Hypophyllanthin

Names

[ Name ]:
Hypophyllanthin

[Synonym ]:
(7R,8R,9S)-9-(3,4-Dimethoxyphenyl)-4-methoxy-7,8-bis(methoxymethyl)-6,7,8,9-tetrahydronaphtho[1,2-d][1,3]dioxole
UNII:22ZZ21E33P
Naphtho[1,2-d]-1,3-dioxole, 9-(3,4-dimethoxyphenyl)-6,7,8,9-tetrahydro-4-methoxy-7,8-bis(methoxymethyl)-, (7R,8R,9S)-
Hypophyllanthin
Hypophyllantin

Biological Activity

[Description]:

Hypophyllanthin is a major lignan in Phyllanthus spp, with strong anti-inflammatory activity. Hypophyllanthin directly inhibits P-glycoprotein (P-gp) activity and did not interfere with multidrug resistance protein 2 (MRP2) activity[1][2].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Membrane Transporter/Ion Channel >> P-glycoprotein

[Target]

P-gp[2]

[In Vitro]

Hypophyllanthin down-regulates COX-2, TNF-α, and IL-1β gene expressions in U937 macrophages by interfering with the activation of NF-κB, MAPKs, and Akt[1].

[References]

[1]. Harikrishnan H, et al. Anti-Inflammatory Effects of Hypophyllanthin and Niranthin Through Downregulation of NF-κB/MAPKs/PI3K-Akt Signaling Pathways. Inflammation. 2018 Jun;41(3):984-995.

[2]. Sukhaphirom N, et al. Phyllanthin and hypophyllanthin inhibit function of P-gp but not MRP2 in Caco-2 cells. J Pharm Pharmacol. 2013 Feb;65(2):292-9.

Chemical & Physical Properties

[ Density]:
1.158

[ Boiling Point ]:
511.1±50.0 °C at 760 mmHg

[ Melting Point ]:
129-130℃

[ Molecular Formula ]:
C₂₄H₃₀O₇

[ Molecular Weight ]:
430.491

[ Flash Point ]:
200.8±30.0 °C

[ Exact Mass ]:
430.199158

[ PSA ]:
64.61000

[ LogP ]:
3.77

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.536

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22

Synthetic Route

Click to get detail synthetic route

Related Compounds

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