi.org/10.1016/0040-4020(82) 85040-0.
- Kouno, I., Shigeko, S., Jiang, Z.H., Tanaka, T., 1997. Prenylated C6-C3 compounds from root bark of Illicium anisatum. Phytochemistry 46, 1389-1392. https://doi.org/ 10.1016/S0031-9422(97)00483-4.
- Lin, Q., 2001a. Taxonomy of the genus Illicium linn. Bull. Bot. Res. 21, 161-174. https:// doi.org/10.3969/j.issn.1673-5102.2001.02.001.
- Lin, Q., 2001b. Taxonomy of the genus Illicium linn. Bull. Bot. Res. 21, 321-334. https:// doi.org/10.3969/j.issn.1673-5102.2001.03.001.
- Liu, Y.L., Li, W.R., Wang, X.J., Wang, R.B., Li, M., Zhang, J.P., Yong, J.Y., Bao, X.Q., Zhang, D., Ma, S.G., 2020. Highly oxidized sesquiterpenes from the fruits of Illicium lanceolatum. A. C. Smith. Phytochem. 172, 112281. https://doi.org/10.1016/j. phytochem.2020.112281.
- Ma, S.G., Gao, R.M., Li, Y.H., Jiang, J.D., Gong, N.B., Li, L., Lu, Y., Tang, W.Z., Liu, Y.B., Qu, J., Lu, H.N., Li, Y., Yu, S.S., 2013. Antiviral spirooliganones A and B with unprecedented skeletons from the roots of Illicium oligandrum. Org. Lett. 15, 4450-4453. https://doi.org/10.1021/ol401992s.
- Ma, S.G., Gao, Y., Wang, H.Q., Li, L., Liu, Y.B., Qu, J., Li, Y., Xu, S., Lv, H.N., Li, Y.H., Yu, S.S., 2016. Antiviral mono- and bis-prenylated C6-C3 derivatives from the roots of Illicium oligandrum. Tetrahedron 72, 3003-3013. https://doi.org/10.1016/j. tet.2016.04.016.
- Ma, S.G., Tang, W.Z., Liu, Y.X., Hu, Y.C., Yu, S.S., Zhang, Y., Chen, X.G., Qu, J., Ren, J.H., Liu, Y.B., Xu, S., Liu, J., Liu, Y.Y., Li, Y., Lu, H.N., Wu, X.F., 2011. Prenylated C6-C3 compounds with molecular diversity from the roots of Illicium oligandrum. Phytochemistry 72, 115-125. https://doi.org/10.1016/j.phytochem.2010.10.021.
- Schievano, E., Morelato, E., Facchin, C., Mammi, S., 2013. Characterization of markers of botanical origin and other compounds extracted from unifloral honeys. J. Agric. Food Chem. 61, 1747-1755. https://doi.org/10.1021/jf302798d.
- Song, L.Y., Yao, H.L., Tong, R.B., 2014. Biomimetic asymmetric total syntheses of spirooliganones A and B. Org. Lett. 16, 3740-3743. https://doi.org/10.1021/ ol501593m.
- Su, G.Z., Wang, R.B., Li, Y., Li, L., Liu, Y.B., Qu, J., Li, Y.H., Zhang, D., Yu, D.Q., Ma, S.G., Yu, S.S., 2021. Bioactive prenylated C6-C3 derivatives from the stems and leaves of Illicium fargesii. Bioorg. Chem. 110, 104734. https://doi.org/10.1016/j. bioorg.2021.104734.
- Takaoka, S., Takaoka, N., Minoshima, Y., Huang, J.M., Kubo, M., Harada, K., Hioki, H., Fukuyama, Y., 2009. Isolation, synthesis, and neurite outgrowth-promoting activity of illicinin A from the flowers of Illicium anisatum. Tetrahedron 65, 8354-8361. https://doi.org/10.1016/j.tet.2009.08.015.
- Tang, W.Z., Ma, S.G., Qu, J., Yu, S.S., Liu, Y.B., Su, D.M., Liu, J., 2011. Dimeric prenylated C6-C3 compounds from the stem bark of Illicium oligandrum. J. Nat. Prod. 74, 1268-1271. https://doi.org/10.1021/np100651n.
- Tang, W.Z., Ma, S.G., Yu, S.S., Qu, J., Liu, Y.B., Liu, J., 2009. Rearranged prenylated C6- C3 compounds and a highly oxygenated seco -prezizaane-type sesquiterpene from the stem bark of Illicium oligandrum. J. Nat. Prod. 72, 1017-1021. https://doi.org/ 10.1021/np9001702.
- Todoroki, Y., Hirai, N., Koshimizu, K., 1994. 8'- and 9'-Methoxyabscisic acids as antimetabolic analogs of abscisic acid. Biosci. Biotechnol. Biochem. 58, 707-715. https://doi.org/10.1271/bbb.58.707.
- Wang, R.B., Ma, S.G., Jamieson, C.S., Gao, R.M., Liu, Y.B., Li, Y., Wang, X.J., Li, Y.H., Houk, K.N., Qu, J., Yu, S.S., 2021. Library construction of stereochemically diverse isomers of spirooliganin: their total synthesis and antiviral activity. Chem. Sci. 2021 (12), 7003-7011. https://doi.org/10.1039/D1SC01277K.
- Wang, Y.X., Li, Y.H., Li, Y.H., Gao, R.M., Wang, H.Q., Liu, Y.X., Gao, L.M., Lu, Q.N., Jiang, J.D., Song, D.Q., 2011. Synthesis, structure-activity relationship and in vitro biological evaluation of N-arylethyl isoquinoline derivatives as coxsackievirus B3
- Wei, L., Xiao, M.X., Xie, Z.X., 2014. Total syntheses of ( )-spirooliganones A and B. Org. Lett. 16, 2784-2786. https://doi.org/10.1055/s-0034-1379081.
- Xi, F.M., Ma, S.G., Liu, Y.B., Li, L., Yu, S.S., 2016. Artaboterpenoids A and B, bisabolenederived sesquiterpenoids from Artabotrys hexapetalus. Org. Lett. 18, 3374-3377. https://doi.org/10.1021/acs.orglett.6b01519.
- Yakushijin, K., Tohshima, T., Kitagawa, E., Suzuki, R., Sekikawa, J., Morishita, T., Murata, H., Lu, S.T., Furukawa, H., 1984. Studies on the constituents of the plants of Illicium species. III. structure elucidations of novel phytoquinoids, illicinones and illifunones from Illicium tashiroi MAXIM. and I. arborescens. HAYATA. Chem. Pharm. Bull. 32, 11-22. https://doi.org/10.1248/cpb.32.11.
- Zhao, N., Ren, X.D., Ren, J.H., Lu, H.N., Ma, S.G., Gao, R.M., Li, Y.H., Xu, S., Li, L., Yu, S. S., 2015. Total syntheses of ( )-spirooliganones A and B and their diastereoisomers: absolute stereochemistry and inhibitory activity against coxsackie virus. B3. Org.
- Zhuang, P.Y., Zhang, G.J., Wang, X.J., Zhang, Y., Yu, S.S., Ma, S.G., Liu, Y.B., Qu, J., Li, Y., Xu, S., Lu, H.N., Chen, X., Li, L., Si, Y.K., Zhang, D., 2013. Prenylated C6-C3 compounds from the roots of Illicium henryi. Phytochemistry 86, 176-183. https:// doi.org/10.1016/j.phytochem.2012.10.002.