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{{Excessive citations|date=December 2024}} |
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{{Chembox |
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{{Chembox |
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| Name = Taxodone |
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| verifiedrevid = 461825977 |
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| ImageFile = Taxodone.png |
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| Name = Taxodone |
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| ImageSize = |
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| ImageAlt = Taxodone |
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| ImageFile = Taxodone.png |
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| ImageSize = |
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| ImageFile1 = Taxodone Ball.png |
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| ImageAlt = Taxodone |
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| ImageSize1 = |
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| ImageAlt1 = Taxodone 3d |
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| ImageFile1 = Taxodone Ball.png |
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| ImageSize1 = |
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| IUPACName = (4b''S'',8a''S'',9''S'')-4,9-Dihydroxy-4b,8,8-trimethyl-2-propan-2-yl-6,7,8a,9-tetrahydro-5''H''-phenanthren-3-one |
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| ImageAlt1 = Taxodone 3d |
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| IUPACName_hidden = yes |
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| OtherNames = 6,11-Dihydroxyabieta-7,9(11),13-trien-12-one, NSC122420, AC1L9XIL, CID457961 |
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| IUPACName = 6α,11-Dihydroxyabieta-7,9(11),13-trien-12-one |
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| SystematicName = (4b''S'',8a''S'',9''S'')-4,9-Dihydroxy-4b,8,8-trimethyl-2-(propan-2-yl)-5,6,7,8,8a,9-hexahydrophenanthren-3(4b''H'')-one |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = NSC122420, AC1L9XIL, CID457961 |
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| CASNo = 19039-02-2 |
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| Section1 = {{Chembox Identifiers |
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| PubChem = 275528 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| ChemSpiderID = 242416 |
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| CASNo = 19039-02-2 |
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| SMILES = O=C1\C(=C/C=2/C(=C1/O)3(C)((O)C=2)C(C)(C)CCC3)C(C)C |
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| PubChem = 275528 |
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| InChI = 1/C20H28O3/c1-11(2)13-9-12-10-14(21)18-19(3,4)7-6-8-20(18,5)15(12)17(23)16(13)22/h9-11,14,18,21,23H,6-8H2,1-5H3/t14-,18-,20+/m0/s1 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| InChIKey = QEAIMIKGLGBTSA-ADLFWFRXBH |
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| ChemSpiderID = 242416 |
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| StdInChI = 1S/C20H28O3/c1-11(2)13-9-12-10-14(21)18-19(3,4)7-6-8-20(18,5)15(12)17(23)16(13)22/h9-11,14,18,21,23H,6-8H2,1-5H3/t14-,18-,20+/m0/s1 |
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| SMILES = O=C1\C(=C/C=2/C(=C1/O)3(C)((O)C=2)C(C)(C)CCC3)C(C)C |
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| StdInChIKey = QEAIMIKGLGBTSA-ADLFWFRXSA-N |
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| InChI = 1/C20H28O3/c1-11(2)13-9-12-10-14(21)18-19(3,4)7-6-8-20(18,5)15(12)17(23)16(13)22/h9-11,14,18,21,23H,6-8H2,1-5H3/t14-,18-,20+/m0/s1 |
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| InChIKey = QEAIMIKGLGBTSA-ADLFWFRXBH |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C20H28O3/c1-11(2)13-9-12-10-14(21)18-19(3,4)7-6-8-20(18,5)15(12)17(23)16(13)22/h9-11,14,18,21,23H,6-8H2,1-5H3/t14-,18-,20+/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = QEAIMIKGLGBTSA-ADLFWFRXSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C = 20| H = 28 | O = 3 |
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| C = 20| H = 28 | O = 3 |
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| Appearance = Golden crystalline solid |
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| Appearance = Golden crystalline solid |
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| MeltingPtCL = 176 |
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| MeltingPtC = 176 to 177 |
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| Solubility = Insoluble |
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| MeltingPtCH = 177 |
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| SolubleOther = Soluble |
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| Solubility = Insoluble |
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| Solvent = chloroform, alcohol, hexane, ether}} |
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| SolubleOther = Soluble |
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| Section8 = {{Chembox Related |
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| Solvent = chloroform, alcohol, hexane, ether}} |
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| OtherCompounds = ] |
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| Section8 = {{Chembox Related |
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| OtherCpds = ] |
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'''Taxodone''' is a naturally occurring ] found in '']'' (Bald Cypress), '']'' (Rosemary), several ] species and other plants, along with its oxidized rearrangement product, taxodione. Taxodone and taxodione exhibit ],<ref name=SMK68>{{cite journal | author = Kupchan, S. M.; Karim, A; Marcks, C. | title = Tumor inhibitors. XXXIV. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium distichum| journal = ] | year = 1968| volume = 90 | pages = 5923 | issue = 21 | doi = 10.1021/ja01023a061}}</ref><ref>{{cite journal | author = Zaghloul AM, Gohar AA, Naiem ZA, Abdel Bar FM | title = Taxodione, a DNA-binding compound from Taxodium distichum L. (Rich.). | journal = ] | year = 2008| volume = 63 | issue = 5–6| pages = 355–360}}</ref><ref name=salhyp>{{cite journal | author = Ayhan Ulubelen, Gülaçti Topçu, Hee-Byung Chai and John M. Pezzuto | title = Cytotoxic Activity of Diterpenoids Isolated from Salvia hypargeia | journal = ] | year = 1999| volume = 37 | issue = 2 | pages = 148–151 | doi = 10.1076/phbi.37.2.148.6082}}</ref> ],<ref name=bacmeta>{{cite journal | author = Vivek K. Bajpai and Sun Chul Kan | title = Antibacterial abietane-type diterpenoid, taxodone from ''Metasequoia glyptostroboides'' Miki ex Hu| journal = ] | year = 2010| volume = 35| pages = 533–538| issue = 4 | doi = 10.1007/s12038-010-0061-z}}</ref><ref name=bacmeta2>{{cite journal | author = Vivek K. Bajpai, Minkyun Na, Sun Chul Kang | title = The role of bioactive substances in controlling foodborne pathogens derived from ''Metasequoia glyptostroboides'' Miki ex Hu| journal = ] | year = 2010| volume = 48| pages = 1945–1949 | doi = 