山楂酸

山楂酸
	IUPAC名; 2α,3β-Dihydroxyolean-12-en-28-oic acid
	系统名; (4aS,6aS,6bR,8aR,10R,11R,12aR,12bR,14bS)-10,11-Dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid
别名	马斯里酸、2α-羟基齐墩果酸
识别
CAS号	4373-41-5
PubChem	73659
ChemSpider	66312
SMILES	CC1(C)[C@@H](O)[C@H](O)C[C@@]2(C)[C@]([H])1CC[C@]3(C)[C@@]([H])2CC=C4[C@](C)3CC[C@]5([C@](O)=O)[C@]([H])4CC(C)(C)CC5;
ChEBI	66682
KEGG	C16939
性质
化学式	C30H48O4
摩尔质量	472.7 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

山楂酸（英語：Maslinic acid），别名马斯里酸或2α-羟基齐墩果酸，是一种齐墩果烷型五环三萜酸，存在于山楂，油橄榄、枇杷叶、桔梗、广藿香、鼠尾草等植物中。在油橄榄和山楂表皮果蜡含量最高，苹果表皮果蜡也有一定的山楂酸^[1]^[2]^[3]。其主要从油橄榄中提取，亦可以齐墩果酸为原料合成制备^[2]。研究表明其具有多种药理活性。

药理活性

体外研究表明山楂酸可以抑制丝氨酸蛋白酶活性，因该酶是HIV病毒在体内扩散所需的关键酶，因此山楂酸可能作为治疗HIV的一个突破点^[4]。其对肠癌细胞也具备体外抑制增殖活性^[5]。在大鼠身上，山楂酸能提高兴奋性氨基酸转运蛋白2（英语：Excitatory amino acid transporter 2）（EAAT2）对谷氨酸吸收，来减缓谷氨酸毒性作用^[6]。在老鼠肝脏中，山楂酸可起到糖原磷酸化酶抑制剂作用^[7]^[8]，这一点可以在虹鳟鱼上证实，暴露于山楂酸后，糖原开始在鱼肝中积累^[9]。

临床意义

山楂酸已被证实具有抗氧化活性，能清除活性氧和活性氮物种^[10]^[11]。它还对小鼠巨噬细胞中的TNF-α和IL-6等促炎细胞因子具有抑制作用^[11]。这些作用均有利于蛋白质合成、促进生长发育和强化关节^[12]。当老年人服用山楂酸，并配以力量训练后可增强肌肉质量^[13]。

参考文献

^ 焦志敏，陈龙胜，许舒雯，陈兰，任凤莲. HPLC测定油橄榄不同部位山楂酸的含量. 林产化学与工业. 2010, 30 (2): 23-26.
^ ^2.0 ^2.1 李宣，何迎春，周芳亮. 山楂酸药理作用及其机制的研究进展. 中国现代医学杂志. 2021, 31 (8): 49-53. doi:10.3969/j.issn.1005-8982.2021.08.009.
^ 张林晨，张小琴，张俊平. 山楂酸药理作用的研究进展. 药学实践与服务. 2024, 42 (5): 185-189. doi:10.12206/j.issn.2097-2024.202307052.
^ University of Granada. Compound From Olive-pomace Oil Inhibits HIV Spread. sciencedaily.com. 11 July 2007 [2009-06-16].
^ Juan ME, Planas JM, Ruiz-Gutierrez V, Daniel H, Wenzel U. Antiproliferative and apoptosis-inducing effects of maslinic and oleanolic acids, two pentacyclic triterpenes from olives, on HT-29 colon cancer cells (PDF). Br J Nutr. 2008, 100 (1): 36–43. PMID 18298868. doi:10.1017/S0007114508882979 .
^ Guan T, Qian Y, Guan T, Qian Y, Tang X, Huang M, Huang L, Li Y, Sun M. Maslinic acid, a natural inhibitor of glycogen phosphorylase, reduces cerebral ischemic injury in hyperglycemic rats by GLT-1 up-regulation. J. Neurosci. Res. November 2011, 89 (11): 1829–39. PMID 21800347. doi:10.1002/jnr.22671 .
^ Márquez Martín A, De La Puerta Vázquez R, Fernández-Arche A, Ruiz-Gutiérrez V. Supressive effect of maslinic acid from pomace olive oil on oxidative stress and cytokine production in stimulated murine macrophages. Free Radical Research. 2006, 40 (3): 295–302. ISSN 1071-5762. PMID 16484046. doi:10.1080/10715760500467935 （英语）.
^ Wen X, Sun H, Liu J, Wu G, Zhang L, Wu X, Ni P. Pentacyclic triterpenes. Part 1: The first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases. Bioorganic & Medicinal Chemistry Letters. 2005-11-15, 15 (22): 4944–4948. ISSN 0960-894X. PMID 16169219. doi:10.1016/j.bmcl.2005.08.026.
^ Vlietinck A, De Bruyne T, Apers S, Pieters L. Plant-Derived Leading Compounds for Chemotherapy of Human Immunodeficiency Virus (HIV) Infection (PDF). Planta Medica. 1998, 64 (02): 97–109. ISSN 0032-0943. PMID 9525100. doi:10.1055/s-2006-957384  （英语）.
^ Conlon, Ian; Raff, Martin. Size Control in Animal Development. Cell. 1999-01-22, 96 (2): 235–244. PMID 9988218. doi:10.1016/S0092-8674(00)80563-2  （英语）.
^ ^11.0 ^11.1 Montilla MP, Agil A, Navarro MC, Jiménez MI, García-Granados A, Parra A, Cabo MM. Antioxidant Activity of Maslinic Acid, a Triterpene Derivative Obtained from Olea europaea. Planta Medica. 2003, 69 (5): 472–474. ISSN 0032-0943. PMID 12802735. doi:10.1055/s-2003-39698 （英语）.
^ Nierding, Axel. Acide Maslinique: Propriétés Et Bienfaits [Maslinic Acid: Properties And Benefits]. Polyvalents. [2023-12-25] （法语）.
^ Nagai N, Yagyu S, Sakane N. Maslinic acid derived from olive fruit in combination with resistance training improves muscle mass and mobility functions in the elderly. Journal of Clinical Biochemistry and Nutrition. 2019, 64 (3): 224–230. PMC 6529705 . PMID 31138956. doi:10.3164/jcbn.18-104.

