植烷酸

植烷酸
	IUPAC名; （7反,11反）-3,7,11,15-四甲基十六烷酸
別名	植烷酸
識別
CAS號	14721-66-5
PubChem	468706
ChemSpider	411797
SMILES	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCCC(C)CC(=O)O;
MeSH	Phytanic+acid
性質
化學式	C20H40O2
摩爾質量	312.53 g·mol⁻¹
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

植烷酸（英語：Phytanic acid，或3,7,11,15-四甲基十六烷酸）是一種支鏈脂肪酸，人類可以通過食用乳製品、反芻動物脂肪以及某些魚類^[1]而獲得該物質。估計西方飲食每天可以提供50～100毫克的植烷酸^[2]。在一項牛津大學做的研究中，食用肉食的個人，平均來說血漿中植烷酸濃度的幾何平均數比純素食主義者高6.7倍^[3]。

人類病理學

不像大多數脂肪酸，植烷酸不能夠通過β-氧化被代謝。相反，它在過氧物酶體中經歷α-氧化，在那裏，它被脫掉一個碳而轉換為降植烷酸 ^[4]。降植烷酸在過氧物酶體經歷數輪迴β-氧化以形成中鏈脂肪酸，這樣就可以在線粒體中被降解成二氧化碳以及水。

患有成人雷夫敘姆病的個體，由PHYH基因中的突變所導致的常染色體隱性神經障礙妨礙了進行α-氧化的活性，且使得他們的血液以及組織中積累了大量的植烷酸^[5]。這常會導致周圍神經病變、小腦共濟失調、色素性視網膜炎、嗅覺喪失症以及聽力喪失^[6]。

其他生物體中的存在情況

在反芻動物中，攝入的植物在消化道發酵中釋放出葉綠醇，這種物質是葉綠素的一部分，之後葉綠醇被轉變成植烷酸並被儲存於脂肪中^[7]。最近，間接的證據已經證明大型類人猿（倭黑猩猩、黑猩猩屬、大猩猩以及猩猩），與人不同，在植物的後腸發酵過程中獲得數量可觀的植烷酸^[8]。

