Taxodone was first isolated in 1968 from the seeds of Taxodium distichum (Bald Cypress) by S. Morris Kupchan and coworkers.[1] They reported the structure determination and basic chemistry of taxodone and its oxidized rearrangement product, taxodione.[11][12] Taxodone occurs naturally in the form of (+)-taxodone.
Taxodone, taxodione and their reaction products have been used as archeological and geological biomarkers.[31][32][33][34][35][36][37]
Analogs of taxodone and taxodione have also been isolated. 2-hydroxy taxodone and 2-hydroxy-taxodione have been found in Salvia texana (Texas Sage).[38] 5,6-Didehydro-7-hydroxy-taxodone was found in Salvia munzii.[14] 7-Hydroxytaxodione, 7,7‘-bistaxodione, and 11,11‘-didehydroxy-7,7‘-dihydroxytaxodione were found in Salvia montbretti.[19][20]
The use of taxodone and taxodione to inhibit hair growth has been patented.[41][42][43] Treatment of benign prostate enlargement with taxodone has also been patented.[44]
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.[70][71] As taxodone readily decomposes into taxodione this synthesis of taxodone also constitutes a formal synthesis of taxodione as well.
Since the synthesis of taxodone there have been additional syntheses of taxodione and analogs.[6][72][73]
^ abcdKupchan, S. M.; Karim, A; Marcks, C. (1968). "Tumor inhibitors. XXXIV. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium distichum". J. Am. Chem. Soc.90 (21): 5923–5924. doi:10.1021/ja01023a061. PMID5679178.
^Kupchan, S. M.; Karim, A; Marcks, C. (1969). "Tumor inhibitors. XLVIII. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium distichum". J. Org. Chem.34 (12): 3912–3918. doi:10.1021/jo01264a036. PMID5357534.
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^Hsiu-Hui Chana, Tsong-Long Hwangb, Chung-Ren Sua, Mopur Vijaya Bhaskar Reddya and Tian-Shung Wu (2011). "Anti-inflammatory, anticholinesterase and antioxidative constituents from the roots and the leaves of Salvia nipponica Miq. var. formosana". Phytomedicine. 18 (2–3): 148–150. doi:10.1016/j.phymed.2010.06.017. PMID21115331.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^Sabri, N. N., Abou-Donia, A. A., Assad, A. M., Ghazy, N. M., El-lakany, A. M., Tempesta, M. S. and Sanson D. R. (1989). "Abietane diterpene quinones from the roots of Salvia verbenaca and S. lanigera". Planta Medica. 55 (6): 582. doi:10.1055/s-2006-962111. PMID17262492. S2CID10020492.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^Benjamın Rodrıguez (2003). "A Methoxyabietane Diterpenoid from the Root of Salvia phlomoides and Structural Correction of Another Diterpene from Cryptomeria japonica". Z. Naturforsch.58b: 324–327.
^A. Zdravkov; A. Bechtel; R. F. Sachsenhofer; J. Kortenski; R. Gratzer (2011). "Vegetation differences and diagenetic changes between two Bulgarian lignite deposits – Insights from coal petrology and biomarker composition". Organic Geochemistry. 42 (3): 237–254. Bibcode:2011OrGeo..42..237Z. doi:10.1016/j.orggeochem.2010.12.006.
^Kenneth E. Peters; Clifford C. Walters; J. Michael Moldowan (2005). "The Biomarker Guide: Biomarkers and isotopes in petroleum systems and Earth History". 2: 546. {{cite journal}}: Cite journal requires |journal= (help)
^C. R. Tirapelli; S. R. Ambrosio; F. B. da Costa; A. M. de Oliveira (2008). "Diterpenes: a therapeutic promise for cardiovascular diseases". Recent Patents on Cardiovascular Drug Discovery. 3 (1): 1–8. doi:10.2174/157489008783331689. PMID18221123.
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^Johnson, W. S.; Shenvi, A. B.; Boots, S. G. (1982). "An approach to taxodione involving biomimetic polyene cyclization methodology". Tetrahedron. 38 (10): 1397–1404. doi:10.1016/0040-4020(82)80219-6.
^Stevens, R. V.; Bisaochi, G. G. (1982). "Benzocyclobutenones as synthons for the synthesis of C-11 oxygenated diterpenoids. Application to the total synthesis of (.+-.)-taxodione". J. Org. Chem.47 (12): 2396–2399. doi:10.1021/jo00133a032.
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