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Chemical Compound Review:

d-Pimaric acid 7-ethenyl-1,4a,7-trimethyl- 3,4,4b,5,6,9,10...

Synonyms: PIMARIC ACID, AG-K-14506, Usic acid, SureCN10819486, IBS-L0127093, ...

Rubio, J. et al., Imaizumi, Y. et al., Ohwada, T. et al., Nakanishi, T. et al., Sugimoto, N. et al.

Nakanishi, Inatomi, Murata, Iida, Inada, Lang, Murata, Rubio, Calderón, Flores, Castroa, Céspedes, Ohwada, Nonomura, Maki, Sakamoto, Ohya, Muraki, Imaizumi, Imaizumi, Sakamoto, Yamada, Hotta, Ohya, Muraki, Uchiyama, Ohwada,

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High impact information on Usic acid

Effects of pimaric acid (PiMA) and eight closely related compounds on large-conductance K(+) (BK) channels were examined using human embryonic kidney (HEK) 293 cells, in which either the alpha subunit of BK channel (HEKBKalpha) or both alpha and beta1 (HEKBKalphabeta1) subunits were heterologously expressed [1].
Two new phenol glucosides termed juniperosides I (1) and II (2) were isolated, together with known two biflavones, cupressuflavone and amentoflavone and a diterpene, 3beta-hydroxy sandaracopimaric acid, from leaves of Juniperus occidentalis HOOK [2].
Fractionation with n-hexane/ethyl acetate (1:1 v/v) by open column chromatography of the oleoresin from Pinus oocarpa Schiede yielded two diterpenes, pimaric acid (1) and dehydroabietic acid (5), the sesquiterpene longifolene (3) and a diterpenic mixture containing pimaric acid (1), isopimaric acid (4) and dehydroabietic acid (5) [3].

Biological context of Usic acid

Structure-activity relationship (SAR) studies of the dehydroabietic acid derivatives and related non-aromatic compounds such as pimaric acid revealed the importance of the carboxyl functionality and an appropriate hydrophobic moiety of the molecules for BK channel-opening ability [4].

Analytical, diagnostic and therapeutic context of Usic acid

Quantification of the main constituent, sandaracopimaric acid, was performed by HPLC and its content in the product was determined to be 11.6% [5].

References

Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit. Imaizumi, Y., Sakamoto, K., Yamada, A., Hotta, A., Ohya, S., Muraki, K., Uchiyama, M., Ohwada, T. Mol. Pharmacol. (2002) [Pubmed]
Phytochemical study on American plants I. Two new phenol glucosides, together with known biflavones and diterpene, from leaves of Juniperus occidentalis Hook. Nakanishi, T., Inatomi, Y., Murata, H., Iida, N., Inada, A., Lang, F.A., Murata, J. Chem. Pharm. Bull. (2002) [Pubmed]
Trypanocidal activity of oleoresin and terpenoids isolated from Pinus oocarpa. Rubio, J., Calderón, J.S., Flores, A., Castroa, C., Céspedes, C.L. Z. Naturforsch., C, J. Biosci. (2005) [Pubmed]
Dehydroabietic acid derivatives as a novel scaffold for large-conductance calcium-activated K+ channel openers. Ohwada, T., Nonomura, T., Maki, K., Sakamoto, K., Ohya, S., Muraki, K., Imaizumi, Y. Bioorg. Med. Chem. Lett. (2003) [Pubmed]
Identification of the main constituents in sandarac resin, a natural gum base. Sugimoto, N., Kuroyanagi, M., Kato, T., Sato, K., Tada, A., Yamazaki, T., Tanamoto, K. Shokuhin Eiseigaku Zasshi (2006) [Pubmed]

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