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Monotropein

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-M2013

  • Specification : 98%

  • CAS number : 5945-50-6

  • Formula : C16H22O11

  • Molecular Weight : 390.34

  • PUBCHEM ID : 73466

  • Volume : 20mg

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Catalogue Number

BF-M2013

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

390.34

Appearance

White crystalline powder

Botanical Source

Morinda officinalis

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

C1=CC(C2C1C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)O)(CO)O

Synonyms

Cyclopenta[c]pyran-4-carboxylic acid, 1-(β-D-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-, (1S,4aS,7R,7aS)-/(1S,2S,6S,9R)-9-hydroxy-9-(hydroxymethyl)-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxabicyclo[4.3.0]nona-4,7-diene-5-carboxylic acid/Morinda officinalis How/(1S,4aS,7R,7aS)-1-(β-D-Glucopyranosyloxy)-7-hydroxy-7-(hydroxymethyl)-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid

IUPAC Name

(1S,4aS,7R,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylic acid

Density

1.7±0.1 g/cm3

Solubility

Methanol; Water; DMSO

Flash Point

262.0±26.4 °C

Boiling Point

717.6±60.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C16H22O11/c17-3-8-10(19)11(20)12(21)15(26-8)27-14-9-6(1-2-16(9,24)5-18)7(4-25-14)13(22)23/h1-2,4,6,8-12,14-15,17-21,24H,3,5H2,(H,22,23)/t6-,8-,9-,10-,11+,12-,14+,15+,16+/m1/s1

InChl Key

HPWWQPXTUDMRBI-NJPMDSMTSA-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#:5945-50-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29908987

Abstract

Estrogen deficiency and inflammation are known to play important roles in bone metabolism and occurrence of osteoporosis. Monotropein as an iridoid glycoside is reported to decrease estrogen deficiency-induced bone loss and inhibit inflammatory response in LPS-induced RAW 264.7 macrophages. However, the effect of monotropein on bone loss in chronic inflammatory conditions remains unclear. It was found in the present study that monotropein significantly inhibited bone mass reduction and improved bone micro-architectures by enhancing bone formation and blocking increased secretion of inflammatory cytokines in osteoporotic mice induced by combined ovariectomy and LPS. Our in vitro experiment further demonstrated that monotropein was able to increase the proliferation and activity of alkaline phosphatase (ALP), bone matrix mineralization and the expression of bone matrix protein osteopontin (OPN) in osteoblastic MC3T3-E1 cells injured by LPS. In addition, monotropein significantly decreased the production of IL-6 and IL-1β, inhibited the nuclear translocation of p65 and NF-κB P50, and down-regulated the phosphorylation of NF-κB p65 and IKK, indicating that monotropein could attenuate inflammatory impairment to MC3T3-E1 cells by suppressing the activation of NF-κB pathway. All these results suggest that monotropein may prove to be a promising candidate for the prevention and treatment of inflammatory bone loss.

Copyright © 2018 Elsevier B.V. All rights reserved.

KEYWORDS

Inflammation; Monotropein; NF-κB pathway; Osteoblast; Osteoporosis; Ovariectomy

Title

Monotropein attenuates ovariectomy and LPS-induced bone loss in mice and decreases inflammatory impairment on osteoblast through blocking activation of NF-κB pathway.

Author

He YQ1, Yang H2, Shen Y3, Zhang JH1, Zhang ZG4, Liu LL5, Song HT6, Lin B6, Hsu HY7, Qin LP1, Han T8, Xin HL9, Zhang QY10.

Publish date

2018 Aug 1

PMID

29278309

Abstract

Attenuating oxidative stress-induced damage and promoting endothelial progenitor cell (EPC) differentiation are critical for ischaemic injuries. We suggested monotropein (Mtp), a bioactive constituent used in traditional Chinese medicine, can inhibit oxidative stress-induced mitochondrial dysfunction and stimulate bone marrow-derived EPC (BM-EPC) differentiation. Results showed Mtp significantly elevated migration and tube formation of BM-EPCs and prevented tert-butyl hydroperoxide (TBHP)-induced programmed cell death through apoptosis and autophagy by reducing intracellular reactive oxygen species release and restoring mitochondrial membrane potential, which may be mediated viamTOR/p70S6K/4EBP1 and AMPK phosphorylation. Moreover, Mtp accelerated wound healing in rats, as indicated by reduced healing times, decreased macrophage infiltration and increased blood vessel formation. In summary, Mtp promoted mobilization and differentiation of BM-EPCs and protected against apoptosis and autophagy by suppressing the AMPK/mTOR pathway, improving wound healing in vivo. This study revealed that Mtp is a potential therapeutic for endothelial injury-related wounds.

© 2017 The Authors. Journal of Cellular and Molecular Medicine published by John Wiley & Sons Ltd and Foundation for Cellular and Molecular Medicine.

KEYWORDS

angiogenesis; autophagy; endothelial progenitor cells; wound healing

Title

Monotropein promotes angiogenesis and inhibits oxidative stress-induced autophagy in endothelial progenitor cells to accelerate wound healing.

Author

Wang C1,2, Mao C1,2, Lou Y1,2, Xu J1,2, Wang Q1,2, Zhang Z1,2, Tang Q1,2, Zhang X1,2, Xu H1,2, Feng Y1,2.

Publish date

2018 Mar

PMID

25466264

Abstract

Osteoarthritis, characterized by a loss of articular cartilage accompanied with inflammation, is the most common age-associated degenerative disease. Monotropein, an iridoids glycoside isolated from the roots of Morinda officinalis How, has been demonstrated to exhibit anti-inflammatory activity. In the present study, monotropein was firstly to exhibit cartilage protective activity by down regulating the pro-inflammatory cytokines in the knee synovial fluid in vivo. The anti-apoptotic and anti-catabolic effects of monotropein on rat OA chondrocytes treated by IL-1β were investigated in vitro. In cultured chondrocytes, monotropein attenuated apoptosis in a dose-dependent manner in response to IL-1β stimulation. Moreover, treatment with monotropein, the expressions of MMP-3 and MMP-13 were significantly decreased, the expression of COL2A1 was increased. Taken together, these findings suggested that monotropein exerted anti-apoptosis and anti-catabolic activity in chondrocytes, which might support its possible therapeutic role in OA.

Title

Monotropein exerts protective effects against IL-1β-induced apoptosis and catabolic responses on osteoarthritis chondrocytes.

Author

Wang F, Wu L, Li L, Chen S.

Publish date

2014 Dec


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