10.1016/j.fct.2010.04.041 | issue = 7}}</ref><ref name=tada2010>{{cite journal | author = Tada M, Kurabe J, Yoshida T, Ohkanda T, Matsumoto Y. | title = Syntheses and antibacterial activities of diterpene catechol derivatives with abietane, totarane and podocarpane skeletons against methicillin-resistant Staphylococcus aureus and Propionibacterium acnes | journal = ] | year = 2010| volume = 58 | issue = 6 | pages = 818–824 | doi = 10.1248/cpb.58.818}}</ref> ],<ref name=oxbar>{{cite journal | author = Ufuk Kolak, Ahmed Kabouche, Mehmet Öztürk, Zahia Kabouche, Gülaçtl Topçu, Ayhan Ulubelen | title = Antioxidant diterpenoids from the roots of ''Salvia barrelieri''| journal = ] | year = 2009| volume = 20| pages = 320–327| issue = 4 | doi = 10.1002/pca.1130}}</ref> ],<ref name=funtax>{{cite journal | author = Norihisa Kusumoto, Tatsuya Ashitani, Tetsuya Murayama, Koichi Ogiyama and Koetsu Takahashi | title = Antifungal Abietane-Type Diterpenes from the Cones of ''Taxodium distichum'' Rich| journal = ] | year = 2010| volume = 36| pages = 1381–1386| issue = 12 | doi = 10.1007/s10886-010-9875-2}}</ref> ],<ref name=insectax>{{cite journal | author = Norihisa Kusumoto, Tatsuya Ashitani, Yuichi Hayasaka, Tetsuya Murayama, Koichi Ogiyama and Koetsu Takahashi | title = Antitermitic Activities of Abietane-type Diterpenes from ''Taxodium distichum'' Cones| journal = ] | year = 2009| volume = 35| pages = 635–642| issue = 6 | doi = 10.1007/s10886-009-9646-0}}</ref> and antifeedant <ref>{{cite journal | author = M. C. Ballesta-Acosta1, M. J. Pascual-Villalobos and B. Rodríguez | title = Short communication. The antifeedant activity of natural plant products towards the larvae of Spodoptera littoralis | journal = ] | year = 2008| volume = 6 | issue = 1 | pages = 85–91}}</ref> activities. |
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'''Taxodone''' is a naturally occurring ] found in '']'' (bald cypress), '']'' (rosemary), several ] species and other plants, along with its oxidized rearrangement product, taxodione. Taxodone and taxodione exhibit ],<ref name=SMK68>{{cite journal |author1=Kupchan, S. M. |author2=Karim, A |author3=Marcks, C. | title = Tumor inhibitors. XXXIV. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium distichum| journal = ] | year = 1968| volume = 90 | pages = 5923–5924 | issue = 21 | doi = 10.1021/ja01023a061|pmid=5679178 |bibcode=1968JAChS..90.5923K }}</ref><ref>{{cite journal |author1=Zaghloul A. M. |author2=Gohar A. A. |author3=Naiem Z. A. |author4=Abdel Bar F. M. | title = Taxodione, a DNA-binding compound from Taxodium distichum L. (Rich.). | journal = ] | year = 2008| volume = 63 | issue = 5–6| pages = 355–360|doi=10.1515/znc-2008-5-608 |pmid=18669020 |s2cid=23956301 |doi-access=free }}</ref><ref name=salhyp>{{cite journal | author = ], Gülaçti Topçu, Hee-Byung Chai and John M. Pezzuto | title = Cytotoxic Activity of Diterpenoids Isolated from Salvia hypargeia | journal = ] | year = 1999| volume = 37 | issue = 2 | pages = 148–151 | doi = 10.1076/phbi.37.2.148.6082}}</ref> ],<ref name=bacmeta>{{cite journal |author1=Vivek K. Bajpai |author2=Sun Chul Kan |name-list-style=amp | title = Antibacterial abietane-type diterpenoid, taxodone from ''Metasequoia glyptostroboides'' Miki ex Hu| journal = ] | year = 2010| volume = 35| pages = 533–538| issue = 4 | doi = 10.1007/s12038-010-0061-z|pmid=21289435 |s2cid=25656295 }}</ref><ref name=bacmeta2>{{cite journal |author1=Vivek K. Bajpai |author2=Minkyun Na |author3=Sun Chul Kang | title = The role of bioactive substances in controlling foodborne pathogens derived from ''Metasequoia glyptostroboides'' Miki ex Hu| journal = ] | year = 2010| volume = 48| pages = 1945–1949 | doi = 10.1016/j.fct.2010.04.041 |pmid=20435080 | issue = 7}}</ref><ref name=tada2010>{{cite journal |author1=Tada M. |author2=Kurabe J. |author3=Yoshida T. |author4=Ohkanda T. |author5=Matsumoto Y. | title = Syntheses and antibacterial activities of diterpene catechol derivatives with abietane, totarane and podocarpane skeletons against methicillin-resistant Staphylococcus aureus and Propionibacterium acnes | journal = ] | year = 2010| volume = 58 | issue = 6 | pages = 818–824 | doi = 10.1248/cpb.58.818|pmid=20522992 | doi-access = free }}</ref> ],<ref name=oxbar>{{cite journal |author1=Ufuk Kolak |author2=Ahmed Kabouche |author3=Mehmet Öztürk |author4=Zahia Kabouche |author5=Gülaçtl Topçu |author6=Ayhan Ulubelen |author-link6=Ayhan Ulubelen | title = Antioxidant diterpenoids from the roots of ''Salvia barrelieri''| journal = ] | year = 2009| volume = 20| pages = 320–327| issue = 4 | doi = 10.1002/pca.1130|pmid=19402189 |bibcode=2009PChAn..20..320K }}</ref> ],<ref name=funtax>{{cite journal | author = Norihisa Kusumoto, Tatsuya Ashitani, Tetsuya Murayama, Koichi Ogiyama and Koetsu Takahashi | title = Antifungal Abietane-Type Diterpenes from the Cones of ''Taxodium distichum'' Rich| journal = ] | year = 2010| volume = 36| pages = 1381–1386| issue = 12 | doi = 10.1007/s10886-010-9875-2| pmid = 21072573| bibcode = 2010JCEco..36.1381K| s2cid = 11861719}}</ref> ],<ref name=insectax>{{cite journal | author = Norihisa Kusumoto, Tatsuya Ashitani, Yuichi Hayasaka, Tetsuya Murayama, Koichi Ogiyama and Koetsu Takahashi | title = Antitermitic Activities of Abietane-type Diterpenes from ''Taxodium distichum'' Cones| journal = ] | year = 2009| volume = 35| pages = 635–642| issue = 6 | doi = 10.1007/s10886-009-9646-0| pmid = 19475449| bibcode = 2009JCEco..35..635K| s2cid = 42622420}}</ref> and ]<ref>{{cite journal | author = M. C. Ballesta-Acosta1, M. J. Pascual-Villalobos and B. Rodríguez | title = Short communication. The antifeedant activity of natural plant products towards the larvae of Spodoptera littoralis | journal = ] | year = 2008| volume = 6 | issue = 1 | pages = 85–91 | doi=10.5424/sjar/2008061-304| doi-access = free }}</ref> activities. |
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==Discovery== |
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==Discovery== |
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Taxodone was first isolated in 1968 from the seeds of '']'' (Bald Cypress) by S. Morris Kupchan and coworkers.<ref name=SMK68/> They reported the structure determination and basic chemistry of taxodone and its oxidized rearrangement product, taxodione.<ref>{{cite journal | author = Kupchan, S. M.; Karim, A; Marcks, C. | title = Tumor inhibitors. XLVIII. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium distichum | journal = ] | year = 1969| volume = 34 | pages = 3912 | issue = 12 | doi = 10.1021/jo01264a036}}</ref><ref>{{cite journal | author = Hanson, R. C.; Lardy, H. A.; Kupchan, S. M. | title = Inhibition of phosphofructokinase by quinone methide and alpha-methylene lactone tumor inhibitors | journal = ] | year = 1970| volume = 168 | pages = 378| issue = 3929|doi=10.1126/science.168.3929.378}}</ref> Taxodone occurs naturally in the form of (+)-taxodone. |
