3809
T3D3755
Emodin
Emodin is found in dock. Emodin is present in Cascara sagrada.Emodin is a purgative resin from rhubarb, Polygonum cuspidatum, the buckthorn and Japanese Knotweed (Fallopia japonica). The term may also refer to any one of a series of principles isomeric with the emodin of rhubarb. (Wikipedia)
Emodin has been shown to exhibit anti-inflammatory, signalling, antibiotic, muscle building and anti-angiogenic functions (A3049, A7853, A7854, A7855, A7857).
518-82-1
3220
C15H10O5
White powder.
266 - 268°C
Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Emodin is moderately cytotoxic and can inhibit the growth of many cell types by interfering with the cell cycle, possibly by stimulating the expression of p53 and p21. Alternatively, it may do this by creating DNA strand breaks and/or non-covalently binding to DNA and inhibiting the catalytic activity of topoisomerase II. It may also induce apoptosis by inhibiting the electron transport chain, producing reactive oxygen species. Emodin is a strong inhibitor of tyrosine-protein kinase Lck and other tyrosine kinase receptors, which likely contributes to its growth suppressing activity. It may act as a chemopreventive agent by activating DNA repair machinery.
Emodin can also inhibit metastasis by interfering with the activity of matrix metalloproteinases, either directly or through through inhibition of focal adhesion kinase, mitogen-activated protein kinase, and RAC-alpha serine/threonine-protein kinase activation, and partial inhibition of transcription factor AP-1 and nuclear factor NF-kappa-B (NF-kB) transcriptional activities.
Emodin exerts its purgative effects by acting directly or indirectly on colon epithelial cells. This activates the underlying smooth muscle cells, leading to muscle contractility. Possible mechanisms for this effect includes enhancing the hormone motilin, activating muscarinic receptors by triggering the release of acetylcholine, stimulating the protein kinase C-alpha pathway for increased calcium sensibility, inhibiting the secretion of the hormone somatostatin, increasing fluid electrolyte accumulation in the distal ileum and colon, and inhibiting the activity of Na+/K+-ATPase and/or potassium channels.
Emodin's antiinflammatory action is due to its specific inhibition of the transcription factor NF-kB. It also regulates angiogenesis by inhibiting the enzymes casein kinase II and nitric oxide synthase and has shown potent estrogen receptor binding affinity. Emodin can induce the microsomal enzyme cytochrome P-450 1A1, perpetuating its own metabolic activation. (A3043, A3044, A3045, A3046, A3047, A3048, A3049, A3050, A3051, A3052, A3053, A3054)
Emodin is biotransformed by the microsomal cytochrome P450 enzymes into active hydroxyemodins such as omega-hydroxyemodin and 2-hydroxyemodin. Emodin glycoside is carried unabsorbed to the large intestine, where it is metabolized to the active aglycones by intestinal bacterial flora. (A3043, A3046)
LD50: 35 mg/kg (Intraperitoneal, Mouse) (L135)
No indication of carcinogenicity to humans (not listed by IARC).
Emodin is a mycotoxin and naturally occurring anthraquinone present in the roots and barks of numerous plants, such as rhubarb. It is an active ingredient of Chinese herbs, including Rheum officinale and Polygonam cuspidatum. Emodin is also produced as a secondary metabolite by molds and lichens such as Aspergillus wentii. It has been used as a laxative and also investigated as a potential chemotherapeutic drug. (A3043)
Chronic use can cause disturbances in electrolyte balance, especially potassium deficiency, and fluid imbalance. Emodin may also cause damage to kidney cells. (A3043, A3044)
Emodin has purgative properties and causes diarrhea. (A3043)
2010-05-14T14:53:47Z
2014-12-24T20:26:30Z
http://en.wikipedia.org/wiki/Emodin
C10343
42223
DB07715
EMO
true
CC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1O)C2=O
C15H10O5
InChI=1S/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3
InChIKey=RHMXXJGYXNZAPX-UHFFFAOYSA-N
270.2369
270.05282343
Exogenous
Solid
HMDB35214
CHEMBL289277
3107