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28-Deoxonimbolide

Names

[ CAS No. ]:
126005-94-5

[ Name ]:
28-Deoxonimbolide

[Synonym ]:
28-Deoxonimbolide
Methyl [(2aR,5aR,6S,6aR,8R,9aR,10aS,10bR,10cS)-8-(3-furyl)-2a,5a,6a,7-tetramethyl-5-oxo-2a,5a,6,6a,8,9,9a,10a,10b,10c-decahydro-2H,5H-cyclopenta[b]furo[2',3',4':4,5]naphtho[2,3-d]furan-6-yl]acetate
2H,5H-Cyclopenta[d]naphtho[2,3-b:1,8-b'c']difuran-6-acetic acid, 8-(3-furanyl)-2a,5a,6,6a,8,9,9a,10a,10b,10c-decahydro-2a,5a,6a,7-tetramethyl-5-oxo-, methyl ester, (2aR,5aR,6S,6aR,8R,9aR,10aS,10bR,10cS)-

Biological Activity

[Description]:

28-Deoxonimbolide is a nimbin (HY-N3187) type limonoid, that can be isolated from Azadirachta indica seed extracts. 28-Deoxonimbolide shows anticancer activity. 28-Deoxonimbolide induces apoptotic cell death in HL60 cells via both the mitochondrial- and the death receptor-mediated pathways[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Signaling Pathways >> Apoptosis >> Caspase

[Target]

Caspase-8

Caspase-9

Caspase-3


[In Vitro]

28-Deoxonimbolide (1-100 μM,48 小时) 对 HL60 (白血病)、A549 (肺)、AZ521 (胃)、SK-BR-3 (乳腺)、CRL1579 (黑色素瘤)和 RPMI1788 (正常淋巴细胞) 显示强有力的细胞毒性[1]。 28-Deoxonimbolide (30 μM, 0-24 h) 诱导 HL60 细胞凋亡[1]。 28-Deoxonimbolide (30 μM, 0-24 h) 可增加裂解的 caspases-8、-9 和 -3 的水平[1]。 Cell Cytotoxicity Assay[1] Cell Line: HL60, A549, AZ521, SK-BR-3, CRL1579 cells, RPMI1788 Concentration: 1-100 μM Incubation Time: 48 h Result: Exhibited potent cytotoxic activity against HL60 (leukemia), A549 (lung), AZ521 (stomach), SK-BR-3 (breast), and CRL1579 (melanoma) cells, with IC50 values of 2.7 μM, 9.3 μM, 2.4 μM, 1.7 μM, 14.2 μM, and 2.7 μM, respectively. Apoptosis Analysis[1] Cell Line: HL60 cells Concentration: 30 μM Incubation Time: 8 and 24 h Result: Induced early apoptosis in HL60 cells. The ratio of early apoptotic cells was increased after 8 h (10.9% vs 6.1% of negative control) and 24 h (18.7% vs 3.5% of negative control), and that of late apoptotic cells (upper right) was increased after 24 h (28.1% vs 2.9% of negative control). Western Blot Analysis[1] Cell Line: HL60 cells Concentration: 30 μM Incubation Time: 8 and 24 h Result: Diminished the levels of procaspases-8, -9, and -3, and then increased the levels of cleaved caspases-8, -9, and -3.

[References]

[1]. Kikuchi T, et al. Cytotoxic and apoptosis-inducing activities of limonoids from the seeds of Azadirachta indica (neem). J Nat Prod. 2011 Apr 25;74(4):866-70.  

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
554.2±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C27H32O6

[ Molecular Weight ]:
452.539

[ Flash Point ]:
289.0±30.1 °C

[ Exact Mass ]:
452.219879

[ PSA ]:
74.97000

[ LogP ]:
3.64

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.589

Safety Information

[ Hazard Codes ]:
Xi


Related Compounds