Euonymus alatus

Euonymus Alatus does not appear to have much evidence for it at this time, and mostly it is in the exploratory stages of figuring out what the main bioactives are. It appears to be a very good source of the standard flavonoid compounds, and some of them (Quercetin in particular) have a variety of different conjugates. Additionally, a large variety of lignans exist in the stems and may be bioactive.

Surprisingly, not too many unique molecules have been isolated from this herb; the benefits seem to be due to the common ingredients that are found in many different herbs and foods.

Currently, the only evidence that can be somewhat applied to daily life is the inhibition of α-glucosidase seen in vitro and once replicated in rats. This may lessen the spike in blood glucose in response to a starchy meal, but by no means is Euonymus Alatus remarkably potent or novel in this regard; the active components here seem to be ones that are found in many other plants as well.

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Not enough evidence exists at this moment in time to recommend an effective dose

Edit1. Sources and Composition

Euonymus alatus (Gui Jeon Wu) is a plant of which its stems have been used traditionally for cancer treatment.^[1] And has also been used for blood circulation and eliminating blood clots, reducing pain, and treating dysmenorrhea in Asian medicine.^[2]

1.1. Composition

The bioactives that are fairly unique to Euonymus Alatus include:

• Three glycosides of Cardenolide where the 3-carbon is attached by Rhamnose (To give Acovenosigenin A 3-O-α-L-rhamnopyranoside), Rhamnose attached to a Glucose (the diglycoside known as Euonymoside A), and then a triglycoside of Rhamnose with two glucose sugars in a chain (Euonymusoside A)^[3]
• 2-{1-(Hydroxy methyl)-4-hydroxy-3,5-dimethoxy-phenyl}-propan-1,3-diol (1.8% ethanol extract), 5R,6S-6,9,10-trihydroxy-megastigma-7-en-3-one (2.25% ethanolic extract) and 2-{4-(3-Hydroxy-propenyl)-3,5-dimethoxy-phenyl}-propane-1,3-diol;^[4]

With more common bioactives (found in many herbs) being:

• 5-caffeoylquinic acid (Chlorogenic Acid) from the stems^[5][5] at 4.5% of an 80% ethanolic extract;^[4] also the metabolite 3,4-dihydroxycinnamic acid (caffeic acid)^[6]
• Lignan compounds including (+)-syringaresinol and De-4′-methylyangabin^[7]
• Sesquilignans Hedyotol C and threo-buddlenol B^[7]
• Dilignans Hedyotisol C and Hedyotisol B^[7]
• Neolignans such as (−)- and (+)- simulanol, (-)- and (+)-dihydrodehyrodiconiferyl alcohol, and guaiacylglycerol-8-O-4′-(coniferyl alcohol) ether (both 7R,8S and 7S,8R configurations)^[7]
• Grasshopper ketone (2.55% methanolic extract)^[4]
• Syringin (2.65% methanolic extract)^[4]
• (+)-usnic acid and benzoic acids^[8]
• Quercetin at 0.011-0.016mg/g (50% ethanolic extract),^[9] Quercetin-3-O-D-galactopyronoside at 5.5% ethanolic extract,^[4] and Rutin at 0.265-0.275mg/g of the 50% ethanolic extract (seems to be best to concentrate Quercetin structures from E.Alatus).^[9] The related Quercetin structures Hyperoside and Quercitrin have also been isolated from this plant, as well as Quercetin 3,7-dirhamnoside^[10]
• Kaempferol^[11] and its 3,7-dirhamnoside Kaempferitrin^[10]
• Apigenin-3-O-L-rhamnopyranoside^[4]
• Catechin, dehydrodicatechin A, and catechin lactone A^[10]
• Daucosterol^[8]
• Symplocoside^[10]
• Taxifolin^[4]
• Naringenin^[4]
• Aromadendrin,^[4] which may fluctuate wildly^[12]

The total flavonoid content of Euonymus Alatus is 235.7mg/kg fresh weight.^[13]

Edit2. Pharmacology

2.1. Enzymatic Interactions

Euonymus Alatus extract appears to be effective in inhibiting the aromatase enzyme in myometrial and leiomyomal cells (uterus related).^[14] Whether it affects other aromatase enzymes is not known, but if it does it may increase circulating testosterone levels.

