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褪黑素

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褪黑素
Melatonin.svg
Melatonin molecule ball.png
临床资料
AHFS英语American Society of Health-System Pharmacists/Drugs.com消费者药物信息
给药途径口服、舌下、皮肤
ATC码
法律规范状态
法律规范
药物动力学数据
生物利用度30–50%
药物代谢肝脏 via CYP1A2 mediated 6-hydroxylation
生物半衰期35–50 分钟
排泄途径肾脏
识别信息
CAS号73-31-4  ✓
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.725 编辑维基数据链接
化学信息
化学式C13H16N2O2
摩尔质量232.278 g/mol
3D model (JSmol)
  (verify)

褪黑素,或称褪黑激素松果体素美拉托宁,化学名为N-乙酰基-5-甲氧基色胺[1],是一种生命必需的小分子吲哚胺类物质[2],在动物植物真菌细菌中皆有发现。在动物体内,褪黑素是一种调节生物钟的激素[3];而其作用在其他生物体内可能不同,同样,褪黑素在动物体内的合成过程也不同于其他物种[4]

褪黑素可以用来帮助入睡和治疗睡眠障碍。其可以口服也可以通过喷雾或透皮贴剂的方式给药。褪黑素在美国加拿大非处方药,在中国大陆保健食品(如脑白金的主要成分),在台湾是未经政府许可的药物[5] [6]。在其他的一些国家,褪黑素可能需要凭处方使用,或者不可用。

发现

20世纪初,人们发现有一种物质可以使蛙皮肤中的黑色素褪变成白色[2]。1958年从牛的松果体内分离提取出了该物质,并命名为褪黑素[7]

开始人们普遍认为褪黑素仅在动物体内存在。随着研究的深入,才发现褪黑素在细菌微生物真菌藻类以及植物中也存在[8]

褪黑素的产生

在高等动物中,褪黑素是由松果体中的松果体细胞色氨酸在4种的作用下经4步连续酶促反应转化而成[9]松果体产生的褪黑素是内分泌激素,会进入血液视网膜胃肠道则产生旁泌性激素下丘脑视交叉上核英语Suprachiasmatic nucleus会由视网膜接收每日光暗的规律,从而影响褪黑素的制造。

植物体内的褪黑素也是由色氨酸经过4步连续酶促反应转化而成, 但至少需要6种酶的参与[10]

在人体内,5-羟色胺(又称为血清素)在N-乙酰基转移酶催化下与乙酰辅酶A反应转化为N-乙酰-5-羟色胺,然后N-乙酰-5-羟色胺再在乙酰血清素O-甲基转移酶英语Acetylserotonin O-methyltransferase催化下被S-腺苷甲硫氨酸甲基化为褪黑素。

有些植物,例如稻米,也会制造褪黑素,哺乳类动物进食含有褪黑素的食物后,褪黑素会被吸收,溶入体内的褪黑素[11][12]

功效

在动物中,褪黑激素参与同步昼夜节律,包括睡眠 - 觉醒时间、血压调节和季节性繁殖。它的大部分作用是激活褪黑激素受体,而另一部分则是它作为抗氧化剂的作用。在植物中,它具有抵抗氧化应激的作用[2],还可促进种子萌发、调节植物的碳氮代谢、果实发育以及改善果实品质和产量[13]。褪黑激素也存在于各种食物中。但中央神经系统才是控制内分泌系统旁泌性系统的主要组织(曾经被人误认为褪黑素)[14][15]

制造机制

在正常情况下,由视网膜感知环境中的蓝光亮度,给出的光暗信号传递给松果体,令其在黑暗的情况下制造褪黑素,因此褪黑素亦称“黑暗荷尔蒙”。褪黑素的分泌于晚间中段时间最多,然后在晚间后段时间较少、再随时间逐渐减少至天明。在古代,在温带生活的人于冬季会有十到八小时生活在黑暗当中,而篝火和白炽灯的光中蓝光的成分很少;反之,现代人广泛使用日光灯,身处黑暗的时间减至八小时以下。即使是微弱的灯光下褪黑素的产生都会受到一定程度的影响,在强光下的影响就更大。缺乏褪黑素被认为很可能是夜班工作者得癌病的成因[16],而现代于晚间亮灯的习惯亦被认为是发达国家越来越多人得癌症的原因之一[17]

