An iridoid glycoside with diverse biological activities
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Monotropein

Item No. 27595

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,4aS,7R,7aS)-1-(β-D-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-cyclopenta[c]pyran-4-carboxylic acid
CAS Number
5945-50-6
Synonyms
  • NSC 291303
  • NSC 88926
Molecular Formula
C16H22O11
Formula Weight
390.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
λmax
236 nm
SMILES
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]
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
InChi Key
HPWWQPXTUDMRBI-NJPMDSMTSA-N
Origin
Plant/Morindae officinalis radix
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Monotropein is an iridoid glycoside originally isolated from M. officinalis roots and has diverse biological activities.1,2,3,4,5 It increases cell viability and migration of bone marrow-derived endothelial progenitor cells (BM-EPCs) when used at concentrations ranging from 0.1 to 1,000 μM.1 Monotropein inhibits apoptosis and reduces levels of matrix metalloproteinase-3 (MMP-3) and MMP-13 in chondrocytes.2 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.3 Monotropein (100 and 200 mg/kg) 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; Item No. 23250). 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.4 Monotropein (20 and 30 mg/kg) reduces acetic acid-induced writhing in mice and carrageenan-induced paw edema in rats.5 It also decreases macrophage infiltration and wound healing time and increases blood vessel formation in a rat model of wound healing.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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).