 | |
| 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 | |
| UNII | |
| |
| |
| 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): | |
LD50 (median dose) | 3.03 mg/kg (IP, mice)[1] |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Bupleurotoxin (BETX) is a highlytoxicpolyyne compound isolated primarily from therhizomes ofBupleurum longiradiatum, apoisonous plant native toNortheast China.[1][2][3] It is astructural isomer ofcicutoxin andoenanthotoxin, and all three are powerfulcentral nervous systemstimulants andconvulsants by acting as potentantagonists ofGABAA receptor.[4][5]
Bupleurotoxin and its derivative acetylbupleurotoxin are responsible for numerous poisoning cases caused byB. longiradiatum.[1][2] Historically,B. longiradiatum, particularly in Northeast China, was used as a substitute forBupleurum chinense andBupleurum scorzonerifolium in thetraditional Chinese medicineChaihu (Radix Bupleuri), leading to sporadic poisoning incidents.[6] In the early 1970s, a severe poisoning outbreak occurred inMulan County,Heilongjiang, followed by other incidents, some of which were fatal, resulting inB. longiradiatum being explicitly listed as toxic and prohibited in the 1977 edition of thePharmacopoeia of the People's Republic of China.[1][6][7] Research intoB. 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 occasional poisoning cases thereafter, primarily due to misidentification or mistaken use.[3]
Bupleurotoxin is almost exclusively found inB. longiradiatum, and is only found in trace or non-detectable amount in otherBupleurum species, thus can be used as a chemical marker to identify and exclude the toxicB. longiradiatum contaminant in Chinese medicine supplies.[7][8][9]