Sibiricine

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Sibiricine
Names
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
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(26-8-25-14)7-12(10)20(21)18(22)11-2-3-13-17(27-9-24-13)16(11)19(20)23/h2-3,6-7,19,23H,4-5,8-9H2,1H3/t19-,20-/m0/s1
    Key: BQZZTMXCHPNTCL-PMACEKPBSA-N
  • O=C6c2c(c1OCOc1cc2)[C@H](O)[C@@]65N(C)CCc4cc3OCOc3cc45
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).

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

  1. ^ Southon, Ian W.; Buckingham, John (15 January 1989). Dictionary of Alkaloids, Second Edition with CD-ROM. CRC Press. p. 971. ISBN 978-0-412-24910-5.
  2. ^ "KNApSAcK Metabolite Information - C00029012". www.knapsackfamily.com.
  3. ^ a b c 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.
  4. ^ 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. Bibcode:2016NatSR...632101W. doi:10.1038/srep32101. PMC 5004179. PMID 27572696.
  5. ^ a b 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.
  6. ^ CID 632652 from PubChem
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