Cheilanthifoline

Last updated
Cheilanthifoline
(-)-(S)-Cheilanthifoline.svg
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
PubChem CID
  • 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 Yes check.svgY
    Key: FVXCQULKSPVRPK-HNNXBMFYSA-N Yes check.svgY
  • 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) [1]
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 . [1] [2] 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. [3] [4]

Contents

Biosynthesis

Cheilanthifoline is produced from the benzylisoquinoline alkaloid, scoulerine, by the enzyme (S)-cheilanthifoline synthase. [4] [5]

Scoulerine-S.png
scoulerine
+ NADPH
 
 
O2
2 H2O
Cheilanthifoline
 
 
 
(-)-(S)-Cheilanthifoline.svg
cheilanthifoline
+ NADP+
 

Scoulerine is one of the products derived from (S)-reticuline. [1]

Metabolism

Cheilanthifoline is the precursor to other alkaloids. [4] [6] For example, (S)-stylopine (also known as tetrahydrocoptisine) is produced when the enzyme (S)-stylopine synthase forms a second methylenedioxy ring: [7]

(-)-(S)-Cheilanthifoline.svg
cheilanthifoline
+ NADPH
 
 
O2
2 H2O
Cheilanthifoline
 
 
 
Stylopine.svg
(S)-stylopine
+ NADP+
 

References

  1. 1 2 3 Mascavage, Linda M.; Jasmin, Serge; Sonnet, Philip E.; Wilson, Michael; Dalton, David R. (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 (2012). "Antimalarial alkaloids from a Bhutanese traditional medicinal plant Corydalis dubia". Journal of Ethnopharmacology. 143 (1): 310–3. doi:10.1016/j.jep.2012.06.037. PMID   22796506.
  3. ↑ Hagel, Jillian; Morris, Jeremy S; Lee, Eun-Jeong; Desgagne-Penix, Isabel; Bross, Crystal D; Chang, Limei; Chen, Xue; Farrow, Scott C; Zhang, Te (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, Ya; Kong, Lingzhe; Li, Qi; Wang, Yifan; Wang, Yongmiao; An, Zhoujie; Ma, Yuwei; Tian, Lixia; Duan, Baozhong; Sun, Wei; Gao, Ranran; Chen, Shilin; Xu, Zhichao (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. ↑ 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.
  6. ↑ Tian, Ya; Kong, Lingzhe; Li, Qi; Wang, Yifan; Wang, Yongmiao; An, Zhoujie; Ma, Yuwei; Tian, Lixia; Duan, Baozhong; Sun, Wei; Gao, Ranran; Chen, Shilin; Xu, Zhichao (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.
  7. ↑ 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.
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