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Arteannuin B

$476

  • Brand : BIOFRON

  • Catalogue Number : BD-P0600

  • Specification : 98.0%(HPLC)

  • CAS number : 50906-56-4

  • Formula : C15H20O3

  • Molecular Weight : 248.32

  • PUBCHEM ID : 6543478

  • Volume : 25mg

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Catalogue Number

BD-P0600

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

248.32

Appearance

White crystalline powder

Botanical Source

Artemisia annua Linn.; Artemisia carvifolia / Constit. of Artemisia annua

Structure Type

Sesquiterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1CCC2C(=C)C(=O)OC23C1CCC4(C3O4)C

Synonyms

Quinghaosu II/Arsinous acid,dimethyl-,2-hydroxyethyl ester/(1aR,1bR,4aS,7R,7aS,9aR)-7,9a-Dimethyl-4-methylenedecahydro-3H-oxireno[7,8]naphtho[8a,1-b]furan-3-one/Arteannuin B/Arsinigsaeureglykolester/3H-Oxireno[7,8]naphtho[8a,1-b]furan-3-one, decahydro-7,9a-dimethyl-4-methylene-, (1aR,1bR,4aS,7R,7aS,9aR)-/arteanniun L

IUPAC Name

(1R,5S,8R,9S,12R,14R)-8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.01,5.012,14]tetradecan-3-one

Applications

Arteannuin B co-occurs with artemisinin, which is the potent antimalarial principle of the Chinese medicinal herb Artemisia annua (Asteraceae)[1].

Density

1.2±0.1 g/cm3

Solubility

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

Flash Point

168.5±20.5 °C

Boiling Point

398.7±35.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C15H20O3/c1-8-4-5-11-9(2)12(16)17-15(11)10(8)6-7-14(3)13(15)18-14/h8,10-11,13H,2,4-7H2,1,3H3/t8-,10+,11+,13-,14-,15-/m1/s1

InChl Key

QWQSMEDUZQDVLA-USPGQWGOSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:50906-56-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

31652784

Abstract

Metabolic engineering is an integrated bioengineering approach, which has made considerable progress in producing terpenoids in plants and fermentable hosts. Here, the full biosynthetic pathway of artemisinin, originating from Artemisia annua, was integrated into the moss Physcomitrella patens. Different combinations of the five artemisinin biosynthesis genes were ectopically expressed in P. patens to study biosynthesis pathway activity, but also to ensure survival of successful transformants. Transformation of the first pathway gene, ADS, into P. patens resulted in the accumulation of the expected metabolite, amorpha-4,11-diene, and also accumulation of a second product, arteannuin B. This demonstrates the presence of endogenous promiscuous enzyme activity, possibly cytochrome P450s, in P. patens. Introduction of three pathway genes, ADS-CYP71AV1-ADH1 or ADS-DBR2-ALDH1 both led to the accumulation of artemisinin, hinting at the presence of one or more endogenous enzymes in P. patens that can complement the partial pathways to full pathway activity. Transgenic P. patens lines containing the different gene combinations produce artemisinin in varying amounts. The pathway gene expression in the transgenic moss lines correlates well with the chemical profile of pathway products. Moreover, expression of the pathway genes resulted in lipid body formation in all transgenic moss lines, suggesting that these may have a function in sequestration of heterologous metabolites. This work thus provides novel insights into the metabolic response of P. patens and its complementation potential for A. annua artemisinin pathway genes. Identification of the related endogenous P. patens genes could contribute to a further successful metabolic engineering of artemisinin biosynthesis, as well as bioengineering of other high-value terpenoids in P. patens.

KEYWORDS

Physcomitrella patens; artemisinin; biotechnology; malaria; sesquiterpenoids

Title

Insights into Heterologous Biosynthesis of Arteannuin B and Artemisinin in Physcomitrella patens.

Author

Ikram NKK1,2, Kashkooli AB3,4, Peramuna A5, Krol ARV6, Bouwmeester H7,8, Simonsen HT9.

Publish date

2019 Oct 23;

PMID

29381342

Abstract

A fast, simple, efficient, and high-throughput analytical protocol using deep eutectic solvents (DES) for mechanochemical extraction (MCE) combined with direct analysis in real time mass spectrometry (DART-MS) was developed to quantify heat-labile bioactive compounds artemisinin (AN), arteannuin B, and artemisinic acid from Aretemisia annua. MCE is performed at room temperature, and target analytes are released into DESs within seconds; this method demonstrated multiple advantages over traditional extraction methods and organic solvents. DART-MS was then used for the structure confirmation and quantification for the three artemisinin major components extracted from plants of five locations. Liquid chromatography (LC) measurements were performed as well for results verification and comparison, and the amounts obtained were consistent between the two techniques. DART-MS showed advantages in simplicity, low limit of detection (5-15 ng mL-1), and superior speed (10-20 s), but with slightly higher relative standard deviation (0.7-10.8%). The entire protocol can be accomplished in a few minutes from raw materials to quantitative results. This study aims to establish a methodology combining high-efficiency sample pretreatment and rapid chemical analysis from complex matrixes, where the time-consuming separation procedure can be eliminated. Additionally, the use of toxic organic solvents needed in the process of chemical extraction and analysis is largely avoided. In general, this investigation provides a robust analytical procedure that can be widely used in many areas of research and industrial activities.

