From Wikipedia, the free encyclopedia
Sibiricine
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Names
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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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Identifiers
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ChEMBL
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ChemSpider
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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
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O=C6c2c(c1OCOc1cc2)[C@H](O)[C@@]65N(C)CCc4cc3OCOc3cc45
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Properties
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C20H17NO6
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Molar mass
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367.357 g·mol−1
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
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
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^ 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.
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^
"KNApSAcK Metabolite Information - C00029012". www.knapsackfamily.com.
- ^
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.
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^ 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.
- ^
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.
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^
CID 632652 from
PubChem