Corydaline

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Corydaline
Corydaline.svg
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
PubChem CID
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]

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<span class="mw-page-title-main">Bulbocapnine</span> Chemical compound

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Jatrorrhizine is a protoberberine alkaloid found in some plant species, such as Enantia chlorantha (Annonaceae). Synonyms that may be encountered include jateorrhizine, neprotin, jatrochizine, jatrorhizine, and yatrorizine.

<span class="mw-page-title-main">Palmatine</span> Chemical compound

Palmatine is a protoberberine alkaloid found in several plants including Phellodendron amurense, Coptis Chinensis and Corydalis yanhusuo, Tinospora cordifolia, Tinospora sagittata, Phellodendron amurense, Stephania yunnanensis.

<span class="mw-page-title-main">Matrine</span> Chemical compound

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Corydalis yanhusuo is a plant species in the genus Corydalis. The Chinese name for Corydalis yanhusuo is yan hu suo. The Japanese common name is engosaku (エンゴサク) and the Korean common name is hyeonhosaek (현호색). English common names include yanhusuo, corydalis, and Asian corydalis. The tuber of this plant, frequently mislabeled as the root, is an important therapeutic agent in traditional Chinese medicine. It is native to high-altitude grasslands across China including in the provinces of Anhui, Henan, Hubei, Hunan, Jiangsu, and Zhejiang, but is more widely cultivated.

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<i>Corydalis mucronifera</i> Species of flowering plant

Corydalis mucronifera is a plant which does not have a common name as it is quite rare in nature. This plant has also previously been recorded as Corydalis boweri. Being as rare as it is, it has only been found in two regions: China and Tibet. The range where the plant can be found is small as it is only found near rocky beaches or high mountain ranges at altitudes between 4200 and 5300 meters. Corydalis mucronifera is small in size and displays a variety of colors: purple, yellow, white, and cream. The plant has similar structures to other plants found in Europe and North America as it displays a racemose corymb. Due to its herbal properties, it is currently being studied in medicine for its inhibitory properties; these properties are focused in studies regarding neurodegenerative disorders.

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. 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.