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106500-25-8

106500-25-8 structure
106500-25-8 structure
  • Name: Azadirachtin B
  • Chemical Name: X5T1RMZ28I
  • CAS Number: 106500-25-8
  • Molecular Formula: C33H42O14
  • Molecular Weight: 662.678
  • Catalog: Signaling Pathways Anti-infection Influenza Virus
  • Create Date: 2018-07-21 02:51:50
  • Modify Date: 2024-01-16 16:10:53
  • Azadirachtin B is an limonoid isolated from seed kernels of Azadirachta indica. Azadirachtin B increases alkaline phosphatase (ALP) activity and stimulates osteoblast differentiation. Azadirachtin B is active against the Epstein-Barr virus early antigen (EBV-EA). Azadirachtin B has insecticidal, nematocidal, anticancer, anti-inflammatory, antiviral and osteogenic properties[1][2][3].

Name X5T1RMZ28I
Synonyms Dimethyl (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-3,8-dihydroxy-4-[(1S,2S,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-4-methyl-10-{[(2E)-2-methyl-2-b 
utenoyl]oxy}octahydro-1H-furo[3',4':4,4a]naphtho[1,8-bc]furan-5,10a(8H)-dicarboxylate
X5T1RMZ28I
1H,7H-Naphtho[1,8a-c:4,5-b'c']difuran-5,10a(8H)-dicarboxylic acid, octahydro-3,8-dihydroxy-4-methyl-10-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]oxy]-4-[(1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-, dimethyl ester, (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-
Description Azadirachtin B is an limonoid isolated from seed kernels of Azadirachta indica. Azadirachtin B increases alkaline phosphatase (ALP) activity and stimulates osteoblast differentiation. Azadirachtin B is active against the Epstein-Barr virus early antigen (EBV-EA). Azadirachtin B has insecticidal, nematocidal, anticancer, anti-inflammatory, antiviral and osteogenic properties[1][2][3].
Related Catalog
Target

Plutella xylostella[1] Alkaline phosphatase (ALP)[2] Epstein-Barr virus early antigen (EBV-EA)[3]

In Vitro Azadirachtin B (1 pM-100 µM; 48 hours; Osteoblast cells) treatment shows highest proliferation at 10 nM and 100 pM concentrations in osteoblast cells[1]. Azadirachtin B increases expression of RunX-2 ∼2.5 fold at 10 nM concentration, ALP expression ∼2.8 fold at 10 nM and 100 pM concentration and OCN expression ∼2.5 folds at 10 nM as compared with control[1]. Azadirachtin B (Compound 4) exhibits toxicity to the diamondback moth (Plutella xylostella) with an LD50 of 4.85-1.06 µg/g body weight, in 92 h[2]. Azadirachtin B (compound 21) exhibits moderate or potent inhibitory effects (IC50 value of 384 mol ratio/32 pmol TPA) against the Epstein-Barr virus early antigen (EBV-EA) activation induced by tetradecanoylphorbol-13-acetate (TPA)[3]. Cell Proliferation Assay[1] Cell Line: Osteoblast cells Concentration: 1 pM, 100 pM, 10 nM, 1 µM, 100 µM Incubation Time: 48 hours Result: Showed highest proliferation at 10 nM and 100 pM concentrations in osteoblast cells.
In Vivo On evaluation of Azadirachtin B (compound 21; oral administration) for its anti-tumor-initiating activity on the two-stage carcinogenesis of mouse skin tumor induced by peroxynitrite (ONOO-; PN) as an initiator and TPA as a promoter, this exhibited marked inhibitory activity[3].
References

[1]. Kushwaha P, et al. Azadirachta indica triterpenoids promote osteoblast differentiation and mineralization in vitro and in vivo. Bioorg Med Chem Lett. 2016 Aug 1;26(15):3719-24.

[2]. Kanokmedhakul S, et al. Azadirachtin derivatives from seed kernels of Azadirachta excelsa. J Nat Prod. 2005 Jul;68(7):1047-50.

[3]. Akihisa T, et al. Melanogenesis inhibitory, anti-inflammatory, and chemopreventive effects of limonoids from the seeds of Azadirachta indicia A. Juss. (neem). J Oleo Sci. 2009;58(11):581-94.

Density 1.5±0.1 g/cm3
Boiling Point 780.5±60.0 °C at 760 mmHg
Molecular Formula C33H42O14
Molecular Weight 662.678
Flash Point 246.6±26.4 °C
Exact Mass 662.257446
LogP 1.31
Vapour Pressure 0.0±6.1 mmHg at 25°C
Index of Refraction 1.628
Storage condition -20°C
Hazard Codes Xn