Lambertianic acid

Last updated
Lambertianic acid
Lambertianic acid.svg
Names
IUPAC name
methyl (1S,4aR,5S,8aR)-5-[2-(furan-3-yl)ethyl]-4a-methyl-6-methylidene-1,2,3,4,5,7,8,8a-octahydronaphthalene-1-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C20H28O3/c1-14-6-8-18-16(19(21)22-3)5-4-11-20(18,2)17(14)9-7-15-10-12-23-13-15/h10,12-13,16-18H,1,4-9,11H2,2-3H3/t16-,17-,18+,20-/m0/s1 X mark.svgN
    Key: XZOUFGJMCGQXNM-GNBUJSLZSA-N
  • CC12CCCC(C1CCC(=C)C2CCC3=COC=C3)C(=O)OC
Properties
C20H28O3
Molar mass 316.441 g·mol−1
Density 1.09 g/cm3
Melting point °C
Boiling point 428 °C
insoluble
Hazards
Flash point 213 °C [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lambertianic acid is a naturally occurring organic compound classified as a diterpenoid with the molecular formula C20H28O3. This is a tricyclic carboxylic acid first isolated from the oleoresin of the Lambert pine ( Pinus lambertiana ), from which it derives its name. The acid is a member of the abietane family of diterpenes, characterized by its aromatic C-ring. [2]

Contents

Structure

Lambertianic acid is based on the abietane carbon skeleton. Its structure consists of three fused six-membered rings (phenanthrene framework) with a carboxylic acid (–COOH) group at the C-18 position (the fourth carbon of the original abietane side chain) and three conjugated double bonds in rings B and C at the positions 8, 11, and 13. This conjugated system contributes to its reactivity and spectroscopic properties. [3] Lambertianic acid is an optical isomer of daniellic acid. [4]

Natural occurences

Lambertianic acid was first reported by Dauben and German [5] in the mid-20th century as a major acidic constituent of the oleoresin (a mixture of resin acids and terpenes) of the sugar pine ( Pinus lambertiana ). [6] The acid is biosynthesized in pine trees from geranylgeranyl pyrophosphate via the diterpenoid pathway and serves as a defensive compound against insects and pathogens. The compound has also been found, often in smaller quantities, in other Pinus species and some species of the Lamiaceae family. [7]

Physical properties

The acid is soluble in common organic solvents (e.g., chloroform, methanol, ethyl acetate, DMSO) and insoluble in water.

Uses

Reports indicate that the acid may offer health benefits by mitigating obesity, allergies, and various cancers such as those of the breast, liver, lung, and prostate. Its anticancer effects stem from suppressing the proliferation and survival of cancer cells. [8] [9]

Lambertianic acid is structurally related to several other commercially and biologically important resin acids:

References

  1. ↑ "Lambertianic Acid" . Retrieved 9 February 2026.
  2. ↑ Terpenoids and Steroids. Chemical Society. 1975. ISBN   978-0-85186-296-5 . Retrieved 9 February 2026.
  3. ↑ Dauben, W. G.; German, V. F. (1 January 1966). "The structure of lamertianic acid: A new diterpenic acid". Tetrahedron . 22 (2): 679–683. doi:10.1016/0040-4020(66)80037-6. ISSN   0040-4020 . Retrieved 9 February 2026.
  4. ↑ Çiçek, Serhat Sezai; Wenzel-Storjohann, Arlette; Girreser, Ulrich; Tasdemir, Deniz (1 February 2020). "Biological Activities of Two Major Copaiba Diterpenoids and Their Semi-synthetic Derivatives". Revista Brasileira de Farmacognosia. 30 (1): 18–27. doi:10.1007/s43450-020-00002-y. ISSN   1981-528X . Retrieved 9 February 2026.
  5. ↑ Bulletin of the Institute for Chemical Research, Kyoto University. Institute for Chemical Research, Kyoto University. 1967. p. 242. Retrieved 9 February 2026.
  6. ↑ Proceedings. 1974. p. 48. Retrieved 9 February 2026.
  7. ↑ Rahman, Atta-ur (8 February 2021). Studies in Natural Products Chemistry. Elsevier. p. 237. ISBN   978-0-12-819486-7 . Retrieved 9 February 2026.
  8. ↑ Shahinozzaman, Md; Islam, Moutushi; Basak, Bristy; Sultana, Arifa; Emran, Rashiduzzaman; Ashrafizadeh, Milad; Islam, A T M Rafiqul (1 September 2021). "A review on chemistry, source and therapeutic potential of lambertianic acid". Zeitschrift fur Naturforschung C . 76 (9–10): 347–356. doi:10.1515/znc-2020-0267. ISSN   1865-7125 . Retrieved 9 February 2026.
  9. ↑ Hee, Cho, Chan; Hyeon, Chae, Si; Hee, Um, Sung; Seulah, Lee,; Sik, Yu, Jae; Sung, Kang, Ki; Hyun, Kim, Ki (January 2025). "Lambertianic Acid from Platycladus orientalis Inhibits Muscle Atrophy in Dexamethasone-Induced C2C12 Muscle Atrophy Cells". Plants . 14 (9). doi:10.3390/plant. ISSN   2223-7747 . Retrieved 9 February 2026.{{cite journal}}: CS1 maint: extra punctuation (link) CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)
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