Two new β-hydroxy amino acid-coupled secoiridoids from the fl ower buds of Lonicera japonica:Isolation, structure elucidation, semisynthesis, and biological activities

Wei-Xia Song Yong-Chun Yang Jian-Gong Shi

Citation:  Wei-Xia Song, Yong-Chun Yang, Jian-Gong Shi. Two new β-hydroxy amino acid-coupled secoiridoids from the fl ower buds of Lonicera japonica:Isolation, structure elucidation, semisynthesis, and biological activities[J]. Chinese Chemical Letters, 2014, 25(9): 1215-1219. doi: 10.1016/j.cclet.2014.05.037 shu

Two new β-hydroxy amino acid-coupled secoiridoids from the fl ower buds of Lonicera japonica:Isolation, structure elucidation, semisynthesis, and biological activities

    通讯作者: Jian-Gong Shi,
  • 基金项目:

    Innovative Research Team in University (PCSIRT, No. IRT1007) (PCSIRT, No. IRT1007)

摘要: Two new β-hydroxy amino acid-coupled secoiridoids, named serinosecologanin (1) and threoninosecologanin (2), were isolated from an aqueous extract of the flower buds of Lonicera japonica. Their uncommon structures including absolute configurations were determined by spectroscopic data analysis, and confirmed by semisynthesis from the co-occurring secologanin (3) and secologanic acid (4). Compounds 1 and 2 exhibited resistant activity against β-glucosidase from almonds and hesperidinase from Aspergillus niger, they also showed activity against the release of glucuronidase in rat polymorphonuclear leukocytes induced by the platelet-activating factor with inhibition rates of (34.9±3.1)% and (53.6±2.6)%, respectively.

English

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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.[1] Jiangsu New Medical College, Dictionary of Traditional Chinese Medicine, Shanghai Science and Technology Publishing House, Shanghai, 1977, pp. 1403-1405.

    2. [2] R. Mehrotra, C. Singh, S.P. Popli, Isolation of secoxyloganin from Lonicera japonica and its conversion into secologanin, J. Nat. Prod. 51 (1988) 319-321.[2] R. Mehrotra, C. Singh, S.P. Popli, Isolation of secoxyloganin from Lonicera japonica and its conversion into secologanin, J. Nat. Prod. 51 (1988) 319-321.

    3. [3] H. Kawai, M. Kuroyanagi, A. Ueno, Iridoid glycosides from Lonicera japonica Thunb, Chem. Pharm. Bull. 36 (1988) 3664-3666.[3] H. Kawai, M. Kuroyanagi, A. Ueno, Iridoid glycosides from Lonicera japonica Thunb, Chem. Pharm. Bull. 36 (1988) 3664-3666.

    4. [4] K.H. Son, J.O. Park, K.C. Chung, et al., Flavonoids from the aerial parts of Lonicera japonica, Arch. Pharm. Res. 15 (1992) 365-370.[4] K.H. Son, J.O. Park, K.C. Chung, et al., Flavonoids from the aerial parts of Lonicera japonica, Arch. Pharm. Res. 15 (1992) 365-370.

    5. [5] L. Tomassini, M.F. Cometa, M. Serafini, M. Nicoletti, Isolation of secoiridoid artifacts from Lonicera japonica, J. Nat. Prod. 58 (1995) 1756-1758.[5] L. Tomassini, M.F. Cometa, M. Serafini, M. Nicoletti, Isolation of secoiridoid artifacts from Lonicera japonica, J. Nat. Prod. 58 (1995) 1756-1758.

    6. [6] R.W. Teng, D.Z. Wang, C.X. Chen, Two triterpenoid saponins from Lonicera japonica, Chin. Chem. Lett. 11 (2000) 337-340.[6] R.W. Teng, D.Z. Wang, C.X. Chen, Two triterpenoid saponins from Lonicera japonica, Chin. Chem. Lett. 11 (2000) 337-340.

