Citation: Yue-Ping Jiang, Qing-Lan Guo, Yu-Feng Liu, Jian-Gong Shi. Codonopiloneolignanin A, a polycyclic neolignan with a new carbon skeleton from the roots of Codonopsis pilosula[J]. Chinese Chemical Letters, ;2016, 27(01): 55-58. doi: 10.1016/j.cclet.2015.11.009 shu

Codonopiloneolignanin A, a polycyclic neolignan with a new carbon skeleton from the roots of Codonopsis pilosula

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: 14 July 2015
Available Online: 6 August 2015
Fund Project: Financial support from the National Natural Science Foundation of China(Nos. 30825044, 21132009) (Nos. 30825044, 21132009) and the National Science and Technology Project of China(Nos. 2012ZX09301002-002, 2011ZX09307-002-01) are acknowledged. (PCSIRT, No. IRT1007)

A neolignan codonopiloneolignanin A(1) with a novel 2,9:2',9:7,7'-tricyclo-8,'-neolignane skeleton was isolated from an aqueous extract of the Codonopsis pilosula roots. Its structure including the absolute configuration was elucidated by extensive spectroscopic analysis, including 2D NMR and electronic circular dichroism calculation. The proposed biosynthetic pathway of compound 1 is also discussed.
- Codonopsis pilosula,
- Campanulaceae,
- Neolignan,
- 2,9:2',9:7,7'-Tricyclo-8,9'-neolignane,
- Codonopiloneolignanin A
1. [1]
  [1] Jiangsu New Medical College, Dictionary of Traditional Chinese Medicine, Shanghai Science and Technology Publishing House, Shanghai, 1986, pp. 1837-1839.
2. [2]
  [2] Z.T. Wang, Q. Du, G.J. Xu, et al., Investigations on the protective action of Condonopsis pilosula(Dangshen) extract on experimentally-induced gastric ulcer in rats, Gen. Pharm. 28(1997) 469-473.
3. [3]
  [3] B.E. Shan, Y. Yaoshida, T. Sugiura, U. Yamashita, Stimulating activity of Chinese medicinal herbs on human lymphocytes in vitro, Int. J. Immunopharm. 21(1999) 149-159.
4. [4]
  [4] B. Singh, H. Song, X.D. Liu, et al., Dangshen(Codonopsis pilosula) and baiguo(Gingko biloba) enhance learning and memory, Altern. Ther. Health Med. 10(2004) 52-56.
5. [5]
  [5] C.S. Yoo, S.J. Kim, Methanol extract of Codonopsis pilosula inhibits inducible nitric oxide synthase and protein oxidation in lipopolysaccharide-stimulated raw cells, Trop. J. Pharm. Res. 12(2013) 705-710.
6. [6]
  [6] K.H. Tsai, N.H. Lee, G.Y. Chen, et al., Dung-shen(Codonopsis pilosula) attenuated the cardiac-impaired insulin-like growth factor Ⅱ receptor pathway on myocardial cells, Food Chem. 138(2013) 1856-1867.
7. [7]
  [7] Z.T. Wang, G.J. Xu, M. Hattori, et al., Constituents of the roots of Codonopsis pilosula, Shoyakugaku Zasshi 42(1988) 339-342.
8. [8]
  [8] T.T. Thuy, T. Van Sung, L. Wessjohann, Chemical constituents of the roots of Codonopsis pilosula, J. Chem. 41(2003) 119-123.
9. [9]
  [9] Q. He, E.Y. Zhu, Z.T. Wang, et al., Study on chemical constituents of Codonopsis pilosula, Chin. Pharm. J. 41(2006) 10-16.
10. [10]
  [10] H.Y. Qi, R. Wang, Y. Liu, Y.P. Shi, Studies on the chemical constituents of Codonopsis pilosula, J. Chin. Med. Mater. 34(2011) 546-548.
11. [11]
  [11] D. Wakana, N. Kawahara, Y. Goda, Two new pyrrolidine alkaloids, codonopsinol C and codonopiloside A, isolated from Codonopsis pilosula, Chem, Pharm. Bull. 61(2013) 1315-1317.
12. [12]
  [12] C.X. Yang, Y.Q. Gou, J.Y. Chen, et al., Structural characterization and antitumor activity of a pectic polysaccharide from Codonopsis pilosula, Carbohydr. Polym. 98(2013) 886-895.
13. [13]
  [13] 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.
14. [14]
  [14] 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.
15. [15]
  [15] 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.
16. [16]
  [16] 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.
17. [17]
  [17] 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.
18. [18]
  [18] Y. Yu, Z.B. Jiang, W.X. Song, et al., Glucosylated caffeoylquinic acid derivatives from the flower buds of Lonicera japonica, Acta Pharm. Sin. B 5(2015) 210-214.
