| Identification | Back Directory | [Name]
bruceine D | [CAS]
21499-66-1 | [Synonyms]
BRUCEIND
Nsc318801
Picras-3-ene-2,16-dione, 13,20-epoxy-1,11,12,14,15-pentahydroxy-, (1β,11β,12α,15β)-
(1beta,11beta,12alpha,15beta)-13,20-Epoxy-1,11,12,14,15-pentahydroxypicras-3-ene-2,16-dione | [Molecular Formula]
C20H26O9 | [MDL Number]
MFCD00221753 | [MOL File]
21499-66-1.mol | [Molecular Weight]
410.42 |
| Chemical Properties | Back Directory | [Melting point ]
294-295℃ | [Boiling point ]
661.3±55.0 °C(Predicted) | [density ]
1.60 | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMSO: 100 mg/mL (243.65 mM) | [form ]
Solid | [pka]
11.55±0.70(Predicted) | [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| |
| Hazard Information | Back Directory | [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 |
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