Title

High-Throughput Analysis for Artemisinins with Deep Eutectic Solvents Mechanochemical Extraction and Direct Analysis in Real Time Mass Spectrometry.

Author

Wang J1, Zhou Y1, Wang M1, Bi W1, Li H1, Chen DDY1,2.

Publish date

2018 Mar 6

PMID

28880869

Abstract

BACKGROUND:
Daodi-herb is a part of Chinese culture, which has been naturally selected by traditional Chinese medicine clinical practice for many years. Sweet wormwood herb is a kind of Daodi-herb, and comes from Artemisia annua L. Artemisinin is a kind of effective antimalarial drug being extracted from A. annua. Because of artemisinin, Sweet wormwood herb earns a reputation. Based on the Pharmacopoeia of the People’s Republic of China (PPRC), Sweet wormwood herb can be used to resolve summerheat-heat, and prevent malaria. Besides, it also has other medical efficacies. A. annua, a medicinal plant that is widely distributed in the world contains many kinds of chemical composition. Research has shown that compatibility of artemisinin, scopoletin, arteannuin B and arteannuic acid has antimalarial effect. Compatibility of scopoletin, arteannuin B and arteannuic acid is conducive to resolving summerheat-heat. Chemical constituents in A. annua vary significantly according to geographical locations. So, distribution of A. annua may play a key role in the characteristics of efficacy and chemical constituents of Sweet wormwood herb. It is of great significance to study this relationship.

OBJECTIVES:
We mainly analyzed the relationship between the chemical constituents (arteannuin B, artemisinin, artemisinic acid, and scopoletin) with special efficacy in A. annua that come from different provinces in china, and analyzed the relationship between chemical constituents and spatial distribution, in order to find out the relationship between efficacy, chemical constituents and distribution.

METHODS:
A field survey was carried out to collect A. annua plant samples. A global positioning system (GPS) was used for obtaining geographical coordinates of sampling sites. Chemical constituents in A. annua were determined by liquid chromatography tandem an atmospheric pressure ionization-electrospray mass spectrometry. Relationship between chemical constituents including proportions, correlation analysis (CoA), principal component analysis (PCA) and cluster analysis (ClA) was displayed through Excel and R software version2.3.2(R), while the one between efficacy, chemical constituents and spatial distribution was presented through ArcGIS10.0, Excel and R software.

RESULTS:
According to the results of CoA, arteannuin B content presented a strong positive correlation with artemisinic acid content (p = 0), and a strong negative correlation with artemisinin content (p = 0). Scopoletin content presented a strong positive correlation with artemisinin content (p = 0), and a strong negative correlation with artemisinic acid content (p = 0). According to the results of PCA, the first two principal components accounted for 81.57% of the total accumulation contribution rate. The contribution of the first principal component is about 45.12%, manly including arteannuin B and artemisinic acid. The contribution of the second principal component is 36.45% of the total, manly including artemisinin and scopoletin. According to the ClA by using the principal component scores, 19 provinces could be divided into two groups. In terms of provinces in group one, the proportions of artemisinin are all higher than 80%. Based on the results of PCA, ClA, percentages and scatter plot analysis, chemical types are defined as “QHYS type”, “INT type” and “QHS type.”

CONCLUSION:
As a conclusion, this paper shows the relationship between efficacy, chemical constituents and distribution. Sweet wormwood herb with high arteannuin B and artemisinic acid content, mainly distributes in northern China. Sweet wormwood herb with high artemisinin and scopoletin content has the medical function of preventing malaria, which mainly distributes in southern China. In this paper, it is proved that Sweet wormwood Daodi herb growing in particular geographic regions, has more significant therapeutical effect and higher chemical constituents compared with other same kind of CMM. And also, it has proved the old saying in China that Sweet wormwood Daodi herb which has been used to resolve summerheat-heat and prevent malaria, which distributed in central China. But in modern time, Daodi Sweet wormwood herb mainly has been used to extract artemisinin and prevent malaria, so the Daod-region has transferred to the southern China.

Title

Differences in chemical constituents of Artemisia annua L from different geographical regions in China.

Author

Zhang X1,2, Zhao Y3, Guo L2, Qiu Z1, Huang L2, Qu X1.

Publish date

2017 Sep 7;