We Offer Worldwide Shipping
Login Wishlist

Triptophenolide

$143

  • Brand : BIOFRON

  • Catalogue Number : BF-T2005

  • Specification : 98%

  • CAS number : 74285-86-2

  • Formula : C20H24O3

  • Molecular Weight : 312.4

  • PUBCHEM ID : 173273

  • Volume : 20mg

In stock

Quantity
Checkout Bulk Order?

Catalogue Number

BF-T2005

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

312.4

Appearance

White crystalline powder

Botanical Source

roots of Tripterygium wilfordii Hook. f.

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(C)C1=C(C2=C(C=C1)C3(CCC4=C(C3CC2)COC4=O)C)O

Synonyms

Triptophenolide/Phenanthro[1,2-c]furan-1(3H)-one, 3b,4,5,9b,10,11-hexahydro-6-hydroxy-9b-methyl-7-(1-methylethyl)-, (3bR,9bS)-/6-hydroxy-9b-methyl-7-propan-2-yl-3,3b,4,5,10,11-hexahydronaphtho[2,1-e]isobenzofuran-1-one/(3bR,9bS)-6-Hydroxy-7-isopropyl-9b-methyl-3b,4,5,9b,10,11-hexahydrophenanthro[1,2-c]furan-1(3H)-one

IUPAC Name

(3bR,9bS)-6-hydroxy-9b-methyl-7-propan-2-yl-3,3b,4,5,10,11-hexahydronaphtho[2,1-e][2]benzofuran-1-one

Density

1.2±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

202.4±21.5 °C

Boiling Point

490.0±45.0 °C at 760 mmHg

Melting Point

232-233ºC

InChl

InChI=1S/C20H24O3/c1-11(2)12-4-6-16-14(18(12)21)5-7-17-15-10-23-19(22)13(15)8-9-20(16,17)3/h4,6,11,17,21H,5,7-10H2,1-3H3/t17-,20+/m0/s1

InChl Key

KPXIBWGPZSPABK-FXAWDEMLSA-N

WGK Germany

RID/ADR

HS Code Reference

2907290000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:74285-86-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31299395

Abstract

Tripterygium wilfordii Hook. f. is a perennial woody vine member of the Celastraceae family. As a traditional Chinese medicine, it contains complex chemical components and exerts various pharmacological activities. In the present study, we identified a glucosyltransferase, TwUGT1, that can catalyze the synthesis of an abietane-type diterpene glucoside, namely, triptophenolide14-O-beta-D-glucopyranoside, and investigated the pharmacological activity of triptophenolide glucoside in diverse cancer cells. Triptophenolide glucoside exhibited significant inhibitory effects on U87-MG, U251, C6, MCF-7, HeLa, K562, and RBL-2H3 cells as determined by pharmacological analysis. The triptophenolide glucoside content of T. wilfordii was analyzed using Agilent Technologies 6490 Triple Quad LC/MS. The glucosyltransferase TwUGT1 belongs to subfamily 88 and group E in family 1. Molecular docking and site-directed mutagenesis of TwUGT1 revealed that the His30, Asp132, Phe134, Thr154, Ala370, Leu376, Gly382, His387, Glu395 and Gln412 residues play crucial roles in the catalytic activity of triptophenolide 14-O-glucosyltransferase. In addition, TwUGT1 was also capable of glucosylating phenolic hydroxyl groups, such as those in liquiritigenin, pinocembrin, 4-methylumbelliferone, phloretin, and rhapontigenin.

Copyright © 2019 Elsevier Ltd. All rights reserved.

KEYWORDS

Anticancer activity; Docking; Glucosyltransferase TwUGT1; Key amino acid residues; Mutagenesis; Tripterygium wilfordii Hook. f.; Triptophenolide 14-O-beta-D-glucopyranoside

Title

A specific UDP-glucosyltransferase catalyzes the formation of triptophenolide glucoside from Tripterygium wilfordii Hook. f.

