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Corydaline

Corydaline
Names
IUPAC name
2,3,9,10-Tetramethoxy-13α-methyl-13aβ-berbine
Systematic 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
KEGG
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).

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]

References

[edit]
  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. 25 (15). Taylor and Francis: 1418–1422. doi:10.1080/14786410802496911. ISSN 1478-6419. PMID 20234973. S2CID 23465603.
  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. PMID 17574358.
  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. PMID 11809332.
  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. PMID 20522959.
  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. PMID 27558975. S2CID 20578877.