Diphyllin

Name: Diphyllin
Brand: MedChemExpress
SKU: HY-N2532
Rating: 4.5 (1 reviews)

Cat. No.: HY-N2532 Purity: 99.90%: FAQs
Data Sheet SDS COA Handling Instructions

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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. Diphyllin is a vacuolar type H⁺-ATPase (V-ATPase) inhibitor with an IC₅₀ value of 17 nM and inhibits lysosomal acidification in human osteoclasts. Diphyllin inhibits NO production with an IC₅₀ of 50 μM and has anticancer and anti-inflammatory activities.

For research use only. We do not sell to patients.

Diphyllin Chemical Structure

CAS No. : 22055-22-7

Size	Price	Stock	Quantity
5 mg	USD 110	In-stock	Estimated Time of Arrival: December 31
10 mg	USD 190	In-stock	Estimated Time of Arrival: December 31
50 mg		Get quote
100 mg		Get quote

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Based on 1 publication(s) in Google Scholar

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HIV HIV-1 HIV-2

Biological Activity
Purity & Documentation
References
Customer Review

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].

IC₅₀ & Target^[1]^[2]

HIV-1

0.38 μM (IC₅₀)

Vacuolar type H⁺-ATPase

17 nM (IC₅₀)

Vesicular stomatitis virus (VSV)

