LIPID MAPS

Common Name

Mulberrin

Systematic Name

2-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-3,8-bis (3-methyl-2-butenyl)-4H-1-benzopyran-4-one

Synonyms

Norartocarpin
Kuwanon C

LM ID

LMPK12110895

Formula

C₂₅H₂₆O₆

Exact Mass

Calculate m/z

422.17294

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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View NP-MRD ID(NMR) spectrum

Category

Main Class

Sub Class

Polyketides [PK]

Flavonoids [PK12]

Flavones and Flavonols [PK1211]

Kuwanon C is a prenylated flavone originally isolated from M. alba that has diverse biological activities, including antioxidant, antibacterial, antiproliferative, and neuroprotective properties.¹ It scavenges DPPH radicals in a cell-free assay (EC50 = 72.99 µg/ml).² It is active against E. coli, S. typhimurium, S. epidermis, and S. aureus (MICs = 10, 25, 6.25, and 6.25 µg/ml, respectively) and inhibits the growth of P388 mouse lymphoma cancer cells (IC50 = 14 µg/ml).^3,4 Kuwanon C (30 mg/kg) improves motor coordination in a rotarod test and decreases neuronal loss in the substantia nigra pars compacta in a mouse model of MPTP-induced Parkinson's disease.⁵

This information has been provided by Cayman Chemical

References

1. Nomura, T., Fukai, T., and Katayanagi, M. Kuwanon A, B, C and oxydihydromorusin, four new flavones from the root bark of the cultivated mulberry tree (Morus alba L.). Chem. Pharm. Bull. 25(3), 529-532 (1977).

2. Mazimba, O., Majinda, R.R.T., and Motlhanka, D. Antioxidant and antibacterial constituents from Morus nigra. Afr. J. Pharma. Pharmaco. 5(6), 751-754 (2011).

3. Sohn, H.-Y., Son, K.H., Kwon, C.-S., et al. Antimicrobial and cytotoxic activity of 18 prenylated flavonoids isolated from medicinal plants: Morus alba L., Morus mongolica Schneider, Broussnetia papyrifera (L.) Vent, Sophora flavescens Ait and Echinosophora koreensis Nakai. Phytomedicine 11(7-8), 666-672 (2004).

4. Ferlinahayati, Syah, Y.M., Juliawaty, L.D., et al. Phenolic constituents from the wood of Morus australis with cytotoxic activity. Z. Naturforsch. C. J. Biosci. 63(1-2), 35-39 (2008).

5. Cao, W., Dong, Y., Zhao, W., et al. Mulberrin attenuates 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine (MPTP)-induced Parkinson’s disease by promoting Wnt/β-catenin signaling pathway. J. Chem. Neuroanat. 98, 63-70 (2019).

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Viridiplantae (#33090)

Flavonoid imported from http://metabolomics.jp/

Morus alba (#3498)

Magnoliopsida (#3398)

Studies on the Constituents of the Cultivated Mulberry Tree. III. Isolation of Four New Flavones, Kuwanon A, B, C and Oxydihydromorusin from the Root Bark of Morus alba L.,
Chem Pharm Bull (Tokyo), 1978

DOI: 10.1248/cpb.26.1453

InChiKey (Click to copy)

UWQYBLOHTQWSQD-UHFFFAOYSA-N

InChi (Click to copy)

InChI=1S/C25H26O6/c1-13(2)5-8-17-20(28)12-21(29)22-23(30)18(9-6-14(3)4)24(31-25(17)22)16-10-7-15(26)11-19(16)27/h5-7,10-12,26-29H,8-9H2,1-4H3

SMILES (Click to copy)

C1(O)=C(C/C=C(\C)/C)C2OC(C3C(O)=CC(O)=CC=3)=C(C/C=C(\C)/C)C(=O)C=2C(O)=C1

HMDB ID

HMDB0029507

METABOLOMICS ID

FL3FALNI0006

PubChem CID