Sterubin

Last updated
Sterubin
Sterubin.png
Names
IUPAC name
(2S)-3′,4′,5-Trihydroxy-7-methoxyflavan-4-one
Systematic IUPAC name
(2S)-2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-2,3-dihydro-4H-1-benzopyran-4-one
Other names
7-Methoxy-3′,4′,5-trihydroxyflavanone
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C16H14O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)8-2-3-10(17)11(18)4-8/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1 Yes check.svgY
    Key: DSAJORLEPQBKDA-AWEZNQCLSA-N Yes check.svgY
  • InChI=1/C16H14O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)8-2-3-10(17)11(18)4-8/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1
    Key: DSAJORLEPQBKDA-AWEZNQCLBS
  • O=C2c3c(O[C@H](c1ccc(O)c(O)c1)C2)cc(OC)cc3O
Properties
C16H14O6
Molar mass 302.28 g/mol
Density 1.458 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sterubin (7-methoxy-3',4',5-trihydroxyflavanone) is a bitter-masking flavanone extracted from Yerba Santa ( Eriodictyon californicum ) a plant growing in America. [1]

Sterubin is one of the four flavanones identified by Symrise in this plant which elicit taste-modifying properties. The others are homoeriodictyol, its sodium salt, and eriodictyol. [2]

Recent research has demonstrated some neuroprotective properties of Sterubin in vitro, but more research is needed before it can be considered a true drug candidate. [3] [4] [5]

Related Research Articles

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Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.

<span class="mw-page-title-main">Naringenin</span> Chemical compound

Naringenin is a flavorless, colorless flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit, and is found in a variety of fruits and herbs.

<span class="mw-page-title-main">Neuroprotection</span> Relative preservation of neuronal structure and/or function

Neuroprotection refers to the relative preservation of neuronal structure and/or function. In the case of an ongoing insult the relative preservation of neuronal integrity implies a reduction in the rate of neuronal loss over time, which can be expressed as a differential equation. It is a widely explored treatment option for many central nervous system (CNS) disorders including neurodegenerative diseases, stroke, traumatic brain injury, spinal cord injury, and acute management of neurotoxin consumption. Neuroprotection aims to prevent or slow disease progression and secondary injuries by halting or at least slowing the loss of neurons. Despite differences in symptoms or injuries associated with CNS disorders, many of the mechanisms behind neurodegeneration are the same. Common mechanisms of neuronal injury include decreased delivery of oxygen and glucose to the brain, energy failure, increased levels in oxidative stress, mitochondrial dysfunction, excitotoxicity, inflammatory changes, iron accumulation, and protein aggregation. Of these mechanisms, neuroprotective treatments often target oxidative stress and excitotoxicity—both of which are highly associated with CNS disorders. Not only can oxidative stress and excitotoxicity trigger neuron cell death but when combined they have synergistic effects that cause even more degradation than on their own. Thus limiting excitotoxicity and oxidative stress is a very important aspect of neuroprotection. Common neuroprotective treatments are glutamate antagonists and antioxidants, which aim to limit excitotoxicity and oxidative stress respectively.

<span class="mw-page-title-main">Rutin</span> Chemical compound

Rutin is the glycoside combining the flavonol quercetin and the disaccharide rutinose. It is a flavonoid glycoside found in a wide variety of plants, including citrus.

<span class="mw-page-title-main">Naringin</span> Chemical compound

Naringin is a flavanone-7-O-glycoside between the flavanone naringenin and the disaccharide neohesperidose. The flavonoid naringin occurs naturally in citrus fruits, especially in grapefruit, where naringin is responsible for the fruit's bitter taste. In commercial grapefruit juice production, the enzyme naringinase can be used to remove the bitterness created by naringin. In humans naringin is metabolized to the aglycone naringenin by naringinase present in the gut.

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<span class="mw-page-title-main">Hesperidin</span> Chemical compound

Hesperidin is a flavanone glycoside found in citrus fruits. Its aglycone is hesperetin. Its name is derived from the word "hesperidium", for fruit produced by citrus trees.

<span class="mw-page-title-main">Chrysin</span> Chemical compound

Chrysin, also called 5,7-dihydroxyflavone, is a flavone found in honey, propolis, the passion flowers, Passiflora caerulea and Passiflora incarnata, and in Oroxylum indicum. It is extracted from various plants, such as the blue passion flower. Following oral intake by humans, chrysin has low bioavailability and rapid excretion. It is under basic research to evaluate its safety and potential biological effects.

