Bruceantin

Bruceantin is a chemical compound that was first isolated from the plant Brucea antidysenterica in 1973.^[2] Chemically, it is classified as a secotriterpenoid and a quassinoid.

Quick facts Names, Identifiers ...

Bruceantin

Names
IUPAC name Methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
Other names Bruceantine
Identifiers
CAS Number	41451-75-6 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:3188
ChEMBL	ChEMBL509895
ChemSpider	4444686
KEGG	C08749
PubChem CID	5281304
UNII	S3NW88DI4T
InChI InChI=1S/C28H36O11/c1-11(2)12(3)7-17(30)39-20-22-27-10-37-28(22,25(35)36-6)23(33)19(32)21(27)26(5)9-15(29)18(31)13(4)14(26)8-16(27)38-24(20)34/h7,11,14,16,19-23,31-33H,8-10H2,1-6H3/b12-7+/t14-,16+,19+,20+,21+,22+,23-,26-,27+,28-/m0/s1 Key: IRQXZTBHNKVIRL-GOTQHHPNSA-N
SMILES CC1=C(C(=O)C[C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@H]4[C@H](C(=O)O3)OC(=O)/C=C(\C)/C(C)C)(OC5)C(=O)OC)O)O)C)O
Properties
Chemical formula	C28H36O11
Molar mass	548.585 g·mol−1
Melting point	225–226 °C (437–439 °F; 498–499 K)[1]
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)	mouse (male, IV) 1.95 mg/kg mouse (female, IV) 2.58 mg/kg[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Close

Bucreantin has attracted interest as a potential antitumor drug because of its antineoplastic activity.^[3] It inhibits the peptidyl transferase elongation reaction, resulting in decreased protein and DNA synthesis.^[3] Bruceantin also has antibiotic, antiamoebic,^[4] and antimalarial activity.^[3]

Phase I and II clinical trials were conducted for the treatment of metastatic breast cancer and melanoma, but tumor regression was not observed and clinical development was terminated.^[5][6]