Author

Ma B1, Liu X1, Lu Y1, Ma X2, Wu X1, Wang X1, Jia M3, Su P4, Tong Y4, Guan H1, Jiang Z1, Gao J1, Huang L4, Gao W5

Publish date

2019 Oct

PMID

27881165

Abstract

BACKGROUND:
Tripterygium wilfordii Radix, a well-known traditional medicine in china which is used for treatment of inflammation, pain, tumor and immune regulation for centuries in china, accompany with the serious toxic side effects. This study was carried out for simultaneously analyzing the four main components (triptolide, triptophenolide, demethylzeylasteral and celastrol) in Tripterygium wilfordii Radix under different drying processes, which was important for reducing the toxicity and quality control of Tripterygium wilfordii Radix in future.

METHODS:
The terpenes were extracted by using ultrasonic method with ethyl acetate from root or cortex of Tripterygium wilfordii Radix, and the sensitive and rapid HPLC-PDA method was developed for simultaneous quantification of triptolide, triptophenolide, demethylzeylasteral and celastrol in root and cortex of Tripterygium wilfordii Radix for evaluation of the impacts by different drying processes.

RESULTS:
The four compounds in their respective determined arrange had good linearity of 0.9998≦R2≦0.9999 and the average recoveries were range from 94.69 to 100.28%, RSDs were within 0.27 to 2.42%, respectively. The contents of triptolide, triptophenolide, demethylzeylasteral and celastrol in different Tripterygium wilfordii Radix individuals were varied greatly at different drying temperatures. Under different temperatures, the contents of triptolide, triptophenolide, demethylzeylasteral, and celastrol were 37.94-70.31 mg/g, 0-1.807 mg/g, 0.3513-9.205 mg/g, 3.202-15.31 mg/g, respectively. The suitable drying temperature of terpenoids in root of wild and cultivate are 80 °C and 60 °C, the suitable drying temperature of terpenoids in cortex is 40 °C.

CONCLUSIONS:
The method established is high sensitivity, accuracy, reliability and suitable for the simultaneous analysis of terpenoids in Tripterygium wilfordii Radix. The data provide a scientific basis and reference for the quality control of herb and preparations related to Tripterygium wilfordii Radix.

KEYWORDS

Drying temperature; HPLC-PDA analysis; Terpenoids; Tripterygium wilfordii Radix

Title

Comparative analysis of four terpenoids in root and cortex of Tripterygium wilfordii Radix by different drying methods.

Author

Wang T1,2, Shen F1, Su S3, Bai Y1, Guo S1, Yan H1, Ji T1, Wang Y4, Qian D1, Duan JA5.

Publish date

2016 Nov 23

PMID

22256754

Abstract

OBJECTIVE:
To investigate chemical constituents of the root bark of Tripterygium hypoglaucum.

METHOD:
Compounds were isolated by column chromatography on silica gel and Sephadex LH-20, and their structures were identified on the basis of spectral data (MS, 1H-NMR and 13C-NMR).

RESULT:
Twelve compounds were isolated and identified as friedelin (1), 3-oxo-olean-9(11),12-diene (2), canophyllal (3), 3-acetoxy oleanolic acid (4), triptophenolide (5), triptonoterpene methyl ether (6), tricosanoic acid (7), beta-sitosterol (8), stearic acid (9), glut-5-en-3beta,28-diol (10), palmitic acid (11) and daucostorol (12).

CONCLUSION:
Compounds 1, 2, 3, 7 and 10 were isolated from T. hypoglaucum and 7 from the genus Tripterygium for the first time.

Title

[Chemical constituents from root bark of Tripterygium hypoglaucum].

Author

Liu Z1, Zhao R, Zou Z.

Publish date

2011 Sep


Description :

Triptophenolide is a colorless crystalline plate isolated from ethyl acetate extracts of Tripterygium wilfordii. IC50 value:Target:In vitro: Triptophenolide can remarkably inhibit the delayed type hypersensitivity (DTH) reaction induced by DNCB and BSA; and diminished the peripheral blood ANAE+lymphocytes in rats and micc. Moreover, triptophenolide can dramatically increase the amount of total serum complement and significautly decrcase the serum antibody products (1gG ) of rats and mice. The phagocytosis of perioneal exudate macrophages in mice present double effects in vitro [1].In vivo: