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Ecliptasaponin A

$225

  • Brand : BIOFRON

  • Catalogue Number : BF-E2008

  • Specification : 98%

  • CAS number : 78285-90-2

  • Formula : C36H58O9

  • Molecular Weight : 634.84

  • PUBCHEM ID : 476537

  • Volume : 20mg

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Catalogue Number

BF-E2008

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

634.84

Appearance

White crystalline powder

Botanical Source

Eclipta prostrata

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(CCC2(C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)OC6C(C(C(C(O6)CO)O)O)O)C)C(=O)O)C

Synonyms

Gleditsoside B/Olean-12-en-28-oic acid, 3-(β-D-glucopyranosyloxy)-16-hydroxy-, (3β,16α)-/(3β,16α)-3-(β-D-Glucopyranosyloxy)-16-hydroxyolean-12-en-28-oic acid/Gleditschoside B/Echynocystinsaeure-monosid/Echinocystic acid-3-O-glucoside/Ecliptasaponin A

IUPAC Name

(4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Density

1.27±0.1 g/cm3

Solubility

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

Flash Point

228.6±26.4 °C

Boiling Point

752.6±60.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C36H58O9/c1-31(2)14-15-36(30(42)43)20(16-31)19-8-9-23-33(5)12-11-25(45-29-28(41)27(40)26(39)21(18-37)44-29)32(3,4)22(33)10-13-34(23,6)35(19,7)17-24(36)38/h8,20-29,37-41H,9-18H2,1-7H3,(H,42,43)/t20-,21+,22-,23+,24+,25-,26+,27-,28+,29-,33-,34+,35+,36+/m0/s1

InChl Key

WYDPEADEZMZKNM-ZBKPBKBGSA-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#:78285-90-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31807521

Abstract

BACKGROUND:
Non-small cell lung cancer (NSCLC) is one of the causes of carcinomas mortality worldwide. Ecliptasaponin A (ES), a natural product extracted from the plant known as Eclipta prostrata, has been reported as an anti-cancer drug against various cancer cell lines. However, the exact mechanisms of ES have not yet been fully characterized.

METHODS:
Numerous studies have been done to support that ES has a powerful inhibiting effect on the growth of cancers via the activation of apoptosis and autophagy. To explore the underlying mechanisms of anti-cancer and investigate the relationships of the apoptosis and autophagy, we used apoptosis signal-regulating kinase 1 (ASK1) inhibitor (GS-4997), c-Jun N-terminal kinase (JNK) inhibitor (SP600125), and autophagy inhibitor [chloroquine (CQ) and 3-methyladenine (3-MA)].

RESULTS:
ES could potently suppress cell viability and induces apoptotic cell death of human lung cancer cells H460 and H1975. ES activated apoptosis via ASK1/JNK pathway, GS-4997 and SP600125 can attenuated these effects. Furthermore, ES could triggered autophagy in lung cancer cell lines, and the autophagy inhibitor 3-MA and CQ reversed ES-induced apoptosis in H460 and H1975 cells. Furthermore, SP600125 can inhibit autophagy.

CONCLUSIONS:
This study showed that ES induces apoptosis in human lung cancer cells by triggering enhanced autophagy and ASK1/JNK pathway, which may thus be a promising agent against lung cancer.

2019 Annals of Translational Medicine. All rights reserved.

KEYWORDS

Ecliptasaponin A (ES); Lung cancer; apoptosis; apoptosis signal-regulating kinase 1 (ASK1); autophagy; c-Jun N-terminal kinase (JNK)

Title

Ecliptasaponin A induces apoptosis through the activation of ASK1/JNK pathway and autophagy in human lung cancer cells.

Author

Han J1, Lv W1, Sheng H1, Wang Y1, Cao L1, Huang S1, Zhu L1, Hu J1.

Publish date

2019 Oct

PMID

30380653

Abstract

Osteoarthritis (OA) is the common form of arthritis and is characterized by disability and cartilage degradation. Although natural product extracts have been reported to have anti-osteoarthritic effects, the potential bioactivity of Ryupunghwan (RPH), a traditional Korean medicinal botanical formula that contains Astragalus membranaceus, Turnera diffusa, Achyranthes bidentata, Angelica gigas, Eclipta prostrata, Eucommia ulmoides, and Ilex paraguariensis, is not known well. Therefore, the inhibitory effects of single compounds isolated from RPH on the OA-related molecules were investigated using IL-1β-stimulated chondrosarcoma SW1353 (SW1353) cell model. Two bioactive compounds, isomucronulatol 7-O-β-d-glucoside (IMG) and ecliptasaponin A (ES) were isolated and purified from RPH using column chromatography, and then the structures were analyzed using ESI-MS, ¹H-NMR, and 13C-NMR spectrum. The expression or amount of matrix metalloproteinase 13 (MMP13), COX1/2, TNF-α, IL-1β or p65 was determined by RT-PCR, Western blot, and enzyme-linked immunosorbent assay (ELISA). RPH pretreatment reduced the expression and amounts of MMP13, and the expression of collagen II, COX1/2, TNF-α, IL-1β or p65, which were increased in IL-1β-stimulated SW1353 cells. IMG reduced the expression of all OA-related molecules, but the observed inhibitory effect was less than that of RPH extract. The other single compound ES showed the reduced expression of all OA-related molecules, and the effect was stronger than that in IMG (approximately 100 fold). Combination pretreatment of both single components remarkably reduced the expression of MMP13, compared to each single component. These synergic effects may provide potential molecular modes of action for the anti-osteoarthritic effects of RPH observed in clinical and animal studies.

KEYWORDS

IL-1β; Ryupunghwan (natural product mixture); chondrosarcoma cells; ecliptasaponin A; isomucronulatol 7-O-β-d-glucoside; osteoarthritis

Title

Inhibition of Osteoarthritis-Related Molecules by Isomucronulatol 7-O-β-d-glucoside and Ecliptasaponin A in IL-1β-Stimulated Chondrosarcoma Cell Model.

Author

Hong GU1, Lee JY2, Kang H3, Kim TY4, Park JY5, Hong EY6, Shin YH7, Jung SH8, Chang HB9, Kim YH10, Kwon YI11, Ro JY12,13.

Publish date

2018 Oct 29

PMID

26378987

Abstract

A sensitive, rapid and specific high-performance liquid chromatography tandem mass spectrometry method (HPLC-MS/MS) was developed to determine ecliptasaponin A in rat plasma and tissues after oral administration. Ginsenoside Rg1 was used as the internal standard (IS). The plasma and tissues samples were prepared by liquid-liquid extraction with ethyl acetate and separated on an Eclipse Plus C18 column (2.1 mm × 150 mm, 5 µm) at a flow rate of 0.4 mL/min using acetonitrile and water (containing 0.05% acetic acid) as the mobile phase. The tandem mass detection was carried out with eletrospray ionization in negative mode. Quantification was performed by using multiple reaction monitoring (MRM), which monitored the fragmentation of m/z 633.4→587.2 for ecliptasaponin A and m/z 859.4→637.4 for the IS. The calibration curves obtained were linear in different matrices, and the lower limit of quantification (LLOQ) achieved was 0.5 ng/mL both for rat plasma and tissues. The intra- and inter-day precisions were below 15%. This method was successfully applied to pharmacokinetic study of ecliptasaponin A in rat plasma and tissues after oral administration.

Copyright © 2015 John Wiley & Sons, Ltd.

KEYWORDS

Eclipta prostrate L; Ecliptasaponin A; LC-MS/MS; pharmacokinetics

Title

Determination of ecliptasaponin A in rat plasma and tissues by liquid chromatography-tandem mass spectrometry.

Author

Zhao J1, Liu E1,2, Han L1,2, Wang L1, Zhang Y1,2, Wang T1,2, Fang S1,2, Gao X1.

Publish date

2016 Jun


Description :

Ecliptasaponin A , a pentacyclic triterpenoid saponin, is one of major compounds separated from Eclipta prostrate[1]. Eclipta prostrate is considered as a nourishing herbal medicine with pleiotropic effects, including anti-inflammatory, hepatoprotective, antioxidant, and immunomodulatory[2].