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Taxodone was first isolated in 1968 from the seeds of '']'' (Bald Cypress) by S. Morris Kupchan and coworkers.<ref name=SMK68/> They reported the structure determination and basic chemistry of taxodone and its oxidized rearrangement product, taxodione.<ref>{{cite journal |author1=Kupchan, S. M. |author2=Karim, A |author3=Marcks, C. | title = Tumor inhibitors. XLVIII. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium distichum | journal = ] | year = 1969| volume = 34 | pages = 3912–3918 | issue = 12 | doi = 10.1021/jo01264a036|pmid=5357534 }}</ref><ref>{{cite journal |author1=Hanson, R. C. |author2=Lardy, H. A. |author3=Kupchan, S. M. | title = Inhibition of phosphofructokinase by quinone methide and alpha-methylene lactone tumor inhibitors | journal = ] | year = 1970| volume = 168 | pages = 378–380| issue = 3929|doi=10.1126/science.168.3929.378|pmid=4244949 |bibcode=1970Sci...168..378H |s2cid=86616738 }}</ref> Taxodone occurs naturally in the form of (+)-taxodone. |
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==Occurrence== |
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==Occurrence== |
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Taxodone and/or taxodione have been identified in several plants besides '']'' including: '']'' (Rosemary),<ref>{{cite journal | author = El-Lakany, Abdalla M.| title = Chlorosmaridione; A Novel Chlorinated Diterpene Quinone Methide from Rosemarinus officinalis L | journal = ] | year = 2004| volume = 10 | issue = 2 | pages = 59–62}}</ref> '']'',<ref name=oxbar/> '']'' (Dawn Redwood),<ref name=bacmeta/> '']'' (San Diego Sage),<ref name=salmun>{{cite journal | author = Luis, J. G.; Grillo, T. A. | title = New diterpenes from Salvia munzii: chemical and biogenetic aspects | journal = ] | year = 1993| volume = 49| pages = 6277 | doi = 10.1016/S0040-4020(01)87965-5 | issue = 28}}</ref> '']'',<ref>{{cite journal | author = Simoes, F.; Michavila, A.; Rodriguez, B.; Garcia Alvarez, M. C.; Mashooda, H.| journal = ] | year = 1986| volume = 25| pages = 755 | doi = 10.1016/0031-9422(86)88043-8 | title = A quinone methide diterpenoid from the root of Salvia moorciuftiana | issue = 3}}</ref> '']'',<ref>{{cite journal | author = Gulacti Topcu1, Esra N. Altiner, Seyda Gozcu, Belkis Halfon, Zeynep Aydogmus, J. M. Pezzuto, Bing-Nan Zhou, David G. I. Kingston| title = Studies on Di- and Triterpenoids from Salvia staminea with Cytotoxic Activity | journal = ] | year = 2003| volume = 69| issue = 5 | pages = 464–467 | doi = 10.1055/s-2003-39705}}</ref> '']'' (Cleveland Sage),<ref>{{cite journal | author = Iván C. Guerrero, Lucía S. Andrés, Leticia G. León, Rubén P. Machín, José M. Padrón, Javier G. Luis, and José Delgadillo| title = Abietane Diterpenoids from ''Salvia pachyphylla'' and ''S. clevelandii'' with Cytotoxic Activity against Human Cancer Cell Lines| journal = ] | year = 2006| volume = 69| pages = 1803–1805| issue = 12 | doi = 10.1021/np060279i}}</ref> '']'',<ref name=salhyp/> '']'',<ref>{{cite journal | author = M. Fraga, Carmen E. Díaz, Ana Guadaño, and Azucena González-Coloma| title = Diterpenes from ''Salvia broussonetii'' Transformed Roots and Their Insecticidal Activity| journal = ] | year = 2005| volume = 53| pages = 5200–5206| issue = 13 | doi = 10.1021/jf058045c}}</ref> ''Salvia montbretii'',<ref name=salmont1>{{cite journal | author = Ayhan Ulubelen, Gülaçti Topcu| title = New Abietane Diterpenoids from Salvia montbretii| journal = ] | year = 1996| volume = 55 | issue = 4 | pages = 441–444}}</ref> |
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Taxodone and/or taxodione have been identified in several plants besides '']'' including: '']'' (Rosemary),<ref>{{cite journal | author = El-Lakany, Abdalla M.| title = Chlorosmaridione; A Novel Chlorinated Diterpene Quinone Methide from Rosemarinus officinalis L | journal = ] | year = 2004| volume = 10 | issue = 2 | pages = 59–62}}</ref> '']'',<ref name=oxbar/> '']'' (Dawn Redwood),<ref name=bacmeta/> '']'' (San Diego Sage),<ref name=salmun>{{cite journal |author1=Luis, J. G. |author2=Grillo, T. A. | title = New diterpenes from Salvia munzii: chemical and biogenetic aspects |journal = ] | year = 1993| volume = 49| pages = 6277–6284 | doi = 10.1016/S0040-4020(01)87965-5 | issue = 28}}</ref> '']'',<ref>{{cite journal |author1=Simoes, F. |author2=Michavila, A. |author3=Rodriguez, B. |author4=Garcia Alvarez, M. C. |author5=Mashooda, H. | journal = ] | year = 1986| volume = 25| pages = 755–756 | doi = 10.1016/0031-9422(86)88043-8 | title = A quinone methide diterpenoid from the root of Salvia moorciuftiana | issue = 3|bibcode=1986PChem..25..755S }}</ref> '']'',<ref>{{cite journal | author = Gulacti Topcu1, Esra N. Altiner, Seyda Gozcu, Belkis Halfon, Zeynep Aydogmus, J. M. Pezzuto, Bing-Nan Zhou, David G. I. Kingston| title = Studies on Di- and Triterpenoids from Salvia staminea with Cytotoxic Activity | journal = ] | year = 2003| volume = 69| issue = 5 | pages = 464–467 | doi = 10.1055/s-2003-39705| pmid = 12802732 | s2cid = 260280222 }}</ref> '']'' (Cleveland Sage),<ref>{{cite journal |author1=Iván C. Guerrero |author2=Lucía S. Andrés |author3=Leticia G. León |author4=Rubén P. Machín |author5=José M. Padrón |author6=Javier G. Luis |author7=José Delgadillo |name-list-style=amp | title = Abietane Diterpenoids from ''Salvia pachyphylla'' and ''S. clevelandii'' with Cytotoxic Activity against Human Cancer Cell Lines| journal = ] | year = 2006| volume = 69| pages = 1803–1805| issue = 12 | doi = 10.1021/np060279i | pmid=17190465}}</ref> '']'',<ref name=salhyp/> '']'',<ref>{{cite journal |author1=M. Fraga |author2=Carmen E. Díaz |author3=Ana Guadaño |author4=Azucena González-Coloma |name-list-style=amp | title = Diterpenes from ''Salvia broussonetii'' Transformed Roots and Their Insecticidal Activity| journal = ] | year = 2005| volume = 53| pages = 5200–5206| issue = 13 | doi = 10.1021/jf058045c|pmid=15969497 |bibcode=2005JAFC...53.5200F }}</ref> ''Salvia montbretii'',<ref name=salmont1>{{cite journal |author1=Ayhan Ulubelen |author-link1 = Ayhan Ulubelen|author2=Gülaçti Topcu | title = New Abietane Diterpenoids from Salvia montbretii| journal = ] | year = 1996| volume = 55 | issue = 4 | pages = 441–444 | doi=10.1021/np50082a006}}</ref><ref name=salmont2>{{cite journal |author1=Ayhan Ulubelen |author-link1=Ayhan Ulubelen |author2=Gülaçti Topcu | title = Abietane and Rearranged Abietane Diterpenes from Salvia montbretii | journal = ] | year = 1996| volume = 59 | issue = 8 | pages = 734–737 | doi = 10.1021/np9602224}}</ref> ''Salvia nipponica'',<ref>{{cite journal |author1=Ikeshiro Y. |author2=Mase I. |author3=Tomita Y. | title = Abietane-Type Diterpene Quinones from Salvia nipponica | journal = ] | year = 1991| volume = 57 | issue = 6 | pages = 588 | doi = 10.1055/s-2006-960219|pmid=17226213 |s2cid=36064314 }}</ref><ref>{{cite journal | author = Hsiu-Hui Chana, Tsong-Long Hwangb, Chung-Ren Sua, Mopur Vijaya Bhaskar Reddya and Tian-Shung Wu | title = Anti-inflammatory, anticholinesterase and antioxidative constituents from the roots and the leaves of Salvia nipponica Miq. var. formosana | journal = ] | year = 2011| volume = 18 | issue = 2–3 | pages = 148–150 | doi = 10.1016/j.phymed.2010.06.017| pmid = 21115331 }}</ref> '']'' (Wild Clary),<ref>{{cite journal | author = A. Kabouche, Z. Kabouche, R. Touzani and C. Bruneau| title = Diterpenes and sterols from the roots of Salvia verbenaca subsp. clandestina | journal = ] | year = 2008| volume = 44 | issue = 6 | pages = 824–825 | doi = 10.1007/s10600-009-9204-6| bibcode = 2008CNatC..44..824K | s2cid = 28852886 }}</ref> '']'',<ref>{{cite journal |author1=Ik-Soo Lee |author2=Norito Kaneda |author3=Rutt Suttisri |author4=Abdalla M. El-Lakany |author5=Nawal Sabri |author6=A. Douglas Kinghorn |name-list-style=amp | title = New Orthoquinones from the Roots of Salvia lanigera | journal = ] | year = 1998| volume = 64 | pages = 632–634 | doi = 10.1055/s-2006-957536 |pmid=17253304 | issue = 7|s2cid=260249066 }}</ref><ref>{{cite journal | author = Sabri, N. N., Abou-Donia, A. A., Assad, A. M., Ghazy, N. M., El-lakany, A. M., Tempesta, M. S. and Sanson D. R.