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Flavones are a class of flavonoids based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

<i>Eriodictyon californicum</i> Species of flowering plant

Eriodictyon californicum is a species of plant within the family Boraginaceae. It is also known as yerba santa, mountain balm, bear's weed, gum bush, gum plant, and consumptive weed. Less common names include Herbe des Montagnes, Herbe à Ourse, Herbe Sacrée, Herbe Sainte, Hierba Santa, Holy Herb, and Tarweed.

<span class="mw-page-title-main">Taste receptor</span> Type of cellular receptor that facilitates taste

A taste receptor or tastant is a type of cellular receptor which facilitates the sensation of taste. When food or other substances enter the mouth, molecules interact with saliva and are bound to taste receptors in the oral cavity and other locations. Molecules which give a sensation of taste are considered "sapid".

<i>Eriodictyon angustifolium</i> Species of flowering plant

Eriodictyon angustifolium, common name narrowleaf yerba santa, is a perennial shrub.

<i>Eriodictyon crassifolium</i> Species of flowering plant

Eriodictyon crassifolium, or thickleaf yerba santa, is a shrub in the borage family. "Crassifolium" means "thick leaf." The plant has thick, wooly leaves. It is native to California and Baja California.

<span class="mw-page-title-main">Eriodictyol</span> Chemical compound

Eriodictyol is a bitter-masking flavanone, a flavonoid extracted from yerba santa, a plant native to North America. Eriodictyol is one of the four flavanones identified in this plant as having taste-modifying properties, the other three being homoeriodictyol, its sodium salt, and sterubin.

<span class="mw-page-title-main">Homoeriodictyol</span> Chemical compound

Homoeriodictyol is a bitter-masking flavanone extracted from Yerba Santa a plant growing in America.

<i>Eriodictyon parryi</i> Species of plant

Eriodictyon parryi or poodle-dog bush is a tall California mountain shrub with showy purple flowers, which is notable for secreting a severe skin irritant. It is an opportunistic species that grows mostly in areas that have been disturbed by fire. In a dry early spring in Southern California, its semi-dormant leaves can droop and curl into coils like locks of curly hair, hence the popular name based on the metaphor of a poodle's natural hair.

<span class="mw-page-title-main">Isoorientin</span> Chemical compound

Isoorientin is a flavone, a chemical flavonoid-like compound. It is the luteolin-6-C-glucoside. Bioassay-directed fractionation techniques led to isolation of isoorientin as the main hypoglycaemic component in Gentiana olivieri. Studies also showed that isoorientin is a potential neuroprotective compound against Alzheimer's disease.

<span class="mw-page-title-main">Xanthohumol</span> Chemical compound

Xanthohumol is a natural product found in the female inflorescences of Humulus lupulus, also known as hops. This compound is also found in beer and belongs to a class of compounds that contribute to the bitterness and flavor of hops. Xanthohumol is a prenylated chalconoid, biosynthesized by a type III polyketide synthase (PKS) and subsequent modifying enzymes.

<span class="mw-page-title-main">Yerba buena</span> Number of aromatic plants

Yerba buena or hierba buena is the Spanish name for a number of aromatic plants, most of which belong to the mint family. Yerba buena translates as "good herb". The specific plant species regarded as yerba buena varies from region to region, depending on what grows wild in the surrounding landscape, or which species is customarily grown in local gardens. Perhaps the most common variation of this plant is spearmint. The term has been used to cover a number of aromatic true mints and mint relatives of the genera Clinopodium, Satureja or Micromeria. All plants so named are associated with medicinal properties, and some have culinary value as herbal teas or seasonings as well.

References

  1. Patricia Kaminski and Richard Katz. Yerba Santa Eriodictyon californicum. Flower Essence Society.
  2. Ley JP, Krammer G, Reinders G, Gatfield IL, Bertram HJ (July 2005). "Evaluation of bitter masking flavanones from Herba Santa (Eriodictyon californicum (H. and A.) Torr., Hydrophyllaceae)". J. Agric. Food Chem. 53 (15): 6061–6. doi:10.1021/jf0505170. PMID   16028996.
  3. Wolfgang Fischer; Antonio Currais; Zhibin Liang; Antonio Pinto; Pamela Maher (February 2019). "Old age-associated phenotypic screening for Alzheimer's disease drug candidates identifies sterubin as a potent neuroprotective compound from Yerba santa". Redox Biology. 21: 101089. doi:10.1016/j.redox.2018.101089. PMC   6309122 . PMID   30594901.
  4. Zhibin Liang; Pamela Maher (November 2022). "Structural Requirements for the Neuroprotective and Anti-Inflammatory Activities of the Flavanone Sterubin". Antioxidants. 11 (11): 2197. doi: 10.3390/antiox11112197 . PMC   9686938 . PMID   36358569.
  5. Batya Swift Yasgur. . (Paywalled) Medscape. February 2019.