Edit3. Interactions with Fat Mass

3.1. Mechanism

Some flavonoid compounds from Euonymus Alatus appear to prevent triglyceride accumulation into differentiating 3T3-L1 adipocytes, with most potency at 25uM concentration coming from quercetin 3,7-dirhamnoside (79.1% of control; set at 100%), hyperoside (71.3%), kaempferitrin (62.3%), catechin lactone A (79.9%) and dehydrodicatechin A (70.2%);^[10] hyperoside has been reported with this inhibitory potency previously^[15] but may not be the consensus due to differing data elsewhere.^[16][17] The potency of these compounds is comparable to 25uM of Resveratrol, with kaempferitrin trending to be more potent.^[10]

Both Kaempferol and Quercetin in Euonymus Alatus appear to be able to bind to the PPARγ receptor too weakly to induce adipocyte proliferation, and may block the pro-adipogenic effects of PPARγ agonists such as Rosiglitazone due to higher affinity (thus acting as receptor modulators).^[11] Despite these mechanisms, both appear to enhance glucose uptake into adipocytes.^[11]

Edit4. Interactions with Glucose Metabolism

4.1. Absorption

Euonymus alatus methanolic extract has inhibitory potential on the α-glucosidase enzyme with an IC₅₀ value of 272µg/mL (in a yeast assay),^[18] and of 8 compounds purified from the plant for interactions with the α-glucosidase noted that 6 compounds had more efficacy than the active control Arcabose (IC₅₀ 679.7µM) including catechin (119.1µM), quercetin 3,7-dirhamnoside (39.6µM), hyperoside (31.6µM), kaempferitrin (23.0µM), catechin lactone A (71.8µM) and dehydrodicatechin A (102.5µM).^[10] Another compound (quercitrin) was found inactive on this assay^[10] but has been noted elsewhere to have an IC₅₀ of 38.4 µM.^[19]

Components have inhibitory potential on alpha-glucosidase, a carbohydrate digestive enzyme

When 500mg/kg of Euonymus Alatus (methanolic extract) is given to rats alongside a 1g/kg bolus of starch and having blood measured for the next 4 hours, supplementation was able to reduce the subsequent AUC of glucose by 25.5% relative to starch control;^[18] fecal analysis was not performed.

Inhibition of starch absorption has been noted to occur in rats following concomitant ingestion of Euonymus Alatus and starch

4.2. Mechanisms

17.2mg/kg of an ethyl acetate fraction with a high flavonoid concentration (bioequivalent to 400mg/kg dry weight) is able to, over 7 days, reduce fasting blood glucose slightly in normal mice and more significantly in alloxan-induced diabetic mice; either of equal potency to or lesser than the active control of 140mg/kg Metformin (relatively low dose of Metformin).^[20] Over 4 weeks, this extraction was more effective than 140mg/kg Metformin in reducing fasting blood glucose in Alloxan-induced diabetic mice.^[20] One other study compared Euonymus Alatus (700mg/kg ethanolic extract) against Metformin (250mg/kg) and noted that while both were effective in reducing fasting blood glucose that Metformin was more potent.^[2]

Edit5. Inflammation and Immunology

5.1. Mechanisms

Euonymus Alatus (80% methanolic extract) can inhibit nF-kB activation at 10-30ug/mL with an IC₅₀ of IC₅₀ value of 11.83μg/mL, via inhibiting the IKKβ pathway.^[21] Anti-inflammatory effects in this same in vitro model (RAW264.7 macrophage activation via LPS) have been noted to occur with all lignan compounds that were not dilignans^[7] (although flavonoids and isoprenoids may also be active^[4]) and the methanolic extract also appears to inhibit JNK1 (40.6%), JNK2 (28.7%), and JNK3 (32.9%) activation.^[21]

General anti-inflammatory properties in macrophage stimulation tests

At least one study has noted that, without incubation with LPS or another pro-inflammatory insult, that Euonymus Alatus was able to increase nF-kB activity and inflammatory biomarkers vicariously though recombinant IFNγ.^[22]

Edit6. Interactions with Oxidation

6.1. Oxidation

In cultured rat hepatocytes (liver cells) Euonymus Alatus appears to both exert direct anti-oxidant abilities and enhance anti-oxidant enzymes.^[23]

