Difference between revisions of "Kaurane"
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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 (5''S'',8''S'',9''S'',10''S'',13''S'',15''R'')-stereochemistry, and is drawn with the five-membered ring receding into the plane of the image.<ref name="IUPAC">{{IUPAC natural products 1999}}.</ref> CAS conventional kaurane has (5''S'',8''R'',9''S'',10''S'',13''R'',15''R'')-stereochemistry, and is drawn with the five-membered ring protruding from the plane of the image.<ref name="CAS">{{citation | contribution = 57817-89-7 – Kaur-16-en-18-oic acid, 13-[(2-''O''-β-<small>D</small>-glucopyranosyl-β-<small>D</small>-glucopyranosyl)oxy]-, β-<small>D</small>-glucopyranosyl ester, (4α)- | url = http://www.commonchemistry.org/ChemicalDetail.aspx?ref=57817-89-7 | title = Common Chemistry | publisher = Chemical Abstracts Service | accessdate = 2009-09-05}}.</ref> 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. | 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 (5''S'',8''S'',9''S'',10''S'',13''S'',15''R'')-stereochemistry, and is drawn with the five-membered ring receding into the plane of the image.<ref name="IUPAC">{{IUPAC natural products 1999}}.</ref> CAS conventional kaurane has (5''S'',8''R'',9''S'',10''S'',13''R'',15''R'')-stereochemistry, and is drawn with the five-membered ring protruding from the plane of the image.<ref name="CAS">{{citation | contribution = 57817-89-7 – Kaur-16-en-18-oic acid, 13-[(2-''O''-β-<small>D</small>-glucopyranosyl-β-<small>D</small>-glucopyranosyl)oxy]-, β-<small>D</small>-glucopyranosyl ester, (4α)- | url = http://www.commonchemistry.org/ChemicalDetail.aspx?ref=57817-89-7 | title = Common Chemistry | publisher = Chemical Abstracts Service | accessdate = 2009-09-05}}.</ref> 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. | ||
| − | The name ''ent''-kaurane is sometimes used to refer to the CAS conventional kaurane and so to distinguish it from the IUPAC stereochemistry. It is also possible to explicitly specify the stereochemistry at carbons 8 and 13, giving: | + | The name ''ent''-kaurane is sometimes used to refer to the CAS conventional kaurane,<ref>{{citation | first1 = Fumihiro | last1 = Nagashima | first2 = Hironao | last2 = Tanaka | first3 = Shigeru | last3 = Takaoka | first4 = Yoshinori | last4 = 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 | first1 = Francisco Javier | last1 = Arriaga-Giner | first2 = Angel | last2 = Rumbero | first3 = Eckhard | last3 = Wollenweber | title = 16α,19-Diacetoxy-''ent''-kaurane, a New Natural Diterpene from the Exudate of ''Ozothamnus scutellifolius'' (Asteraceae) | journal = Z. Naturforsch. C | volume = 54 | pages = 602–4 | year = 1999}}. {{citation | title = Three New Cytotoxic ''ent''-Kaurane Diterpenoids from ''Isodon weisiensis'' C. Y. Wu | first1 = Lan | last1 = Ding | first2 = Zhang-Jing | last2 = Zhang | first3 = Guo-An | last3 = Liu | first4 = Dong-Juan | last4 = Yang | first5 = Guo-Cong | last5 = Guo | first6 = Han | last6 = Wang | first7 = Kun | last7 = Sun | journal = Helv. Chim. Acta | volume = 88 | issue = 9 | year = 2005 | pages = 2502–7 | doi = 10.1002/hlca.200590185}}. {{citation | first1 = Ronan | last1 = Batista | first2 = Pablo A. | last2 = García | first3 = Maria A. | last3 = Castro | first4 = José M. Miguel | last4 = del Corral | first5 = Arturo | last5 = San Feliciano | first6 = Alaíde B. | last6 = 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 | last1 = Zhao | first1 = Yong | last2 = Pu | first2 = Jian-Xin | last3 = Huang | first3 = Sheng-Xiong | last4 = Ding | first4 = Li-Sheng | last5 = Wu | first5 = Ying-Li | last6 = Li | first6 = Xian | last7 = Yang | first7 = Li-Bin | last8 = Xiao | first8 = Wei-Lie | last9 = Chen | first9 = Guo-Qiang | last10 = Sun | first10 = Han-Dong | title = ''ent''-Kaurane diterpenoids from ''Isodon pharicus'' | journal = J. Nat. Prod. | year = 2009 | volume = 72 | issue = 6 | pages = 988–93 | doi = 10.1021/np9000366 | pmid = 19425589}}.</ref> and so to distinguish it from the IUPAC stereochemistry, in particular by the [[International Union of Biochemistry and Molecular Biology]] (IUBMB).<ref>{{citation | url = http://www.expasy.org/cgi-bin/nicezyme.pl?1.14.13.78 | contribution = EC 1.14.13.78 – ''ent''-kaurene oxidase | title = ExPASy Proteomics Server | publisher = Swiss Institute of Bioinformatics | accessdate = 2009-09-05}}. {{citation | url = http://www.expasy.org/cgi-bin/nicezyme.pl?1.14.13.79 | contribution = EC 1.14.13.79 – ''ent''-kaureneic acid oxidase | title = ExPASy Proteomics Server | publisher = Swiss Institute of Bioinformatics | accessdate = 2009-09-05}}.</ref> It is also possible to explicitly specify the stereochemistry at carbons 8 and 13, giving: |