[1] 焦志敏，陈龙胜，许舒雯，陈兰，任凤莲. HPLC测定油橄榄不同部位山楂酸的含量. 林产化学与工业. 2010, 30 (2): 23-26.

[:0-2] 2.0 ^2.1 李宣，何迎春，周芳亮. 山楂酸药理作用及其机制的研究进展. 中国现代医学杂志. 2021, 31 (8): 49-53. doi:10.3969/j.issn.1005-8982.2021.08.009.

[3] 张林晨，张小琴，张俊平. 山楂酸药理作用的研究进展. 药学实践与服务. 2024, 42 (5): 185-189. doi:10.12206/j.issn.2097-2024.202307052.

[4] University of Granada. Compound From Olive-pomace Oil Inhibits HIV Spread. sciencedaily.com. 11 July 2007 [2009-06-16].

[5] Juan ME, Planas JM, Ruiz-Gutierrez V, Daniel H, Wenzel U. Antiproliferative and apoptosis-inducing effects of maslinic and oleanolic acids, two pentacyclic triterpenes from olives, on HT-29 colon cancer cells (PDF). Br J Nutr. 2008, 100 (1): 36–43. PMID 18298868. doi:10.1017/S0007114508882979 .

[6] Guan T, Qian Y, Guan T, Qian Y, Tang X, Huang M, Huang L, Li Y, Sun M. Maslinic acid, a natural inhibitor of glycogen phosphorylase, reduces cerebral ischemic injury in hyperglycemic rats by GLT-1 up-regulation. J. Neurosci. Res. November 2011, 89 (11): 1829–39. PMID 21800347. doi:10.1002/jnr.22671 .

[7] Márquez Martín A, De La Puerta Vázquez R, Fernández-Arche A, Ruiz-Gutiérrez V. Supressive effect of maslinic acid from pomace olive oil on oxidative stress and cytokine production in stimulated murine macrophages. Free Radical Research. 2006, 40 (3): 295–302. ISSN 1071-5762. PMID 16484046. doi:10.1080/10715760500467935 （英语）.

[8] Wen X, Sun H, Liu J, Wu G, Zhang L, Wu X, Ni P. Pentacyclic triterpenes. Part 1: The first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases. Bioorganic & Medicinal Chemistry Letters. 2005-11-15, 15 (22): 4944–4948. ISSN 0960-894X. PMID 16169219. doi:10.1016/j.bmcl.2005.08.026.

[9] Vlietinck A, De Bruyne T, Apers S, Pieters L. Plant-Derived Leading Compounds for Chemotherapy of Human Immunodeficiency Virus (HIV) Infection (PDF). Planta Medica. 1998, 64 (02): 97–109. ISSN 0032-0943. PMID 9525100. doi:10.1055/s-2006-957384  （英语）.

[10] Conlon, Ian; Raff, Martin. Size Control in Animal Development. Cell. 1999-01-22, 96 (2): 235–244. PMID 9988218. doi:10.1016/S0092-8674(00)80563-2  （英语）.

[montilla-11] 11.0 ^11.1 Montilla MP, Agil A, Navarro MC, Jiménez MI, García-Granados A, Parra A, Cabo MM. Antioxidant Activity of Maslinic Acid, a Triterpene Derivative Obtained from Olea europaea. Planta Medica. 2003, 69 (5): 472–474. ISSN 0032-0943. PMID 12802735. doi:10.1055/s-2003-39698 （英语）.

[12] Nierding, Axel. Acide Maslinique: Propriétés Et Bienfaits [Maslinic Acid: Properties And Benefits]. Polyvalents. [2023-12-25] （法语）.

[pmid31138956-13] Nagai N, Yagyu S, Sakane N. Maslinic acid derived from olive fruit in combination with resistance training improves muscle mass and mobility functions in the elderly. Journal of Clinical Biochemistry and Nutrition. 2019, 64 (3): 224–230. PMC 6529705 . PMID 31138956. doi:10.3164/jcbn.18-104.

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