Structure Database (LMSD)

Common Name
Jaceosidin
Systematic Name
Synonyms
LM ID
LMPK12111235
Formula
C17H14O7
Exact Mass
Calculate m/z
330.073955
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Flavones and Flavonols [PK1211]

Biological Context

Jaceosidin is a natural methylated trihydroxyflavone first isolated from plants of the Compositae family. Like many flavones, jaceosidin has antioxidative actions on cells in culture.1 It induces cell cycle arrest and apoptosis in cancer cells, suggesting potential roles in cancer therapy.2,3,4 Jaceosidin also blocks cell signaling related to inflammation, including activation of NF-κB and induced expression of cyclooxygenase 1, inducible nitric oxide synthase, and matrix metalloproteinase-9.1,5

This information has been provided by Cayman Chemical

References

1. Woo, S.M., and Kwon, T.K. Jaceosidin induces apoptosis through Bax activation and down-regulation of Mcl-1 and c-FLIP expression in human renal carcinoma Caki cells. Chem. Biol. Interact. 260, 168-175 (2016).
2. Lv, W., Sheng, X., Chen, T., et al. Jaceosidin induces apoptosis in human ovary cancer cells through mitochondrial pathway. J. Biomed. Biotechnol. 394802 (2008).
3. Lee, J.-G., Kim, J.-H., Ahn, J.-H., et al. Jaceosidin, isolated from dietary mugwort (Artemisia princeps), induces G2/M cell cycle arrest by inactivating cdc25C-cdc2 via ATM-Chk1/2 activation. Food Chem. Toxicol. 55, 214-221 (2013).
4. Kim, M.-J., Han, J.-M., Jin, Y.-Y., et al. In vitro antioxidant and anti-inflammatory activities of Jaceosidin from Artemisia princeps Pampanini cv. Sajabal. Arch. Pharm. Res. 31(4), 42-437 (2008).
5. Jeong, M.A., Lee, K.W., Yoon, D.-Y., et al. Jaceosidin, a pharmacologically active flavone derived from Artemisia argyi, inhibits phorbol-ester-induced upregulation of COX-2 and MMP-9 by blocking phosphorylation of ERK-1 and -2 in cultured human mammary epithelial cells. Ann. N. Y. Acad. Sci. 1095, 458-466 (2007).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Viridiplantae (#33090)
Flavonoid imported from http://metabolomics.jp/

String Representations

InChiKey (Click to copy)
GLAAQZFBFGEBPS-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C17H14O7/c1-22-13-5-8(3-4-9(13)18)12-6-10(19)15-14(24-12)7-11(20)17(23-2)16(15)21/h3-7,18,20-21H,1-2H3
SMILES (Click to copy)
C1(O)=CC2OC(C3C=C(OC)C(O)=CC=3)=CC(=O)C=2C(O)=C1OC

Other Databases

CHEBI ID
66103
METABOLOMICS ID
FL3FECNS0009
PubChem CID
5379096
Cayman ID
19758

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 3
Aromatic Rings 3
Rotatable Bonds 3
Van der Waals Molecular Volume 273.29
Topological Polar Surface Area 109.36
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 7
logP 3.49
Molar Refractivity 86.13

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Updated at
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