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Lupeol

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-L2007

  • Specification : 98%

  • CAS number : 545-47-1

  • Formula : C30H50O

  • Molecular Weight : 426.72

  • PUBCHEM ID : 259846

  • Volume : 20mg

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Catalogue Number

BF-L2007

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

426.72

Appearance

White crystalline powder

Botanical Source

Crataegus pinnatifida

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

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

Synonyms

Lup-20(29)-en-3-ol, (3β)-/Cautchicol/Fagarsterol/Fagarasterol/monogynolb/Clerodol/Lup-20(29)-en-3β-ol (8CI)/Lupeol/b-viscol/MONOGYNOL/(3b)-Lup-20(29)-en-3-ol/Monogynol B/(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-Isopropenyl-3a,5a,5b,8,8,11a-hexamethylicosahydro-1H-cyclopenta[a]chrysen-9-ol/Lup-20(29)-en-3b-ol/(3β)-Lup-20(29)-en-3-ol/β-Viscol/Lupenol/(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-Hexamethyl-1-(1-propen-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol/Lup-20(29)-en-3-β-ol (8CI)

IUPAC Name

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

Density

1.0±0.1 g/cm3

Solubility

Methanol; Chloroform; Acetone; Ethyl Acetate

Flash Point

216.9±12.4 °C

Boiling Point

488.1±14.0 °C at 760 mmHg

Melting Point

215-216ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2906190000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:545-47-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31561200

Abstract

Cleome arabica is a medicinal plant contains diverse bioactive compounds and terpenoids are the major components. However, the isolation and purification of the active triterpenes from this plant involve long and complicated procedures. The present work investigates the triterpenes profiles of different tissues, besides that, describes the isolation, heterologous expression and functional characterization of C. arabica gene coding for triterpenes synthases. The phytochemical investigation through GC-MS revealed significant accumulation of pentacyclic triterpenes in leaves and siliques at mature stage compared to the stems and roots of C. arabica. Among the pentacyclic triterpenes, the lupeol reached the highest level of 320 μg/g DW in leaves at maturity stage compared to the other tissues. The biosynthesis of a pentacyclic triterpene was investigated through isolation and cloning of a full-length oxidosqualene cyclase cDNA (CaOSC) from mature leaves of C. arabica. The bioinformatic analyses revealed that CaOSC was highly homologous with the characterized lupeol synthases and shared 79.3% identity to camelliol C synthase from A. thaliana. Heterologous expression of CaOSC gene in Saccharomyces cerevisiae synthesized lupeol as a single product. The lupeol biosynthesis was exponentially increased after induction through the fermentation process reaching the maximum of 2.33 μg/ml for 240 h. Furthermore, organ-specific expression of lupeol gene was exactly matched the accumulation pattern in different tissues of C. arabica during phenological cycle. Thus, the identified CaOSC will be useful in enhancing triterpene yield for industrial purposes.

Copyright © 2019 Elsevier Masson SAS. All rights reserved.

KEYWORDS

Cleome arabica; Heterologous expression; Lupeol; Oxidosqualene cyclase; Pentacyclic triterpene

Title

Unravelling triterpene biosynthesis through functional characterization of an oxidosqualene cyclase (OSC) from Cleome arabica L.

Author

Ladhari A1, Chappell J2.

Publish date

2019 Nov

PMID

31309269

Abstract

Betulinic acid (BA) and its derivatives possess potent pharmacological activity against cancer and HIV. As with many phytochemicals, access to BA is limited by the requirement for laborious extraction from plant biomass where it is found in low amounts. This might be alleviated by metabolically engineering production of BA into an industrially relevant microbe such as Saccharomyces cerevisiae (yeast), which requires complete elucidation of the corresponding biosynthetic pathway. However, while cytochrome P450 enzymes (CYPs) that can oxidize lupeol into BA have been previously identified from the CYP716A subfamily, these generally do not seem to be specific to such biosynthesis and, in any case, have not been shown to enable high-yielding metabolic engineering. Here RoCYP01 (CYP716A155) was identified from the BA-producing plant Rosmarinus officinalis (rosemary) and demonstrated to effectively convert lupeol into BA, with strong correlation of its expression and BA accumulation. This was further utilized to construct a yeast strain that yields > 1 g/L of BA, providing a viable route for biotechnological production of this valuable triterpenoid.

KEYWORDS

Betulinic acid; Cytochrome P450; Synthetic biology; Yeast

Title

Identification of RoCYP01 (CYP716A155) enables construction of engineered yeast for high-yield production of betulinic acid.

Author

Huang J1, Zha W1, An T1, Dong H1, Huang Y2, Wang D2, Yu R1, Duan L3,4, Zhang X2, Peters RJ5, Dai Z6, Zi J7.

Publish date

2019 Sep;

PMID

31251318

Abstract

Tephrosia purpurea (L.) Pers., commonly known as “sarpunkha” and “wild indigo”, is being used in traditional systems of medicine to treat liver disorders, spleen and kidney. In the present study, a validated High Performance Thin Layer Chromatography (HPTLC) method was established for the estimation of lupeol, β-sitosterol and rotenone in various extracts of T. purpurea with the aim to see the effect of seasons on the quantity of aforesaid phytoconstituents. The plant material was collected in summer (April), rainy (August) and winter (December) during 2013-2014 from Lucknow, India. The method was validated in terms of precision, repeatability, specificity, sensitivity linearity and robustness. The method permits reliable quantification and showed good resolution on silica gel with toluene-ethyl acetate-formic acid (9:1:1 v/v/v) as mobile phase, and characteristic bands of β-sitosterol, rotenone and lupeol were observed at Rf 0.38, 0.45 and 0.52, respectively. The content of aforesaid phytoconstituents varies from season to season and extract to extract. Our finding indicated that winter season (December) may not be appropriate for collection of T. purpurea for the preparation of therapeutic formulations because of the high content of rotenone, a known insecticide that is responsible for Parkinson’s disease and associated with heart failure, fatty liver and liver necrosis.

© The Author(s) 2019. Published by Oxford University Press. All rights reserved. For Permissions, please email: journals.permissions@oup.com.

Title

A Validated HPTLC Densitometric Method for Determination of Lupeol, β-Sitosterol and Rotenone in Tephrosia purpurea: A Seasonal Study.

Author

Khatoon S1, Irshad S1, Pandey MM1, Rastogi S1, Rawat AKS1.

Publish date

2019 Aug 16


Description :

Lupeol is a novel androgen receptor inhibitor.