| title = Abietane diterpene quinones from the roots of Salvia verbenaca and S. lanigera| journal = ] | year = 1989| volume = 55| pages = 582 | doi = 10.1055/s-2006-962111 | pmid = 17262492| issue = 6| s2cid = 10020492}}</ref> '']'',<ref>{{cite journal |author1=Li M. |author2=Zhang J. S. |author3=Ye Y. M. |author4=Fang J. N. | title = Constituents of the roots of Salvia prionitis | journal = ] | year = 2000 | volume = 63| issue = 1| pages = 139–141 | doi = 10.1021/np990357k|pmid=10650097 }}</ref> '']'',<ref>{{cite journal |author1=Y. Tezuka |author2=R. Kasimu |author3=J. X. Li |author4=P. Basnet |author5=K. Tanaka |author6=T. Namba |author7=S. Kadot | title = Constituents of Roots of Salvia deserta SCHANG. (Xinjiang-Danshen)| journal = ] | year = 1998| volume = 46| issue = 1 | pages = 107–112 | doi=10.1248/cpb.46.107|doi-access=free }}</ref> ''Salvia phlomoides'',<ref>{{cite journal | author = Benjamın Rodrıguez| title = A Methoxyabietane Diterpenoid from the Root of Salvia phlomoides and Structural Correction of Another Diterpene from Cryptomeria japonica| journal = ] | year = 2003| volume = 58b| pages = 324–327}}</ref><ref>{{cite journal |author1=J. A. Hueso-Rodrıguez |author2=M. L. Jimeno |author3=B. Rodrıguez |author4=G. Savona |author5=M. Bruno | title = Abietane diterpenoids from the root of Salvia phlomoides | journal = ] | year = 1983| volume = 22| pages = 2005–2009 | doi = 10.1016/0031-9422(83)80033-8 | issue = 9|bibcode=1983PChem..22.2005H }}</ref> and ''] hereroensis''<ref>{{cite journal | author = Olga Batista, M. Fátima Simões, José Nascimento, Sofia Riberio, Aida Duartea, Benjamín Rodríguez and Maria C. de la Torreb | title = A rearranged abietane diterpenoid from Plectranthus hereroensis | journal = ] | year = 1996| volume = 41 | issue = 2 | pages = 571–573 | doi = 10.1016/0031-9422(95)00646-X| pmid = 8821435 | bibcode = 1996PChem..41..571B }}</ref> |
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<ref name=salmont2>{{cite journal | author = Ayhan Ulubelen, Gülaçti Topcu| title = Abietane and Rearranged Abietane Diterpenes from Salvia montbretii | journal = ] | year = 1996| volume = 59 | issue = 8 | pages = 734–737 | doi = 10.1021/np9602224}}</ref> ''Salvia nipponica'',<ref>{{cite journal | author = Ikeshiro Y, Mase I, Tomita Y.| title = Abietane-Type Diterpene Quinones from Salvia nipponica | journal = ] | year = 1991| volume = 57 | issue = 6 | pages = 588 | doi = 10.1055/s-2006-960219}}</ref><ref>{{cite journal | author = Hsiu-Hui Chana, Tsong-Long Hwangb, Chung-Ren Sua, Mopur Vijaya Bhaskar Reddya and Tian-Shung Wu | title = Anti-inflammatory, anticholinesterase and antioxidative constituents from the roots and the leaves of Salvia nipponica Miq. var. formosana | journal = ] | year = 2011| volume = 18 | issue = 2–3 | pages = 148–150 | doi = 10.1016/j.phymed.2010.06.017}}</ref> '']'' (Wild Clary),<ref>{{cite journal | author = A. Kabouche, Z. Kabouche, R. Touzani and C. Bruneau| title = Diterpenes and sterols from the roots of Salvia verbenaca subsp. clandestina | journal = ] | year = 2008| volume = 44 | issue = 6 | pages = 824–825 | doi = 10.1007/s10600-009-9204-6}}</ref> '']'',<ref>{{cite journal | author = Ik-Soo Lee, Norito Kaneda, Rutt Suttisri, Abdalla M. El-Lakany, Nawal Sabri, and A. Douglas Kinghorn| title = New Orthoquinones from the Roots of Salvia lanigera | journal = ] | year = 1998| volume = 64 | pages = 632 | doi = 10.1055/s-2006-957536 | issue = 7}}</ref><ref>{{cite journal | author = Sabri, N.N., Abou-Donia, A.A., Assad, A.M., Ghazy, N.M., El-lakany, A.M., Tempesta, M.S. and Sanson D.R.| title = Abietane diterpene quinones from the roots of Salvia verbenaca and S. lanigera| journal = ] | year = 1989| volume = 55| pages = 582 | doi = 10.1055/s-2006-962111 | issue = 6}}</ref>'']'',<ref>{{cite journal | author = Li M, Zhang JS, Ye YM, Fang JN | title = Constituents of the roots of Salvia prionitis | journal = ] | year = 2000 | volume = 63| issue = 1| pages = 139–141 | doi = 10.1021/np990357k}}</ref> '']'',<ref>{{cite journal | author = Y. Tezuka, R. Kasimu, J. X. Li, P. Basnet, K. Tanaka, T. Namba, S. Kadot| title = Constituents of Roots of Salvia deserta SCHANG. (Xinjiang-Danshen)| journal = ] | year = 1998| volume = 46| issue = 1 | pages = 107–112}}</ref> ''Salvia phlomoides'',<ref>{{cite journal | author = Benjamın Rodrıguez| title = A Methoxyabietane Diterpenoid from the Root of Salvia phlomoides and Structural Correction of Another Diterpene from Cryptomeria japonica| journal = ] | year = 2003| volume = 58b| pages = 324–327}}</ref><ref>{{cite journal | author = J. A. Hueso-Rodrıguez, M. L. Jimeno, B. Rodrıguez, G. Savona, M. Bruno | title = Abietane diterpenoids from the root of Salvia phlomoides | journal = ] | year = 1983| volume = 22| pages = 2005 | doi = 10.1016/0031-9422(83)80033-8 | issue = 9}}</ref> and ''] hereroensis'' <ref>{{cite journal | author = Olga Batista, M. Fátima Simões, José Nascimento, Sofia Riberio, Aida Duartea, Benjamín Rodríguez and Maria C. de la Torreb | title = A rearranged abietane diterpenoid from Plectranthus hereroensis | journal = ] | year = 1996| volume = 41 | issue = 2 | pages = 571–573 | doi = 10.1016/0031-9422(95)00646-X}}</ref> |
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Taxodone, taxodione and their reaction products have been used as archeological and geological biomarkers.<ref>{{cite journal | author = A. Otto, H. Walther, W. Püttmann| title = Sesqui- and diterpenoid biomarkers preserved in Taxodium-rich Oligocene oxbow lake clays, Weisselster basin, Germany | journal = ] | year = 1997 | volume = 26| pages = 105–115 | issue = 1–2 | doi = 10.1016/S0146-6380(96)00133-7}}</ref><ref>{{cite journal | author = A. Otto, H. Walther, W. Püttmann | title = Molecular composition of a leaf- and root-bearing Oligocene Oxbow Lake Clay in the Weisselster Basin, Germany | journal = ] | year = 1994| volume = 22| pages = 275–286 | issue = 2 | doi = 10.1016/0146-6380(94)90174-0}}</ref><ref>{{cite journal | author = Angelika Otto, Bernd R. T. Simoneit, William C. Rember | title = Resin compounds from the seed cones of three fossil conifer species from the Miocene Clarkia flora, Emerald Creek, Idaho, USA, and from related extant species | journal = ] | year = 2003| volume = 126 | pages = 225–241 | doi = 10.1016/S0034-6667(03)00088-5 | issue = 3–4}}</ref><ref>{{cite journal | author = Maya Stefanova, Bernd R.T. Simoneit | title = Polar aromatic biomarkers of Miocene-aged Chukurovo resinite and correlation with a progenitor macrofossil | journal = ] | year = 2008 | volume = 75| issue = 3 | pages = 166–174 | doi = 10.1016/j.coal.2008.05.003}}</ref><ref>{{cite journal | author = A. Zdravkov, A. Bechtel, R.F. Sachsenhofer, J. Kortenski, R. Gratzer | title = Vegetation differences and diagenetic changes between two Bulgarian lignite deposits – Insights from coal petrology and biomarker composition| journal = ] | year = 2011| volume = 42 | issue = 3| pages = 237–254 | doi = 10.1016/j.orggeochem.2010.12.006}}</ref><ref>{{cite journal | author = Yann Hautevelle, Raymond Michels, Fabrice Malartre, Alain Trouiller | title = Vascular plant biomarkers as proxies for palaeoflora and palaeoclimatic changes at the Dogger/Malm transition of the Paris Basin (France)| journal = ] | year = 2006| volume = 37| issue = 5 | pages = 610–625 | doi = 10.1016/j.orggeochem.2005.12.010}}</ref><ref>{{cite journal| author = Kenneth E. Peters, Clifford C. Walters, J. Michael Moldowan| title = The Biomarker Guide: Biomarkers and isotopes in petroleum systems and Earth History| year = 2005| volume = 2 | pages = 546}}</ref> |