    7. [7] R. Kakuda, M. Imai, Y. Yaoita, et al., Secoiridoid glycosides from the flower buds of Lonicera japonica, Phytochemistry 55 (2000) 879-881.[7] R. Kakuda, M. Imai, Y. Yaoita, et al., Secoiridoid glycosides from the flower buds of Lonicera japonica, Phytochemistry 55 (2000) 879-881.

    8. [8] C.W. Choi, H.A. Jung, S.S. Kang, et al., Antioxidant constituents and a new triterpenoid glycoside from Flos Lonicerae, Arch. Pharm. Res. 30 (2007) 1-7.[8] C.W. Choi, H.A. Jung, S.S. Kang, et al., Antioxidant constituents and a new triterpenoid glycoside from Flos Lonicerae, Arch. Pharm. Res. 30 (2007) 1-7.

    9. [9] 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.[9] 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.

    10. [10] 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.[10] 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.

    11. [11] C.Y. Chen, W.H. Peng, L.C. Wu, C.C. Wu, S.L. Hsu, Luteolin ameliorates experimental lung fibrosis both in vivo and in vitro: implications for therapy of lung fibrosis, J. Agric. Food Chem. 58 (2010) 11653-11661.[11] C.Y. Chen, W.H. Peng, L.C. Wu, C.C. Wu, S.L. Hsu, Luteolin ameliorates experimental lung fibrosis both in vivo and in vitro: implications for therapy of lung fibrosis, J. Agric. Food Chem. 58 (2010) 11653-11661.

    12. [12] 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.[12] 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.

    13. [13] Z.F. Zheng, Q.J. Zhang, R.Y. Chen, et al., Four new N-contained iridoid glycosides from flower buds of Lonicera japonica, J. Asian Nat. Prod. Res. 14 (2012) 729-737.[13] Z.F. Zheng, Q.J. Zhang, R.Y. Chen, et al., Four new N-contained iridoid glycosides from flower buds of Lonicera japonica, J. Asian Nat. Prod. Res. 14 (2012) 729-737.

    14. [14] 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.[14] 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.

    15. [15] 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.[15] 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.

    16. [16] 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.[16] 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.

    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.[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, Chin. J. Chin. Mater. Med. 38 (2013) 1378-1385.[18] F. Wang, Y.P. Jiang, X.L. Wang, et al., Chemical constituents from flower buds of Lonicera japonica, Chin. J. Chin. Mater. Med. 38 (2013) 1378-1385.

    19. [19] C. Bluchel, C.V. Ramana, A. Vasella, et al., Synthesis of monosaccharide-derived spirocyclic cyclopropylamines and their evaluation as glycosidase inhibitors, Helv. Chim. Acta 86 (2003) 2998-3036.[19] C. Bluchel, C.V. Ramana, A. Vasella, et al., Synthesis of monosaccharide-derived spirocyclic cyclopropylamines and their evaluation as glycosidase inhibitors, Helv. Chim. Acta 86 (2003) 2998-3036.

    20. [20] P. Marfey, Determination of D-amino acids II: use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene, Carlsberg Res. Commun. 49 (1984) 591-596.[20] P. Marfey, Determination of D-amino acids II: use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene, Carlsberg Res. Commun. 49 (1984) 591-596.

    21. [21] L.F. Tietze, C. Bä rtels, J. Fennen, Biomimetic synthesis of the monoterpene alkaloids xylostosidine and loxylostosidine A and of similar unnatural compounds by transformations of the monoterpene glycoside secologanin, Liebigs Ann. Chem. 1989 (1989) 1241-1245.[21] L.F. Tietze, C. Bä rtels, J. Fennen, Biomimetic synthesis of the monoterpene alkaloids xylostosidine and loxylostosidine A and of similar unnatural compounds by transformations of the monoterpene glycoside secologanin, Liebigs Ann. Chem. 1989 (1989) 1241-1245.

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  • 收稿日期:  2014-03-17
  • 网络出版日期:  2014-04-29
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