Citation: Youzhe Chen, Chengbo Xu, Weiping Wang, Xiaoliang Wang, Qinglan Guo, Jiangong Shi. Phthalide-derived oxaspiroangelioic acids A–C with an unprecedented carbon skeleton from an aqueous extract of the Angelica sinensis root head[J]. Chinese Chemical Letters, ;2021, 32(10): 3257-3260. doi: 10.1016/j.cclet.2021.03.004 shu

Phthalide-derived oxaspiroangelioic acids A–C with an unprecedented carbon skeleton from an aqueous extract of the Angelica sinensis root head

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

guonina@imm.ac.cn

shijg@imm.ac.cn

Received Date: 6 February 2021
Revised Date: 19 February 2021
Accepted Date: 1 March 2021
Available Online: 3 March 2021

Figures(4)

Three phthalide-derived analogues, oxaspiroangelioic acids A–C (1–3), were isolated as minor components of an aqueous extract of the Angelica sinensis root heads (guitou). Oxaspiroangelioic acids A and B were racemates separated into enantiomers by chiral HPLC. Their structures including absolute configurations were determined by spectroscopic data analysis, single crystal X-ray diffraction, exciton chirality method and electronic circular dichroism (ECD) calculation. These compounds share an undescribed carbon skeleton, for which biosynthetic pathways are proposed. Compound 1 and its enantiomers showed almost identical activity inhibiting Tandem of P domains in a weak inwardly rectifying K⁺ channel 1 (TREK-1).
- Umbelliferae,
- Angelica sinensis,
- Phthalide-derived analogues,
- Oxaspiroangelioic acids A–C
1. [1]
  Jiangsu New Medical College, Dictionary of Traditional Chinese Medicine, Shanghai Science and Technology Publishing House, Shanghai, 1977, pp. 876-879.
2. [2]
  I.L.I. Hook, J. Ethnopharm. 152(2014) 1-13. doi: 10.1016/j.jep.2013.12.018
3. [3]
  W.L. Wei, R. Zeng, C.M. Gu, Y. Qu, L.F. Huang, J. Ethnopharm. 190(2016) 116-141. doi: 10.1016/j.jep.2016.05.023
4. [4]
  W. Gong, Y. Zhou, X. Li, et al., Molecules 21 (2016) 549. doi: 10.3390/molecules21050549
5. [5]
  W. Gong, Y. Zhou, X. Li, et al., Molecules 21(2016) 549. doi: 10.1007/s10600-018-2248-8
6. [6]
  L. Zhang, J. Lv, Chem. Nat. Comp. 54(2018) 13-17. doi: 10.1016/j.fitote.2018.06.016
7. [7]
  J.L. Lv, L.B. Zhang, L.M. Gao, Fitoterapia 129(2018) 102-107. doi: 10.1021/acs.orglett.8b00017
8. [8]
  J. Zou, G.D. Chen, H. Zhao, et al., Org. Lett. 20(2018) 884-887. doi: 10.1039/C9CC02681A
9. [9]
  J. Zou, G.D. Chen, H. Zhao, et al., Chem. Commun. 55(2019) 6221-6224. doi: 10.1021/acs.orglett.9b02172
10. [10]
  B. Sheng, Y. Vo, P. Lan, et al., Org. Lett. 21(2019) 6295-6299. doi: 10.1021/acs.jnatprod.8b00962
11. [11]
  K. Duric, Y. Liu, S.N. Chen, et al., J. Nat. Prod. 82(2019) 2400-2408. doi: 10.1016/j.cclet.2017.12.001
12. [12]
  L. Meng, Q. Guo, M. Chen, et al., Chin. Chem. Lett. 29(2018) 1257-1260. doi: 10.1016/j.apsb.2018.03.009
13. [13]
  Q. Guo, H. Xia, X. Meng, et al., Acta Pharm. Sin. B 8(2018) 409-419. doi: 10.1016/j.apsb.2018.08.005
14. [14]
  Q. Guo, C. Xu, M. Chen, et al., Acta Pharm. Sin. B 8(2018) 933-943. doi: 10.1021/acs.orglett.7b03956
15. [15]
  Q. Guo, H. Xia, G. Shi, et al., Org. Lett. 20(2018) 816-819. doi: 10.1021/acs.orglett.9b02479
16. [16]
  Y. Wu, S. Shao, Q. Guo, et al., Org. Lett. 21(2019) 6850-6854.
17. [17]
  J. Cai, Q.L. Guo, R.F. Li, et al., Acta Pharm. Sin. 54(2019) 1075-1081. doi: 10.1016/j.apsb.2019.09.001
18. [18]
  Q. Guo, D. Li, C. Xu, et al., Acta Pharm. Sin. B 10(2020) 895-902. doi: 10.1016/j.ejmech.2020.112071
19. [19]
  C. Xu, Y. Xin, M. Chen, et al., Eur. J. Med. Chem. 189(2020)112071. doi: 10.1016/j.apsb.2020.01.013
20. [20]
  Q. Guo, H. Xia, Y. Wu, et al., Acta Pharm. Sin. B 10(2020) 1954-1965. doi: 10.1016/j.cclet.2020.11.067
21. [21]
  Y. Chen, Q. Guo, C. Xu, et al., Chin. Chem. Lett. 32(2021) 1657-1659.
1. [1]
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2. [2]
  Jiao Li , Chenyang Zhang , Chuhan Wu , Yan Liu , Xuejian Zhang , Xiao Li , Yongtao Li , Jing Sun , Zhongmin Su . Defined organic-octamolybdate crystalline superstructures derived Mo₂C@C as efficient hydrogen evolution electrocatalysts. Chinese Chemical Letters, 2024, 35(6): 108782-. doi: 10.1016/j.cclet.2023.108782
3. [3]
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4. [4]
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5. [5]
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10. [10]
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11. [11]
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12. [12]
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13. [13]
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14. [14]
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15. [15]
  Xinyi Luo , Ke Wang , Yingying Xue , Xiaobao Cao , Jianhua Zhou , Jiasi Wang . Digital PCR-free technologies for absolute quantitation of nucleic acids at single-molecule level. Chinese Chemical Letters, 2025, 36(2): 109924-. doi: 10.1016/j.cclet.2024.109924
16. [16]
  Lei Wan , Yizhou Tong , Xi Lu , Yao Fu . Cobalt-catalyzed reductive alkynylation to construct C(sp)-C(sp³) and C(sp)-C(sp²) bonds. Chinese Chemical Letters, 2024, 35(7): 109283-. doi: 10.1016/j.cclet.2023.109283
17. [17]
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18. [18]
  Hao Deng , Yuxin Hui , Chao Zhang , Qi Zhou , Qiang Li , Hao Du , Derek Hao , Guoxiang Yang , Qi Wang . MXene−derived quantum dots based photocatalysts: Synthesis, application, prospects, and challenges. Chinese Chemical Letters, 2024, 35(6): 109078-. doi: 10.1016/j.cclet.2023.109078
19. [19]
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20. [20]
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