淡水海綿都含有例如4,8,12-三甲基十三烷酸, 植烷酸以及降植烷酸之類的類萜，這表明這些酸對於海生和淡水海綿來說具有化學分類學意義^[9]。

昆蟲，例如黃櫨跳甲，被報道可以使用葉綠醇及其代謝產物（例如植烷酸）作為防止自己被捕食的化學威懾劑^[10]。這些化合物攝取自它的宿主植物。

轉錄調控劑

植烷酸及其代謝產物被報道說可以結合併激活轉錄因子過氧化物酶體增殖物激活受體α^[11]以及視黃酸受體^[12]。

參考文獻

^ Brown, P. J.; et al. The determination of phytanic acid and phytol in certain foods and the application of this knowledge to the choice of suitable convenience foods for patients with Refsum's disease. Journal of Human Nutrition and Dietetics. 1993, 6: 295–305. doi:10.1111/j.1365-277x.1993.tb00375.x.
^ Steinberg, D. Phytanic acid storage disease (Refsum's disease). In: Metabolic Basis of Inherited Disease. Edited by Stanbury JB, Wyngarden JB, Fredericksen DS, Goldstein JL, Brown MS, 5th edn. New York: McGraw Hill; 1983: 731-747.
^ Naomi E. Allen, Philip B. Grace, Annette Ginn, Ruth C. Travis, Andrew W. Roddam, Paul N. Appleby, Timothy Key. Phytanic acid: measurement of plasma concentrations by gas-liquid chromatography-mass spectrometry analysis and associations with diet and other plasma fatty acids. The British Journal of Nutrition. 2008-03, 99 (3): 653–659 [2019-02-12]. ISSN 0007-1145. PMID 17868488. doi:10.1017/S000711450782407X. （原始內容存檔於2009-03-01）.
^ D. M. van den Brink, R. J. A. Wanders. Phytanic acid: production from phytol, its breakdown and role in human disease. Cellular and molecular life sciences: CMLS. 2006-08, 63 (15): 1752–1765 [2019-02-12]. ISSN 1420-682X. PMID 16799769. doi:10.1007/s00018-005-5463-y.
^ G. Quintaliani, U. Buoncristiani, A. Orecchini, P. Pierini, R. Ricci, G. P. Reboldi. The Umbria Regional Registry for hemodialyzed and transplanted patients. Preliminary experience with an informatic procedure. Contributions to Nephrology. 1994, 109: 96–99 [2019-02-12]. ISSN 0302-5144. PMID 7956237.
^ R. J. A. Wanders, J. C. Komen. Peroxisomes, Refsum's disease and the alpha- and omega-oxidation of phytanic acid. Biochemical Society Transactions. 2007-11, 35 (Pt 5): 865–869 [2019-02-13]. ISSN 0300-5127. PMID 17956234. doi:10.1042/BST0350865. （原始內容存檔於2014-10-22）.
^ N. M. Verhoeven, R. J. Wanders, B. T. Poll-The, J. M. Saudubray, C. Jakobs. The metabolism of phytanic acid and pristanic acid in man: a review. Journal of Inherited Metabolic Disease. 1998-10, 21 (7): 697–728 [2019-02-12]. ISSN 0141-8955. PMID 9819701. （原始內容存檔於2016-06-04）.
^ Paul A. Watkins, Ann B. Moser, Cicely B. Toomer, Steven J. Steinberg, Hugo W. Moser, Mazen W. Karaman, Krishna Ramaswamy, Kimberly D. Siegmund, D. Rick Lee, John J. Ely, Oliver A. Ryder, Joseph G. Hacia. Identification of differences in human and great ape phytanic acid metabolism that could influence gene expression profiles and physiological functions. BMC physiology. 2010-10-08, 10: 19 [2019-02-12]. ISSN 1472-6793. PMC 2964658 . PMID 20932325. doi:10.1186/1472-6793-10-19. （原始內容存檔於2014-04-16）.
^ Rezanka, T.; Dembitsky, V. M. Isoprenoid polyunsaturated fatty acids from freshwater sponges. Journal of Natural Products. 1993, 56: 1898–1904. doi:10.1021/np50101a005.
^ Venci, F.V.; Morton, T.C. The shield defense of the sumac flea beetle, Blepharida rhois (Chrysomelidae: Alticinae). Chemoecology. 1998, 8: 25–32.
^ J. Gloerich, N. van Vlies, G. A. Jansen, S. Denis, J. P. N. Ruiter, M. A. van Werkhoven, M. Duran, F. M. Vaz, R. J. A. Wanders, S. Ferdinandusse. A phytol-enriched diet induces changes in fatty acid metabolism in mice both via PPARalpha-dependent and -independent pathways. Journal of Lipid Research. 2005-04, 46 (4): 716–726 [2019-02-13]. ISSN 0022-2275. PMID 15654129. doi:10.1194/jlr.M400337-JLR200.
^ S. Kitareewan, L. T. Burka, K. B. Tomer, C. E. Parker, L. J. Deterding, R. D. Stevens, B. M. Forman, D. E. Mais, R. A. Heyman, T. McMorris, C. Weinberger. Phytol metabolites are circulating dietary factors that activate the nuclear receptor RXR. Molecular Biology of the Cell. 1996-08, 7 (8): 1153–1166 [2019-02-12]. ISSN 1059-1524. PMC 275969 . PMID 8856661.

外部連結

[1] Brown, P. J.; et al. The determination of phytanic acid and phytol in certain foods and the application of this knowledge to the choice of suitable convenience foods for patients with Refsum's disease. Journal of Human Nutrition and Dietetics. 1993, 6: 295–305. doi:10.1111/j.1365-277x.1993.tb00375.x.

[2] Steinberg, D. Phytanic acid storage disease (Refsum's disease). In: Metabolic Basis of Inherited Disease. Edited by Stanbury JB, Wyngarden JB, Fredericksen DS, Goldstein JL, Brown MS, 5th edn. New York: McGraw Hill; 1983: 731-747.

