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Heterophyllin B

$431

  • Brand : BIOFRON

  • Catalogue Number : BD-P0040

  • Specification : 98.0%(HPLC)

  • CAS number : 145459-19-4

  • PUBCHEM ID : 102022989

  • Volume : 25mg

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Catalogue Number

BD-P0040

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

-20℃

Molecular Weight

Appearance

White crystalline powder

Botanical Source

Pseudostellaria heterophylla (Miq.)Pax ex Pax et Hoffm./Root of Pseudostellaria heterophylla

Structure Type

Miscellaneous

Category

Standards;Natural Pytochemical;API

SMILES

CCC(C)C1C(=O)NC(C(=O)NCC(=O)NCC(=O)NC(C(=O)N2CCCC2C(=O)N3CCCC3C(=O)N4CCCC4C(=O)N1)CC(C)C)CC5=CC=CC=C5

Synonyms

Cyclo(glycylglycyl-L-leucyl-L-prolyl-L-prolyl-L-prolyl-L-isoleucyl-L-phenylalanyl)/Heterophyllin B

IUPAC Name

(3S,9S,15S,24S,27S,30S)-24-benzyl-27-[(2S)-butan-2-yl]-15-(2-methylpropyl)-1,7,13,16,19,22,25,28-octazatetracyclo[28.3.0.03,7.09,13]tritriacontane-2,8,14,17,20,23,26,29-octone

Density

1.3±0.1 g/cm3

Solubility

Methanol; Acetontrile

Flash Point

655.1±34.3 °C

Boiling Point

1159.7±65.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C40H58N8O8/c1-5-25(4)34-37(53)44-27(21-26-12-7-6-8-13-26)35(51)42-22-32(49)41-23-33(50)43-28(20-24(2)3)38(54)47-18-10-15-30(47)40(56)48-19-11-16-31(48)39(55)46-17-9-14-29(46)36(52)45-34/h6-8,12-13,24-25,27-31,34H,5,9-11,14-23H2,1-4H3,(H,41,49)(H,42,51)(H,43,50)(H,44,53)(H,45,52)/t25-,27-,28-,29-,30-,31-,34-/m0/s1

InChl Key

KYAVLJJQNUHRMR-PPLFBOPFSA-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#:145459-19-4) 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

31749814

Abstract

Plant cyclic peptides (CPs) are a large group of small molecule metabolites found in a wide variety of plants, including traditional Chinese medicinal plants. However, the majority of plant CPs have not been studied for their biosynthetic mechanisms, including heterophyllin B (HB), which is one of the characteristic chemical components of Pseudostellaria heterophylla. Here, we screened the precursor gene (prePhHB) of HB in P. heterophylla and functionally identified its correctness in vivo and in vitro. First, we developed a new method to screen the precursors of HB from 16 candidate linear peptides. According to transcriptome sequencing data, we cloned the genes that encoded the HB precursor peptides and confirmed that the prePhHB-encoded precursor peptide could enzymatically synthesize HB. Next, we generated the transgenic tobacco that expressed prePhHB, and the results showed that HB was detected in transgenic tobacco. Moreover, we revealed that prePhHB gene expression is positively correlated with HB accumulation in P. heterophylla. Mutations in the prePhHB gene may influence the accumulation of HB in P. heterophylla. These results suggest that HB is ribosomally synthesized and posttranslationally modified peptide (RiPP) derived from the precursor gene prePhHB-encoded precursor peptide, and the core peptide sequence of HB is IFGGLPPP in P. heterophylla. This study developed a new idea for the rapid identification of Caryophyllaceae-type CP precursor peptides via RNA-sequencing data mining.

KEYWORDS

Pseudostellaria heterophylla; cyclic peptide; gene; heterophyllin B; prePhHB.

