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

1.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

Corresponding author: Jian-Gong Shi,
Received Date: 17 March 2014
Available Online: 29 April 2014
Fund Project:

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.
- Lonicera japonica,
- Caprifoliaceae,
- β-Hydroxy amino acid-coupled secoirridoid,
- Isolation,
- Structure elucidation,
- Semisynthesis,
- Biological activity
1. [1]
  [1] Jiangsu New Medical College, Dictionary of Traditional Chinese Medicine, Shanghai Science and Technology Publishing House, Shanghai, 1977, pp. 1403-1405.
2. [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.
3. [3]
  [3] H. Kawai, M. Kuroyanagi, A. Ueno, Iridoid glycosides from Lonicera japonica Thunb, Chem. Pharm. Bull. 36 (1988) 3664-3666.
4. [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.
5. [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.
6. [6]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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.
1. [1]
  Feng Wu , Xuemin Kong , Yixuan Liu , Shuli Wang , Zhong Chen , Xu Hou . Microfluidic-based isolation of circulating tumor cells with high-efficiency and high-purity. Chinese Chemical Letters, 2024, 35(8): 109754-. doi: 10.1016/j.cclet.2024.109754
2. [2]
  Chunmao Yuan , Yanrong Zeng , Lei Huang , Yu Mou , Jun Jin , Ping Yi , Yanmei Li , Xiaojiang Hao . Hymoins A–C, three unusual polycyclic polyprenylated acylphloroglucinols with lipid-lowering activity from Hypericum monogynum. Chinese Chemical Letters, 2025, 36(3): 109859-. doi: 10.1016/j.cclet.2024.109859
3. [3]
  Kun Zou , Yihang Xiao , Jinyu Yang , Mingxuan Wu . Facile semisynthesis of histone H3 enables nucleosome probes for investigation of histone H3K79 modifications. Chinese Chemical Letters, 2024, 35(10): 109497-. doi: 10.1016/j.cclet.2024.109497
4. [4]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
5. [5]
  Aimin Fu , Chunmei Chen , Qin Li , Nanjin Ding , Jiaxin Dong , Yu Chen , Mengsha Wei , Weiguang Sun , Hucheng Zhu , Yonghui Zhang . Niduenes A−F, six functionalized sesterterpenoids with a pentacyclic 5/5/5/5/6 skeleton from endophytic fungus Aspergillus nidulans. Chinese Chemical Letters, 2024, 35(9): 109100-. doi: 10.1016/j.cclet.2023.109100
6. [6]
  Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
7. [7]
  Wei Sun , Anjing Liao , Li Lei , Xu Tang , Ya Wang , Jian Wu . Research progress on piperidine-containing compounds as agrochemicals. Chinese Chemical Letters, 2025, 36(1): 109855-. doi: 10.1016/j.cclet.2024.109855
8. [8]
  Anjing Liao , Wei Sun , Yaming Liu , Han Yan , Zhi Xia , Jian Wu . Pyrrole and pyrrolidine analogs: The promising scaffold in discovery of pesticides. Chinese Chemical Letters, 2025, 36(3): 110094-. doi: 10.1016/j.cclet.2024.110094
9. [9]
  Ali Dai , Zhiguo Zheng , Liusheng Duan , Jian Wu , Weiming Tan . Small molecule chemical scaffolds in plant growth regulators for the development of agrochemicals. Chinese Chemical Letters, 2025, 36(4): 110462-. doi: 10.1016/j.cclet.2024.110462
10. [10]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
11. [11]
  Jian Song , Shenghui Wang , Qiuge Liu , Xiao Wang , Shuo Yuan , Hongmin Liu , Saiyang Zhang . N-Benzyl arylamide derivatives as novel and potent tubulin polymerization inhibitors against gastric cancers: Design, structure–activity relationships and biological evaluations. Chinese Chemical Letters, 2025, 36(2): 109678-. doi: 10.1016/j.cclet.2024.109678
12. [12]
  Yiyue Ding , Qiuxiang Zhang , Lei Zhang , Qilu Yao , Gang Feng , Zhang-Hui Lu . Exceptional activity of amino-modified rGO-immobilized PdAu nanoclusters for visible light-promoted dehydrogenation of formic acid. Chinese Chemical Letters, 2024, 35(7): 109593-. doi: 10.1016/j.cclet.2024.109593
13. [13]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
14. [14]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
15. [15]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
16. [16]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
17. [17]
  Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
18. [18]
  Yulin Mao , Jingyu Ma , Jiecheng Ji , Yuliang Wang , Wanhua Wu , Cheng Yang . Crown aldoxime ethers: Their synthesis, structure, acid-catalyzed/photo-induced isomerization and adjustable guest binding. Chinese Chemical Letters, 2024, 35(11): 109927-. doi: 10.1016/j.cclet.2024.109927
19. [19]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
20. [20]
  Luyan Shi , Ke Zhu , Yuting Yang , Qinrui Liang , Qimin Peng , Shuqing Zhou , Tayirjan Taylor Isimjan , Xiulin Yang . Phytic acid-derivative Co₂B-CoPO_x coralloidal structure with delicate boron vacancy for enhanced hydrogen generation from sodium borohydride. Chinese Chemical Letters, 2024, 35(4): 109222-. doi: 10.1016/j.cclet.2023.109222

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(663)
HTML views(6)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142