Corydaline

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Corydaline
Corydaline.svg
Names
Preferred IUPAC name
(13S,13aR)-2,3,9,10-Tetramethoxy-13-methyl-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C22H27NO4/c1-13-15-6-7-18(24-2)22(27-5)17(15)12-23-9-8-14-10-19(25-3)20(26-4)11-16(14)21(13)23/h6-7,10-11,13,21H,8-9,12H2,1-5H3/t13-,21+/m0/s1
    Key: VRSRXLJTYQVOHC-YEJXKQKISA-N
  • InChI=1/C22H27NO4/c1-13-15-6-7-18(24-2)22(27-5)17(15)12-23-9-8-14-10-19(25-3)20(26-4)11-16(14)21(13)23/h6-7,10-11,13,21H,8-9,12H2,1-5H3/t13-,21+/m0/s1
    Key: VRSRXLJTYQVOHC-YEJXKQKIBZ
  • C[C@@H]1[C@@H]2C3=CC(=C(C=C3CCN2CC4=C1C=CC(=C4OC)OC)OC)OC
  • C[C@@H]1[C@@H]2C3=CC(=C(C=C3CCN2CC4=C1C=CC(=C4OC)OC)OC)OC
Properties
C22H27NO4
Molar mass 369.461 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Corydaline is an acetylcholinesterase inhibitor isolated from Corydalis yanhusuo.[1]

Corydaline is a pharmacologically active isoquinoline alkaloid isolated from Corydalis tubers. It also has diverse biological activities. It exhibits the antiacetylcholinesterase(AChE; IC50 = 15 μM),[2] antiallergic, antinociceptive, and gastric emptying activities.

Corydaline exhibited strong nematocidal activity, showed little cytotoxicity and represents a potential treatment for Strongyloidiasis. Corydaline is nematocidal against S. ratti and S. venezuelensis third instar larvae with 50% paralysis (PC50) values of 18 and 30 μM, respectively.[3]

Corydaline exhibits gastrointestinal modulatory, antinociceptive, anti-allergic, and anti-parasitic activities. Corydaline (1 and 3 mg/kg) increases gastric emptying in rat models of apomorphine- and laparotomy-induced delayed gastric emptying.[4] Corydaline is currently in clinical trials as a potential treatment for functional dyspepsia.

In animal models, corydaline increases gastric emptying and small intestine transit speed and induces gastric relaxation.

In other animal models, corydaline inhibits chemically-induced pain. Additionally, this compound may inhibit mast cell-dependent smooth muscle contraction of the aorta.

It inhibits thrombin-induced platelet aggregation in vitro (IC50 = 54.16 μg/ml).[5]

WARNING This product is not for human or veterinary use.

References[]

  1. ^ Xiao, Hai-Tao; Peng, Jiao; Liang, Yan; Yang, Jie; Bai, Xue; Hao, Xiao-Yan; Yang, Fu-Mei; Sun, Qian-Yun (September 2011). "Acetylcholinesterase inhibitors from Corydalis yanhusuo". Natural Product Research. Taylor and Francis. 25 (15): 1418–1422. doi:10.1080/14786410802496911. ISSN 1478-6419. PMID 20234973.
  2. ^ Adsersen, Anne; Kjølbye, Anne; Dall, Ole; Jäger, Anna K. (August 2007). "Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Corydalis cava Schweigg. & Kort". Journal of Ethnopharmacology. 113 (1): 179–182. doi:10.1016/j.jep.2007.05.006.
  3. ^ Satou, Tadaaki; Koga, Masataka; Matsuhashi, Rinako; Koike, Kazuo; Tada, Isao; Nikaido, Tamotsu (March 2002). "Assay of nematocidal activity of isoquinoline alkaloids using third-stage larvae of Strongyloides ratti and S. venezuelensis". Veterinary Parasitology. 104 (2): 131–138. doi:10.1016/S0304-4017(01)00619-7.
  4. ^ Lee, Tae Ho; Son, Miwon; Kim, Sun Yeou (2010). "Effects of Corydaline from Corydalis Tuber on Gastric Motor Function in an Animal Model". Biological and Pharmaceutical Bulletin. 33 (6): 958–962. doi:10.1248/bpb.33.958. ISSN 0918-6158.
  5. ^ Zhang, Qian; Chen, Cen; Wang, Feng-Qin; Li, Chun-Hong; Zhang, Qi-Hui; Hu, Yuan-Jia; Xia, Zhi-Ning; Yang, Feng-Qing (2016-12-01). "Simultaneous screening and analysis of antiplatelet aggregation active alkaloids from Rhizoma Corydalis". Pharmaceutical Biology. 54 (12): 3113–3120. doi:10.1080/13880209.2016.1211714. ISSN 1388-0209.
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