bruceine D Chemical Properties

Melting point:

294-295℃

Boiling point:

661.3±55.0 °C(Predicted)

Density 

1.60

storage temp. 

2-8°C

solubility 

DMSO: 100 mg/mL (243.65 mM)

pka

11.55±0.70(Predicted)

form 

Solid

color 

White to off-white

InChIKey

JBDMZGKDLMGOFR-SOKPEVJONA-N

SMILES

[C@@]123CO[C@@]4([C@@H](O)[C@H](O)C1[C@@]1(C)[C@H](O)C(C=C(C)[C@]1([H])C[C@@]2([H])OC(=O)[C@H](O)[C@]34O)=O)C |&1:0,3,4,6,9,11,17,20,25,27,r|

bruceine D Usage And Synthesis

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from the fruit of Brucea javanica.

Uses

Bruceine D is a Notch inhibitor with anti-cancer activity and induces apoptosis in several human cancer cells. Bruceine D is an effective botanical insect antifeedant with outstanding systemic properties, causing potent pest growth inhibitory activity[1][2]. Bruceine D has strong anthelmintic activity against D. intermedius with an EC50 value of 0.57 mg/L[3].

Definition

ChEBI: A quassinoid that is 13,20-epoxypicras-3-ene substituted by hydroxy groups at positions 1, 11, 12, 14 and 15 and oxo groups at positions 2 and 16. Isolated from the ethanol extract of the stem of Brucea mollis, it exhibits cytotoxic activity.

References

[1] Mao G,et al. Bruceine D Isolated from Brucea Javanica (L.) Merr. as a Systemic Feeding Deterrent for Three Major Lepidopteran Pests. J Agric Food Chem. 2019 Apr 17;67(15):4232-4239. DOI:10.1021/acs.jafc.8b06511
[2] Cheng Z, et al. Bruceine D inhibits hepatocellular carcinoma growth by targeting β-catenin/jagged1 pathways. Cancer Lett. 2017 Sep 10;403:195-205. DOI:10.1016/j.canlet.2017.06.014
[3] Yong Wang, et al. In vivo anthelmintic activity of bruceine A and bruceine D from Brucea javanica against Dactylogyrus intermedius (Monogenea) in goldfish (Carassius auratus). Vet Parasitol. 2011 Apr 19;177(1-2):127-33. DOI:10.1016/j.vetpar.2010.11.040

bruceine D(21499-66-1)Related Product Information

• bruceine A
• brusatol
• (-)-13,20-Epoxy-1β,11β,12α,14,15β,21-hexahydroxypicrasa-3-ene-2,16-dione
• yadanziolide A
• bruceine B
• YADANZIOLIDE-C
• (+)-13,20-Epoxy-1β,6α,11β,12α,14,15β,21-heptahydroxypicrasa-3-ene-2,16-dione
• YADANZIOSIDE-L
• (-)-DIHYDROCARVYL ACETATE
• (+)-Isobutyl D-lactate
• delta-Dodecalactone
• Undecanolactone
• (R)-BETA-HYDROXY-BETA-METHYL-DELTA-VALEROLACTONE
• delta-Nonalactone
• DL-LEUCIC ACID
• 5-Hydroxyoctanoic acid lactone
• 2-ISOBUTYL-4-HYDROXY-4-METHYLTETRAHYDROPYRAN
• Lactic acid isoamyl ester