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SML0310

Sigma-Aldrich

Tryptanthrin

≥98% (HPLC)

Synonym(s):

Couroupitine A, Indolo(2,1-b)quinazoline-6,12-dione, NSC 349447, Tryptanthrine

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About This Item

Empirical Formula (Hill Notation):
C15H8N2O2
CAS Number:
13220-57-0
Molecular Weight:
248.24
MDL number:
MFCD00012073
UNSPSC Code:
12352200
PubChem Substance ID:
329825315
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

faintly yellow to dark yellow

solubility

DMSO: 2 mg/mL (warmed)

storage temp.

2-8°C

SMILES string

O=C1C2=NC3=CC=CC=C3C(N2C4=C1C=CC=C4)=O

InChI

1S/C15H8N2O2/c18-13-10-6-2-4-8-12(10)17-14(13)16-11-7-3-1-5-9(11)15(17)19/h1-8H

InChI key

VQQVWGVXDIPORV-UHFFFAOYSA-N

Biochem/physiol Actions

Tryptanthrin is a plant alkaloid with anti-inflammatory and anti cancer activities. Tryptanthrin blocks leukotriene production in neutrophils and in whole blood assays, and in an in vivo rat pleurisy model. The compound also inhibits P-glycoprotein, and sensitizes resistant cancer cell lines to killing by cytotoxic agents.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tobias Mohn et al.
Planta medica, 73(2), 151-156 (2007-01-20)
An HPLC method has been developed and validated for the quantification of the pharmacologically active principles tryptanthrin (1), 1,3-dihydro-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylene]-2 H-indol-2-one (indolinone) (3), indirubin (4), alpha-linolenic acid (2), and indigo (5), an isomer of indirubin, in extracts from the traditional anti-inflammatory
Sung-Tsai Yu et al.
Biochemical and biophysical research communications, 358(1), 79-84 (2007-05-08)
Development of agents to overcome multidrug resistance (MDR) is important in cancer chemotherapy. Up to date, few chemicals have been reported to down-regulate MDR1 gene expression. We evaluated the effect of tryptanthrin on P-glycoprotein (P-gp)-mediated MDR in a breast cancer
Hui-Man Cheng et al.
BMC complementary and alternative medicine, 17(1), 439-439 (2017-09-04)
Indigo naturalis is a Traditional Chinese Medicine (TCM) ingredient long-recognized as a therapy for several inflammatory conditions, including psoriasis. However, its mechanism is unknown due to lack of knowledge about the responsible chemical entity. We took a different approach to
C Vlachos et al.
The British journal of dermatology, 167(3), 496-505 (2012-04-27)
The aryl hydrocarbon receptor (AhR) is a nuclear receptor and transcriptional regulator with pleiotropic effects. The production of potent AhR ligands by Malassezia yeasts, such as indirubin, indolo[3,2-b]carbazole (ICZ), tryptanthrin and malassezin, has been associated with the pathogenesis of seborrhoeic
Man Hagiyama et al.
Experimental and therapeutic medicine, 23(4), 274-274 (2022-03-08)
Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) uses its S1 spike protein to bind to angiotensin-converting enzyme 2 (ACE2) on human cells in the first step of cell entry. Tryptanthrin, extracted from leaves of the indigo plant, Polygonum tinctorium, using
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