*(8''S'',13''S'')-kaurane (IUPAC conventional) | *(8''S'',13''S'')-kaurane (IUPAC conventional) | ||
*(8''R'',13''R'')-kaurane (CAS conventional) | *(8''R'',13''R'')-kaurane (CAS conventional) | ||
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==Further reading== | ==Further reading== | ||
*{{citation | first1 = Jeong-Hyung | last1 = Lee | first2 = Tae Hyeon | last2 = Koo | first3 = Bang Yeon | last3 = Hwang | first4 = Jung Joon | last4 = Lee | title = 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 | first1 = Jeong-Hyung | last1 = Lee | first2 = Tae Hyeon | last2 = Koo | first3 = Bang Yeon | last3 = Hwang | first4 = Jung Joon | last4 = Lee | title = 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}}. | ||
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*{{citation | last1 = Nagashima | first1 = Fumihiro | last2 = Kondoh | first2 = Masuo | last3 = Uematsu | first3 = Toshinari | last4 = Nishiyama | first4 = Akiko | last5 = Saito | first5 = Sayaka | last6 = Sato | first6 = Masao | last7 = Asakawa | first7 = 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 | doi = 10.1248/cpb.50.808}}. | *{{citation | last1 = Nagashima | first1 = Fumihiro | last2 = Kondoh | first2 = Masuo | last3 = Uematsu | first3 = Toshinari | last4 = Nishiyama | first4 = Akiko | last5 = Saito | first5 = Sayaka | last6 = Sato | first6 = Masao | last7 = Asakawa | first7 = 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 | doi = 10.1248/cpb.50.808}}. | ||
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*{{citation | first1 = Maurizio | last1 = Bruno | first2 = Franco | last2 = Piozzi | first3 = Nelly Apostolides | last3 = Arnold | first4 = K. Hüsnü Can | last4 = Başer | first5 = Nurhayat | last5 = Tabanca | first6 = Neşe | last6 = Kirimer | 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 | journal = Turk. J. Chem. | volume = 29 | issue = 1 | year = 2005 | pages = 61–64}}. | *{{citation | first1 = Maurizio | last1 = Bruno | first2 = Franco | last2 = Piozzi | first3 = Nelly Apostolides | last3 = Arnold | first4 = K. Hüsnü Can | last4 = Başer | first5 = Nurhayat | last5 = Tabanca | first6 = Neşe | last6 = Kirimer | 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 | journal = Turk. J. Chem. | volume = 29 | issue = 1 | year = 2005 | pages = 61–64}}. | ||
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*{{citation | last1 = Kim | first1 = Ki Hyun | last2 = Choi | first2 = Sang Un | last3 = Lee | first3 = Kang Ro | title = Diterpene glycosides from the seeds of ''Pharbitis nil'' | journal = J. Nat. Prod. | year = 2009 | volume = 72 | issue = 6 | pages = 1121–27 | doi = 10.1021/np900101t | pmid = 19435339}}. | *{{citation | last1 = Kim | first1 = Ki Hyun | last2 = Choi | first2 = Sang Un | last3 = Lee | first3 = Kang Ro | title = Diterpene glycosides from the seeds of ''Pharbitis nil'' | journal = J. Nat. Prod. | year = 2009 | volume = 72 | issue = 6 | pages = 1121–27 | doi = 10.1021/np900101t | pmid = 19435339}}. | ||
*{{citation | title = An efficient microwave-assisted extraction process of stevioside and rebaudioside-A from ''Stevia rebaudiana'' (Bertoni) | last1 = Jaitak | first1 = Vikas | last2 = Bikram Singh | first2 = Bandna | last3 = Kaul | first3 = V. K. | journal = Phytochem. Anal. | year = 2009 | volume = 20 | issue = 3 | pages = 240–45 | doi = 10.1002/pca.1120 | pmid = 19358287}}. | *{{citation | title = An efficient microwave-assisted extraction process of stevioside and rebaudioside-A from ''Stevia rebaudiana'' (Bertoni) | last1 = Jaitak | first1 = Vikas | last2 = Bikram Singh | first2 = Bandna | last3 = Kaul | first3 = V. K. | journal = Phytochem. Anal. | year = 2009 | volume = 20 | issue = 3 | pages = 240–45 | doi = 10.1002/pca.1120 | pmid = 19358287}}. | ||
Revision as of 11:03, 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.