19. [19]
  [19] Z.B. Jiang, X.H. Meng, B.Y. Jiang, et al., Two 2-(quinonylcarboxamino)benzoates from the lateral roots of Aconitum carmichaelii, Chin. Chem. Lett. 26(2015) 653-656.
20. [20]
  [20] Q. Guo, Y. Wang, S. Lin, et al., 4-Hydroxybenzyl-substituted amino acid derivatives from Gastrodia elata, Acta Pharm. Sin. B 5(2015) 350-357.
21. [21]
  [21] Q.L. Guo, Y.N. Wang, C.G. Zhu, et al., 4-Hydroxybenzyl-substituted glutathione derivatives from Gastrodia elata, J. Asian Nat. Prod. Res. 17(2015) 439-454.
22. [22]
  [22] Y.F. Liu, M.H. Chen, X.L. Wang, et al., Antiviral enantiomers of a bisindole alkaloid with a new carbon skeleton from the roots of Isatis indigotica, Chin. Chem. Lett. 26(2015) 931-936.
23. [23]
  [23] Y.F. Liu, M.H. Chen, Q.L. Guo, et al., Antiviral glycosidic bisindole alkaloids from the roots of Isatis indigotica, J. Asian Nat. Prod. Res. 17(2015) 689-704.
24. [24]
  [24] Y.P. Jiang, Y.F. Liu, Q.L. Guo, et al., Acetylenes and fatty acids from Codonopsis pilosula, Acta Pharm. Sin. B 5(2015) 215-222.
25. [25]
  [25] Y.P. Jiang, Y.F. Liu, Q.L. Guo, et al., C₁₄-Polyacetylene glucosides from Codonopsis pilosula, J. Asian Nat. Prod. Res. 17(2015) 601-614.
26. [26]
  [26] Chemical Computing Group Inc., Molecular Operating Environment software package, Chemical Computing Group Inc., 2008 hwww.chemcomp.comi(10).
27. [27]
  [27] Gaussian Inc., Gaussian 09, Revision A.1, Gaussian Inc., Wallingford CT, 2009.
28. [28]
  [28] M. Yuda, K. Ohtani, K. Mizutani, et al., Neolignan glycosides from roots of Codonopsis tangshen, Phytochemistry 29(1990) 1989-1993.
29. [29]
  [29] R.Q. Mei, Q. Lv, Y.F. Hu, Y.X. Cheng, Chemical constituents from Codonopsis cordifolioidea, Nat. Prod. Res. Dev. 22(2010) 238-240.
30. [30]
  [30] S.L. Mao, S.M. Sang, A.N. Lao, Z.L. Chen, Studies on the chemical constituents of Codonopisis lanceolata Benth. Et Hook, Nat. Prod. Res. Dev. 12(2000) 1-3.
31. [31]
  [31] X.C. Li, D. Ferreira, Y.Q. Ding, Determination of absolute configuration of natural products:theoretical calculation of electronic circular dichroism as a tool, Curr. Org. Chem. 14(2010) 1678-1697.
32. [32]
  [32] G.P. Moss, Nomenclature of lignans and neolignans(IUPAC recommendations 2000), Pure Appl. Chem. 72(2000) 1493-1523.
1. [1]
  Jiajun Wang , Guolin Yi , Shengling Guo , Jianing Wang , Shujuan Li , Ke Xu , Weiyi Wang , Shulai Lei . Computational design of bimetallic TM₂@g-C₉N₄ electrocatalysts for enhanced CO reduction toward C₂ products. Chinese Chemical Letters, 2024, 35(7): 109050-. doi: 10.1016/j.cclet.2023.109050
2. [2]
  Ruiheng Liang , Huizhong Wu , Zhongzheng Hu , Ge Song , Xuyang Zhang , Omotayo A. Arotiba , Minghua Zhou . Hierarchical Fe-Bi/Bi₇O₉I₃/OVs microspheres coupled with natural air diffusion electrode to achieve efficient heterogeneous visible-light-driven photoelectro-Fenton degradation of tetracycline without aeration. Chinese Chemical Letters, 2025, 36(4): 110136-. doi: 10.1016/j.cclet.2024.110136
3. [3]
  Yuan Teng , Zichun Zhou , Jinghua Chen , Siying Huang , Hongyan Chen , Daibin Kuang . Dual atom-bridge effect promoting interfacial charge transfer in 2D/2D Cs₃Bi₂Br₉/BiOBr epitaxial heterojunction for efficient photocatalysis. Chinese Chemical Letters, 2025, 36(2): 110430-. doi: 10.1016/j.cclet.2024.110430
4. [4]
  Hao GUO , Tong WEI , Qingqing SHEN , Anqi HONG , Zeting DENG , Zheng FANG , Jichao SHI , Renhong LI . Electrocatalytic decoupling of urea solution for hydrogen production by nickel foam-supported Co₉S₈/Ni₃S₂ heterojunction. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2141-2154. doi: 10.11862/CJIC.20240085
5. [5]
  . . University Chemistry, 2024, 39(9): 0-0.
6. [6]
  Cheng PENG , Jianwei WEI , Yating CHEN , Nan HU , Hui ZENG . First principles investigation about interference effects of electronic and optical properties of inorganic and lead-free perovskite Cs₃Bi₂X₉ (X=Cl, Br, I). Chinese Journal of Inorganic Chemistry, 2024, 40(3): 555-560. doi: 10.11862/CJIC.20230282
