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Hypophyllanthin

CAS# 33676-00-5

Hypophyllanthin

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Quality Control of Hypophyllanthin

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Chemical structure

Hypophyllanthin

3D structure

Chemical Properties of Hypophyllanthin

Cas No. 33676-00-5 SDF Download SDF
PubChem ID 358902 Appearance White powder
Formula C24H30O7 M.Wt 430.5
Type of Compound Lignans Storage Desiccate at -20°C
Solubility Soluble in chloroform, diethyl ether and methanol; sparingly soluble in petroleum ether; insoluble in water
Chemical Name (7R,9S)-9-(3,4-dimethoxyphenyl)-4-methoxy-7,8-bis(methoxymethyl)-6,7,8,9-tetrahydrobenzo[g][1,3]benzodioxole
SMILES COCC1CC2=CC(=C3C(=C2C(C1COC)C4=CC(=C(C=C4)OC)OC)OCO3)OC
Standard InChIKey LBJCUHLNHSKZBW-DSSITSQDSA-N
Standard InChI InChI=1S/C24H30O7/c1-25-11-16-8-15-10-20(29-5)23-24(31-13-30-23)22(15)21(17(16)12-26-2)14-6-7-18(27-3)19(9-14)28-4/h6-7,9-10,16-17,21H,8,11-13H2,1-5H3/t16-,17?,21+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Hypophyllanthin

The herbs of Phyllanthus niruri Linn.

Biological Activity of Hypophyllanthin

Description1. Hypophyllanthin and phyllanthin have antitumour effects against Ehrlich Ascites Carcinoma in mice. 2. Hypophyllanthin can modulate the vascular tension via the endothelium-independent mechanisms. 3. Hypophyllanthin can directly inhibit P-gp activity and does not interfere with MRP2 activity, it may reversibly inhibit P-gp function. 4. Hypophyllanthin offers a promising means for treatment of chronic muscle pain. 5. Hypophyllanthin has estrogenic properties against carbofuran induced toxicity in female rats.
TargetsP-gp | Calcium Channel | Potassium Channel | PGE

Hypophyllanthin Dilution Calculator

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Hypophyllanthin Molarity Calculator

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Preparing Stock Solutions of Hypophyllanthin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3229 mL 11.6144 mL 23.2288 mL 46.4576 mL 58.072 mL
5 mM 0.4646 mL 2.3229 mL 4.6458 mL 9.2915 mL 11.6144 mL
10 mM 0.2323 mL 1.1614 mL 2.3229 mL 4.6458 mL 5.8072 mL
50 mM 0.0465 mL 0.2323 mL 0.4646 mL 0.9292 mL 1.1614 mL
100 mM 0.0232 mL 0.1161 mL 0.2323 mL 0.4646 mL 0.5807 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Hypophyllanthin

Phyllanthin and hypophyllanthin inhibit function of P-gp but not MRP2 in Caco-2 cells.[Pubmed:23278697]

J Pharm Pharmacol. 2013 Feb;65(2):292-9.

OBJECTIVES: The purposes of this study were to investigate the inhibitory effects of two lignans, phyllanthin and Hypophyllanthin, on the function of P-glycoprotein (P-gp) and multidrug resistance protein 2 (MRP2), using the in-vitro model of Caco-2 cells. In addition, the effect of prolonged exposure to these two compounds on the expression of active P-gp was also determined. METHODS: The activity of P-gp and MRP2 was determined in the uptake assays by monitoring the intracellular accumulation of their specific substrates (calcein acetoxymethyl ester and 5(6)-carboxy-2',7'-dichlorofluorescein diacetate, respectively) with fluorescence spectroscopy. KEY FINDINGS: Hypophyllanthin and phyllanthin inhibited P-gp function with comparable potencies, but neither compound affected MRP2 activity. When the lignans were washed out before addition of substrate, the inhibitory action of both compounds against P-gp function was lost. These results suggested the reversibility of the inhibition. Moreover, prolonged exposure of the Caco-2 cells to both lignans (up to 7 days) had no effect on P-gp function. CONCLUSIONS: Phyllanthin and Hypophyllanthin directly inhibited P-gp activity and did not interfere with MRP2 activity. It was likely that both phyllanthin and Hypophyllanthin could reversibly inhibit P-gp function.

