Lupeolic acid | CAS:87355-32-6 | Manufacturer ChemFaces

Lupeolic acid

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Description:

Lupeolic acid has anti-inflammatory activity.

Targets:

COX | PGE

In vitro:

J Nat Prod. 2014 Jun 27;77(6):1445-51.

Tetra- and pentacyclic triterpene acids from the ancient anti-inflammatory remedy frankincense as inhibitors of microsomal prostaglandin E(2) synthase-1.[Pubmed: 24844534 ]

The microsomal prostaglandin E2 synthase (mPGES)-1 is the terminal enzyme in the biosynthesis of prostaglandin (PG)E2 from cyclooxygenase (COX)-derived PGH2. We previously found that mPGES-1 is inhibited by boswellic acids (IC50 = 3-30 μM), which are bioactive triterpene acids present in the anti-inflammatory remedy frankincense.
METHODS AND RESULTS:
Here we show that besides boswellic acids, additional known triterpene acids (i.e., tircuallic acid, Lupeolic acid, and roburic acid) isolated from frankincense suppress mPGES-1 with increased potencies. In particular, 3α-acetoxy-8,24-dienetirucallic acid (6) and 3α-acetoxy-7,24-dienetirucallic acid (10) inhibited mPGES-1 activity in a cell-free assay with IC50 = 0.4 μM, each. Structure-activity relationship studies and docking simulations revealed concrete structure-related interactions with mPGES-1 and its cosubstrate glutathione. COX-1 and -2 were hardly affected by the triterpene acids (IC50 > 10 μM).
CONCLUSIONS:
Given the crucial role of mPGES-1 in inflammation and the abundance of highly active triterpene acids in frankincence extracts, our findings provide further evidence of the anti-inflammatory potential of frankincense preparations and reveal novel, potent bioactivities of tirucallic acids, roburic acids, and Lupeolic acids.

Lupeolic acid Description

Source:	From Boswellia carterii
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Structure Identification:

J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 5;791(1-2):21-30.

Analysis of pentacyclic triterpenic acids from frankincense gum resins and related phytopharmaceuticals by high-performance liquid chromatography. Identification of lupeolic acid, a novel pentacyclic triterpene.[Pubmed: 12798161]

CONCLUSIONS:
An HPLC gradient method with photodiode array detection was developed for the simultaneous analysis of 12 different pentacyclic triterpenic acids in Indian and African frankincense gum resins as well as in related phytopharmaceuticals. The triterpenic acids were obtained by an exhaustive extraction procedure. Identification of the compounds was based on retention times, UV-spectra and add on technique with standards isolated from African frankincense.
CONCLUSIONS:
The method allows differentiation of frankincense of different origin and standardization of frankincense-based phytopharmaceuticals. Further, this is the first report identifying a novel pentacyclic triterpene, Lupeolic acid, as a constituent of frankincense gum resins.

Product Name	Lupeolic acid
Price:	$413 / 5mg
CAS No.:	87355-32-6
Catalog No.:	CFN96255
Molecular Formula:	C₃₀H₄₈O₃
Molecular Weight:	456.7 g/mol
Purity:	>=98%
Type of Compound:	Triterpenoids
Physical Desc.:	Powder
Source:	From Boswellia carterii
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Anti-inflammatory Compound Library Triterpenoids Compound Library PGE Inhibitor Library COX Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.1896 mL	10.9481 mL	21.8962 mL	43.7924 mL	54.7405 mL
5 mM	0.4379 mL	2.1896 mL	4.3792 mL	8.7585 mL	10.9481 mL
10 mM	0.219 mL	1.0948 mL	2.1896 mL	4.3792 mL	5.4741 mL
50 mM	0.0438 mL	0.219 mL	0.4379 mL	0.8758 mL	1.0948 mL
100 mM	0.0219 mL	0.1095 mL	0.219 mL	0.4379 mL	0.5474 mL

CFN96184	Lup-20(29)-ene-3bate,23-diol	163060-07-9	442.7	C₃₀H₅₀O₂
CFN96255	Lupeolic acid	87355-32-6	456.7	C₃₀H₄₈O₃
CFN96583	Lupeol acetate	1617-68-1	468.77	C₃₂H₅₂O₂
CFN99057	Lupeol caffeate	103917-26-6	588.9	C₃₉H₅₆O₄
CFN97717	Lup-20(29)-ene-2alpha,3beta-diol	61448-03-1	442.73	C₃₀H₅₀O₂
CFN97128	Glochidiol	6610-56-6	442.7	C₃₀H₅₀O₂
CFN98360	3-Epiglochidiol	29028-10-2	442.7	C₃₀H₅₀O₂
CFN97122	3-Epiglochidiol diacetate	6587-37-7	526.8	C₃₄H₅₄O₄
CFN89288	11beta-Hydroxylupeol	49776-92-3	442.72	C₃₀H₅₀O₂
CFN91560	Obtusalin	125164-64-9	442.7	C₃₀H₅₀O₂