Monotropein | CAS# 5945-50-6 | Iridoid Glycoside

MedKoo Cat#: 574021 | Name: Monotropein

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Monotropein is an iridoid glycoside. It increases cell viability and migration of bone marrow-derived endothelial progenitor cells (BM-EPCs), inhibits apoptosis, and reduces levels of matrix metalloproteinase-3 (MMP-3) and MMP-13 in chondrocytes. It inhibits LPS-induced nuclear translocation of NF-κB and reduces COX-2, inducible nitric oxide synthase (iNOS), TNF-α, and IL-1β mRNA expression in RAW 264.7 cells. Monotropein also reduces colonic myeloperoxidase (MPO) activity, COX-2 and iNOS mRNA expression, and disease severity in a mouse model of ulcerative colitis induced by dextran sulfate sodium (DSS). It increases bone mineral content, bone mineral density, and improves bone microstructure in ovariectomized mice when administered at doses of 40 or 80 mg/kg. Monotropein decreases macrophage infiltration and wound healing time and increases blood vessel formation in a rat model of wound healing.

Chemical Structure

Monotropein

CAS#5945-50-6

Theoretical Analysis

MedKoo Cat#: 574021

Name: Monotropein

CAS#: 5945-50-6

Chemical Formula: C16H22O11

Exact Mass: 390.1162

Molecular Weight: 390.34

Elemental Analysis: C, 49.23; H, 5.68; O, 45.09

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 330.00
10mg	USD 560.00
25mg	USD 1,050.00
50mg	USD 2,000.00

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Related CAS #

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Synonym

Monotropein, NSC 291303, NSC 88926

IUPAC/Chemical Name

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

InChi Key

HPWWQPXTUDMRBI-NJPMDSMTSA-N

InChi Code

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

SMILES Code

OC[C@@]1(O)C=C[C@]2([H])C(C(O)=O)=CO[C@@H](O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@]21[H]

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Monotropein is an iridoid glycoside isolated Morinda officinalis.

In vitro activity:

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. Reference: Int Immunopharmacol. 2014 Dec;23(2):575-80. https://pubmed.ncbi.nlm.nih.gov/25466264/

In vivo activity:

This study aimed to explore the role of MON (monotropein) in doxorubicin (DOX)-induced cardiotoxicity. This study showed that MON treatment mitigated DOX-induced myocardial damage and improved cardiac dysfunction. In addition, DOX-treated mice displayed higher levels of inflammation and oxidative stress, while MON treatment also reversed these pathological changes. Moreover, DOX-treated mice were more susceptible to ventricular fibrillation, whereas MON reduced ventricular fibrillation incidence. Reference: Biochem Biophys Res Commun. 2023 Jan 1;638:14-22. https://pubmed.ncbi.nlm.nih.gov/36436337/

	Solvent	mg/mL	mM
Solubility
	DMSO	78.0	199.83
	Water	54.6	139.94

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 390.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Wang F, Wu L, Li L, Chen S. Monotropein exerts protective effects against IL-1β-induced apoptosis and catabolic responses on osteoarthritis chondrocytes. Int Immunopharmacol. 2014 Dec;23(2):575-80. doi: 10.1016/j.intimp.2014.10.007. Erratum in: Int Immunopharmacol. 2023 Mar;116:109633. PMID: 25466264. 2. Jiang F, Xu XR, Li WM, Xia K, Wang LF, Yang XC. Monotropein alleviates H2O2‑induced inflammation, oxidative stress and apoptosis via NF‑κB/AP‑1 signaling. Mol Med Rep. 2020 Dec;22(6):4828-4836. doi: 10.3892/mmr.2020.11548. Epub 2020 Sep 29. PMID: 33173962; PMCID: PMC7646929. 3. Fang Z, Wei W, Jiang X. Monotropein attenuates doxorubicin-induced oxidative stress, inflammation, and arrhythmia via the AKT signal pathway. Biochem Biophys Res Commun. 2023 Jan 1;638:14-22. doi: 10.1016/j.bbrc.2022.11.058. Epub 2022 Nov 19. PMID: 36436337. 4. Zhang Q, Hu S, He Y, Song Z, Shen Y, Zhao Z, Zhang Q, Qin L, Zhang Q. Monotropein Protects against Inflammatory Bone Loss and Suppresses Osteoclast Formation and Bone Resorption by Inhibiting NFATc1 via NF-κB and Akt/GSK-3β Pathway. Nutrients. 2022 Sep 24;14(19):3978. doi: 10.3390/nu14193978. PMID: 36235631; PMCID: PMC9571677.

In vitro protocol:

In vivo protocol:

1. Fang Z, Wei W, Jiang X. Monotropein attenuates doxorubicin-induced oxidative stress, inflammation, and arrhythmia via the AKT signal pathway. Biochem Biophys Res Commun. 2023 Jan 1;638:14-22. doi: 10.1016/j.bbrc.2022.11.058. Epub 2022 Nov 19. PMID: 36436337. 2. Zhang Q, Hu S, He Y, Song Z, Shen Y, Zhao Z, Zhang Q, Qin L, Zhang Q. Monotropein Protects against Inflammatory Bone Loss and Suppresses Osteoclast Formation and Bone Resorption by Inhibiting NFATc1 via NF-κB and Akt/GSK-3β Pathway. Nutrients. 2022 Sep 24;14(19):3978. doi: 10.3390/nu14193978. PMID: 36235631; PMCID: PMC9571677.

1. Wang, C., Mao, C., Lou, Y., et al. Monotropein promotes angiogenesis and inhibits oxidative stress-induced autophagy in endothelial progenitor cells to accelerate wound healing. J. Cell. Mol. Med. 22(3), 1583-1600 (2018). 2. Wang, F., Wu, L., Li, L., et al. Monotropein exerts protective effects against IL-1β-induced apoptosis and catabolic responses on osteoarthritis chondrocytes. Int. Immunopharmacol. 23(2), 575-580 (2014). 3. Shin, J.-S., Yun, K.-J., Chung, K.-S., et al. Monotropein isolated from the roots of Morinda officinalis ameliorates proinflammatory mediators in RAW 264.7 macrophages and dextran sulfate sodium (DSS)-induced colitis via NF-κB inactivation. Food Chem. Toxicol. 53, 263-271 (2013). 4. Zhang, Z., Zhang, Q., Yang, H., et al. Monotropein isolated from the roots of Morinda officinalis increases osteoblastic bone formation and prevents bone loss in ovariectomized mice. Fitoterapia 110, 166-172 (2016). 5. Choi, J., Lee, K.-T., Choi, M.-Y., et al. Antinociceptive anti-inflammatory effect of Monotropein isolated from the root of Morinda officinalis. Biol. Pharm. Bull. 28(10), 1915-1918 (2005).