References

1. Inhibitory effect of methanol extract of Euonymus alatus on matrix metalloproteinase-9
2. Park SH, Ko SK, Chung SH. Euonymus alatus prevents the hyperglycemia and hyperlipidemia induced by high-fat diet in ICR mice. J Ethnopharmacol. (2005)
3. Kitanaka S, et al. Cytotoxic cardenolides from woods of Euonymus alata. Chem Pharm Bull (Tokyo). (1996)
4. Jeong EJ, et al. Inhibitory constituents of Euonymus alatus leaves and twigs on nitric oxide production in BV2 microglia cells. Food Chem Toxicol. (2011)
5. Jin UH, et al. A phenolic compound, 5-caffeoylquinic acid (chlorogenic acid), is a new type and strong matrix metalloproteinase-9 inhibitor: isolation and identification from methanol extract of Euonymus alatus. Life Sci. (2005)
6. Park WH, Kim SH, Kim CH. A new matrix metalloproteinase-9 inhibitor 3,4-dihydroxycinnamic acid (caffeic acid) from methanol extract of Euonymus alatus: isolation and structure determination. Toxicology. (2005)
7. Jeong EJ, et al. Inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 macrophage cells by lignans isolated from Euonymus alatus leaves and twigs. Bioorg Med Chem Lett. (2011)
8. Fang ZF, et al. {Studies on chemical constituents from Euonymus alatus II}. Zhongguo Zhong Yao Za Zhi. (2008)
9. Zhang F, et al. Microwave-assisted extraction of rutin and quercetin from the stalks of Euonymus alatus (Thunb.) Sieb. Phytochem Anal. (2009)
10. Zhang Y, et al. A new flavan-3-ol lactone and other constituents from Euonymus alatus with inhibitory activities on α-glucosidase and differentiation of 3T3-L1 cells. Nat Prod Res. (2012)
11. Fang XK, Gao J, Zhu DN. Kaempferol and quercetin isolated from Euonymus alatus improve glucose uptake of 3T3-L1 cells without adipogenesis activity. Life Sci. (2008)
12. Chen Y, et al. {Determination of aromadendrin in Euonymus alatus by HPLC}. Zhongguo Zhong Yao Za Zhi. (2010)
13. Chon SU, et al. Total phenolics level, antioxidant activities and cytotoxicity of young sprouts of some traditional Korean salad plants. Plant Foods Hum Nutr. (2009)
14. Lee TK, et al. Inhibitory effects of Scutellaria barbata D. Don. and Euonymus alatus Sieb. on aromatase activity of human leiomyomal cells. Immunopharmacol Immunotoxicol. (2004)
15. An Y, et al. Inhibitory effects of flavonoids from Abelmoschus manihot flowers on triglyceride accumulation in 3T3-L1 adipocytes. Fitoterapia. (2011)
16. Yahagi T, Daikonya A, Kitanaka S. Flavonol acylglycosides from flower of Albizia julibrissin and their inhibitory effects on lipid accumulation in 3T3-L1 cells. Chem Pharm Bull (Tokyo). (2012)
17. Effects of Eucommia ulmoides Oliver leaf extract on 3T3-L1 differentiation into adipocytes
18. Lee SK, et al. Inhibitory activity of Euonymus alatus against alpha-glucosidase in vitro and in vivo. Nutr Res Pract. (2007)
19. Lai YC, et al. Triterpenes as α-glucosidase inhibitors from Fagus hayatae. Phytochemistry. (2012)
20. Fang XK, et al. Alleviating effects of active fraction of Euonymus alatus abundant in flavonoids on diabetic mice. Am J Chin Med. (2008)
21. Oh BK, et al. Euonymus alatus extract attenuates LPS-induced NF-κB activation via IKKβ inhibition in RAW 264.7 cells. J Ethnopharmacol. (2011)
22. Chung HS, et al. Activation of inducible nitric oxide synthase by Euonymus alatus in mouse peritoneal macrophages. Clin Chim Acta. (2002)
23. Kim KW, et al. Effects on lipid peroxidation and antioxidative enzymes of Euonymus alatus in cultured rat hepatocytes. Basic Clin Pharmacol Toxicol. (2009)

(Common misspellings for Euonymus alatus include euronymus, eurymus, eunymus, euonimus, eunimus, euronimus)

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