Difference between revisions of "Kaurane"
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*{{citation | author = Fumihiro Nagashima, Hironao Tanaka, Shigeru Takaoka and Yoshinori Asakawa | 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 = Fumihiro Nagashima, Hironao Tanaka, Shigeru Takaoka and Yoshinori Asakawa | 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 | pages = 622–27 | doi = 10.1590/S0103-50532007000300020}}. | *{{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 | pages = 622–27 | doi = 10.1590/S0103-50532007000300020}}. | ||
| + | *{{citation | title = Three New Cytotoxic ''ent''-Kaurane Diterpenoids from ''Isodon weisiensis'' C. Y. Wu | author = Z.-J. Zhang, L. Ding | journal = Helv. Chim. Acta | volume = 88 | issue = 9 | year = 2005 | pages = 2502–7}}. | ||
| + | *{{citation | author = NAGASHIMA Fumihiro; KONDOH Masuo; UEMATSU Toshinari; NISHIYAMA Akiko; SAITO Sayaka; SATO Masao; ASAKAWA Yoshinori | title = Cytotoxic and apoptosis-inducing ''ent''-kaurane-type diterpenoids from the Japanese liverwort ''Jungermannia truncata'' nees | journal = Chem. Pharm. Bull. | year = 2002 | volume = 50 | issue = 6 | pages = 808–13}}. | ||
| + | *{{citation | title = 16α,19-Diacetoxy-''ent''-kaurane, a New Natural Diterpene from the Exudate of ''Ozothamnus scutellifolius'' (Asteraceae) | author = Fco. Javier Arriaga-Giner, Angel Rumbero and Eckhard Wollenweber | journal = Z. Naturforsch. | volume = 54c | pages = 602–4 | year = 1999}}. | ||
| + | *{{citation | title = Kaurane Diterpenoids from Three ''Sideritis'' Species | url = http://journals.tubitak.gov.tr/chem/issues/kim-05-29-1/kim-29-1-7-0402-1.pdf | author = Maurizio BRUNO, Franco PIOZZI Nelly Apostolides ARNOLD, K. H¨usn¨u Can BAS�ER3, Nurhayat TABANCA, Ne�se KIRIMER | journal = Turk. J. Chem. | volume = 29 | year = 2005 | pages = 61–64}}. | ||
| + | |||
| + | ==External links== | ||
| + | *[http://chemistry.about.com/od/factsstructures/ig/Chemical-Structures---K/Kaurane.-0xj.htm Kaurane Chemical Structure] (shows the IUPAC conventional structure) | ||
| + | *[http://www.find-health-articles.com/msh-diterpenes-kaurane.htm Diterpenes, Kaurane – Research News and Information] | ||
[[Category:Diterpenes]] | [[Category:Diterpenes]] | ||
Revision as of 09:51, 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 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. J. Biol. Chem., 277 (21), 18411–20. DOI: 10.1074/jbc.M201368200.
- Fumihiro Nagashima, Hironao Tanaka, Shigeru Takaoka and Yoshinori Asakawa 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), 622–27. DOI: 10.1590/S0103-50532007000300020.
- Z.-J. Zhang, L. Ding Three New Cytotoxic ent-Kaurane Diterpenoids from Isodon weisiensis C. Y. Wu. Helv. Chim. Acta 2005, 88 (9), 2502–7.
- NAGASHIMA Fumihiro; KONDOH Masuo; UEMATSU Toshinari; NISHIYAMA Akiko; SAITO Sayaka; SATO Masao; ASAKAWA Yoshinori Cytotoxic and apoptosis-inducing ent-kaurane-type diterpenoids from the Japanese liverwort Jungermannia truncata nees. Chem. Pharm. Bull. 2002, 50 (6), 808–13.
- Fco. Javier Arriaga-Giner, Angel Rumbero and Eckhard Wollenweber 16α,19-Diacetoxy-ent-kaurane, a New Natural Diterpene from the Exudate of Ozothamnus scutellifolius (Asteraceae). Z. Naturforsch. 1999, 54c, 602–4.
- Maurizio BRUNO, Franco PIOZZI Nelly Apostolides ARNOLD, K. H¨usn¨u Can BAS�ER3, Nurhayat TABANCA, Ne�se KIRIMER Kaurane Diterpenoids from Three Sideritis Species. Turk. J. Chem. 2005, 29, 61–64, <http://journals.tubitak.gov.tr/chem/issues/kim-05-29-1/kim-29-1-7-0402-1.pdf>.
External links
- Kaurane Chemical Structure (shows the IUPAC conventional structure)
- Diterpenes, Kaurane – Research News and Information
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