A diarylnonanoid with diverse biological activities
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Malabaricone B

Item No. 29911

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-(2,6-dihydroxyphenyl)-9-(4-hydroxyphenyl)-1-nonanone
CAS Number
63335-24-0
Synonyms
  • NSC 287967
  • NSC 630196
Molecular Formula
C21H26O4
Formula Weight
342.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 20 mg/mlEthanol: 10 mg/ml
λmax
223, 270 nm
SMILES
OC1=C(C(CCCCCCCCC2=CC=C(O)C=C2)=O)C(O)=CC=C1
InChi Code
InChI=1S/C21H26O4/c22-17-14-12-16(13-15-17)8-5-3-1-2-4-6-9-18(23)21-19(24)10-7-11-20(21)25/h7,10-15,22,24-25H,1-6,8-9H2
InChi Key
KOAPDMKKECXPHX-UHFFFAOYSA-N
Origin
Plant/Myristica malabarica
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

    $160

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    10 mg

    $303

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    25 mg

    $710

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    Product Description

    Malabaricone B is a diarylnonanoid that has been found in Myristica and has diverse biological activities, including enzyme inhibitory, antimicrobial, anticancer, and antioxidant properties.1,2,3,4,5 It is an inhibitor of sphingomyelin synthase 1 and -2 (IC50s = 3.5 and 2.5 µM, respectively, in fibroblast cell lysates).1 It is active against the bacteria S. aureus, B. subtilis, and S. durans (MIC = 1 µg/ml for all) and three strains of the fungus C. albicans (MICs = 4-16 µg/ml).2 It is cytotoxic to A549, A375, Jurkat, A431, U937, and MCF-7 cells (IC50s = 8.1, 26.7, 27.4, 9.5, 27.5, and 9.3 µM, respectively) but not non-cancerous INT407, HEK293, or WI-38 cells.3 It increases the levels of intracellular reactive oxygen species (ROS) and induces apoptosis in A549 cells. It reduces the formation of thiobarbituric acid reactive substrates (TBARS) by 28.2% in rat liver mitochondria when used at a concentration of 2 µg/ml but scavenges only 5% of 2,2-diphenyl-picrylhydrazyl (DPPH; Item No. 14805) radicals at 7 µg/ml.4 Malabaricone B (10, 15, and 20 mg/kg) reduces stomach ulceration in a mouse model of indomethacin-induced gastric ulcer.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Othman, M.A., Yuyama, K., Murai, Y., et al. Malabaricone C as natural sphingomyelin synthase inhibitor against diet-induced obesity and its lipid metabolism in mice. Med. Chem. Lett. 10(8), 1154-1158 (2019).

    2. Orabi, K.Y., Mossa, J.S., and El-Feraly, F.S. Isolation and characterization of two antimicrobial agents from mace (Myristica fragrans). J. Nat. Prod. 54(3), 856-859 (1991).

    3. Tyagi, M., Maity, B., Saha, B., et al. Spice-derived phenolic, malabaricone B induces mitochondrial damage in lung cancer cells via a p53-independent pathway. Food Funct. 9(11), 5715-5727 (2018).

    4. Patro, B.S., Bauri, A.K., Mishra, S., et al. Antioxidant activity of Myristica malabarica extracts and their constituents. J. Agric. Food Chem. 53(17), 6912-6918 (2005).

    5. Banerjee, D., Bauri, A.K., Guha, R.K., et al. Healing properties of malabaricone B and malabaricone C, against indomethacin-induced gastric uleration and mechanism of action. Eur. J. Pharm. 578(2-3), 300-312 (2008).