Cellular Effect

Cell Line	Type	Value	Description	References
A2058	IC₅₀	2.6 μM Compound: 1	Cytotoxicity against human A2058 cells incubated for 24 hrs by AlamarBlue staining based analysis Cytotoxicity against human A2058 cells incubated for 24 hrs by AlamarBlue staining based analysis	[PMID: 36857518]
A549	IC₅₀	2.02 μM Compound: 1	Cytotoxicity against human A549 cells incubated for 24 hrs by MTS assay Cytotoxicity against human A549 cells incubated for 24 hrs by MTS assay	[PMID: 36857518]
A549	IC₅₀	24.01 μM Compound: 1	Cytotoxicity against human A549 cells measured after 3 days by MTT assay Cytotoxicity against human A549 cells measured after 3 days by MTT assay	[PMID: 36857518]
A549	IC₅₀	8 μM Compound: 5a	Anticancer activity against Homo sapiens (human) A549 cells assessed as decrease in cell growth after 3 days by MTT assay Anticancer activity against Homo sapiens (human) A549 cells assessed as decrease in cell growth after 3 days by MTT assay	10.1007/s00044-012-0245-1
A549	IC₅₀	8 μM Compound: Diphyllin	Cytotoxicity against Homo sapiens (human) A549 cells after 72 hr by MTT assay Cytotoxicity against Homo sapiens (human) A549 cells after 72 hr by MTT assay	10.1007/s00044-011-9937-1
A549	IC₅₀	8.8 μM Compound: 1	Cytotoxicity against human A549 cells incubated for 24 hrs by AlamarBlue staining based analysis Cytotoxicity against human A549 cells incubated for 24 hrs by AlamarBlue staining based analysis	[PMID: 36857518]
Calu-1	IC₅₀	31.8 μM Compound: 1	Cytotoxicity against human Calu-1 cells incubated for 24 hrs by AlamarBlue staining based analysis Cytotoxicity against human Calu-1 cells incubated for 24 hrs by AlamarBlue staining based analysis	[PMID: 36857518]
EBC-1	IC₅₀	14.8 μM Compound: 1	Cytotoxicity against human EBC-1 cells incubated for 24 hrs by AlamarBlue staining based analysis Cytotoxicity against human EBC-1 cells incubated for 24 hrs by AlamarBlue staining based analysis	[PMID: 36857518]
ECa-109 cell line	IC₅₀	0.21 μM Compound: 1	Antiproliferative activity against human Eca-109 cells measured after 2 days by CCK-8 method Antiproliferative activity against human Eca-109 cells measured after 2 days by CCK-8 method	[PMID: 36857518]
HCT-116	ED₅₀	0.8 μg/mL Compound: 3	Cytotoxicity against human HCT116 cells by MTT assay Cytotoxicity against human HCT116 cells by MTT assay	[PMID: 11908984]
HCT-116	IC₅₀	3.54 μM Compound: 1	Cytotoxicity against human HCT116 cells after 72 hrs by sulforhodamine B and MTT assay Cytotoxicity against human HCT116 cells after 72 hrs by sulforhodamine B and MTT assay	[PMID: 22119124]
HCT-116	IC₅₀	48.5 μM Compound: 5a	Anticancer activity against Homo sapiens (human) HCT116 cells assessed as decrease in cell growth after 3 days by MTT assay Anticancer activity against Homo sapiens (human) HCT116 cells assessed as decrease in cell growth after 3 days by MTT assay	10.1007/s00044-012-0245-1
HEK293	IC₅₀	> 100 μM Compound: 5a	Cytotoxicity against Homo sapiens (human) HEK293 cells assessed as decrease in cell growth after 3 days by MTT assay Cytotoxicity against Homo sapiens (human) HEK293 cells assessed as decrease in cell growth after 3 days by MTT assay	10.1007/s00044-012-0245-1
HEK293	IC₅₀	774.4 μM Compound: Diphyllin	Cytotoxicity against Homo sapiens (human) HEK293 cells after 72 hr by MTT assay Cytotoxicity against Homo sapiens (human) HEK293 cells after 72 hr by MTT assay	10.1007/s00044-011-9937-1
Hep 3B2	ED₅₀	3.6 μg/mL Compound: 3	Cytotoxicity against human Hep3B cells by MTT assay Cytotoxicity against human Hep3B cells by MTT assay	[PMID: 11908984]
HepG2	IC₅₀	> 500 μM Compound: 1	Cytotoxicity against Homo sapiens (human) HepG2 cells after 3 days by MTT assay Cytotoxicity against Homo sapiens (human) HepG2 cells after 3 days by MTT assay	10.1007/s00044-009-9172-1
HepG2	ED₅₀	0.4 μg/mL Compound: 3	Cytotoxicity against human HepG2 cells by MTT assay Cytotoxicity against human HepG2 cells by MTT assay	[PMID: 11908984]
HepG2	IC₅₀	21.6 μM Compound: 1	Cytotoxicity against human HepG2 cells incubated for 24 hrs by AlamarBlue staining based analysis Cytotoxicity against human HepG2 cells incubated for 24 hrs by AlamarBlue staining based analysis	[PMID: 36857518]
HT-29	IC₅₀	19.5 μM Compound: 1	Cytotoxicity against human HT-29 cells incubated for 24 hrs by AlamarBlue staining based analysis Cytotoxicity against human HT-29 cells incubated for 24 hrs by AlamarBlue staining based analysis	[PMID: 36857518]
HT-29	ED₅₀	2.5 μg/mL Compound: 3	Cytotoxicity against human HT-29 cells by MTT assay Cytotoxicity against human HT-29 cells by MTT assay	[PMID: 11908984]
K562	IC₅₀	1.67 μM Compound: 1	Cytotoxicity against human K562 cells after 72 hrs by sulforhodamine B and MTT assay Cytotoxicity against human K562 cells after 72 hrs by sulforhodamine B and MTT assay	[PMID: 22119124]
K562	IC₅₀	2.38 μM Compound: Diphyllin	Cytotoxicity against human etoposide-sensitive K562 cells after 72 hrs by CellTiter96 AQueous one solution cell proliferation assay Cytotoxicity against human etoposide-sensitive K562 cells after 72 hrs by CellTiter96 AQueous one solution cell proliferation assay	[PMID: 29656990]
K562	IC₅₀	23.46 μM Compound: 1	Cytotoxicity against adriamycin-selected multi drug-resistant human K562 cells after 72 hrs by sulforhodamine B and MTT assay Cytotoxicity against adriamycin-selected multi drug-resistant human K562 cells after 72 hrs by sulforhodamine B and MTT assay	[PMID: 22119124]
KB	IC₅₀	0.78 μM Compound: 1	Cytotoxicity against human KB cells after 72 hrs by sulforhodamine B and MTT assay Cytotoxicity against human KB cells after 72 hrs by sulforhodamine B and MTT assay	[PMID: 22119124]
KB	IC₅₀	3.15 μM Compound: 1	Cytotoxicity against vincristine-selected multi drug-resistant human KB cells after 72 hrs by sulforhodamine B and MTT assay Cytotoxicity against vincristine-selected multi drug-resistant human KB cells after 72 hrs by sulforhodamine B and MTT assay	[PMID: 22119124]
KB	IC₅₀	5.3 μM Compound: 5a	Anticancer activity against Homo sapiens (human) KB cells assessed as decrease in cell growth after 3 days by MTT assay Anticancer activity against Homo sapiens (human) KB cells assessed as decrease in cell growth after 3 days by MTT assay	10.1007/s00044-012-0245-1
KB	IC₅₀	5.3 μM Compound: Diphyllin	Cytotoxicity against Homo sapiens (human) KB cells after 72 hr by MTT assay Cytotoxicity against Homo sapiens (human) KB cells after 72 hr by MTT assay	10.1007/s00044-011-9937-1
MCF7	IC₅₀	0.54 μM Compound: 1	Cytotoxicity against human MCF7 cells after 72 hrs by sulforhodamine B and MTT assay Cytotoxicity against human MCF7 cells after 72 hrs by sulforhodamine B and MTT assay	[PMID: 22119124]
MONO-MAC-6	IC₅₀	3.9 μM Compound: 1	Cytotoxicity against human MONO-MAC-6 cells incubated for 24 hrs by AlamarBlue staining based analysis Cytotoxicity against human MONO-MAC-6 cells incubated for 24 hrs by AlamarBlue staining based analysis	[PMID: 36857518]
NCI-H838	IC₅₀	16 μM Compound: 1	Cytotoxicity against human NCI-H838 cells incubated for 24 hrs by AlamarBlue staining based analysis Cytotoxicity against human NCI-H838 cells incubated for 24 hrs by AlamarBlue staining based analysis	[PMID: 36857518]
PC-3	IC₅₀	3.8 μM Compound: 1	Cytotoxicity against human PC-3 cells incubated for 24 hrs by AlamarBlue staining based analysis Cytotoxicity against human PC-3 cells incubated for 24 hrs by AlamarBlue staining based analysis	[PMID: 36857518]
Platelet	IC₅₀	> 100 μM Compound: 10	Inhibition of arachidonic acid-induced platelet aggregation in rabbit platelet-rich blood by turbidimetric method Inhibition of arachidonic acid-induced platelet aggregation in rabbit platelet-rich blood by turbidimetric method	[PMID: 8988600]
SW480	IC₅₀	3.4 μM Compound: 5a	Anticancer activity against Homo sapiens (human) SW480 cells assessed as decrease in cell growth after 3 days by MTT assay Anticancer activity against Homo sapiens (human) SW480 cells assessed as decrease in cell growth after 3 days by MTT assay	10.1007/s00044-012-0245-1
SW480	IC₅₀	3.4 μM Compound: Diphyllin	Cytotoxicity against Homo sapiens (human) SW480 cells after 72 hr by MTT assay Cytotoxicity against Homo sapiens (human) SW480 cells after 72 hr by MTT assay	10.1007/s00044-011-9937-1
TE-1	IC₅₀	0.28 μM Compound: 1	Antiproliferative activity against human TE-1 cells measured after 2 days by CCK-8 method Antiproliferative activity against human TE-1 cells measured after 2 days by CCK-8 method	[PMID: 36857518]
U-87MG ATCC	IC₅₀	26.1 μM Compound: 1	Cytotoxicity against human U87 cells incubated for 24 hrs by AlamarBlue staining based analysis Cytotoxicity against human U87 cells incubated for 24 hrs by AlamarBlue staining based analysis	[PMID: 36857518]
Vero C1008	IC₅₀	> 100 μM Compound: 1	Cytotoxicity against African green monkey Vero E6 cells incubated for 48 hrs by CCK-8 assay Cytotoxicity against African green monkey Vero E6 cells incubated for 48 hrs by CCK-8 assay	[PMID: 36857518]

