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Structure Database (LMSD)

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Common Name

Abietic acid

Systematic Name

Synonyms

LM ID

LMPR0104050001

Formula

C₂₀H₃₀O₂

Exact Mass

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302.22458

Status

Curated

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Classification

Biological Context

Abietic acid is an abietane diterpene originally isolated from wood resin that has diverse biological activities, including enzyme inhibitory, antiproliferative, antibacterial, and anti-obesity properties.^1,2,3,4,5,6 It inhibits soybean 5-lipoxygenase (5-LO) and rat prostate testosterone 5α-reductase in cell-free assays (IC50s = 29.5 and 56 μM, respectively).^2,3 Abietic acid selectively inhibits proliferation of HeLa cervical cancer cells over noncancerous Vero cells (IC50s = 15 and 53 μM, respectively) and inhibits the growth of S. epidermidis, P. acnes, and S. mitis bacteria (MICs = 8, 4, and 16 μg/ml, respectively).^4,5 It induces expression of fatty acid binding protein 2 (FABP2) and lipoprotein lipase (LPL) in differentiated 3T3-L1 mouse adipocytes when used at a concentration of 25 μM.⁷ Abietic acid (40 mg/kg per day) also decreases body and adipose tissue weight in mice fed a high-fat diet.⁶

This information has been provided by Cayman Chemical

References

1. Harris, G.C., and Sanderson, T.F. Resin acids; an improved method of isolation of resin acids the isolation of a new abietic-type acid, neoabietic acid. J. Am. Chem. Soc. 70(1), 334-339 (1948).

2. Ulusu, N.N., Ercil, D., Sakar, M.K., et al. Abietic acid inhibits lipoxygenase activity. Phytother. Res. 16(1), 88-90 (2002).

3. Roh, S.-S., Park, M.-K., and Kim, Y.-U. Abietic acid from Resina Pini of Pinus species as a testosterone 5α-reductase inhibitor. J. Health Sci. 56(4), 451-455 (2010).

4. González, M.A., Pérez-Guaita, D., Correa-Royero, J., et al. Synthesis and biological evaluation of dehydroabietic acid derivatives. Eur. J. Med. Chem. 45(2), 811-816 (2010).

5. Helfenstein, A., Vahermo, M., Nawrot, D.A., et al. Antibacterial profiling of abietane-type diterpenoids. Bioorg. Med. Chem. 25(1), 132-137 (2017).

6. Hwang, K.H., Ahn, J.Y., Kim, S., et al. Abietic acid has an anti-obesity effect in mice fed a high-fat diet. J. Med. Food 14(9), 1052-1056 (2011).

7. Takahashi, N., Kawada, T., Goto, T., et al. Abietic acid activates peroxisome proliferator-activated receptor-γ (PPARγ) in RAW264.7 macrophages and 3T3-L1 adipocytes to regulate gene expression involved in inflammation and lipid metabolism. FEBS Lett. 550(1-3), 190-194 (2003).

String Representations

InChiKey (Click to copy)

RSWGJHLUYNHPMX-ONCXSQPRSA-N

InChi (Click to copy)

InChI=1S/C20H30O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h7,12-13,16-17H,5-6,8-11H2,1-4H3,(H,21,22)/t16-,17+,19+,20+/m0/s1

SMILES (Click to copy)

[C@@]12([H])CC=C3C=C(CC[C@]3([H])[C@@]1(C)CCC[C@@]2(C)C(=O)O)C(C)C