Hydrangenol

Last updated
Hydrangenol
Hydrangenol.svg
Names
Preferred IUPAC name
8-Hydroxy-3-(4-hydroxyphenyl)-1H-2-benzopyran-1-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • 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 X mark.svgN
    Key: DGKDFNDHPXVXHW-UHFFFAOYSA-N X mark.svgN
  • InChI=1/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
    Key: DGKDFNDHPXVXHW-UHFFFAOYAS
  • C1C(OC(=O)C2=C1C=CC=C2O)C3=CC=C(C=C3)O
Properties
C15H12O4
Molar mass 256.25 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Hydrangenol is a dihydroisocoumarin. It can be found in Hydrangea macrophylla , as well as its 8-O-glucoside. [1] (−)-Hydrangenol 4′-O-glucoside [2] and (+)-hydrangenol 4′-O-glucoside [3] can be found in Hydrangeae Dulcis Folium, the processed leaves of H. macrophylla var. thunbergii.

Related Research Articles

<i>Hydrangea macrophylla</i> Species of flowering plant in the family Hydrangeaceae

Hydrangea macrophylla is a species of flowering plant in the family Hydrangeaceae, native to Japan. It is a deciduous shrub growing to 2 m (7 ft) tall by 2.5 m (8 ft) broad with large heads of pink or blue flowers in summer and autumn. Common names include bigleaf hydrangea, French hydrangea, lacecap hydrangea, mophead hydrangea, penny mac and hortensia. It is widely cultivated in many parts of the world in many climates. It is not to be confused with H. aspera 'Macrophylla'.

Momordin is one of several saponins derived from oleanolic acid, a triterpenoid. These chemical compounds are found in some plants of the genus Momordica, which includes the bitter melon and the balsam apple, as well as in other Asian herbal medicine plants such as Kochia scoparia and Ampelopsis radix.

Gentianella nitida is a species of plant in the Gentianaceae family. It is one of two types of hercampuri, which is traditionally used in herbal medicine as an infusion, the other type of hercampuri being Gentianella alborosea. Gentianella nitida has been used in Peruvian folk medicine since before the time of the Incas. These small shrubs are native to the high Andes of Peru. The Junin Province is a region of Peru that grows hercampuri.

Allixin Chemical compound

Allixin is a phytoalexin found in garlic bulbs. It was first isolated and characterized in 1989. When garlic is stored for long periods of time, it can form visible accumulations of crystalline allixin on its surface, particularly in areas where tissue has become necrotic. After 2 years of storage, the amount of allixin accumulated can approach 1% of the dry weight of the cloves. Since allixin has weak antimicrobial activity, these high concentrations are thought to be produced by the garlic bulb to protect itself from further damage from microorganisms.

Phyllodulcin Chemical compound

Phyllodulcin is a dihydroisocoumarin found in Hydrangea macrophylla and Hydrangea serrata. It is a sweetener 400–800 times sweeter than sugar.

Thunberginol A Chemical compound

Thunberginol A is an isocoumarin found in Hydrangea macrophylla and the herbal preparation hydrangeae dulcis folium which is produced from its leaves.

Thunberginol B Chemical compound

Thunberginol B is an isocoumarin found in Hydrangeae Dulcis Folium, the processed leaves of Hydrangea macrophylla var. thunbergii.

Thunberginol C Chemical compound

Thunberginol C is a dihydroisocoumarin found in Hydrangeae Dulcis Folium, the processed leaves of Hydrangea macrophylla var. thunbergii.

Thunberginol D Chemical compound

Thunberginol D is a dihydroisocoumarin found in Hydrangeae Dulcis Folium, the processed leaves of Hydrangea macrophylla var. thunbergii.

Thunberginol E Chemical compound

Thunberginol E is a dihydroisocoumarin found in Hydrangeae Dulcis Folium, the processed leaves of Hydrangea macrophylla var. thunbergii.

Thunberginol F Chemical compound

Thunberginol F is a phthalide found in Hydrangea macrophylla.

Thunberginol G Chemical compound

Thunberginol G is a dihydroisocoumarin found in Hydrangeae Dulcis Folium, the processed leaves of Hydrangea macrophylla var. thunbergii.

Tergallic acids are trimers of gallic acid, often found naturally in the form of glycosides. Tergallic acid O- or C-glucosides that can be found in acorns of several Quercus (oak) species. The dehydrated tergallic acid C-glucoside and tergallic acid O-glucoside can be characterised in the acorns of Quercus macrocarpa. Dehydrated tergallic-C-glucoside can be found in the cork from Quercus suber.

Kaempferol 7-<i>O</i>-glucoside Chemical compound

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Pedunculagin Chemical compound

Pedunculagin is an ellagitannin. It is formed from casuarictin via the loss of a gallate group.

Anthocyanin 3-O-glucoside 6″-O-hydroxycinnamoyltransferase is an enzyme forming delphinidin 3-(6-p-coumaroyl)glucoside from delphinidin 3-O-glucoside (myrtillin) and p-coumaroyl-CoA.

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Catechin-7-<i>O</i>-glucoside Chemical compound

Catechin-7-O-glucoside is a flavan-3-ol glycoside formed from catechin.

Lupeol synthase is an enzyme with systematic name (3S)-2,3-epoxy-2,3-dihydrosqualene mutase . This enzyme catalyses the following chemical reaction

Taxillusin Chemical compound

Taxillusin is a flavonol found in the parasitic plant Taxillus kaempferi. It is a galloylated 3-O-glucoside of quercetin.

References

  1. Matsuda, Hisashi; Simoda, Hiroshi; Yamahara, Johji; Yoshikawa, Masayuki (1999). "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". Biological & Pharmaceutical Bulletin. 22 (8): 870–872. doi: 10.1248/bpb.22.870 . PMID   10480329. INIST:1959604.
  2. Yoshikawa, M; Uchida, E; Chatani, N; Kobayashi, H; Naitoh, Y; Okuno, Y; Matsuda, H; Yamahara, J; Murakami, N (1992). "Thunberginols C, D, and E, new antiallergic and antimicrobial dihydroisocoumarins, and thunberginol G 3′-O-glucoside and (−)-hydrangenol 4′-O-glucoside, new dihydroisocoumarin glycosides, from Hydrangeae Dulcis Folium". Chemical & Pharmaceutical Bulletin. 40 (12): 3352–3354. doi: 10.1248/cpb.40.3352 . PMID   1363465.
  3. Yoshikawa, M; Matsuda, H; Shimoda, H; Shimada, H; Harada, E; Naitoh, Y; Miki, A; Yamahara, J; Murakami, N (1996). "Development of bioactive functions in Hydrangeae Dulcis Folium. V. On the antiallergic and antimicrobial principles of Hydrangeae Dulcis Folium. (2). Thunberginols C, D, and E, thunberginol G 3′-O-glucoside, (−)-hydrangenol 4′-O-glucoside, and (+)-hydrangenol 4′-O-glucoside". Chemical & Pharmaceutical Bulletin. 44 (8): 1440–1447. doi: 10.1248/cpb.44.1440 . PMID   8795265. INIST:3226693.