Minquartynoic acid

Last updated
Minquartynoic acid
Minquartynoic acid.svg
Names
IUPAC name
(17S)-17-hydroxyoctadeca-9,11,13,15-tetraynoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C18H20O3/c1-17(19)15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18(20)21/h17,19H,4,6,8,10,12,14,16H2,1H3,(H,20,21)/t17-/m0/s1
    Key: MTWGWIOCIREVRF-KRWDZBQOSA-N
  • CC(C#CC#CC#CC#CCCCCCCCC(=O)O)O
Properties
C18H20O3
Molar mass 284.355 g·mol−1
Appearancegrey-yellow needles [1]
Melting point 95 °C (203 °F; 368 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Minquartynoic acid is an unsaturated, conjugated, and hydroxylated fatty acid containing four triple bonds and belonging to the class of polyyne and alkynoic acids. It was only discovered in 1989. [2] The acid is optically active, but there are conflicting data regarding the rotation of the natural S-isomer. [3]

Contents

Discovery

The acid was initially isolated by R.J. Marles, N.R. Farnsworth and D.A. Neill in 1989 from the stem of the Amazonian tree Minquartia guianensis . [4] [5]

Natural occurrence

The acid occurs only in small quantities in the bark or twigs of a few plant species, such as Minquartia guianensis , Ochanostachys amentacea , [6] and Coula edulis , [7] all of the family Olacaceae .

Synthesis

Minquartynoic acid can be synthesized starting from azelaic acid monomethyl ester in a seven-step synthesis. [8] Another synthesis of the compound has also been published. [9]

An infusion of the acid has been used by Ecuadorian indigenous people to treat intestinal parasitic infections, lung cancer, and tuberculosis; also, it has been applied topically to treat skin irritations and muscle pain. [10]

Uses

In in vitro studies, minquartynoic acid was antiviral against HIV and cytotoxic against ten different cancer cell lines, including leukemia cells. [11] [12] In other studies, it has shown activity against malaria and Leishmania. [3]

References

  1. ↑ Gunstone, Frank D.; Harwood, John L.; Padley, Fred B. (21 July 1994). The Lipid Handbook, Second Edition. CRC Press. p. 226. ISBN   978-0-412-43320-7 . Retrieved 11 April 2025.
  2. ↑ Gung, Benjamin W. (2009). "Total synthesis of polyyne natural products" . Comptes Rendus. Chimie (in French). 12 (3–4): 489–505. doi:10.1016/j.crci.2008.08.014. ISSN   1878-1543 . Retrieved 11 April 2025.
  3. 1 2 Rasmussen, Hasse Bonde; Christensen, Søren Brøgger; Kvist, Lars Peter; Kharazmi, Arzalan; Huansi, Andrea Gonzales (1 September 2000). "Absolute Configuration and Antiprotozoal Activity of Minquartynoic Acid" . Journal of Natural Products . 63 (9): 1295–1296. Bibcode:2000JNAtP..63.1295R. doi:10.1021/np990604k. ISSN   0163-3864. PMID   11000043 . Retrieved 11 April 2025.
  4. ↑ Nigg, H. N.; Seigler, D. (29 June 2013). Phytochemical Resources for Medicine and Agriculture. Springer Science & Business Media. p. 145. ISBN   978-1-4899-2584-8 . Retrieved 11 April 2025.
  5. ↑ Hostettmann, Kurt (19 December 2018). Chemistry, Biological and Pharmacological Properties of Medicinal Plants from the Americas. Routledge. ISBN   978-1-351-46108-5 . Retrieved 11 April 2025.
  6. ↑ Wiart, Christophe (5 December 2021). Medicinal Plants in the Asia Pacific for Zoonotic Pandemics, Volume 3: Family Bixaceae to Portulacaceae. CRC Press. p. 184. ISBN   978-1-000-47726-9 . Retrieved 11 April 2025.
  7. ↑ Fort, Diana M; King, Steven R; Carlson, Thomas J; Nelson, Susan T (1 June 2000). "Minquartynoic acid from Coula edulis" . Biochemical Systematics and Ecology . 28 (5): 489–490. Bibcode:2000BioSE..28..489F. doi:10.1016/S0305-1978(99)00079-4. ISSN   0305-1978. PMID   10725606 . Retrieved 11 April 2025.
  8. ↑ Gung, Benjamin W.; Dickson, Hamilton (1 July 2002). "Total Synthesis of (−)-Minquartynoic Acid: An Anti-Cancer, Anti-HIV Natural Product" . Organic Letters. 4 (15): 2517–2519. doi:10.1021/ol026145n. ISSN   1523-7060. PMID   12123365 . Retrieved 11 April 2025.
  9. ↑ Sabitha, Gowravaram; Reddy, Ch. Srinivas; Yadav, J. S. (26 June 2006). "Total syntheses of the highly potent anti-cancer polyacetylenes, (S)-18-hydroxyminquartynoic acid, (S)-minquartynoic acid and (E)-15,16-dihydrominquartynoic acid" . Tetrahedron Letters . 47 (26): 4513–4516. doi:10.1016/j.tetlet.2006.03.118. ISSN   0040-4039 . Retrieved 11 April 2025.
  10. ↑ Marles, Robin J.; Farnsworth, Norman R.; Neill, David A. (1 March 1989). "Isolation Of A Novel Cytotoxic Polyacetylene From A Traditional Anthelmintic Medicinal Plant, Minquartia guianensis" . Journal of Natural Products. 52 (2): 261–266. Bibcode:1989JNAtP..52..261M. doi:10.1021/np50062a007. ISSN   0163-3864 . Retrieved 11 April 2025.
  11. ↑ Rashid, Mohammad A.; and Boyd, Michael R. (1 January 2001). "Absolute Stereochemistry and Anti-HIV Activity of Minquartynoic Acid, A Polyacetylene from Ochanostachys amentacea 1a" . Natural Product Letters . 15 (1): 21–26. doi:10.1080/10575630108041253. ISSN   1057-5634. PMID   11547419 . Retrieved 11 April 2025.
  12. ↑ Dembitsky, Valery M. (2006). "Anticancer activity of natural and synthetic acetylenic lipids" . Lipids . 41 (10): 883–924. doi:10.1007/s11745-006-5044-3. ISSN   1558-9307. PMID   17180879 . Retrieved 11 April 2025.
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