ChemicalBook Product Catalog Natural Products Terpenes moronic acid

moronic acid

Product Namemoronic acid
CAS6713-27-5
MFC30H46O3
MW454.68
EINECS
MOL File6713-27-5.mol

Chemical Properties

Melting point	212 °C(dec.)
Boiling point	550.0±50.0 °C(Predicted)
Density	1.09±0.1 g/cm3(Predicted)
solubility	Chloroform: Sparingly soluble: 1-10 mg/ml Methanol: Slightly soluble: 0.1-1 mg/ml
form	Solid
pka	4.59±0.70(Predicted)
color	White to off-white

Usage And Synthesis

Chemical Properties

White crystalline needles; m. p. 210±2128C; [a]D 25: + 298 (c 0.41, CHCl3); IR (CHCl3): nmax = 3514 to 2800 (COOH), 1731 (COOH), 1695 (CO), 1457 cm-1 (C = C). EI :m/z (rel. int.) = 454 [M+, C30H46O3] (13), 410 (53), 408 (9), 248 (33), 235 (87), 191 (97), 189 (95), 163 (30), 119 (35), 95 (39), 69 (30). 1H-NMR (CDCl3, 300 MHz): d = 12.00 ± 10.00 (1H, COOH), 5.16 (1H, s, H-19), 2.47 (2H, m, H-2), 2.27 ± 2.04 (m), 1.98 (2H, m, H-1), 1.70 ± 1.20 (CH and CH2), 1.08, 1.03, 1.02, 1.00, 0.97, 0.94, 0.79 (21H, 7 s, 7CH3). 13C-NMR (CDCl3, 75 MHz, multiplicities by the DEPT pulse sequences): d = 218.2 (s, C-3), 182.3 (s, C-28), 136.5 (s, C-18), 133.2 (d, C-19), 54.8 (d, C-5), 50.4 (d, C-9), 47.9 (s, C-17), 47.2 (s, C-4), 42.5 (s, C-14), 41.4 (d, C-13), 40.5 (s, C-8), 39.8 (t, C-1), 36.9 (s, C-10), 34.0 (t, C-7), 33.8 (t, C-2), 33.5 (t, C-22), 33.4 (t, C-21), 33.3 (t, C-16), 32.0 (s, C-20), 30.3 (q, C-29), 29.3 (t, C-15), 29.0 (q, C-30), 26.8 (q, C-24), 26.0 (t, C-12), 21.4 (t, C-11), 20.9 (q, C-23), 19.6 (t, C6), 16.4 (q, C-26), 15.8 (q, C-25), 14.8 (q, C-27).

Uses

Moronic Acid and its derivatives can have antidiabetic activity by inhibiting PTP-1B. Moronic Acid is also shown sustained antidiabetic and antihyperglycemic action possibly mediated by an insulin sensitization in rat models.

Definition

ChEBI: Moronic acid is a pentacyclic triterpenoid that is olean-18-ene substituted at position 3 by an oxo group and position 28 by a carboxy group. It has a role as a metabolite, an anti-HSV-1 agent and an anti-HIV agent. It derives from a hydride of an oleanane.

General Description

Moronic acid is a fatty acid found in the seeds of Morus alba. It has been shown to have anti-infective properties by binding to the bacterial efflux protein, which is responsible for transporting toxic compounds out of the cell. The binding of moronic acid to the efflux protein prevents it from functioning and leads to increased expression of proinflammatory genes, ultimately leading to cell death. Moronic acid has also been shown to bind to a receptor on Staphylococcus aureus that is responsible for regulating virulence factors, leading to decreased production of proteins such as coagulase and proteases. Moronic acid also binds with oleanolic acid and inhibits the growth of Mycobacterium tuberculosis in vitro.

in vivo

Moronic Acid (5-10 mg/kg, i.g., once daily, 20 days) regulates the ROS - NF - κB - NLRP3 signaling pathway in mice by inhibiting ROS, improving inflammatory bowel disease^[2].
Moronic Acid extends the survival time of HSV-1 infected mice and slows the progression of skin lesions^[3].

Animal Model:	Mice induced by DSS^[2]
Dosage:	5, 10 mg/kg; daily; 20 days
Administration:	i.g.
Result:	Inhibited intestinal macrophage M1 polarization, inhibited the expression of inflammatory factors, and reduced ROS-NF-κB-NLRP3 signaling levels.

IC 50

NLRP3

References

[1] MKHUSELI KOKI. Phytochemical Investigation and Biological Studies on Selected Searsia Species.[J]. Plants-Basel, 2022. DOI: 10.3390/plants11202793
[2] JUNKO ITO. Anti-AIDS Agents. 48. 1 Anti-HIV Activity of Moronic Acid Derivatives and the New Melliferone-Related Triterpenoid Isolated from Brazilian Propolis[J]. Journal of Natural Products , 2001, 64 10: 1278-1281. DOI: 10.1021/np010211x
[3] SHUILIANG RUAN Li Z. Moronic acid improves intestinal inflammation in mice with chronic colitis by inhibiting intestinal macrophage polarization[J]. Journal of Biochemical and Molecular Toxicology, 2022, 36 11. DOI: 10.1002/jbt.23188
[4] K. YASUKAWA. Inhibitory Effects of Brazilian Propolis on Tumor Promotion in Two-Stage Mouse Skin Carcinogenesis[J]. Journal of Pharmacy and Nutrition Sciences, 2012, 24 1. DOI: 10.6000/1927-5951.2012.02.01.10
[5] MARÍA RIOS1. Cytotoxic Activity of Moronic Acid and Identification of the New Triterpene 3,4-seco-Olean-18-ene-3,28-dioic Acid from Phoradendron reichenbachianum[J]. Planta medica, 2001, 101 1: 443-446. DOI:10.1055/s-2001-15823.

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