Pain Modulation by Lignans (Phyllanthin and Hypophyllanthin) and Tannin (Corilagin) Rich Extracts of Phyllanthus amarus in Carrageenan-induced Thermal and Mechanical Chronic Muscle Hyperalgesia.[Pubmed:25974715]

Phytother Res. 2015 Aug;29(8):1202-10.

The current study was aimed at evaluating the antihyperalgesic effects of lignans (phyllanthin and Hypophyllanthin) and tannin (corilagin) rich three standardized extracts of Phyllanthus amarus in a model of chronic musculoskeletal inflammatory pain. Three percent carrageenan injected in the gastrocnemius muscle produced hyperalgesia to mechanical and heat stimuli ipsilaterally, which spreads to the contralateral side within 7 to 9 days. To investigate the effects on chronic thermal and mechanical hypersensitivity, three extracts of P. amarus in three doses (100, 200, and 400 mg/kg) were administered to animals intraperitoneally from 14th day to 22nd day after intramuscular injection of carrageenan. It was observed that intraperitoneal administrations of Phyllanthus extracts showed antihyperalgesic activity, as they elevated thermal and mechanical threshold, which was supported by histopathological observations along with reduction in prostaglandin E2 (PGE2) concentration. In conclusion, we strongly suggest that the observed antihyperalgesic and antiinflammatory effects of P. amarus in current pain model are mediated via spinal or supraspinal neuronal mechanisms, mainly by inhibition of PGE2. Modulation of chronic muscular inflammation may be due to presence of phytoconstituents like phyllanthin, Hypophyllanthin, and corilagin, which offers a promising means for treatment of chronic muscle pain.

1H- and 13C-nmr assignments of phyllanthin and hypophyllanthin: lignans that enhance cytotoxic responses with cultured multidrug-resistant cells.[Pubmed:8385184]

J Nat Prod. 1993 Feb;56(2):233-9.

Complete 1H-nmr data and unambiguous assignments of the 13C-nmr spectra of phyllanthin [1] and Hypophyllanthin [2] were obtained through extensive nmr studies, including homonuclear COSY, homonuclear decoupling, APT, HETCOR, nOe difference, selective INEPT, and COLOC experiments. The absolute configuration of Hypophyllanthin [2] was determined by cd. Neither of these lignans demonstrated significant cytotoxic activity when evaluated with a battery of cultured mammalian cells, but both were found to enhance the cytotoxic response mediated by vinblastine with multidrug-resistant KB cells. In addition, 1 was found to displace the binding of vinblastine with membrane vesicles derived from this cell line, suggesting an interaction with the P-glycoprotein.

Endothelium-independent effects of phyllanthin and hypophyllanthin on vascular tension.[Pubmed:21893171]

Fitoterapia. 2011 Dec;82(8):1231-6.

The purpose of this study was to investigate the modulating effects of phyllanthin and Hypophyllanthin on vascular tension, using in the in vitro model of isolated rat aorta. Our results indicated that both phyllanthin and Hypophyllanthin significantly relaxed the sustained contraction induced by phenylephrine (PE) in a concentration-dependent manner. In addition, endothelial removal had no significant influence on the vasorelaxation responses of the aortic rings toward these two compounds. Furthermore, both compounds inhibited the contraction of aortic muscle provoked by either PE (1 muM) or KCl (40 mM) as well as the spontaneous contraction of the Ca(2)(+)-depleted muscle. In high K(+)-Ca(2)(+) free solution, phyllanthin (100 muM), but not Hypophyllanthin, significantly inhibited the contractile responses upon cumulative addition of CaCl(2). Both compounds (100 muM) significantly inhibited PE-induced contraction in Ca(2)(+)-free condition, but could not affect caffeine-induced contraction. Taken together, phyllanthin and Hypophyllanthin could modulate the vascular tension via the endothelium-independent mechanisms. The modulating effects of both compounds were possibly involved with the blockade of Ca(2)(+) entry into vascular smooth muscle cells and inhibition of PE-mediated Ca(2)(+) release from sarcoplasmic reticulum.

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.

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