参见

参考文献

  1. ^ Melatonin. Sleepdex. [17 August 2011]. (原始内容存档于2015-09-24). 
  2. ^ 2.0 2.1 2.2 Liu, Deshuai; Yao, Lei; Xu, Weirong; Feng, Mei; Yao, Wenkong. Research Progress of Melatonin in Plant Stress Resistance. Chinese Bulletin of Botany. 2022-01-01, 57 (1): 111. doi:10.11983/CBB21146. 
  3. ^ Hardeland, Rüdiger; Pandi-Perumal, S.R.; Cardinali, Daniel P. Melatonin. The International Journal of Biochemistry & Cell Biology. 2006, 38 (3): 313–316. PMID 16219483. doi:10.1016/j.biocel.2005.08.020. 
  4. ^ Lewis, Alan. Melatonin and the Biological Clock. McGraw-Hill. 1999: 7. ISBN 0879837349 (英语). 
  5. ^ 国内市尚未开放…褪黑激素是禁药 偷卖将遭重罚 - 生活 - 自由时报电子报页面存档备份,存于互联网档案馆),2016-04-25
  6. ^ 存档副本. [2022-02-22]. (原始内容存档于2022-02-22). 
  7. ^ Lerner, Aaron B.; Case, James D.; Takahashi, Yoshiyata; Lee, Teh H.; Mori, Wataru. ISOLATION OF MELATONIN, THE PINEAL GLAND FACTOR THAT LIGHTENS MELANOCYTES 1. Journal of the American Chemical Society. 1958-05, 80 (10): 2587–2587. doi:10.1021/ja01543a060. 
  8. ^ Tan, Dun-Xian; Manchester, Lucien C.; Hardeland, Rüdiger; Lopez-Burillo, Silvia; Mayo, Juan C.; Sainz, Rosa M.; Reiter, Russel J. Melatonin: a hormone, a tissue factor, an autocoid, a paracoid, and an antioxidant vitamin: Melatonin: a multi-functional molecule. Journal of Pineal Research. 2003-01, 34 (1): 75–78. doi:10.1034/j.1600-079X.2003.02111.x. 
  9. ^ Fernández-Mar, M.I.; Mateos, R.; García-Parrilla, M.C.; Puertas, B.; Cantos-Villar, E. Bioactive compounds in wine: Resveratrol, hydroxytyrosol and melatonin: A review. Food Chemistry. 2012-02, 130 (4): 797–813. doi:10.1016/j.foodchem.2011.08.023. 
  10. ^ Back, Kyoungwhan; Tan, Dun-Xian; Reiter, Russel J. Melatonin biosynthesis in plants: multiple pathways catalyze tryptophan to melatonin in the cytoplasm or chloroplasts. Journal of Pineal Research. 2016-11, 61 (4): 426–437. doi:10.1111/jpi.12364. 
  11. ^ Hattori A, Migitaka H, Iigo M, Itoh M, Yamamoto K, Ohtani-Kaneko R, Hara M, Suzuki T, Reiter R. Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates.. Biochem Mol Biol Int. 1995, 35 (3): 627–34. PMID 7773197. 
  12. ^ Uz T, Arslan A, Kurtuncu M, Imbesi M, Akhisaroglu M, Dwivedi Y, Pandey G, Manev H. The regional and cellular expression profile of the melatonin receptor MT1 in the central dopaminergic system.. Brain Res Mol Brain Res. 2005, 136 (1-2): 45–53. PMID 15893586. 
  13. ^ Erdal, Serkan. Melatonin promotes plant growth by maintaining integration and coordination between carbon and nitrogen metabolisms. Plant Cell Reports. 2019-08, 38 (8): 1001–1012. doi:10.1007/s00299-019-02423-z. 
  14. ^ Richardson G. The human circadian system in normal and disordered sleep.. J Clin Psychiatry. 2005,. 66 Suppl 9: 3–9; quiz 42–3. PMID 16336035. 
  15. ^ Perreau-Lenz S, Pévet P, Buijs R, Kalsbeek A. The biological clock: the bodyguard of temporal homeostasis.. Chronobiol Int. 2004, 21 (1): 1–25. PMID 15129821. 
  16. ^ Schernhammer E, Rosner B, Willett W, Laden F, Colditz G, Hankinson S. Epidemiology of urinary melatonin in women and its relation to other hormones and night work.. Cancer Epidemiol Biomarkers Prev. 2004, 13 (62): 936–43. PMID 15184249. 
  17. ^ Pauley S. Lighting for the human circadian clock: recent research indicates that lighting has become a public health issue.. Med Hypotheses. 2004, 63 (4): 588–96. PMID 15325001. 

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褪黑素
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