Citation:
Wei-Xia Song, Qing-Lan Guo, Yong-Chun Yang, Jian-Gong Shi. Two homosecoiridoids from the fl ower buds of Lonicera japonica[J]. Chinese Chemical Letters,
;2015, 26(5): 517-521.
doi:
10.1016/j.cclet.2014.11.035
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Two new homosecoiridoids, named loniaceticiridoside (1) and lonimalondialiridoside (2), were isolated from an aqueous extract of the flower buds of Lonicera japonica. Their structures including the absolute configuration were determined by extensive spectroscopic studies, especially by 2D NMR and CD data analysis. A proposed biosynthetic pathway and preliminary investigations of the biological activity of compounds 1 and 2 are also discussed.
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-
-
[1]
[1] Jiangsu New Medical College, Dictionary of Traditional Chinese Medicine, Shanghai Science and Technology Publishing House, Shanghai, 1977, pp. 1403-1405.
-
[2]
[2] R.W. Teng, D.Z. Wang, C.X. Chen, Two triterpenoid saponins from Lonicera japonica, Chin. Chem. Lett. 11 (2000) 337-340.
-
[3]
[3] R. Kakuda, M. Imai, Y. Yaoita, M. Koichi, K. Masao, Secoiridoid glycosides from the flower buds of Lonicera japonica, Phytochemistry 55 (2000) 879-881.
-
[4]
[4] C.W. Choi, H.A. Jung, S.S. Kang, J.S. Choi, Antioxidant constituents and a new triterpenoid glycoside from Flos Lonicerae, Arch. Pharm. Res. 30 (2007) 1-7.
-
[5]
[5] D.Q. Yu, R.Y. Chen, L.J. Huang, et al., The structure and absolute configuration of Shuangkangsu: a novel natural cyclic peroxide from Lonicera japonica (Thunb.), J. Asian Nat. Prod. Res. 10 (2008) 851-856.
-
[6]
[6] L.M. Lin, X.G. Zhang, J.J. Zhu, et al., Two new triterpenoid saponins from the flowers and buds of Lonicera japonica, J. Asian Nat. Prod. Res. 10 (2008) 925-929.
-
[7]
[7] E.J. Lee, J.S. Kim, H.P. Kim, J.H. Lee, S.S. Kang, Phenolic constituents from the flower buds of Lonicera japonica and their 5-lipoxygenase inhibitory activities, Food Chem. 120 (2010) 134-139.
-
[8]
[8] Z.F. Zheng, Q.J. Zhang, R.Y. Chen, D.Q. Yu, Four new N-contained iridoid glycosides from flower buds of Lonicera japonica, J. Asian Nat. Prod. Res. 14 (2012) 729-737.
-
[9]
[9] M.H. Chen, L. Lin, L. Li, et al., Enantiomers of an indole alkaloid containing unusual dihydrothiopyran and 1,2,4-thiadiazole rings from the root of Isatis indigotica, Org. Lett. 14 (2012) 5668-5671.
-
[10]
[10] Y. Tian, Q.L. Guo, W.D. Xu, et al., A minor diterpenoid with a new 6/5/7/3 fusedring skeleton from Euphorbia micractina, Org. Lett. 16 (2014) 3950-3953.
-
[11]
[11] W.D. Xu, Y. Tian, Q.L. Guo, Y.C. Yang, J.G. Shi, Secoeuphoractin, a minor diterpenoid with a new skeleton from Euphorbia micractina, Chin. Chem. Lett. 25 (2014) 1531-1534.
-
[12]
[12] W.X. Song, S. Li, S.J. Wang, et al., Pyridinium alkaloid-coupled secoiridoids from the flower buds of Lonicera japonica, J. Nat. Prod. 71 (2008) 922-925.
-
[13]
[13] Y. Yu, W.X. Song, C.G. Zhu, et al., Homosecoiridoids from the flower buds of Lonicera japonica, J. Nat. Prod. 74 (2011) 2151-2160.
-
[14]
[14] Y. Yu, C.G. Zhu, S.J. Wang, et al., Homosecoiridoid alkaloids with amino acid units from the flower buds of Lonicera japonica, J. Nat. Prod. 76 (2013) 2226-2233.
-
[15]
[15] W.X. Song, Y.C. Yang, J.G. Shi, Two new β-hydroxy amino acid-coupled secoiridoids from the flower buds of Lonicera japonica: isolation, structure elucidation, semisynthesis, and biological activities, Chin. Chem. Lett. 25 (2014) 1215-1219.
-
[16]
[16] Z.B. Jiang, W.X. Song, J.G. Shi, Two new 1-(6'-O-acyl-β-D-glucopyranosyl)pyridinium- 3-carboxylates from the flower buds of Lonicera japonica, Chin. Chem. Lett. 26 (2015) 69-72.
-
[17]
[17] F. Wang, Y.P. Jiang, X.L. Wang, et al., Aromatic glycosides from the flower buds of Lonicera japonica, J. Asian Nat. Prod. Res. 15 (2013) 492-501.
-
[18]
[18] F. Wang, Y.P. Jiang, X.L. Wang, et al., Chemical constituents from flower buds of Lonicera japonica, China J. Chin. Mater. Med. 38 (2013) 1378-1385.
-
[19]
[19] N. Harada, K. Nakanishi, Determining the chiralities of optically active glycols, J. Am. Chem. Soc. 91 (1969) 3989-3991.
-
[20]
[20] M. Koreeda, N. Harada, K. Nakanishi, Exciton chirality methods as applied to conjugated enones, esters, and lactones, J. Am. Chem. Soc. 96 (1974) 266-268.
-
[21]
[21] A. Itoh, K. Fujii, S. Tomatsu, et al., Six secoiridoid glucosides from Adina racemosa, J. Nat. Prod. 66 (2003) 1212-1216.
-
[22]
[22] A. Itoh, N. Oya, E. Kawaguchi, et al., Secoiridoid glucosides from Strychnos spinosa, J. Nat. Prod. 68 (2005) 1434-1436.
-
[23]
[23] L.F. Tietze, C. Bärtels, Synthesis of bridged homoiridoids from secologanin by tandem-Knoevenagel-hetero-Diels-Alder reactions, Liebigs Ann. Chem. 1991 (1991) 155-160.
-
[24]
[24] Y. Kashiwada, Y. Omichi, S. Kurimoto, et al., Conjugates of a secoiridoid glucoside with a phenolic glucoside from the flower buds of Lonicera japonica Thunb, Phytochemistry 96 (2013) 423-429.
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