- Note
- Published:
Inhibitory effects of l-pipecolic acid from the edible mushroom, Sarcodon aspratus, on angiotensin I-converting enzyme
Journal of Wood Science volume 54, pages 179–181 (2008)
Abstract
The aqueous extract of the edible mushroom Sarcodon aspratus showed inhibitory effects against angiotensin I-converting enzyme (ACE). l-Pipecolic acid (l-piperidine-2-carboxylic acid) was isolated from a hot-water extract in a 0.02% yield as an active principle. The mode of inhibition of l-pipecolic acid was found to be competitive, whereas its d-isomer showed no significant inhibitory effects against ACE, suggesting that the configuration of the carboxyl group in the molecule plays an important role in the enzyme inhibition.
References
Hollenberg NK (1979) Pharmacologic interrupting the reninangiotensin system. Ann Rev Pharmacol 19:559–582
Cheung HS, Cushman DW (1973) Inhibition of homogeneous angiotensin-converting enzyme of rabbit lung by synthetic venom peptides of Bothrops jararaca. Biochim Biophys Acta 293:451–463
Li G-H, Le G-W, Shi Y-H, Shrestha S (2004) Angiotensin I-converting enzyme inhibitory peptides derived from food proteins and their physiological and pharmacological effects. Nutr Res 24:469–486
Choi HS, Cho HY, Yang HC, Ra KS, Suh HJ (2001) Angiotensin I-converting enzyme inhibitor from Grifola frondosa. Food Res Int 34:177–182
Lee DH, Kim JH, Park JS, Choi YJ, Lee JS (2004) Isolation and characterization of a novel angiotensin I-converting enzyme inhibitory peptide derived from the edible mushroom Tricholoma giganteum. Peptides 25:621–627
Sakamoto Y, Takeuchi A, Sato T, Obara K, Takai K, Fujino K, Hirose T, Inagaki Y (2001) Identification of antihypertensive substance in an aqueous extract from fruit body of Mycoleptodonoides aitchisonii. Oyo Yakuri/Pharmacometrics 61:221–229
Tateishi K, Hosono T, Shimazu S, Fujimoto M (2000) Anti-allergenic properties of the fruiting bodies of Sarcodon asptatus (in Japanese). Nippon Shokuhin Kagaku Kogaku Kaishi 47:281–286
Kiyoto M, Suzuki H, Hara T, Yagi Y, Cho N-S, Aoyama M (2005) Moderate angiotensin I converting enzyme (ACE) inhibitor from the fruit body of Sarcodon aspratus. Mushroom Sci Biotechnol 13:189–194
Suzuki H, Kiyoto M, Nobuyama N, Hara T, Yagi Y, Togashi I, Aoyama M (2006) Moderate angiotensin I converting enzyme (ACE) inhibitors from the edible mushroom Pleurotus citrinopileatus Singer (Agaricomycetideae). Int J Med Mushrooms 8:45–47
Cushman DW, Cheung HS (1971) Spectrophotometric assay and properties of the angiotensin-converting enzyme of rabbit lung. Biochem Pharmacol 20:1637–1648
Bush K, Henry PR, Slusarchyk DS (1984) Muraceins — muranyl peptides produced by Nocardia orientalis as angiotensinconverting enzyme inhibitors. I. Taxonomy, fermentation and biological properties. J Antibiot 37:330–335
Oh C-H, Kim J-H, Kim K-R, Mabry TJ (1995) Rapid gas chromatographic screening of edible seeds, nuts and beans for nonprotein and protein amino acids. J Chromatogr A 708:131–141
Inoue H, Sakata Y, Fukunaga K, Nishio H, Tsuruta Y (2004) Sensitive determination of pipecolic acid in serum by high-performance liquid chromatography using 4-(5,6-dimethoxy-2-phthalimidinyl)-2-methoxyphenylsulfonyl chloride as a fluorescent labeling reagent. Anal Chim Acta 511:267–271
Kerckaert I, Poll BT, Espeel M, Duran M, Roeleveld ABC, Wanders RJA, Roels F (2000) Hepatic peroxisomes in isolated hyperpipecolic acidaemia: evidence supporting its classification as a single peroxisomal enzyme deficiency. Virchows Arch 436:459–465
Kusano G, Ogawa H, Takahashi A, Nozoe S, Yokoyama K (1987) A new amino acid, (2S, 3R)-(-)-3-hydroxybaikiain from Russula subnigricans Hongo. Chem Pharm Bull 35:3482–3486
Stefan R-I, Nejem RM, Staden JF, Aboul-Enein HY (2003) Biosensors for the enantioselective analysis of pipecolic acid. Sensor Actuat B-Chem 94:271–275
Fujita T, Fujita M, Kodama T, Hada T, Higashino K (2003) Determination of d-and l-pipecolic acid in food samples including processed foods. Ann Nutr Metab 47:165–169
Ondetti MA, Cushman DW (1982) Enzymes of the reninangiotensin system and their inhibitors. Ann Rev Biochem 51:283–308
Tzakos AG, Naqvi N, Comporozos K, Pierattelli R, Theodorou V, Husain A, Gerothanassis IP (2006) The molecular basis for the selection of captopril cis and trans conformations by angiotensin I converting enzyme. Bioorg Med Chem Lett 16:5084–5087
Moulin M, Deleu C, Larher FR, Bouchereau A (2002) High-performance liquid chromatography determination of pipecolic acid after precolumn ninhydrin derivatization using domestic microwave. Anal Biochem 308:320–327
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kiyoto, M., Saito, S., Hattori, K. et al. Inhibitory effects of l-pipecolic acid from the edible mushroom, Sarcodon aspratus, on angiotensin I-converting enzyme. J Wood Sci 54, 179–181 (2008). https://doi.org/10.1007/s10086-007-0923-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10086-007-0923-7
Key words
- Angiotensin I-converting enzyme (ACE)
- Antihypertensive agent
- l-Pipecolic acid
- Sarcodon aspratus