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Taxodone, taxodione and their reaction products have been used as archeological and geological biomarkers.<ref>{{cite journal |author1=A. Otto |author2=H. Walther |author3=W. Püttmann | title = Sesqui- and diterpenoid biomarkers preserved in Taxodium-rich Oligocene oxbow lake clays, Weisselster basin, Germany | journal = ] | year = 1997 | volume = 26| pages = 105–115 | issue = 1–2 | doi = 10.1016/S0146-6380(96)00133-7|bibcode=1997OrGeo..26..105O }}</ref><ref>{{cite journal |author1=A. Otto |author2=H. Walther |author3=W. Püttmann | title = Molecular composition of a leaf- and root-bearing Oligocene Oxbow Lake Clay in the Weisselster Basin, Germany | journal = ] | year = 1994| volume = 22| pages = 275–286 | issue = 2 | doi = 10.1016/0146-6380(94)90174-0|bibcode=1994OrGeo..22..275O }}</ref><ref>{{cite journal |author1=Angelika Otto |author2=Bernd R. T. Simoneit |author3=William C. Rember | title = Resin compounds from the seed cones of three fossil conifer species from the Miocene Clarkia flora, Emerald Creek, Idaho, USA, and from related extant species | journal = ] | year = 2003| volume = 126 | pages = 225–241 | doi = 10.1016/S0034-6667(03)00088-5 | issue = 3–4|bibcode=2003RPaPa.126..225O }}</ref><ref>{{cite journal |author1=Maya Stefanova |author2=Bernd R.T. Simoneit | title = Polar aromatic biomarkers of Miocene-aged Chukurovo resinite and correlation with a progenitor macrofossil | journal = ] | year = 2008 | volume = 75| issue = 3 | pages = 166–174 | doi = 10.1016/j.coal.2008.05.003|bibcode=2008IJCG...75..166S }}</ref><ref>{{cite journal |author1=A. Zdravkov |author2=A. Bechtel |author3=R. F. Sachsenhofer |author4=J. Kortenski |author5=R. Gratzer | title = Vegetation differences and diagenetic changes between two Bulgarian lignite deposits – Insights from coal petrology and biomarker composition| journal = ] | year = 2011| volume = 42 | issue = 3| pages = 237–254 | doi = 10.1016/j.orggeochem.2010.12.006|bibcode=2011OrGeo..42..237Z }}</ref><ref>{{cite journal |author1=Yann Hautevelle |author2=Raymond Michels |author3=Fabrice Malartre |author4=Alain Trouiller | title = Vascular plant biomarkers as proxies for palaeoflora and palaeoclimatic changes at the Dogger/Malm transition of the Paris Basin (France)| journal = ] | year = 2006| volume = 37| issue = 5 | pages = 610–625 | doi = 10.1016/j.orggeochem.2005.12.010|bibcode=2006OrGeo..37..610H }}</ref><ref>{{cite journal|author1=Kenneth E. Peters |author2=Clifford C. Walters |author3=J. Michael Moldowan | title = The Biomarker Guide: Biomarkers and isotopes in petroleum systems and Earth History| year = 2005| volume = 2 | pages = 546}}</ref> |
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Analogs of taxodone and taxodione have also been isolated. 2-hydroxy taxodone and 2-hydroxy-taxodione have been found in '']'' (Texas Sage).<ref>{{cite journal | author = Gonzalez, A. G.; Aguilar, Z. E.; Luis, J. G; Ravelo, A G.; Dominguez, X. | title = Quinone methide diterpenoids from the roots of Salvia texana | journal = ] | year = 1988| volume = 27| pages = 177}}</ref> 5,6-Didehydro-7-hydroxy-taxodone was found in '']''.<ref name=salmun/> 7-Hydroxytaxodione, 7,7‘-bistaxodione, and 11,11‘-didehydroxy-7,7‘-dihydroxytaxodione were found in ''Salvia montbretti''.<ref name=salmont1/><ref name=salmont2/> |
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Analogs of taxodone and taxodione have also been isolated. 2-hydroxy taxodone and 2-hydroxy-taxodione have been found in '']'' (Texas Sage).<ref>{{cite journal |author1=Gonzalez, A. G. |author2=Aguilar, Z. E. |author3=Luis, J. G |author4=Ravelo, A. G. |author5=Dominguez, X. | title = Quinone methide diterpenoids from the roots of Salvia texana | journal = ] | year = 1988| volume = 27|issue=6 | pages = 1777–1781 | doi=10.1016/0031-9422(88)80442-4|bibcode=1988PChem..27.1777G }}</ref> 5,6-Didehydro-7-hydroxy-taxodone was found in '']''.<ref name=salmun/> 7-Hydroxytaxodione, 7,7‘-bistaxodione, and 11,11‘-didehydroxy-7,7‘-dihydroxytaxodione were found in ''Salvia montbretti''.<ref name=salmont1/><ref name=salmont2/> |
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==Activity== |
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==Activity== |
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Taxodone and taxodione possess '']'' activity against Walker intramuscular ] 256 in rats (25 and 40 mg/kg, respectively) and '']'' activity against cells derived from human ] of the ] (KB) (ED<sub>50</sub> = 0.6 and 3 ug/ml respectively).<ref name=SMK68/> Taxodone and taxodione exhibit ] activity against wood decay fungi, with taxodione being especially active against '']'' and '']''.<ref name=funtax/> Taxodione exhibited the highest ] activity among the tested ]s from the roots of '']''.<ref name=oxbar/> Taxodone showed potent ] effects against foodborne ] ], such as '']'' ATCC 19166, '']'' KCTC 2515, '']'' KCTC 2021, '']'' ATCC 8739, '']'' O157:H7 ATCC 43888, '']'' KCTC 2190, '']'' ATCC 6538 and '']''.KCTC 1916 <ref name=bacmeta/> Taxodone showed potent termicidal activity against the subterranean ], ''Reticulitermes speratus'' Kolbe.<ref name=insectax/> Taxodione depresses neruonal GABAA receptor-operated Cl-current (IGABA).<ref>{{cite journal | author = D Rutherford, M Nielsen, N Tokutomi, N Akaike | title = Effects of plant diterpenes on the neuronal GABAA receptor-operated chloride current | journal = ] | year = 1994| volume = 5| pages = 2569–2572 | doi = 10.1097/00001756-199412000-00041 | issue = 18}}</ref> Taxodione may have potential in treatment of cardiovascular disease.<ref>{{cite journal | author = CR Tirapelli, SR Ambrosio, FB da Costa, AM de Oliveira | title = Diterpenes: a therapeutic promise for cardiovascular diseases | journal = ] | year = 2008 | volume = 3| pages = 1–8 | doi = 10.2174/157489008783331689}}</ref> |
