Cheilanthifoline

Cheilanthifoline
Names
IUPAC name
2-Methoxy-2′H-[1,3]dioxolo[4′,5′:9,10]berbin-3-ol
Systematic IUPAC name
(6aS)-9-Methoxy-6,6a,11,14-tetrahydro-2H,12H-[1,3]dioxolo[4,5-h]isoquinolino[2,1-b]isoquinolin-8-ol
Other names
(S)-Cheilanthifoline
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C19H19NO4/c1-22-18-7-12-4-5-20-9-14-11(2-3-17-19(14)24-10-23-17)6-15(20)13(12)8-16(18)21/h2-3,7-8,15,21H,4-6,9-10H2,1H3/t15-/m0/s1 checkY
    Key: FVXCQULKSPVRPK-HNNXBMFYSA-N checkY
  • COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C5=C(C=C4)OCO5)O
Properties
C19H19NO4
Molar mass 325.364 g·mol−1
Melting point 184 °C (363 °F; 457 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(S)-Cheilanthifoline is a benzylisoquinoline alkaloid (BIA) which has been isolated from Corydalis cheilanthifolia and Argemone mexicana. It is derived from (S)-reticuline, a pivotal intermediate in the biosynthesis of numerous BIAs. (S)-cheilanthifoline is the immediate precursor of the BIA (S)-stylopine ((S)-stylopine synthase/CYP719A20), which is the precursor for the alkaloids protopine and sanguinarine.

Biosynthesis

Cheilanthifoline is produced from the benzylisoquinoline alkaloid, scoulerine, by the enzyme (S)-cheilanthifoline synthase.

2D representation of the chemical structure of scoulerine .
scoulerine
+ NADPH
 
 
O2
2 H2O
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
2D representation of the chemical structure of cheilanthifoline .
cheilanthifoline
+ NADP+
 

Scoulerine is one of the products derived from (S)-reticuline.

Metabolism

Cheilanthifoline is the precursor to other alkaloids. For example, (S)-stylopine (also known as tetrahydrocoptisine) is produced when the enzyme (S)-stylopine synthase forms a second methylenedioxy ring:

2D representation of the chemical structure of cheilanthifoline .
cheilanthifoline
+ NADPH
 
 
O2
2 H2O
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
2D representation of the chemical structure of Q27102969.
(S)-stylopine
+ NADP+
 

References

  1. 1 2 3 Mascavage LM, Jasmin S, Sonnet PE, Wilson M, Dalton DR (2010). "Alkaloids". Ullmann's Encyclopedia of Industrial Chemistry. pp. 56–57. doi:10.1002/14356007.a01_353.pub2. ISBN 978-3-527-30385-4.
  2. ↑ Wangchuk P, Keller PA, Pyne SG, Willis AC, Kamchonwongpaisan S (August 2012). "Antimalarial alkaloids from a Bhutanese traditional medicinal plant Corydalis dubia". Journal of Ethnopharmacology. 143 (1): 310–313. doi:10.1016/j.jep.2012.06.037. PMID 22796506.
  3. ↑ Hagel JM, Morris JS, Lee EJ, Desgagné-Penix I, Bross CD, Chang L, et al. (September 2015). "Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants". BMC Plant Biology. 15 (1) 227. Bibcode:2015BMCPB..15..227H. doi:10.1186/s12870-015-0596-0. PMC 4575454. PMID 26384972.
  4. 1 2 3 Tian Y, Kong L, Li Q, Wang Y, Wang Y, An Z, et al. (November 2024). "Structural diversity, evolutionary origin, and metabolic engineering of plant specialized benzylisoquinoline alkaloids". Natural Product Reports. 41 (11): 1787–1810. doi:10.1039/D4NP00029C. PMID 39360417.
  5. 1 2 Bauer W, Zenk MH (1991). "Two methylenedioxy bridge-forming cytochrome P-450 dependent enzymes are involved in (S)-stylopine biosynthesis". Phytochemistry. 30 (9): 2953–2961. Bibcode:1991PChem..30.2953B. doi:10.1016/S0031-9422(00)98230-X.