Chemistry:Minquartynoic acid

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Minquartynoic acid
Names
IUPAC name
(17S)-17-hydroxyoctadeca-9,11,13,15-tetraynoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
Properties
C18H20O3
Molar mass 284.355 g·mol−1
Appearance grey-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).
Infobox references
Tracking categories (test):

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]

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) (in en). The Lipid Handbook, Second Edition. CRC Press. p. 226. ISBN 978-0-412-43320-7. https://books.google.com/books?id=m9J9pTDZEGEC&dq=Minquartynoic+acid&pg=RA1-PA489. Retrieved 11 April 2025. 
  2. ↑ Gung, Benjamin W. (2009). "Total synthesis of polyyne natural products" (in fr). Comptes Rendus. Chimie 12 (3–4): 489–505. doi:10.1016/j.crci.2008.08.014. ISSN 1878-1543. https://comptes-rendus.academie-sciences.fr/chimie/articles/10.1016/j.crci.2008.08.014/. Retrieved 11 April 2025. 
  3. ↑ 3.0 3.1 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. doi:10.1021/np990604k. ISSN 0163-3864. PMID 11000043. Bibcode: 2000JNAtP..63.1295R. https://pubs.acs.org/doi/10.1021/np990604k. Retrieved 11 April 2025. 
  4. ↑ Nigg, H. N.; Seigler, D. (29 June 2013) (in en). Phytochemical Resources for Medicine and Agriculture. Springer Science & Business Media. p. 145. ISBN 978-1-4899-2584-8. https://books.google.com/books?id=YxT3BwAAQBAJ&dq=Minquartynoic+acid+1989&pg=PA145. Retrieved 11 April 2025. 
  5. ↑ Hostettmann, Kurt (19 December 2018) (in en). Chemistry, Biological and Pharmacological Properties of Medicinal Plants from the Americas. Routledge. ISBN 978-1-351-46108-5. https://books.google.com/books?id=-XuCDwAAQBAJ&dq=Minquartynoic+acid&pg=PA224. Retrieved 11 April 2025. 
  6. ↑ Wiart, Christophe (5 December 2021) (in en). 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. https://books.google.com/books?id=SDlJEAAAQBAJ&dq=Minquartynoic+acid&pg=PA184. 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. doi:10.1016/S0305-1978(99)00079-4. ISSN 0305-1978. PMID 10725606. Bibcode: 2000BioSE..28..489F. https://www.sciencedirect.com/science/article/abs/pii/S0305197899000794. 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. https://pubs.acs.org/doi/10.1021/ol026145n. 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. https://linkinghub.elsevier.com/retrieve/pii/S0040403906005910. 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. doi:10.1021/np50062a007. ISSN 0163-3864. Bibcode: 1989JNAtP..52..261M. https://pubs.acs.org/doi/abs/10.1021/np50062a007. 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. https://www.tandfonline.com/doi/abs/10.1080/10575630108041253. Retrieved 11 April 2025. 
  12. ↑ Dembitsky, Valery M. (2006). "Anticancer activity of natural and synthetic acetylenic lipids" (in en). Lipids 41 (10): 883–924. doi:10.1007/s11745-006-5044-3. ISSN 1558-9307. PMID 17180879. https://aocs.onlinelibrary.wiley.com/doi/10.1007/s11745-006-5044-3. Retrieved 11 April 2025. 



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