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Taxodone and taxodione possess '']'' activity against Walker intramuscular ] 256 in rats (25 and 40 mg/kg, respectively) and '']'' activity against cells derived from human ] of the ] (KB) (ED<sub>50</sub> = 0.6 and 3 ug/ml respectively).<ref name=SMK68/> Taxodone and taxodione exhibit ] activity against wood decay fungi, with taxodione being especially active against '']'' and '']''.<ref name=funtax/> Taxodione exhibited the highest ] activity among the tested ]s from the roots of '']''.<ref name=oxbar/> Taxodone showed potent ] effects against foodborne ] ], such as '']'' ATCC 19166, '']'' KCTC 2515, '']'' KCTC 2021, '']'' ATCC 8739, '']'' O157:H7 ATCC 43888, '']'' KCTC 2190, '']'' ATCC 6538 and '']'' KCTC 1916<ref name=bacmeta/> Taxodone showed potent termicidal activity against the subterranean ], ''Reticulitermes speratus'' Kolbe.<ref name=insectax/> Taxodione depresses neuronal GABAA receptor-operated Cl-current (IGABA).<ref>{{cite journal |author1=D. Rutherford |author2=M. Nielsen |author3=N. Tokutomi |author4=N. Akaike | title = Effects of plant diterpenes on the neuronal GABAA receptor-operated chloride current | journal = ] | year = 1994| volume = 5| pages = 2569–2572 | doi = 10.1097/00001756-199412000-00041 | issue = 18|pmid=7696606 }}</ref> Taxodione may have potential in treatment of cardiovascular disease.<ref>{{cite journal |author1=C. R. Tirapelli |author2=S. R. Ambrosio |author3=F. B. da Costa |author4=A. M. de Oliveira | title = Diterpenes: a therapeutic promise for cardiovascular diseases | journal =Recent Patents on Cardiovascular Drug Discovery| year = 2008 | volume = 3|issue=1 | pages = 1–8 | doi = 10.2174/157489008783331689|pmid=18221123 }}</ref> |
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The use of taxodone and taxodione to inhibit hair growth has been patented.<ref></ref><ref></ref><ref></ref> Treatment of benign prostate enlargement with taxodone has also been patented.<ref></ref> |
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The use of taxodone and taxodione to inhibit hair growth has been patented.<ref></ref><ref></ref><ref></ref> Treatment of benign prostate enlargement with taxodone has also been patented.<ref></ref> |
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==Chemistry== |
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==Chemistry== |
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Taxodone was the first isolated example of a ]<ref>{{cite journal |author1=Karantsios, D. |author2=Scarpa, J. S. |author3=Eugster, C. H. | journal = ] | year = 1966| volume = 49| pages = 1151–1172 | doi = 10.1002/hlca.19660490313 | title = Struktur von Fuerstion | issue = 3}}</ref><ref>{{cite journal |author1=Gonzalez, A. G. |author2=Fraga, B. M. |author3=Gonzalez, C. M. |journal = ] | year = 1983| volume = 84 |issue=29 | pages = 3033–3036 | doi = 10.1016/s0040-4039(00)88088-0 |title=X-ray analysis of netzahualcoyone, a triterpene Quinone methide from ''orthosphenia mexicana''}}</ref><ref>{{cite journal | author = Simoes, F.; Miehavila, A; Rodriguez. B.; Garcia A1varez, M. C.; Mashooda, H.| journal = ] | year = 1986| volume = 25| pages = 755–756 | doi = 10.1016/0031-9422(86)88043-8 | title = A quinone methide diterpenoid from the root of Salvia moorciuftiana | issue = 3| bibcode = 1986PChem..25..755S }}</ref><ref>{{cite journal |author1=Sankaram, A. V. B. |author2=Murthi, M. M. |author3=Bhaskaraiah, K. |author4=Narasimha Rao, G. L. |author5=Suhrahmanyam, M. |author6=Shoolery, J. N. | journal = ] | year = 1988| volume = 29| pages = 245–248 | doi = 10.1016/S0040-4039(00)80066-0 | title = Bharangin, a novel diterpenoid quinonemethide from pygmacopremna herbacea (Roxb.) moldenke | issue = 2}}</ref><ref>{{cite journal |author1=Fernando, H. C. |author2=Gunatilaka, A. A. L. |author3=Kumar, V. |author4=Weexatunga, G. | journal = ] | year = 1988| volume = 29| pages = 387–390 | doi = 10.1016/S0040-4039(00)80104-5 | title = Two new quinone-methides from cassine balae: Revised structure of balaenonol | issue = 3}}</ref><ref>{{cite journal |author1=Sankaram, A. V. B. |author2=Bhaskaraiah, K. |author3=Marthandamurthi. M. |author4=Subrahmanyam, M. | journal = ] | year = 1989| volume = 30| pages = 867–868 | doi = 10.1016/S0040-4039(01)80638-9 | title = Isobharangin, a new biogenetically significant diterpenoid quinonemethide from pygmacopremna herbacea (Roxb.) moldenke | issue = 7}}</ref> with a ] ] adjacent to this reactive ].<ref name=SMK68/> Kupchan demonstrated that taxodone aromatizes to a ] ] upon exposure to mild ]. Air ] of this ] ] affords taxodione. |
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Taxodone was the first isolated example of a ] <ref>{{cite journal | author = Karantsios, D.; Scarpa, J. S.; Eugster, C. H. | journal = ] | year = 1966| volume = 49| pages = 1151 | doi = 10.1002/hlca.19660490313 | title = Struktur von Fuerstion | issue = 3}}</ref> |
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<ref>{{cite journal | author = Gonzalez, A G.; Fraga, B. M.; Gonzalez, C. M.| journal = ] | year = 1983| volume = 84 | pages = 3033}}</ref><ref>{{cite journal | author = Simoes, F.; Miehavila, A; Rodriguez. B.; Garcia A1varez, M. C.; Mashooda, H.| journal = ] | year = 1986| volume = 25| pages = 755 | doi = 10.1016/0031-9422(86)88043-8 | title = A quinone methide diterpenoid from the root of Salvia moorciuftiana | issue = 3}}</ref><ref>{{cite journal | author = Sankaram, A. V. B.; Murthi, M. M.; Bhaskaraiah, K.; Narasimha Rao, G. L.; Suhrahmanyam, M.; Shoolery, J. N.| journal = ] | year = 1988| volume = 29| pages = 245 | doi = 10.1016/S0040-4039(00)80066-0 | title = Bharangin, a novel diterpenoid quinonemethide from pygmacopremna herbacea (Roxb.) moldenke | issue = 2}}</ref><ref>{{cite journal | author = Fernando, H. C.; Gunatilaka, A A L.; Kumar, V.; Weexatunga, G. | journal = ] | year = 1988| volume = 29| pages = 387 | doi = 10.1016/S0040-4039(00)80104-5 | title = Two new quinone-methides from cassine balae: Revised structure of balaenonol | issue = 3}}</ref><ref>{{cite journal | author = Sankaram, A. V. B.; Bhaskaraiah, K.; Marthandamurthi. M.; Subrahmanyam, M.| journal = ] | year = 1989| volume = 30| pages = 867 | doi = 10.1016/S0040-4039(01)80638-9 | title = Isobharangin, a new biogenetically significant diterpenoid quinonemethide from pygmacopremna herbacea (Roxb.) moldenke | issue = 7}}</ref> with a ] ] adjacent to this reactive ].<ref name=SMK68/> Kupchan demonstrated that taxodone aromatizes to a ] ] upon exposure to mild ]. Air ] of this ] ] affords taxodione. |
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==Synthesis== |
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==Synthesis== |