7. [7]
  Xinqiong Li , Guocheng Rao , Xi Peng , Chan Yang , Yanjing Zhang , Yan Tian , Xianghui Fu , Jia Geng . Direct detection of C9orf72 hexanucleotide repeat expansions by nanopore biosensor. Chinese Chemical Letters, 2024, 35(5): 109419-. doi: 10.1016/j.cclet.2023.109419
8. [8]
  Yan Liu , Yang Wang , Jiayi Zhu , Xuxian Su , Xudong Lin , Liang Xu , Xiwen Xing . Employing pH-responsive RNA triplex to control CRISPR/Cas9-mediated gene manipulation in mammalian cells. Chinese Chemical Letters, 2024, 35(9): 109427-. doi: 10.1016/j.cclet.2023.109427
9. [9]
  Hongzhi Zhang , Hong Li , Asif Ali Haider , Junpeng Li , Zhi Xie , Hongming Jiang , Conglin Liu , Rui Wang , Jing Zhu . An unexpected role of lanthanide substitution in thermally responsive phosphors NaLnTe2O7: Eu3+ (Ln = Y and Gd). Chinese Journal of Structural Chemistry, 2025, 44(2): 100509-100509. doi: 10.1016/j.cjsc.2024.100509
10. [10]
  Guo-Ping Yin , Ya-Juan Li , Li Zhang , Ling-Gao Zeng , Xue-Mei Liu , Chang-Hua Hu . Citrinsorbicillin A, a novel homotrimeric sorbicillinoid isolated by LC-MS-guided with cytotoxic activity from the fungus Trichoderma citrinoviride HT-9. Chinese Chemical Letters, 2024, 35(8): 109035-. doi: 10.1016/j.cclet.2023.109035
11. [11]
  Peng Guo , Shicheng Dong , Xiang-Gui Zhang , Bing-Bin Yang , Jun Zhu , Ke-Yin Ye . Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane (9-BBN) borates. Chinese Chemical Letters, 2025, 36(4): 110052-. doi: 10.1016/j.cclet.2024.110052
12. [12]
  Qiuye Wang , Yabing Sun , Liangxue Lai , Haijing Cui , Yonglong Ye , Ming Yang , Weihao Zhu , Bo Yuan , Quanliang Mao , Wenzhi Ren , Aiguo Wu . MMP-9-responsive probe for fluorescence-magnetic resonance dual-mode imaging of hepatocellular carcinoma models with different metastatic capacities. Chinese Chemical Letters, 2025, 36(4): 110212-. doi: 10.1016/j.cclet.2024.110212
13. [13]
  Huizhong Wu , Ruiheng Liang , Ge Song , Zhongzheng Hu , Xuyang Zhang , Minghua Zhou . Enhanced interfacial charge transfer on Bi metal@defective Bi₂Sn₂O₇ quantum dots towards improved full-spectrum photocatalysis: A combined experimental and theoretical investigation. Chinese Chemical Letters, 2024, 35(6): 109131-. doi: 10.1016/j.cclet.2023.109131
14. [14]
  Xuewei BA , Cheng CHENG , Huaikang ZHANG , Deqing ZHANG , Shuhua LI . Preparation and luminescent performance of Sr_1-xZrSi₂O₇∶xDy³⁺ phosphor with high thermal stability. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 357-364. doi: 10.11862/CJIC.20240096
15. [15]
  . . University Chemistry, 2024, 39(7): 0-0.
16. [16]
  Yan Guo , Hongtao Bian , Le Yu , Jiani Ma , Yu Fang . Photochemical reaction mechanism of benzophenone protected guanosine at N7 position. Chinese Chemical Letters, 2025, 36(3): 109971-. doi: 10.1016/j.cclet.2024.109971
17. [17]
  Yiran Tao , Chunlei Dai , Zhaoxiang Xie , Xinru You , Kaiwen Li , Jun Wu , Hai Huang . Redox responsive polymeric nanoparticles enhance the efficacy of cyclin dependent kinase 7 inhibitor for enhanced treatment of prostate cancer. Chinese Chemical Letters, 2024, 35(8): 109170-. doi: 10.1016/j.cclet.2023.109170
18. [18]
  Hui-Juan Wang , Wen-Wen Xing , Zhen-Hai Yu , Yong-Xue Li , Heng-Yi Zhang , Qilin Yu , Hongjie Zhu , Yao-Yao Wang , Yu Liu . Cucurbit[7]uril confined phenothiazine bridged bis(bromophenyl pyridine) activated NIR luminescence for lysosome imaging. Chinese Chemical Letters, 2024, 35(6): 109183-. doi: 10.1016/j.cclet.2023.109183
19. [19]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
20. [20]
  Zhilian Liu , Wengui Wang , Hongxiao Yang , Yu Cui , Shoufeng Wang . Ideological and Political Education Design for the Synthesis of Irinotecan Drug Intermediate 7-Ethyl Camptothecin. University Chemistry, 2024, 39(2): 89-93. doi: 10.3866/PKU.DXHX202306012

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(669)
HTML views(9)

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