A flavonoid glycoside with diverse biological activities
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Rhoifolin

Item No. 35583

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7-[[2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
CAS Number
17306-46-6
Synonyms
  • Apigenin 7-O-Neohesperidoside
Molecular Formula
C27H30O14
Formula Weight
578.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
λmax
268, 334 nm
SMILES
O=C1C2=C(O)C=C(O[C@H]3[C@H](O[C@]4([H])O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@@H](CO)O3)C=C2OC(C5=CC=C(O)C=C5)=C1
InChi Code
InChI=1S/C27H30O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-8,10,18,20-30,32-36H,9H2,1H3/t10-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
InChi Key
RPMNUQRUHXIGHK-PYXJVEIZSA-N
Origin
Plant/Exocarpium Citri Grandis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $32

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    5 mg

    $141

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    10 mg

    $234

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    25 mg

    $542

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    Cayman Chemical
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    Product Description

    Rhoifolin is a flavonoid glycoside that has been found in C. nudiflora and has diverse biological activities.1,2,3,4,5 It inhibits Ezrin phosphorylation, cell migration, and TGF-β1-induced epithelial-to-mesenchymal transition (EMT) in MDA-MB-231 cells when used at concentrations of 10 and 40 µM.1 Rhoifolin inhibits severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) main protease (Mpro), also known as 3C-like protease (3CLpro; IC50 = 27.45 µM).2 It reverses scopolamine-induced memory deficits and inhibits acetylcholinesterase (AChE) activity in zebrafish when administered in the tank water at concentrations of 1, 3, and 5 µg/L.3 Rhoifolin (20 and 40 mg/kg) reduces paw edema and IL-1β, IL-6, and TNF-α levels in a rat model of carrageenan-induced inflammation.4 It also ameliorates cartilage damage in a rat model of osteoarthritis, an effect that can be reversed by the autophagy inhibitor 3-methyladenine (Item No. 13242).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Xiong, L., Lu, H., Hu, Y., et al. In vitro anti-motile effects of rhoifolin, a flavonoid extracted from Callicarpa nudiflora on breast cancer cells via downregulating podocalyxin-ezrin interaction during epithelial mesenchymal transition. Phytomedicine 93, 153486 (2021).

    2. Jo, S., Kim, S., Shin, D.H., et al. Inhibition of SARS-CoV 3CL protease by flavonoids. J. Enzyme Inhib. Med. Chem. 35(1), 145-151 (2020).

    3. Brinza, I., Abd-Alkhalek , A.M., El-Raey , M.A., et al. Ameliorative effects of rhoifolin in scopolamine-induced amnesic zebrafish (Danio rerio) model. Antioxidants (Basel) 9(7), 580 (2020).

    4. Fang, J., Cao, Z., Song, X., et al. Rhoifolin alleviates inflammation of acute inflammation animal models and LPS-Induced RAW264.7 cells via IKKβ/NF-κB signaling pathway. Inflammation 43(6), 2191-2201 (2020).

    5. Yan, J., Ni, B., Sheng, G., et al. Rhoifolin ameliorates osteoarthritis via regulating autophagy. Front. Pharmacol. 12, 661072 (2021).