The name ent-kaurane is sometimes used to refer to the CAS conventional kaurane,[3] and so to distinguish it from the IUPAC stereochemistry, in particular by the International Union of Biochemistry and Molecular Biology (IUBMB).[4] It is also possible to explicitly specify the stereochemistry at carbons 8 and 13, giving:
- (8S,13S)-kaurane (IUPAC conventional)
- (8R,13R)-kaurane (CAS conventional)
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).
- ↑ Nagashima, Fumihiro; Tanaka, Hironao; Takaoka, Shigeru; Asakawa, Yoshinori 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. Arriaga-Giner, Francisco Javier; Rumbero, Angel; Wollenweber, Eckhard 16α,19-Diacetoxy-ent-kaurane, a New Natural Diterpene from the Exudate of Ozothamnus scutellifolius (Asteraceae). Z. Naturforsch. C 1999, 54, 602–4. Ding, Lan; Zhang, Zhang-Jing; Liu, Guo-An; Yang, Dong-Juan; Guo, Guo-Cong; Wang, Han; Sun, Kun Three New Cytotoxic ent-Kaurane Diterpenoids from Isodon weisiensis C. Y. Wu. Helv. Chim. Acta 2005, 88 (9), 2502–7. DOI: 10.1002/hlca.200590185. Batista, Ronan; García, Pablo A.; Castro, Maria A.; del Corral, José M. Miguel; San Feliciano, Arturo; de Oliveira, Alaíde B. 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. Zhao, Yong; Pu, Jian-Xin; Huang, Sheng-Xiong; Ding, Li-Sheng; Wu, Ying-Li; Li, Xian; Yang, Li-Bin; Xiao, Wei-Lie, et al. ent-Kaurane diterpenoids from Isodon pharicus. J. Nat. Prod. 2009, 72 (6), 988–93. PMID 19425589. DOI: 10.1021/np9000366.
- ↑ EC 1.14.13.78 – ent-kaurene oxidase. In ExPASy Proteomics Server; Swiss Institute of Bioinformatics, <http://www.expasy.org/cgi-bin/nicezyme.pl?1.14.13.78>. (accessed 5 September 2009). EC 1.14.13.79 – ent-kaureneic acid oxidase. In ExPASy Proteomics Server; Swiss Institute of Bioinformatics, <http://www.expasy.org/cgi-bin/nicezyme.pl?1.14.13.79>. (accessed 5 September 2009).
Further reading
- Lee, Jeong-Hyung; Koo, Tae Hyeon; Hwang, Bang Yeon; Lee, Jung Joon 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.
- 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. DOI: 10.1248/cpb.50.808.
- 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 (1), 61–64, <http://journals.tubitak.gov.tr/chem/issues/kim-05-29-1/kim-29-1-7-0402-1.pdf>.
- Kim, Ki Hyun; Choi, Sang Un; Lee, Kang Ro Diterpene glycosides from the seeds of Pharbitis nil. J. Nat. Prod. 2009, 72 (6), 1121–27. PMID 19435339. DOI: 10.1021/np900101t.
- Jaitak, Vikas; Bikram Singh, Bandna; 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. DOI: 10.1002/pca.1120.
External links
- Kaurane Chemical Structure (shows the IUPAC conventional structure)
- Diterpenes, Kaurane – Research News and Information
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