Chemistry:Sibiricine
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| IUPAC name
8'-Hydroxy-6-methylspiro[7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-5,7'-8H-cyclopenta[g][1,3]benzodioxole]-6'-one
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C20H17NO6 | |
| Molar mass | 367.357 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Sibiricine is a bioactive isoquinoline alkaloid isolated from Corydalis crispa (Fumariaceae), which is a Bhutanese medicinal plant from the Himalayas.[3][4]
Using high resolution mass spectrometry, the molecular formula of sibiricine is determined to be C20H17NO6.[5] The IUPAC name for sibiricine is 8'-hydroxy-6-methylspiro[7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-5,7'-8H-cyclopenta[g][1,3]benzodioxole]-6'-one.[6] The proton nuclear magnetic resonance (PMR) spectrum of sibiricine at 100 MHz shows that sibiricine is structurally related to ochrobirine and ochotensine.[3][5] With the exception of sibiricine, 8 other alkaloids are extracted by investigating Corydalis crispa. These isoquinoline alkaloids are protopine, 13-oxoprotopine, 13-oxocryptopine, stylopine, coreximine, rheagenine, ochrobirine, and bicuculline.[3]
References
- ↑ Southon, Ian W.; Buckingham, John (15 January 1989) (in en). Dictionary of Alkaloids, Second Edition with CD-ROM. CRC Press. p. 971. ISBN 978-0-412-24910-5. https://books.google.com/books?id=b5xrxX24fJAC.
- ↑ "KNApSAcK Metabolite Information - C00029012". http://www.knapsackfamily.com/knapsack_core/information.php?word=C00029012.
- ↑ 3.0 3.1 3.2 Wangchuk, P.; Keller, P. A.; Pyne, S. G.; Sastraruji, T.; Taweechotipatr, M.; Rattanajak, R.; Tonsomboon, A.; Kamchonwongpaisan, S. (2012). "Phytochemical and biological activity studies of the Bhutanese medicinal plant Corydalis crispa". Natural Product Communications 7 (5): 575–80. doi:10.1177/1934578X1200700507. PMID 22799079. https://ro.uow.edu.au/cgi/viewcontent.cgi?article=8102&context=scipapers.
- ↑ Wangchuk, Phurpa; Giacomin, Paul R.; Pearson, Mark S.; Smout, Michael J.; Loukas, Alex (2016). "Identification of lead chemotherapeutic agents from medicinal plants against blood flukes and whipworms". Scientific Reports 6: 32101. doi:10.1038/srep32101. PMID 27572696. Bibcode: 2016NatSR...632101W.
- ↑ 5.0 5.1 Manske, R. H. F.; Rodrigo, R.; MacLean, D. B.; Gracey, D. E. F.; Saunders, J. K. (1969). "Structure of sibiricine, an alkaloid of Corydalissibirica". Canadian Journal of Chemistry 47 (19): 3585–3588. doi:10.1139/v69-592.
- ↑ CID 632652 from PubChem
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