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Taxodone rearranges easily in the presence of mild ] and reacts readily with ]. Although taxodone shows higher ] and ] activity than taxodione it eluded creation in the laboratory for over 25 years because of its inherent instability. During this time several different groups reported syntheses of the more stable taxodione.<ref>{{cite journal | author = Mori, K.; Matsui, M | title = Diterpenoid total synthesis. XIII Taxodione, a quinone methide tumor inhibitor | journal = ] | year = 1970| volume = 26| pages = 3467–3473 | doi = 10.1016/S0040-4020(01)92926-6 | issue = 14}}</ref><ref>{{cite journal | author = Matsumoto, T.; Tachibana, Y.; Uchida, J.; Fukui, K.| journal = ] | year = 1971| volume = 44| pages = 2766 | doi = 10.1246/bcsj.44.2766 | title = The Total Synthesis of (±)-Taxodione, A Tumor Inhibitor | issue = 10}}</ref><ref>{{cite journal | author = Matsumoto, T.; Ohsuga, Y.; Fukui, K. | title = SYNTHESIS OF TAXODIONE AND METHYL 11-HYDROXY-12-METHOXY-7-OXOABIETA-8,11,13-TRIEN-18-OATE| journal = ] | year = 1974| pages = 297}}</ref><ref>{{cite journal | author = Matsumoto, T.; Osbuga, Y.; Harada, S.; Fukui, K. | journal = ] | year = 1977| volume = 50| pages = 266 | doi = 10.1246/bcsj.50.266 | title = Synthesis of Taxodione, Royleanone, Cryptojaponol, and Methyl 11-Hydroxy-12-methoxy-7-oxoabieta-8,11)13-trien-18-oate}}</ref><ref>{{cite journal | author = Matsumoto. T.; Usui, S.; Morimoto. T.| journal = ] | year = 1977| volume = 50| pages = 1575 | doi = 10.1246/bcsj.50.1575 | title = A Convenient Synthesis of (±)-Taxodione, (±)-Ferruginol, and (±)-Sugiol | issue = 6}}</ref><ref>{{cite journal | author = Ohtsuka, Y.; Tahara, A.| title = Diterpenoids. XLVI. Syntheses of Taxodione, Royleanone and Their Analogues | journal = ] | year = 1978| volume = 26| pages = 2007}}</ref><ref>{{cite journal | author = Snitman, D. L.; Himmelsbach, R. J.; Haltiwanger, R C.; Watt, D. S. | title = A synthesis of (±)-cryptojaponol and (±)-taxodione | journal = ] | year = 1979| volume = 27| pages = 2477–2480}}</ref><ref>{{cite journal | author = Johnson, W. S.; Shenvi, A. B.; Boots, S. G. | journal = ] | year = 1982| volume = 38| pages = 1397 | doi = 10.1016/0040-4020(82)80219-6 | title = An approach to taxodione involving biomimetic polyene cyclization methodology | issue = 10}}</ref><ref>{{cite journal | author = Stevens, R. V.; Bisaochi, G. G.| journal = ] | year = 1982| volume = 47| pages = 2396 | doi = 10.1021/jo00133a032 | title = Benzocyclobutenones as synthons for the synthesis of C-11 oxygenated diterpenoids. Application to the total synthesis of (.+-.)-taxodione | issue = 12}}</ref><ref>{{cite journal | author = Poirier, D.; Jean, M.; Burnell, R H. | title = Alternate Syntheses of Taxodione | journal = ] | year = 1983| volume = 13| pages = 201 | doi = 10.1080/00397918308065989 | issue = 3}}</ref><ref>{{cite journal | author = Banerjee, A K; Carrasco, M. C. | title = Synthetic Approaches to (±)-Taxodione | journal = ] | year = 1988| volume = 13| pages = 281}}</ref> |
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Taxodone rearranges easily in the presence of mild ] and reacts readily with ]. Although taxodone shows higher ] and ] activity than taxodione it eluded creation in the laboratory for over 25 years because of its inherent instability. During this time several different groups reported syntheses of the more stable taxodione.<ref>{{cite journal |author1=Mori, K. |author2=Matsui, M. | title = Diterpenoid total synthesis. XIII Taxodione, a quinone methide tumor inhibitor |journal = ] | year = 1970| volume = 26| pages = 3467–3473 | doi = 10.1016/S0040-4020(01)92926-6 | issue = 14|pmid=5449327 }}</ref><ref>{{cite journal |author1=Matsumoto, T. |author2=Tachibana, Y. |author3=Uchida, J. |author4=Fukui, K. | journal = ] | year = 1971| volume = 44| pages = 2766–2770 | doi = 10.1246/bcsj.44.2766 | title = The Total Synthesis of (±)-Taxodione, A Tumor Inhibitor | issue = 10| doi-access = free }}</ref><ref>{{cite journal |author1=Matsumoto, T. |author2=Ohsuga, Y. |author3=Fukui, K. | title = Synthesis of Taxodione and Methyl 11-hydroxy-12-methoxy-7-oxobieta-8,11,13-trien-18-oate| journal = ] |volume=3 |issue=3 | year = 1974| pages = 297–300|doi=10.1246/cl.1974.297 }}</ref><ref>{{cite journal |author1=Matsumoto, T. |author2=Osbuga, Y. |author3=Harada, S. |author4=Fukui, K. | journal = ] | year = 1977| volume = 50| pages = 266–272 | doi = 10.1246/bcsj.50.266 | title = Synthesis of Taxodione, Royleanone, Cryptojaponol, and Methyl 11-Hydroxy-12-methoxy-7-oxoabieta-8,11)13-trien-18-oate| doi-access = free }}</ref><ref>{{cite journal |author1=Matsumoto. T. |author2=Usui, S. |author3=Morimoto. T. | journal = ] | year = 1977| volume = 50| pages = 1575–1579 | doi = 10.1246/bcsj.50.1575 | title = A Convenient Synthesis of (±)-Taxodione, (±)-Ferruginol, and (±)-Sugiol | issue = 6| doi-access = free }}</ref><ref>{{cite journal |author1=Ohtsuka, Y. |author2=Tahara, A. | title = Diterpenoids. XLVI. Syntheses of Taxodione, Royleanone and Their Analogues | journal = ] | year = 1978| volume = 26|issue=7 | pages = 2007–2013 | doi=10.1248/cpb.26.2007| doi-access = free }}</ref><ref>{{cite journal |author1=Snitman, D. L. |author2=Himmelsbach, R. J. |author3=Haltiwanger, R. C. |author4=Watt, D. S. | title = A synthesis of (±)-cryptojaponol and (±)-taxodione | journal = ] | year = 1979| volume = 20|issue=27 | pages = 2477–2480|doi=10.1016/S0040-4039(01)86325-5}}</ref><ref>{{cite journal |author1=Johnson, W. S. |author2=Shenvi, A. B. |author3=Boots, S. G. |journal = ] | year = 1982| volume = 38| pages = 1397–1404 | doi = 10.1016/0040-4020(82)80219-6 | title = An approach to taxodione involving biomimetic polyene cyclization methodology | issue = 10}}</ref><ref>{{cite journal |author1=Stevens, R. V. |author2=Bisaochi, G. G. | journal = ] | year = 1982| volume = 47| pages = 2396–2399 | doi = 10.1021/jo00133a032 | title = Benzocyclobutenones as synthons for the synthesis of C-11 oxygenated diterpenoids. Application to the total synthesis of (.+-.)-taxodione | issue = 12}}</ref><ref>{{cite journal |author1=Poirier, D. |author2=Jean, M. |author3=Burnell, R. H. | title = Alternate Syntheses of Taxodione | journal = ] | year = 1983| volume = 13| pages = 201–205 | doi = 10.1080/00397918308065989 | issue = 3}}</ref><ref>{{cite journal |author1=Banerjee, A K |author2=Carrasco, M. C. | title = Synthetic Approaches to (±)-Taxodione | journal = ] | year = 1988| volume = 13|issue=4 | pages = 281–287 | doi=10.1080/00397918308066977}}</ref><ref>{{cite journal |author1=Banerjee, A. K |author2=Carrasco, M. C. | journal = ] | year = 1986| pages = 25–31 | doi = 10.1039/p19860000025 | title = Total synthesis of (±)-12-methoxyabieta-8,11,13-trien-6-one, a versatile intermediate for diterpene syntheses}}</ref><ref>{{cite journal |author1=Burnell, P. H. |author2=Jean, M. |author3=Poirer, D. | title = Synthesis of taxodione | journal = ] | year = 1987| volume = 65| pages = 775–781 | doi = 10.1139/v87-132 | issue = 4}}</ref><ref>{{cite journal |author1=Engler, T. A. |author2=Sampath. U. |author3=N aganathan, S. |author4=Van Der Velde, D. |author5=Takusagawa, F. | journal = ] | year = 1989| volume = 54| pages = 5712–5727 | doi = 10.1021/jo00285a018 | title = A new general synthetic approach to diterpenes: Application to syntheses of (.+-.)-taxodione and (.+-.)-royleanone | issue = 24}}</ref><ref>{{cite journal |author1=Haslinger, E. |author2=Michl, G. | journal = ] | year = 1988| volume = 29| pages = 5751–5754 | doi = 10.1016/S0040-4039(00)82181-4 | title = Synthesis of (+)-taxodione from (−)-abietic acid | issue = 45}}</ref><ref>{{cite journal |author1=Haslinger, E. |author2=Michl, G. | journal = ] |volume=1989 |issue=7 | year = 1989| pages = 677–686|title=''missing''|doi=10.1002/jlac.198919890212 }}</ref><ref>{{cite journal |author1=Harring, S. R |author2=Livinghouse, T. | title = A concise biomimetic total synthesis of (±)-taxodione via a BF<sub>3</sub>·MeNO<sub>2</sub> promoted cationic cascade annulation | journal = ] |issue=6 | year = 1992 | pages = 502–503|doi=10.1039/C39920000502 }}</ref><ref>{{cite journal |author1=Ruedi, P. |author2=Eugster, C. H. | journal = ] | year = 1981|volume = 64| pages = 2219–2226 | doi = 10.1002/hlca.19810640728 | title = 14-Hydroxytaxodion: Partialsynthese und Reaktionen | issue = 7}}</ref><ref>{{cite journal |author1=Matsumoto, T. |author2=Kawashima, H. |author3=Iyo, K. | journal = ] | year = 1982| volume = 55|pages = 1168–1173 | doi = 10.1246/bcsj.55.1168 | title = Synthesis of 3.BETA.-hydroxytaxodione and coleons S and T | issue = 4| doi-access = free }}</ref> |
