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T3652

Sigma-Aldrich

Triptolide

from Tripterygium wilfordii, ≥98% (HPLC), solid, immunosuppressant

Synonym(s):

PG 490

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About This Item

Empirical Formula (Hill Notation):
C20H24O6
CAS Number:
38748-32-2
Molecular Weight:
360.40
MDL number:
MFCD00210565
UNSPSC Code:
12352200
PubChem Substance ID:
24900156
NACRES:
NA.77

product name

Triptolide, from Tripterygium wilfordii, ≥98% (HPLC), solid

biological source

Tripterygium wilfordii

Assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

DMSO: soluble

storage temp.

2-8°C

SMILES string

O=C1OCC2=C1CC[C@]3(C)[C@]4(O5)[C@@H]5[C@H]6[C@@](O6)(C(C)C)[C@@H](O)[C@]4(O7)[C@@H]7C[C@]32[H]

InChI

1S/C20H24O6/c1-8(2)18-13(25-18)14-20(26-14)17(3)5-4-9-10(7-23-15(9)21)11(17)6-12-19(20,24-12)16(18)22/h8,11-14,16,22H,4-7H2,1-3H3/t11?,12-,13-,14-,16+,17-,18-,19+,20+/m0/s1

InChI key

DFBIRQPKNDILPW-KTGKZQHOSA-N

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Application

Triptolide has been used as a NF-κB inhibitor to study the inhibition of cell invasion and angiogenesis in human thyroid cancer cells6. Triptolide has also been used to study its apoptotic effects in anaplastic thyroid cancer cells7.

Biochem/physiol Actions

Triptolide is a diterpene triepoxide, the principal active ingredient in extracts from the Chinese herb Tripterygium wilfordii hook (TwHF). It is a potent immunosuppressant and anti-inflammatory. Triptolide has been shown to inhibit the expression of IL-2 in activated T cells at the level of purine-box/nuclear factor and NF-κB mediated transcription activation. It synergizes with cyclosporin A in promoting graft survival in animal models and in suppression of graft versus host disease in allogeneic bone marrow transplants. In addition, it induces apoptosis in tumor cells and potentiates tumor necrosis factor (TNFα) induction of apoptosis in part through the suppression of c-IAP2 and c-IAP1 induction.

Preparation Note

Triptolide is soluble in DMSO. The stock solution should be stored in DMSO at -20 deg C after reconstitution.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H300 + H330,H361f

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 1 Oral - Repr. 2

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Ruidong Li et al.
Oncology reports, 37(1), 442-448 (2016-11-24)
Cellular senescence, an irreversible growth arrest of cells, is involved in protection against cancer. Triptolide (TPL) plays an important role in immunosuppressive, anti-fertility, anti-cystogenesis and anticancer activities. However, effect and mechanism of TPL on cellular senescence-associated antitumor is rarely reported.
Stefano Giustino Manzo et al.
Cancer research, 72(20), 5363-5373 (2012-08-29)
Triptolide is a bioactive ingredient in traditional Chinese medicine that exhibits diverse biologic properties, including anticancer properties. Among its many putative targets, this compound has been reported to bind to XPB, the largest subunit of general transcription factor TFIIH, and
Chundong Song et al.
BMC complementary and alternative medicine, 19(1), 198-198 (2019-08-04)
Endothelial cell inflammation is a central event in the pathogenesis of numerous cardiovascular diseases, including sepsis and atherosclerosis. Triptolide, a principal bioactive ingredient of Traditional Chinese Medicine Tripterygium wilfordii Hook.F., displays anti-inflammatory actions in vivo. However, the mechanisms underlying these
Xiang Wang et al.
Toxicology and applied pharmacology, 310, 32-40 (2016-08-25)
Triptolide (TP), derived from the medicinal plant Triterygium wilfordii Hook. f. (TWHF), is a diterpene triepoxide with variety biological and pharmacological activities. However, TP has been restricted in clinical application due to its narrow therapeutic window especially in reproductive system.
Zhao-Li Zhou et al.
Natural product reports, 29(4), 457-475 (2012-01-25)
Triptolide, a principal bioactive ingredient of Tripterygium wilfordii Hook F, has attracted extensive exploration due to its unique structure of a diterpenoid triepoxide and multiple biological activities. This review will focus on the structural modifications, structure-activity relationships, pharmacology, and clinical
View All Related Papers

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