Molecular Weight

380.35

Formula

C₂₁H₁₆O₇

CAS No.

22055-22-7

Appearance

Solid

Color

Off-white to gray

SMILES

O=C1OCC2=C(O)C3=CC(OC)=C(OC)C=C3C(C4=CC=C(OCO5)C5=C4)=C12

Structure Classification

Initial Source

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

DMSO : 14.29 mg/mL (37.57 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	2.6292 mL	13.1458 mL	26.2916 mL
5 mM	0.5258 mL	2.6292 mL	5.2583 mL
10 mM	0.2629 mL	1.3146 mL	2.6292 mL

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

Concentration _(start)

Volume _(start)

Concentration _(final)

Volume _(final)

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 1.43 mg/mL (3.76 mM); Clear solution

This protocol yields a clear solution of ≥ 1.43 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (14.3 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Protocol 2

Add each solvent one by one: 10% DMSO 90% Corn Oil
Solubility: ≥ 1.43 mg/mL (3.76 mM); Clear solution

This protocol yields a clear solution of ≥ 1.43 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (14.3 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

DMSO +

Tween-80 +

Saline

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Calculation results:

Working solution concentration: mg/mL

Method for preparing stock solution: mg drug dissolved in μL DMSO (Stock solution concentration: mg/mL).

The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).

Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.

If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.

Purity & Documentation

Purity: 99.90%

Select Batch:

Data Sheet (281 KB) SDS (393 KB)

COA (259 KB) LCMS (95 KB)

Handling Instructions (2659 KB)

References

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

[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. [Content Brief]

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

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

DMSO	1 mM	2.6292 mL	13.1458 mL	26.2916 mL	65.7289 mL
	5 mM	0.5258 mL	2.6292 mL	5.2583 mL	13.1458 mL
	10 mM	0.2629 mL	1.3146 mL	2.6292 mL	6.5729 mL
	15 mM	0.1753 mL	0.8764 mL	1.7528 mL	4.3819 mL
	20 mM	0.1315 mL	0.6573 mL	1.3146 mL	3.2864 mL
	25 mM	0.1052 mL	0.5258 mL	1.0517 mL	2.6292 mL
	30 mM	0.0876 mL	0.4382 mL	0.8764 mL	2.1910 mL

Diphyllin Related Classifications

Help & FAQs

Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

Diphyllin22055-22-7VSVHIVProton PumpInfluenza VirusVesicular Stomatitis VirusHuman immunodeficiency virusHIV-1arylnaphthalenelignanantiviralinfluenzaviruscytotoxicityInhibitorinhibitorinhibit

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Diphyllin

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Complete Stock Solution Preparation Table

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