Title

The Biosynthesis of Heterophyllin B in Pseudostellaria heterophylla From prePhHB-Encoded Precursor

Author

Wei Zheng 1 2 , Tao Zhou 1 , Jun Li 1 , Weike Jiang 3 , Jinqiang Zhang 1 , Chenghong Xiao 1 , Dequn Wei 1 , Changgui Yang 1 , Rong Xu 1 , Anhui Gong 1 , Chen Zhang 1 , Yan Bi 1

Publish date

2019 Oct 17

PMID

29561811

Abstract

Heterophyllin B (HB), an active cyclic peptide, is a compound existing in the ethyl acetate extract of Pseudostellaria heterophylla (Miq.) Pax and exhibited the activity of inhibiting the production of NO and cytokines, such as IL-1β and IL-6, in LPS-stimulated RAW 264.7 macrophages. In addition, HB suppressed the production of ROS and the apoptosis induced by LPS in RAW 264.7 macrophages. The underlying mechanism was investigated in the LPS-induced RAW 264.7 cells. The results showed that HB decreased the level of IL-1β and IL-6 expression by qRT-PCR analysis. HB up-regulated the relative ratio of p-AKT/AKT and p-PI3K/PI3K as indicated by western blot analysis. In summary, HB inhibited the LPS-induced inflammation and apoptosis through the PI3K/Akt signaling pathways and represented a potential therapeutic target for treatment of inflammatory diseases.

KEYWORDS

Heterophyllin B; anti-apoptosis; anti-inflammatory effect; anti-oxidative effect.

Title

Heterophyllin B Ameliorates Lipopolysaccharide-Induced Inflammation and Oxidative Stress in RAW 264.7 Macrophages by Suppressing the PI3K/Akt Pathways

Author

Chunjing Yang 1 , Longtai You 2 , Xingbin Yin 3 , Yi Liu 4 , Xin Leng 5 , Wenping Wang 6 , Na Sai 7 , Jian Ni 8

Publish date

2018 Mar 21

PMID

26647768

Abstract

The present study aimed to measure the effect of heterophyllin B (HB) on the adhesion and invasion of ECA-109 human esophageal carcinoma cells, and examine the possible mechanism involved. A Cell Counting kit 8 assay was performed to determine the cell viability. Cell adhesion and invasion were determined following treatment of the ECA-109 cells with HB (0, 10, 25 and 50 µM) for 24 h. The levels of phosphorylated (p-)ATK and p-phosphoinositide 3-kinase (PI3K), and the protein levels of β-catenin were measured using western blot analysis. The mRNA and protein expression levels of E-cadherin, vimentin, snail, matrix metalloproteinase (MMP)2 and MMP9 were detected using reverse transcription-quantitative polymerase chain reaction and western blot analyses, respectively. HB (10, 25 and 50 µM) significantly suppressed the adhesion and invasion of the ECA-109 human esophageal carcinoma cells in a dose-dependant manner. The expression levels of p-ATK, p-PI3K and β-catenin were markedly decreased. The expression of E-cadherin was promoted, whereas the expression levels of snail, vimentin, MMP 2 and MMP 9 were decreased significantly in the ECA-109 cells treated with HB. In addition, HB inhibited the adhesion and invasion induced by PI3K activating peptide in the ECA-109 cells, and the protein expression levels were also adjusted. These results suggested that HB effectively suppressed the adhesion and invasion of the human esophageal carcinoma cells by mediating the PI3K/AKT/β-catenin pathways and regulating the expression levels of adhesion- and invasion-associated genes.

Title

Heterophyllin B Inhibits the Adhesion and Invasion of ECA-109 Human Esophageal Carcinoma Cells by Targeting PI3K/AKT/β-catenin Signaling

Author

Ji-Cheng Tantai 1 , Yao Zhang 2 , Heng Zhao 1

Publish date

2016 Feb


Description :

Heterophyllin B is an active cyclic peptide isolated from Pseudostellaria heterophylla. Heterophyllin B provides a novel strategy for the treatment of esophageal cancer[1].