Difference between revisions of "Kaurane"
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==References== | ==References== | ||
{{reflist}} | {{reflist}} | ||
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| + | ==Further reading== | ||
| + | *{{citation | author = Jeong-Hyung Lee, Tae Hyeon Koo, Bang Yeon Hwang, and Jung Joon Lee |Kaurane Diterpene, Kamebakaurin, Inhibits NF-kappa B by Directly Targeting the DNA-binding Activity of p50 and Blocks the Expression of Antiapoptotic NF-kappa B Target Genes | journal = J. Biol. Chem. | volume = 277 | issue = 21 | pages = 18411–20 | doi = 10.1074/jbc.M201368200}}. | ||
| + | *{{citation | author = Nagashima F.; Tanaka H.; Takaoka S.; Asakawa Y. | title = ENT-kaurane-type diterpenoids from the liverwort ''Jungermannia exsertifolia'' ssp. cordifolia | journal = Phytochemistry | volume = 41 | issue = 4 | year = 1996 | pages = 1129–41 | doi = 10.1016/0031-9422(95)00755-5}}. | ||
| + | *{{citation | author = Ronan Batista; Pablo A. García; Maria A. Castro; José M. Miguel del Corral; Arturo San Feliciano; Alaíde B. de Oliveira | title = New oxidized ''ent''-kaurane and ''ent''-norkaurane derivatives from kaurenoic acid | journal = J. Braz. Chem. Soc. | volume = 18 | issue = 3 | year = 2007 | doi = 10.1590/S0103-50532007000300020 | url = http://www.scielo.br/scielo.php?pid=S0103-50532007000300020&script=sci_arttext}}. | ||
[[Category:Diterpenes]] | [[Category:Diterpenes]] | ||
Revision as of 08:36, 5 September 2009
Kaurane is a parent hydride used in the IUPAC nomenclature of natural products and also, distinctly, in CAS nomenclature. It is a diterpene with a rigid four-ring structure and six chiral centres.
The stereochemistry of the six chiral centres is defined by convention: however, IUPAC and CAS use different conventional stereochemistry, which also leads to a slight difference in numbering between the two systems. IUPAC conventional kaurane has (5S,8S,9S,10S,13S,15R)-stereochemistry, and is drawn with the five-membered ring receding into the plane of the image.[1] CAS conventional kaurane has (5S,8R,9S,10S,13R,15R)-stereochemistry, and is drawn with the five-membered ring protruding from the plane of the image.[2] Carbon-19 (one of the two methyl groups attached to carbon-4) is on the same side of the molecule as the five-membered ring in both systems: hence it is receding into the plane of the image in IUPAC nomenclature and protruding from the plane of the image in CAS nomenclature.
References
- ↑ Revised Section F: Natural Products and Related Compounds (IUPAC Recommendations 1999). Pure Appl. Chem., 71 (4), 587–643. DOI: 10.1351/pac199971040587.
- ↑ 57817-89-7 – Kaur-16-en-18-oic acid, 13-[(2-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-, β-D-glucopyranosyl ester, (4α)-. In Common Chemistry; Chemical Abstracts Service, <http://www.commonchemistry.org/ChemicalDetail.aspx?ref=57817-89-7>. (accessed 5 September 2009).
Further reading
- Jeong-Hyung Lee, Tae Hyeon Koo, Bang Yeon Hwang, and Jung Joon Lee J. Biol. Chem., 277 (21), 18411–20. DOI: 10.1074/jbc.M201368200.
- Nagashima F.; Tanaka H.; Takaoka S.; Asakawa Y. ENT-kaurane-type diterpenoids from the liverwort Jungermannia exsertifolia ssp. cordifolia. Phytochemistry 1996, 41 (4), 1129–41. DOI: 10.1016/0031-9422(95)00755-5.
- Ronan Batista; Pablo A. García; Maria A. Castro; José M. Miguel del Corral; Arturo San Feliciano; Alaíde B. de Oliveira New oxidized ent-kaurane and ent-norkaurane derivatives from kaurenoic acid. J. Braz. Chem. Soc. 2007, 18 (3). doi:10.1590/S0103-50532007000300020, <http://www.scielo.br/scielo.php?pid=S0103-50532007000300020&script=sci_arttext>.
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