[pmid17868488-3] Naomi E. Allen, Philip B. Grace, Annette Ginn, Ruth C. Travis, Andrew W. Roddam, Paul N. Appleby, Timothy Key. Phytanic acid: measurement of plasma concentrations by gas-liquid chromatography-mass spectrometry analysis and associations with diet and other plasma fatty acids. The British Journal of Nutrition. 2008-03, 99 (3): 653–659 [2019-02-12]. ISSN 0007-1145. PMID 17868488. doi:10.1017/S000711450782407X. （原始內容存檔於2009-03-01）.

[pmid16799769-4] D. M. van den Brink, R. J. A. Wanders. Phytanic acid: production from phytol, its breakdown and role in human disease. Cellular and molecular life sciences: CMLS. 2006-08, 63 (15): 1752–1765 [2019-02-12]. ISSN 1420-682X. PMID 16799769. doi:10.1007/s00018-005-5463-y.

[pmid7956237-5] G. Quintaliani, U. Buoncristiani, A. Orecchini, P. Pierini, R. Ricci, G. P. Reboldi. The Umbria Regional Registry for hemodialyzed and transplanted patients. Preliminary experience with an informatic procedure. Contributions to Nephrology. 1994, 109: 96–99 [2019-02-12]. ISSN 0302-5144. PMID 7956237.

[pmid17956234-6] R. J. A. Wanders, J. C. Komen. Peroxisomes, Refsum's disease and the alpha- and omega-oxidation of phytanic acid. Biochemical Society Transactions. 2007-11, 35 (Pt 5): 865–869 [2019-02-13]. ISSN 0300-5127. PMID 17956234. doi:10.1042/BST0350865. （原始內容存檔於2014-10-22）.

[pmid9819701-7] N. M. Verhoeven, R. J. Wanders, B. T. Poll-The, J. M. Saudubray, C. Jakobs. The metabolism of phytanic acid and pristanic acid in man: a review. Journal of Inherited Metabolic Disease. 1998-10, 21 (7): 697–728 [2019-02-12]. ISSN 0141-8955. PMID 9819701. （原始內容存檔於2016-06-04）.

[pmid20932325-8] Paul A. Watkins, Ann B. Moser, Cicely B. Toomer, Steven J. Steinberg, Hugo W. Moser, Mazen W. Karaman, Krishna Ramaswamy, Kimberly D. Siegmund, D. Rick Lee, John J. Ely, Oliver A. Ryder, Joseph G. Hacia. Identification of differences in human and great ape phytanic acid metabolism that could influence gene expression profiles and physiological functions. BMC physiology. 2010-10-08, 10: 19 [2019-02-12]. ISSN 1472-6793. PMC 2964658 . PMID 20932325. doi:10.1186/1472-6793-10-19. （原始內容存檔於2014-04-16）.

[9] Rezanka, T.; Dembitsky, V. M. Isoprenoid polyunsaturated fatty acids from freshwater sponges. Journal of Natural Products. 1993, 56: 1898–1904. doi:10.1021/np50101a005.

[10] Venci, F.V.; Morton, T.C. The shield defense of the sumac flea beetle, Blepharida rhois (Chrysomelidae: Alticinae). Chemoecology. 1998, 8: 25–32.

[pmid15654129-11] J. Gloerich, N. van Vlies, G. A. Jansen, S. Denis, J. P. N. Ruiter, M. A. van Werkhoven, M. Duran, F. M. Vaz, R. J. A. Wanders, S. Ferdinandusse. A phytol-enriched diet induces changes in fatty acid metabolism in mice both via PPARalpha-dependent and -independent pathways. Journal of Lipid Research. 2005-04, 46 (4): 716–726 [2019-02-13]. ISSN 0022-2275. PMID 15654129. doi:10.1194/jlr.M400337-JLR200.

[pmid8856661-12] S. Kitareewan, L. T. Burka, K. B. Tomer, C. E. Parker, L. J. Deterding, R. D. Stevens, B. M. Forman, D. E. Mais, R. A. Heyman, T. McMorris, C. Weinberger. Phytol metabolites are circulating dietary factors that activate the nuclear receptor RXR. Molecular Biology of the Cell. 1996-08, 7 (8): 1153–1166 [2019-02-12]. ISSN 1059-1524. PMC 275969 . PMID 8856661.

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