Kaurane
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.
- Bruno, Maurizio; Piozzi, Franco; Arnold, Nelly Apostolides; Başer, K. Hüsnü Can; Tabanca, Nurhayat; Kirimer, Neşe 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>.
- Zhao, Yong (Y); Pu, Jian-Xin (JX); Huang, Sheng-Xiong (SX); Ding, Li-Sheng (LS); Wu, Ying-Li (YL); Li, Xian (X); Yang, Li-Bin (LB); Xiao, Wei-Lie (WL); Chen, Guo-Qiang (GQ); Sun, Han-Dong (HD) ent-Kaurane diterpenoids from Isodon pharicus. J. Nat. Prod. 2009, 72 (6), 988–93. PMID 19425589.
- Kim, Ki Hyun (KH); Choi, Sang Un (SU); Lee, Kang Ro Diterpene glycosides from the seeds of Pharbitis nil. J. Nat. Prod. 2009, 72 (6), 1121–27. PMID 19435339.
- Jaitak, Vikas (V); Bikram Singh, Bandna (B); Kaul, V K An efficient microwave-assisted extraction process of stevioside and rebaudioside-A from Stevia rebaudiana (Bertoni). Phytochem. Anal. 2009, 20 (3), 240–45. PMID 19358287.
External links
- Kaurane Chemical Structure (shows the IUPAC conventional structure)
- Diterpenes, Kaurane – Research News and Information
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