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Lupenone

$275

  • Brand : BIOFRON

  • Catalogue Number : BF-L4004

  • Specification : 98%(HPLC)

  • CAS number : 1617-70-5

  • Formula : C30H48O

  • Molecular Weight : 424.72

  • PUBCHEM ID : 92158

  • Volume : 25mg

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Catalogue Number

BF-L4004

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

424.72

Appearance

White powder

Botanical Source

Adenophora stricta

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(=C)C1CCC2(C1C3CCC4C5(CCC(=O)C(C5CCC4(C3(CC2)C)C)(C)C)C)C

Synonyms

Lupenone/(1R,3aR,4S,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-Isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta[a]chrysen-9-one/(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-Hexamethyl-1-(1-propen-2-yl)icosahydro-9H-cyclopenta[a]chrysen-9-one/(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-Isopropenyl-3a,5a,5b,8,8,11a-hexamethylicosahydro-9H-cyclopenta[a]chrysen-9-one/Lup-2-en-1-one/(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-Isopropenyl-3a,5a,5b,8,8,11a-hexamethylicosahydro-9H-cyclopenta[a]chrysen-9-on/Lup-20(29)-en-3-one/Lup-20(30)-en-3-one/18-lupen-3-one

IUPAC Name

(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one

Applications

Lupenone, isolated from Rhizoma Musae, belongs to lupane type triterpenoids. Lupenone shows various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity[1][2].

Density

1.0±0.1 g/cm3

Solubility

Methanol; Ethyl Acetate; Petroleum ether; Hexane

Flash Point

278.4±5.7 °C

Boiling Point

487.9±12.0 °C at 760 mmHg

Melting Point

165-167ºC

InChl

InChI=1S/C30H48O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-23,25H,1,9-18H2,2-8H3/t20-,21+,22-,23+,25+,27+,28-,29+,30+/m0/s1

InChl Key

GRBHNQFQFHLCHO-BHMAJAPKSA-N

WGK Germany

RID/ADR

HS Code Reference

2914290000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:1617-70-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

25986900

Abstract

A variety of anthropogenic compounds has been found to be capable of disrupting the endocrine systems of organisms, in laboratory studies as well as in wildlife. The most widely described endpoint is estrogenicity, but other hormonal disturbances, e.g., thyroid hormone disruption, are gaining more and more attention. Here, we present a review and chemical characterization, using principal component analysis, of organic compounds that have been tested for their capacity to bind competitively to the thyroid hormone transport protein transthyretin (TTR). The database contains 250 individual compounds and technical mixtures, of which 144 compounds are defined as TTR binders. Almost one third of these compounds (n = 52) were even more potent than the natural hormone thyroxine (T4). The database was used as a tool to assist in the identification of thyroid hormone-disrupting compounds (THDCs) in an effect-directed analysis (EDA) study of a sediment sample. Two compounds could be confirmed to contribute to the detected TTR-binding potency in the sediment sample, i.e., triclosan and nonylphenol technical mixture. They constituted less than 1 % of the TTR-binding potency of the unfractionated extract. The low rate of explained activity may be attributed to the challenges related to identification of unknown contaminants in combination with the limited knowledge about THDCs in general. This study demonstrates the need for databases containing compound-specific toxicological properties. In the framework of EDA, such a database could be used to assist in the identification and confirmation of causative compounds focusing on thyroid hormone disruption.

Electronic supplementary material
The online version of this article (doi:10.1007/s00216-015-8736-9) contains supplementary material, which is available to authorized users.

KEYWORDS

Thyroid hormone-disrupting compound (THDC), Transthyretin (TTR), Database, Structure-activity relationship (SAR), Effect-directed analysis (EDA), Sediment

Title

Tracing thyroid hormone-disrupting compounds: database compilation and structure-activity evaluation for an effect-directed analysis of sediment

Author

Jana M. Weiss,corresponding author Patrik L. Andersson, Jin Zhang, Eszter Simon, Pim E. G. Leonards, Timo Hamers, and Marja H. Lamoree

Publish date

2015

PMID

29653365

Abstract

There are a large number of new structure compounds with good pharmacological activity in the natural plants, can be applied to the treatment of human diseases. Finding active ingredients from the plants is one of the important ways to develop new drugs. Triterpenes are widespread in plants, and lupenone belongs to lupane type triterpenoids. Lupenone is very common natural ingredient distributed in multi-family plants including Asteraceae, Balanophoraceae, Cactaceae, Iridaceae, Musaceae, Urticaceae, Leguminosae, Bombacaceae, etc., but its distribution has no regular. The consumption of lupenone in vegetarian diet is high in human life. Pharmacological screening of lupenone revealed various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity. Based on these important pharmacological activities, this review provides detailed account of pre-clinical studies conducted to determine the utility of lupenone as a therapeutic and chemopreventive agent for the treatment of various diseases.

Copyright © 2018 Elsevier Masson SAS. All rights reserved.

KEYWORDS

Chagas disease; Diabetes; Inflammation; Lupenone; Tumor; Virus

Title

Beneficial health effects of lupenone triterpene: A review.

Author

Xu F1, Huang X1, Wu H1, Wang X2.

Publish date

2018 Jul;

PMID

30796639

Abstract

The dried rhizome of Musa basjoo Sieb. et Zucc. is Rhizoma Musae. It has been used to treat diabetes in Miao medicine in China. Lupenone was isolated from Rhizoma Musae and has good anti-diabetic activity. Its mechanism of action is unclear. Diabetes is a chronic low-level systemic inflammatory disease, and lupenone has anti-inflammatory activity, but the underlying mechanism is not fully elucidated. In this study, we aimed to construct the drug-target biologic network and predict the anti-inflammatory mechanism of lupenone. The network-based pharmacologic analysis platform was used to identify the target proteins related to inflammation. Furthermore, the effects of lupenone on acute, subacute and diabetic pancreatic inflammation were evaluated. The “component-target-disease” network was constructed using Cytoscape. Lupenone could regulate transcription factor p65, NF-kappa-B inhibitor alpha, transcription factor AP-1, NF-kappa-B essential modulator, nuclear factor NF-kappa-B p105 subunit, epidermal growth factor receptor, hypoxia-inducible factor 1-alpha and other proteins related to the PI3K-Akt, Toll-like receptor and NF-kappa B signaling pathways. In addition, lupenone significantly decreased acute and subacute inflammation in mice as well as the IL-1β and IFN-γ levels in the pancreas of diabetic rats. The above results provide strong support for studying the molecular mechanism of lupenone in the treatment of diabetes from the perspective of anti-inflammation.

KEYWORDS

Diabetes; Inflammation; Lupenone; Network pharmacology; Pancreas; Target

Title

Lupenone is a good anti-inflammatory compound based on the network pharmacology.

Author

Xu F1, Yang L1, Huang X1, Liang Y1, Wang X1, Wu H2.

Publish date

2020 Feb;