Bruceantin

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 ;
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)
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	mouse (male, IV) 1.95 mg/kg; mouse (female, IV) 2.58 mg/kg
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.

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]

References

^ ^a ^b Merck Index, 12th Edition, 1475
^ Kupchan, S. Morris; Britton, Ronald W.; Ziegler, Myra F.; Sigel, Carl W. (1973). "Bruceantin, a new potent antileukemic simaroubolide from Brucea antidysenterica". J. Org. Chem. 38 (1): 178–179. doi:10.1021/jo00941a049. PMID 4682660.
^ ^a ^b ^c "Bruceantin". NCI Cancer Dictionary. National Institutes of Health.
^ Gillin, F. D.; Reiner, D. S.; Suffness, M. (2021). "Bruceantin, a potent amoebicide from a plant, Brucea antidysenterica". Antimicrobial Agents and Chemotherapy. 22 (2): 342–345. doi:10.1128/AAC.22.2.342. PMC 183739. PMID 6100431.
^ Cuendet, Muriel; Pezzuto, John M. (2004). "Antitumor activity of bruceantin: an old drug with new promise". J Nat Prod. 67 (2): 269–272. Bibcode:2004JNAtP..67..269C. doi:10.1021/np030304+. PMID 14987068.
^ "Bruceantin". Inxsight Drugs.

[Merck-1] Merck Index, 12th Edition, 1475

[2] Kupchan, S. Morris; Britton, Ronald W.; Ziegler, Myra F.; Sigel, Carl W. (1973). "Bruceantin, a new potent antileukemic simaroubolide from Brucea antidysenterica". J. Org. Chem. 38 (1): 178–179. doi:10.1021/jo00941a049. PMID 4682660.

[NCI-3] "Bruceantin". NCI Cancer Dictionary. National Institutes of Health.

[4] Gillin, F. D.; Reiner, D. S.; Suffness, M. (2021). "Bruceantin, a potent amoebicide from a plant, Brucea antidysenterica". Antimicrobial Agents and Chemotherapy. 22 (2): 342–345. doi:10.1128/AAC.22.2.342. PMC 183739. PMID 6100431.

[5] Cuendet, Muriel; Pezzuto, John M. (2004). "Antitumor activity of bruceantin: an old drug with new promise". J Nat Prod. 67 (2): 269–272. Bibcode:2004JNAtP..67..269C. doi:10.1021/np030304+. PMID 14987068.

[6] "Bruceantin". Inxsight Drugs.

[1]

[2]

[3]

[4]

[5]

[6]