Chemistry:Cheilanthifoline
-(S)-Cheilanthifoline.svg)
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| 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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| ChemSpider | |
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PubChem CID
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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 | |
(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
- ↑ 1.0 1.1 1.2 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. https://ro.uow.edu.au/cgi/viewcontent.cgi?article=7675&context=scipapers.
- ↑ Hagel, Jillian; Morris, Jeremy S; Lee, Eun-Jeong; Desgagne-Penix, Isabel; Bross, Crystal D; Chang, Limei; Chen, Xue; Farrow, Scott C et al. (2015). "Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants". BMC Plant Biology 15 (1): 227. doi:10.1186/s12870-015-0596-0. PMID 26384972. PMC 4575454. Bibcode: 2015BMCPB..15..227H. http://openlib.tugraz.at/download.php?id=564f2fa60a35b&location=browse.
- ↑ 4.0 4.1 4.2 Tian, Ya; Kong, Lingzhe; Li, Qi; Wang, Yifan; Wang, Yongmiao; An, Zhoujie; Ma, Yuwei; Tian, Lixia et al. (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.
- ↑ "Two methylenedioxy bridge-forming cytochrome P-450 dependent enzymes are involved in (S)-stylopine biosynthesis". Phytochemistry 30 (9): 2953–2961. 1991. doi:10.1016/S0031-9422(00)98230-X. Bibcode: 1991PChem..30.2953B.
- ↑ Tian, Ya; Kong, Lingzhe; Li, Qi; Wang, Yifan; Wang, Yongmiao; An, Zhoujie; Ma, Yuwei; Tian, Lixia et al. (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.
- ↑ "Two methylenedioxy bridge-forming cytochrome P-450 dependent enzymes are involved in (S)-stylopine biosynthesis". Phytochemistry 30 (9): 2953–2961. 1991. doi:10.1016/S0031-9422(00)98230-X. Bibcode: 1991PChem..30.2953B.
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