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Diphyllin

Names

[ CAS No. ]:
22055-22-7

[ Name ]:
Diphyllin

[Synonym ]:
HMS1607M09
7-hydroxyjusticidin B
Bio-0182
Diphyllin

Biological Activity

[Description]:

Diphyllin is an arylnaphthalene lignan isolated from Justicia procumbens and is a potent HIV-1 inhibitor with an IC50 of 0.38 μM. Diphyllin is active against vesicular stomatitis virus (VSV) and influenza virus[1]. Diphyllin is a vacuolar type H+-ATPase (V-ATPase) inhibitor with an IC50 value of 17 nM and inhibits lysosomal acidification in human osteoclasts[2]. Diphyllin inhibits NO production with an IC50 of 50 μM and has anticancer and anti-inflammatory activities[3].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Influenza Virus
Research Areas >> Cancer
Signaling Pathways >> Anti-infection >> HIV
Research Areas >> Infection
Research Areas >> Inflammation/Immunology
Signaling Pathways >> Membrane Transporter/Ion Channel >> Proton Pump

[Target]

HIV-1:0.38 μM (IC50)

Vesicular stomatitis virus (VSV)

Vacuolar type H+-ATPase:17 nM (IC50)


[References]

[1]. Xin-Ya Xu, et al. Anti-HIV Lignans From Justicia Procumbens. Chin J Nat Med. 2019 Dec;17(12):945-952.

[2]. Mette G Sørensen, et al. Diphyllin, a Novel and Naturally Potent V-ATPase Inhibitor, Abrogates Acidification of the Osteoclastic Resorption Lacunae and Bone Resorption. J Bone Miner Res. 2007 Oct;22(10):1640-8.

[3]. Yerra Koteswara Rao, et al. Anti-inflammatory Activities of Constituents Isolated From Phyllanthus Polyphyllus. J Ethnopharmacol. 2006 Jan 16;103(2):181-6.

Chemical & Physical Properties

[ Density]:
1.445g/cm3

[ Boiling Point ]:
638.8ºC at 760 mmHg

[ Melting Point ]:
290 ºC (methanol )

[ Molecular Formula ]:
C21H16O7

[ Molecular Weight ]:
380.34800

[ Flash Point ]:
232.4ºC

[ Exact Mass ]:
380.09000

[ PSA ]:
83.45000

[ LogP ]:
3.62870

[ Vapour Pressure ]:
6.53E-17mmHg at 25°C

[ Index of Refraction ]:
1.679

[ Storage condition ]:
2-8℃

[ Water Solubility ]:
Insuluble (2.4E-3 g/L) (25 ºC)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds