A member of the class of dihydroisocoumarins that is 3,4-dihydroisocoumarin substituted by a hydroxy group at position 8 and a 4-hydroxyphenyl group at position 3. It has been isolated from the roots of Scorzonera judaica and exhibits anti-allergic activity.

Identification

IUPAC Names

8-hydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-1H-isochromen-1-one

Molecular Formula
C15H12O4
Mass
256.25340
Monoisotopic Mass
256.07356
Charge
0
InChI
InChI=1S/C15H12O4/c16-11-6-4-9(5-7-11)13-8-10-2-1-3-12(17)14(10)15(18)19-13/h1-7,13,16-17H,8H2
InChIKey
DGKDFNDHPXVXHW-UHFFFAOYSA-N
SMILES
Oc1ccc(cc1)C1Cc2cccc(O)c2C(=O)O1
Synonyms

8-hydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-1H-2-benzopyran-1-one

Species

scorzonera judaica

NCBI:txid895824-121650157

Europe PubMed Central results


Effects of phyllodulcin, hydrangenol, and their 8-O-glucosides, and thunberginols A and F from Hydrangea macrophylla SERINGE var. thunbergii MAKINO on passive cutaneous anaphylaxis reaction in rats.

Author: Matsuda H, Shimoda H, Yamahara J, Yoshikawa M.

Abstract: We examined the antiallergic effects of phyllodulcin, hydrangenol, and their 8-O-glucosides, and thunberginols A and F isolated from the processed leaves (Hydrangeae Dulcis Folium) and dried leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO using the passive cutaneous anaphylaxis (PCA) reaction. With the exception of phyllodulcin, these constituents were found to significantly inhibit the PCA reaction. Although thunberginol A showed the most potent inhibitory effect, hydrangenol was considered to be the principal antiallergic component in the processed leaves, after taking into account their contents.

Studies of hydrangenol in hydrangea macrophylla Ser. I. Isolation, identification, and biosynthesis from C 14-labelled compounds.

Author: IBRAHIM RK, TOWERS GH.

Abstract: NA

Phenolic compounds from the roots of Jordanian viper's grass, Scorzonera judaica.

Author: Bader A, De Tommasi N, Cotugno R, Braca A.

Abstract: Nine new phenolic compounds, 3S-hydrangenol 40-O-R-L-rhamnopyranoysl-(1-->3)-β-D-glucopyranoside (1), thunberginol F 7-O-β-D-glucopyranoside (2), 2-hydroxy-6-[2-(4-hydroxyphenyl)-2-oxo-ethyl]benzoic acid (3), 2-hydroxy-6-[2-(3,4-dihydroxyphenyl)-2-oxo-ethyl]benzoic acid (4), 2-hydroxy-6-[2-(3,4-dihydroxyphenyl-5-methoxy)-2-oxoethyl]benzoic acid (5), hydrangeic acid 40-O-β-D-glucopyranoside (6), E-3-(3,4-dihydroxybenzylidene)-5-(3,4-dihydroxyphenyl)dihydrofuran-2-one (7), Z-3-(3,4-dihydroxybenzylidene)-5-(3,4-dihydroxyphenyl)-2(3H)-furanone (8), and 4-[β-D-glucopyranosyl)hydroxy]-pinoresinol (9), and nine known compounds were isolated from the roots of Scorzonera judaica. Structures of 1-9 were elucidated by mass spectrometry, extensive 1D and 2D NMR spectroscopy, and CD spectroscopy.All compounds were evaluated for cytotoxic activity.

[Chemical constituents from Hydrangea macrophylla].

Author: Wang ZB, Guo JT, Yang CJ, Meng YH, Wang QH, Yang BY, Kuang HX.

Abstract: <h4>Objective</h4>To investigate chemical constituents from Chinese herbal medicine Hydrangea macrophylla.<h4>Method</h4>The compounds were separated and purified by column chromatography over silica gel, ODS, and preparative HPLC. Their structures were identified by spectral methods including 1H, 13C-NMR and MS.<h4>Result</h4>Eleven compounds were isolated and identified as zeorin, hopane-6, 22-diol (1), botulin (2), betulinic acid (3), 2-ethyl-3-methyl-maleimide-N-beta-D-glucopyranoside (4), uridine (5), thymidine (6), adenosine (7), nicotinamide (8), methyl pyroglutamate (9), hydrangenol (10) and hydrangenol-4'-O-beta-D-glucopyranoside (11), respectively.<h4>Conclusion</h4>Compounds 14 and 7-9 were obtained from the genus Hydrangea for the first time.

Inhibitory effects of hydrangenol derivatives on the activation of hyaluronidase and their antiallergic activities.

Author: Kakegawa H, Matsumoto H, Satoh T.

Abstract: NA

Gut microbiota and the prevalence and incidence of renal stones.

Author: Kim HN, Kim JH, Chang Y, Yang D, Joo KJ, Cho YS, Park HJ, Kim HL, Ryu S.

Abstract: The role of the gut microbiome in the development of renal stone diseases has not been well characterized. This study focused on the taxonomic and functional profiles of gut microbiomes according to the prevalence and incidence of nephrolithiasis. Stool samples from 915 Korean adults were collected at baseline. Participants were followed for a median of 4.0 years. We evaluated the biodiversity of the gut microbiota and taxonomic profiles associated with nephrolithiasis status, using 16S rRNA gene sequencing. Nephrolithiasis status was categorized into three groups: control (no-stone at both baseline and follow-up visits), incidental nephrolithiasis, and prevalent nephrolithiasis. Compared to the control and incidental nephrolithiasis, the prevalent nephrolithiasis showed a reduced evenness in alpha diversity. Nephrolithiasis was associated with a reduced abundance of some key taxa involved in short-chain fatty acid production. Moreover, the abundance of Bifidobacterium, which possess oxalate-degrading ability, was higher in the control. Conversely, there was no significant difference in the bacterial composition between the incidental and prevalent nephrolithiasis. In our study with repeated nephrolithiasis measurements, prevalent renal stones were associated with an altered gut microbiota composition compared to the control. Besides the known oxalate degradation pathway, other functional pathways inferred in this study require further investigation.

Prognosis of cardiogenic shock secondary to culprit left main coronary artery lesion-related myocardial infarction.

Author: Galván-Román F, Fernández-Herrero I, Ariza-Solé A, Sánchez-Salado JC, Puerto E, Lorente V, Gómez-Lara J, Martín-Asenjo R, Gómez-Hospital JA, Comín-Colet J.

Abstract: <h4>Aims</h4>This study aimed to assess, in patients with cardiogenic shock secondary to unprotected left main coronary artery-related myocardial infarction (ULMCA-related AMICS), the incidence and predictors of no recovery of left ventricular function during the admission.<h4>Methods and results</h4>This was an observational study conducted at two tertiary care centres (2012-20). The main outcome measured was death or requirement for heart transplantation (HT) or left ventricular assist devices (LVAD) during the admission. A total of 70 patients were included. Percutaneous coronary intervention (PCI) was successful in 53/70 patients (75.7%). The combined endpoint of death or requirement of HT or LVAD during the admission occurred in 41/70 patients (58.6%). The highest incidence of the primary endpoint was observed among patients with profound shock and occluded left main coronary artery (LMCA) (20/23, 87%, P < 0.001). Although a successful PCI reduced the incidence of the event in the whole cohort (51.9% vs. 82.4% in failed PCI, P = 0.026), this association was not observed among this last group of complex patients (86.7% vs. 87.5% in failed PCI, P = 0.731). The predictive model included left ventricular ejection fraction, baseline ULMCA Thrombolysis In Myocardial Infarction flow, and severity of shock and showed an optimal ability for predicting death or requirements for HT or LVAD during the admission (area under the curve 0.865, P < 0.001).<h4>Conclusions</h4>ULMCA-related AMICS was associated with a high in-hospital mortality or need for HT or LVAD. Prognosis was especially poor among patients with profound shock and baseline occluded LMCA, with a low probability of recovery regardless of successful PCI.