InChI=1S/C18H16O8/c1-23-10-6-8(4-5-9(10)19)17-18(25-3)16(22)13-11(26-17)7-12(24-2)14(20)15(13)21/h4-7,19-21H,1-3H3 |
QQBSPLCHDUCBNM-UHFFFAOYSA-N |
COc1cc(ccc1O)-c1oc2cc(OC)c(O)c(O)c2c(=O)c1OC |
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Inula aschersoniana
(NCBI:txid557639)
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Found in
aerial part
(BTO:0001658).
See:
PubMed
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plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antiviral agent
A substance that destroys or inhibits replication of viruses.
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antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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View more via ChEBI Ontology
5,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxy-4H-1-benzopyran-4-one
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4',5,6-trihydroxy-3,3',7-trimethoxyflavone
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ChEBI
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Quercetagetin 3,7,3'-trimethyl ether
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KEGG COMPOUND
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1441253
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Reaxys Registry Number
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Reaxys
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23370-16-3
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CAS Registry Number
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ChemIDplus
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Trendafilova A, Todorova M, Genova V, Shestakova P, Dimitrov D, Jadranine M, Milosavljevic S (2014) New pseudoguaiane derivatives from Inula aschersoniana Janka var. aschersoniana. Natural product communications 9, 1123-1124 [PubMed:25233586] [show Abstract] The aerial parts of Inula aschersoniana Janka var. aschersoniana afforded parthenolide, diepoxycostunolide, inusoniolide, chrysosplenol C and four new pseudoguaiane-type sesquiterpenoids. Their structures were determined using spectral methods and relative stereochemistry by NOESY correlations. | Son MJ, Kim HK, Huong do TT, Kim YH, Van Sung T, Cuong NM, Woo SH (2011) Chrysosplenol C increases contraction in rat ventricular myocytes. Journal of cardiovascular pharmacology 57, 259-262 [PubMed:21052017] [show Abstract] Chrysosplenol C (4',5,6-trihydroxy-3,3',7-trimethoxyflavone) is a flavone contained in several medicinal plants including Miliusa balansae and Pterocaulon sphacelatum. This compound is known to have an antiviral effect and show cytotoxic activity in several cell lines. In the present study, we explored the effect of chrysosplenol C on contractility in isolated adult rat ventricular myocytes. Chrysosplenol C was isolated from M. balansae, and cell shortenings were measured in field-stimulated single myocytes using a video edge detection method at room temperature. Chrysosplenol C was found to increase cell shortenings in a dose-dependent manner with a half-maximal effective concentration of 45 ± 7.8 μM. Maximal effect of chrysosplenol C, approximately 185% of control, was observed at ≥80 μM. The positive inotropic effect caused by chrysosplenol C was reversible. Time-to-peak contraction and time-to-relengthening were significantly increased by chrysosplenol C. The velocity of cell shortening was slightly accelerated, whereas that of relaxation was not altered by chrysosplenol C. The chrysosplenol C–induced positive inotropic effect was not inhibited by propranolol posttreatment or H-89 pretreatment, suggesting that chrysosplenol C increased contraction independently of β-adrenergic receptor stimulation and protein kinase A. Our findings are the first to demonstrate that chrysosplenol C is a positive inotropic agent in cardiac myocytes. | Huong DT, Luong DV, Thao TT, Sung TV (2005) A new flavone and cytotoxic activity of flavonoid constituents isolated from Miliusa balansae (Annonaceae). Die Pharmazie 60, 627-629 [PubMed:16124409] [show Abstract] A new flavone named miliufavol [8-(2-hydroxybenzyl)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxy-4H-chromen-4-one or 8-C-(o)-hydroxybenzylpachypodol] from Miliusa balansae (Annonaceae) was isolated and structurally elucidated by spectroscopic means besides four known flavones: ombuine, chrysosplenol B, pachypodol and chrysosplenol C. These flavonoids exhibited interesting cytotoxic activity against three human cell lines (KB, Hep-G2, RD) with IC50 values < 5 microg/ml. | Huong DT, Kamperdick C, Sung TV (2004) Homogentisic acid derivatives from Miliusa balansae. Journal of natural products 67, 445-447 [PubMed:15043427] [show Abstract] The new homogentisic acid derivatives miliusol (1b) and miliusolide (2) from Miliusa balansae were isolated and structurally determined by spectroscopic means. The relative configurations of the new 1b and its known acetate 1a were established. Furthermore, the symmetric ether bis(2-hydroxyphenyl)methyl ether 3, which was isolated for the first time from a natural source, the known flavonoids pachypodol and chrysosplenol C, and sodium benzoate were identified. |
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