Cheilanthifoline
| Names | |
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| IUPAC name
2-Methoxy-2′H-[1,3]dioxolo[4′,5′:9,10]berbin-3-ol
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| 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
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| 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).
Infobox references
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(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]
Biosynthesis
Cheilanthifoline is produced from the benzylisoquinoline alkaloid, scoulerine, by the enzyme (S)-cheilanthifoline synthase.[4][5]
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]
References
- ^ a b c 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.
- ^ 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.
- ^ 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.
- ^ a b c 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.
- ^ 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.
- ^ 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.
- ^ 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.