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<ref>{{cite journal | author = Banerjee, A K; Carrasco, M. C. | journal = ] | year = 1986| pages = 25 | doi = 10.1039/p19860000025 | title = Total synthesis of (�)-12-methoxyabieta-8,11,13-trien-6-one, a versatile intermediate for diterpene syntheses}}</ref> |
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<ref>{{cite journal | author = Burnell, P. H.; Jean, M.; Poirer, D. | title = Synthesis of taxodione | journal = ] | year = 1987| volume = 65| pages = 775–781 | doi = 10.1139/v87-132 | issue = 4}}</ref><ref>{{cite journal | author = Engler, T. A.; Sampath. U.; N aganathan, S.; Van Der Velde, D.; Takusagawa, F.| journal = ] | year = 1989| volume = 54| pages = 5712 | doi = 10.1021/jo00285a018 | title = A new general synthetic approach to diterpenes: Application to syntheses of (.+-.)-taxodione and (.+-.)-royleanone | issue = 24}}</ref><ref>{{cite journal | author = Haslinger, E.; Michl, G.| journal = ] | year = 1988| volume = 29| pages = 5751 | doi = 10.1016/S0040-4039(00)82181-4 | title = Synthesis of (+)-taxodione from (−)-abietic acid | issue = 45}}</ref><ref>{{cite journal | author = Haslinger, E.; Michl, G| journal = ] | year = 1989| pages = 677}}</ref><ref>{{cite journal | author = Harring, S. R; Livinghouse, T. | title = A concise biomimetic total synthesis of (±)-taxodione via a BF3·MeNO2 promoted cationic cascade annulation | journal = ] | year = 1992 | pages = 502}}</ref><ref>{{cite journal | author = Ruedi, P.; Eugster, C. H. | journal = ] | year = 1981|volume = 64| pages = 2219 | doi = 10.1002/hlca.19810640728 | title = 14-Hydroxytaxodion: Partialsynthese und Reaktionen | issue = 7}}</ref><ref>{{cite journal | author = Matsumoto, T.; Kawashima, H.; Iyo, K.| journal = ] | year = 1982| volume = 55|pages = 1168 | doi = 10.1246/bcsj.55.1168 | title = Synthesis of 3.BETA.-hydroxytaxodione and coleons S and T | issue = 4}}</ref> |
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In 1993 taxodone was synthesized for the first time in a 16 step sequence utilizing a unique phenol benzylic epoxide electron reorganization in the final step.<ref>{{cite journal | author = Sanchez, Anthony J.; Konopelski, Joseph P. | title = The First Total Synthesis of (±)-Taxodone| journal = ] | year = 1994| pages = 335–336}}</ref><ref>{{cite journal | author = Sanchez, Anthony J.; Konopelski, Joseph P. | title = Phenol Benzylic Epoxide to Quinone Methide Electron Reorganization: The Synthesis of (±)-Taxodone| journal = ] | year = 1994| volume = 59| pages = 5445–5452| issue = 18 | doi = 10.1021/jo00097a057 }}</ref> As taxodone readily decomposes into taxodione this synthesis of taxodone also constitutes a formal synthesis of taxodione as well. |
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In 1993 taxodone was synthesized for the first time in a 16 step sequence utilizing a unique phenol benzylic epoxide electron reorganization in the final step.<ref>{{cite journal |author1=Sanchez, Anthony J. |author2=Konopelski, Joseph P. | title = The First Total Synthesis of (±)-Taxodone| journal = ] | year = 1994| pages = 335–336 | doi=10.1055/s-1994-22844 | volume=1994|issue=5 |s2cid=196814605 }}</ref><ref>{{cite journal |author1=Sanchez, Anthony J. |author2=Konopelski, Joseph P. | title = Phenol Benzylic Epoxide to Quinone Methide Electron Reorganization: The Synthesis of (±)-Taxodone| journal = ] | year = 1994| volume = 59| pages = 5445–5452| issue = 18 | doi = 10.1021/jo00097a057 }}</ref> As taxodone readily decomposes into taxodione this synthesis of taxodone also constitutes a formal synthesis of taxodione as well. |
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Since the synthesis of taxodone there have been additional syntheses of taxodione and analogs.<ref name=tada2010/><ref>{{cite journal |author1=Scott R. Harring |author2=Tom Livinghouse |name-list-style=amp | title = Polyene cascade cyclizations mediated by BF<sub>3</sub>·CH<sub>3</sub>NO<sub>2</sub>. an unusually efficient method for the direct, stereospecific synthesis of polycyclic intermediates via cationic initiation at non-functionalized 3° alkenes. An application to the total synthesis of (±)-taxodione |journal = ] | year = 1994 | volume = 50 | issue = 31 | pages = 9229–9254 | doi = 10.1016/S0040-4020(01)85502-2}}</ref><ref>{{cite journal | author = E. Alvarez-Manzaneda, R. Chahboun, E. Cabrera, E. Alvarez, R. Alvarez-Manzaneda, M. Lachkar and I. Messouri| title = First synthesis of picealactone C. A new route toward taxodione-related terpenoids from abietic acid | journal = ] | year = 2007| volume = 48 | issue = 6 | pages = 989–992 | doi = 10.1016/j.tetlet.2006.12.009}}</ref> |
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Since the synthesis of taxodone there have been additional syntheses of taxodione and analogs.<ref name=tada2010/> |
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<ref>{{cite journal | author = Scott R. Harring and Tom Livinghouse | title = Polyene cascade cyclizations mediated by BF3·CH3NO2. an unusually efficient method for the direct, stereospecific synthesis of polycyclic intermediates via cationic initiation at non-functionalized 3° alkenes. An application to the total synthesis of (±)-taxodione | journal = ] | year = 1994 | volume = 50 | issue = 31 | pages = 9229–9254 | doi = 10.1016/S0040-4020(01)85502-2}}</ref><ref>{{cite journal | author = E. Alvarez-Manzaneda, R. Chahboun, E. Cabrera, E. Alvarez, R. Alvarez-Manzaneda, M. Lachkar and I. Messouri| title = First synthesis of picealactone C. A new route toward taxodione-related terpenoids from abietic acid | journal = ] | year = 2007| volume = 48 | issue = 6 | pages = 989–992 | doi = 10.1016/j.tetlet.2006.12.009}}</ref> |
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==Notes and references== |
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*{{cite journal | author = Sanchez, Anthony J.; Konopelski, Joseph P. | title = Phenol Benzylic Epoxide to Quinone Methide Electron Reorganization: The Synthesis of (±)-Taxodone| journal = ] | year = 1994| volume = 59| pages = 5445–5452| issue = 18 | doi = 10.1021/jo00097a057 }} |
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*{{cite journal |author1=Sanchez, Anthony J. |author2=Konopelski, Joseph P. | title = Phenol Benzylic Epoxide to Quinone Methide Electron Reorganization: The Synthesis of (±)-Taxodone| journal = ] | year = 1994| volume = 59| pages = 5445–5452| issue = 18 | doi = 10.1021/jo00097a057 }} |
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