木兰醇

木兰醇[1]
IUPAC名
3,3′-Neoligna-8,8′-diene-4,4′-diol
系统名
5,5′-Di(prop-2-en-1-yl)[1,1′-biphenyl]-2,2′-diol
别名 木兰酚
厚朴酚
5,5'-二烯丙基-2,2'-联苯酚
识别
CAS号 528-43-8  checkY
PubChem 72300
ChemSpider 65251
SMILES
 
  • C=CCC1=CC(=C(C=C1)O)C2=C(C=CC(=C2)CC=C)O
InChI
 
  • 1/C18H18O2/c1-3-5-13-7-9-17(19)15(11-13)16-12-14(6-4-2)8-10-18(16)20/h3-4,7-12,19-20H,1-2,5-6H2
InChIKey VVOAZFWZEDHOOU-UHFFFAOYAE
KEGG C10651
性质
化学式 C18H18O2
摩尔质量 266.33 g·mol−1
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

木兰醇（英語：Magnolol），又称厚朴酚，是一种有机化合物。是从木兰属厚朴（学名：Houpu magnolia）和荷花玉兰（学名：Magnolia grandiflora）树皮中提取到的一种木脂素[2]。并非所有木兰属植物存在木兰醇，其仅存在于少部分木兰属植物树皮中。此外，同样从木兰属植物树皮中提取的木脂素还有和厚朴酚，其为木兰醇的同分异构体。

生物活性

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在大鼠的体外研究表明木兰醇是一种GABAA受体抑制剂[3]，同时具有抗真菌活性[4]。木兰醇在细胞培养中具有多种成骨细胞刺激和破骨细胞抑制活性，并已被建议作为筛选预防骨质疏松的候选药物[5]。它在大鼠模型中具有抗牙周病活性[6]。木兰醇的结构类似物已被研究并发现是GABAA受体强效的别构调节剂[7]。

木兰醇的二聚体能与PPAR-γ核受体结合，充当该受体的激动剂，该受体是糖尿病研究的对象之一[8]。

木兰醇能与大麻素受体相互作用，且能部分激发大麻素2号受体（英语：Cannabinoid receptor 2）且不与大麻素1号受体（英语：Cannabinoid receptor 1）亲和[9]。

参考文献

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  1. ^ Magnolol （页面存档备份，存于互联网档案馆） at Sigma-Aldrich
  2. ^ Lee, Young-Jung; Lee, Yoot Mo; Lee, Chong-Kil; Jung, Jae Kyung; Han, Sang Bae; Hong, Jin Tae. Therapeutic applications of compounds in the Magnolia family. Pharmacology & Therapeutics. 2011, 130 (2): 157–76. PMID 21277893. doi:10.1016/j.pharmthera.2011.01.010. 
  3. ^ Ai, Jinglu; Wang, Xiaomei; Nielsen, Mogens. Honokiol and Magnolol Selectively Interact with GABAA Receptor Subtypes in vitro. Pharmacology. 2001, 63 (1): 34–41. PMID 11408830. S2CID 19327464. doi:10.1159/000056110. 
  4. ^ Bang, Kyu Ho; Kim, Yoon Kwan; Min, Byung Sun; Na, Min Kyun; Rhee, Young Ha; Lee, Jong Pill; Bae, Ki Hwan. Antifungal activity of magnolol and honokiol. Archives of Pharmacal Research. 2000, 23 (1): 46–9. PMID 10728656. S2CID 22754315. doi:10.1007/BF02976465. 
  5. ^ Kwak, Eun Jung; Lee, Young Soon; Choi, Eun Mi. Effect of Magnolol on the Function of Osteoblastic MC3T3-E1 Cells. Mediators of Inflammation. 2012, 2012: 1–7. PMC 3306956 可免费查阅. PMID 22474400. doi:10.1155/2012/829650 可免费查阅. 
  6. ^ Lu, Sheng-Hua; Huang, Ren-Yeong; Chou, Tz-Chong. Magnolol Ameliorates Ligature-Induced Periodontitis in Rats and Osteoclastogenesis: In Vivo and in Vitro Study. Evidence-Based Complementary and Alternative Medicine. 2013, 2013: 1–12. PMC 3618931 可免费查阅. PMID 23573141. doi:10.1155/2013/634095 可免费查阅. 
  7. ^ Fuchs, Alexander; Baur, Roland; Schoeder, Clara; Sigel, Erwin; Müller, Christa E. Structural analogues of the natural products magnolol and honokiol as potent allosteric potentiators of GABAA receptors. Bioorganic & Medicinal Chemistry. December 2014, 22 (24): 6908–6917. PMID 25456080. doi:10.1016/j.bmc.2014.10.027. 
  8. ^ Dreier, Dominik; Latkolik, Simone; Rycek, Lukas; Schnürch, Michael; Dymáková, Andrea; Atanasov, Atanas G.; Ladurner, Angela; Heiss, Elke H.; Stuppner, Hermann; Schuster, Daniela; Mihovilovic, Marko D.; Dirsch, Verena M. Linked magnolol dimer as a selective PPARγ agonist – Structure-based rational design, synthesis, and bioactivity evaluation. Scientific Reports. 20 October 2017, 7 (1): 13002. PMC 5651862 可免费查阅. PMID 29057944. S2CID 256897195. doi:10.1038/s41598-017-12628-5. 
  9. ^ Rempel, Viktor; Fuchs, Alexander; Hinz, Sonja; Karcz, Tadeusz; Lehr, Matthias; Koetter, Uwe; Müller, Christa E. Magnolia Extract, Magnolol, and Metabolites: Activation of Cannabinoid CB 2 Receptors and Blockade of the Related GPR55. ACS Medicinal Chemistry Letters. 10 January 2013, 4 (1): 41–45. PMC 4027495 可免费查阅. PMID 24900561. doi:10.1021/ml300235q.