Bupleurotoxin

Last updated
Bupleurotoxin
Bupleurotoxin.svg
Names
IUPAC name
(2Z,8E,10E,14S)-heptadeca-2,8,10-trien-4,6-diyne-1,14-diol
Other names
14-Hydroxy-bupleurynol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C17H22O2/c1-2-14-17(19)15-12-10-8-6-4-3-5-7-9-11-13-16-18/h4,6,8,10-11,13,17-19H,2,12,14-16H2,1H3/b6-4+,10-8+,13-11-/t17-/m0/s1
    Key: UPXPHJXYZGEBCW-PFTJZPSUSA-N
  • CCC[C@@H](CC/C=C/C=C/C#CC#C/C=C\CO)O
Properties
C17H22O2
Molar mass 258.361 g·mol−1
Density 1.025 g/cm3
Boiling point 458.7 °C (857.7 °F; 731.8 K)
Hazards
Flash point 213.8 °C (416.8 °F; 486.9 K)
Lethal dose or concentration (LD, LC):
3.03 mg/kg (IP, mice) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bupleurotoxin (BETX) is a highly toxic polyyne compound isolated primarily from the rhizomes of Bupleurum longiradiatum , a poisonous plant native to Northeast China. [1] [2] [3] It is a structural isomer of cicutoxin and oenanthotoxin, and all three are powerful central nervous system stimulants and convulsants by acting as potent antagonists of GABAA receptor. [4] [5]

Bupleurotoxin and its derivative acetylbupleurotoxin are responsible for numerous poisoning cases caused by B. longiradiatum. [1] [2] Historically, B. longiradiatum, particularly in Northeast China, was used as a substitute for Bupleurum chinense and Bupleurum scorzonerifolium in the traditional Chinese medicine Chaihu (Radix Bupleuri), leading to sporadic poisoning incidents. [6] In the early 1970s, a severe poisoning outbreak occurred in Mulan County, Heilongjiang, followed by other incidents, some of which were fatal, resulting in B. longiradiatum being explicitly listed as toxic and prohibited in the 1977 edition of the Pharmacopoeia of the People's Republic of China . [1] [6] [7] Research into B. longiradiatum's toxic constituents began around early 1980s, leading to the isolation and identification of bupleurotoxin and acetylbupleurotoxin in 1986. [1] [3] [8] There are still ocasional poisoning cases thereafter, primarily due to misidentification or mistaken use. [3]

Bupleurotoxin is almost exclusively found in B. longiradiatum, and is only found in trace or non-detectable amount in other Bupleurum species, thus can be used as a chemical marker to identify and exclude the toxic B. longiradiatum contaminant in Chinese medicine supplies. [7] [9]

References

  1. 1 2 3 4 5 Zhao, J. F.; Guo, Y. Z.; Meng, X. S. (1987). "大叶柴胡的毒性成分" [The toxic principles of Bupleurum longiradiatum]. Yao Xue Xue Bao = Acta Pharmaceutica Sinica (in Chinese). 22 (7): 507–511. doi:10.16438/j.0513-4870.1987.07.006. ISSN   0513-4870. PMID   3450149 . Retrieved 2026-01-25.
  2. 1 2 Huang, Hai-Qiang; Zhang, Xi; Shen, Yun-Heng; Su, Juan; Liu, Xiao-Hua; Tian, Jun-Min; Lin, Sheng; Shan, Lei; Zhang, Wei-Dong (2009-12-28). "Polyacetylenes from Bupleurum longiradiatum". Journal of Natural Products. 72 (12): 2153–2157. doi:10.1021/np900534v. ISSN   0163-3864 . Retrieved 2026-01-26.
  3. 1 2 3 Lin, Meiyu; Zhang, Weidong; Su, Juan (2016). "Toxic polyacetylenes in the genus Bupleurum (Apiaceae) – Distribution, toxicity, molecular mechanism and analysis". Journal of Ethnopharmacology. 193: 566–573. doi:10.1016/j.jep.2016.09.052 . Retrieved 2026-01-25.
  4. ↑ Zhang, Zhongxiao; Lu, Cheng; Liu, Xinru; Su, Juan; Dai, Weixing; Yan, Shikai; Lu, Aiping; Zhang, Weidong (2014-02-07). "Global and Targeted Metabolomics Reveal That Bupleurotoxin, a Toxic Type of Polyacetylene, Induces Cerebral Lesion by Inhibiting GABA Receptor in Mice". Journal of Proteome Research. 13 (2): 925–933. doi:10.1021/pr400968c. ISSN   1535-3893 . Retrieved 2026-01-25.
  5. ↑ Wyrembek, Paulina; Negri, Roberto; Appendino, Giovanni; Mozrzymas, Jerzy W. (2012). "Inhibitory effects of oenanthotoxin analogues on GABAergic currents in cultured rat hippocampal neurons depend on the polyacetylenes' polarity". European Journal of Pharmacology. 683 (1–3): 35–42. doi:10.1016/j.ejphar.2012.03.005 . Retrieved 2026-01-26.
  6. 1 2 Xu, Zhengbin; Guo, Xiufang (1981-01-31). "大叶柴胡毒性的探讨". Heilongjiang Medical Journal (in Chinese).
  7. 1 2 Huang, Hai-Qiang; Su, Juan; Zhang, Xi; Shan, Lei; Zhang, Wei-Dong (2011). "Qualitative and quantitative determination of polyacetylenes in different Bupleurum species by high performance liquid chromatography with diode array detector and mass spectrometry". Journal of Chromatography A. 1218 (8): 1131–1138. doi:10.1016/j.chroma.2010.12.007 . Retrieved 2026-01-26.
  8. ↑ Yao, Ru-yu; Zou, Yuan-feng; Chen, Xing-fu (2013). "Traditional Use, Pharmacology, Toxicology, and Quality Control of Species in Genus Bupleurum L." Chinese Herbal Medicines. 5 (4): 245–255. doi:10.1016/S1674-6384(13)60036-2 . Retrieved 2026-01-26.
  9. ↑ Nešić, Milica D.; Nešić, Milan S.; Dimitrijević, Milan Ž.; Radulović, Niko S. (2024-07-26). "Essential Oil Composition of Bupleurum praealtum and Bupleurum affine: New Natural Constituents". Plants. 13 (15): 2076. doi: 10.3390/plants13152076 . ISSN   2223-7747. PMC   11314282 . PMID   39124193.
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