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Taxodone

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Not to be confused with Taxodione.
Taxodone
Taxodone
Taxodone 3d
Names
IUPAC name
(4bS,8aS,9S)-4,9-Dihydroxy-4b,8,8-trimethyl-2-propan-2-yl-6,7,8a,9-tetrahydro-5H-phenanthren-3-one
Other names
6,11-Dihydroxyabieta-7,9(11),13-trien-12-one, NSC122420, AC1L9XIL, CID457961
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=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 checkY
    Key: QEAIMIKGLGBTSA-ADLFWFRXSA-N checkY
  • 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
    Key: QEAIMIKGLGBTSA-ADLFWFRXBH
  • O=C1\C(=C/C=2/C(=C1/O)[C@]3(C)[C@@H]([C@@H](O)C=2)C(C)(C)CCC3)C(C)C
Properties
C20H28O3
Molar mass 316.441 g·mol−1
Appearance Golden crystalline solid
Melting point 176 to 177 °C (349 to 351 °F; 449 to 450 K)
Insoluble
Solubility in chloroform, alcohol, hexane, ether Soluble
Related compounds
Related compounds
 Taxodione
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Taxodone is a naturally occurring diterpenoid found in Taxodium distichum (Bald Cypress), Rosmarinus officinalis (Rosemary), several Salvia species and other plants, along with its oxidized rearrangement product, taxodione. Taxodone and taxodione exhibit anticancer,[1][2][3] antibacterial,[4][5][6] antioxidant,[7] antifungal,[8] insecticide,[9] and antifeedant[10] activities.

Discovery

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.

Occurrence

Taxodone and/or taxodione have been identified in several plants besides Taxodium distichum including: Rosmarinus officinalis (Rosemary),[13] Salvia barrelieri,[7] Metasequoia glyptostroboides (Dawn Redwood),[4] Salvia munzii (San Diego Sage),[14] Salvia moorcroftiana,[15] Salvia staminea,[16] Salvia clevelandii (Cleveland Sage),[17] Salvia hypargeia,[3] Salvia broussonetii,[18] Salvia montbretii,[19][20] Salvia nipponica,[21][22] Salvia verbenaca (Wild Clary),[23] Salvia lanigera,[24][25]Salvia prionitis,[26] Salvia deserta,[27] Salvia phlomoides,[28][29] and Plectranthus hereroensis[30]

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]

Activity

Taxodone and taxodione possess in vivo activity against Walker intramuscular carcinosarcoma 256 in rats (25 and 40 mg/kg, respectively) and in vitro activity against cells derived from human carcinoma of the nasopharynx (KB) (ED50 = 0.6 and 3 ug/ml respectively).[1] Taxodone and taxodione exhibit antifungal activity against wood decay fungi, with taxodione being especially active against Trametes versicolor and Fomitopsis palustris.[8] Taxodione exhibited the highest antioxidant activity among the tested diterpenoids from the roots of Salvia barrelieri.[7] Taxodone showed potent antibacterial effects against foodborne pathogenic bacteria, such as Listeria monocytogenes ATCC 19166, Salmonella typhimurium KCTC 2515, Salmonella enteritidis KCTC 2021, Escherichia coli ATCC 8739, Escherichia coli O157:H7 ATCC 43888, Enterobacter aerogenes KCTC 2190, Staphylococcus aureus ATCC 6538 and Staphylococcus aureus.KCTC 1916[4] Taxodone showed potent termicidal activity against the subterranean termite, Reticulitermes speratus Kolbe.[9] Taxodione depresses neruonal GABAA receptor-operated Cl-current (IGABA).[39] Taxodione may have potential in treatment of cardiovascular disease.[40]

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]

Chemistry

Taxodone was the first isolated example of a quinone methide[45][46][47][48][49][50] with a labile hydrogen adjacent to this reactive chromophore.[1] Kupchan demonstrated that taxodone aromatizes to a catechol ketone upon exposure to mild acid. Air oxidation of this catechol ketone affords taxodione.

Synthesis

Taxodone rearranges easily in the presence of mild acids and reacts readily with nucleophiles. Although taxodone shows higher anticancer and antibacterial 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.[51][52][53][54][55][56][57][58][59][60][61][62][63][64][65][66][67][68][69]

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]

Notes and references

  1. ^ a b c d Kupchan, 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. PMID 5679178.
  2. ^ Zaghloul A. M.; Gohar A. A.; Naiem Z. A.; Abdel Bar F. M. (2008). "Taxodione, a DNA-binding compound from Taxodium distichum L. (Rich.)". Z. Naturforsch. C. 63 (5–6): 355–360. doi:10.1515/znc-2008-5-608. PMID 18669020.
  3. ^ a b Ayhan Ulubelen, Gülaçti Topçu, Hee-Byung Chai and John M. Pezzuto (1999). "Cytotoxic Activity of Diterpenoids Isolated from Salvia hypargeia". Pharmaceutical Biology. 37 (2): 148–151. doi:10.1076/phbi.37.2.148.6082.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ a b c Vivek K. Bajpai & Sun Chul Kan (2010). "Antibacterial abietane-type diterpenoid, taxodone from Metasequoia glyptostroboides Miki ex Hu". Journal of Biosciences. 35 (4): 533–538. doi:10.1007/s12038-010-0061-z. PMID 21289435.
  5. ^ Vivek K. Bajpai; Minkyun Na; Sun Chul Kang (2010). "The role of bioactive substances in controlling foodborne pathogens derived from Metasequoia glyptostroboides Miki ex Hu". Food and Chemical Toxicology. 48 (7): 1945–1949. doi:10.1016/j.fct.2010.04.041. PMID 20435080.
  6. ^ a b Tada M.; Kurabe J.; Yoshida T.; Ohkanda T.; Matsumoto Y. (2010). "Syntheses and antibacterial activities of diterpene catechol derivatives with abietane, totarane and podocarpane skeletons against methicillin-resistant Staphylococcus aureus and Propionibacterium acnes". Chem Pharm Bull. 58 (6): 818–824. doi:10.1248/cpb.58.818. PMID 20522992.
  7. ^ a b c Ufuk Kolak; Ahmed Kabouche; Mehmet Öztürk; Zahia Kabouche; Gülaçtl Topçu; Ayhan Ulubelen (2009). "Antioxidant diterpenoids from the roots of Salvia barrelieri". Phytochemical Analysis. 20 (4): 320–327. doi:10.1002/pca.1130. PMID 19402189.
  8. ^ a b Norihisa Kusumoto, Tatsuya Ashitani, Tetsuya Murayama, Koichi Ogiyama and Koetsu Takahashi (2010). "Antifungal Abietane-Type Diterpenes from the Cones of Taxodium distichum Rich". Journal of Chemical Ecology. 36 (12): 1381–1386. doi:10.1007/s10886-010-9875-2. PMID 21072573.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  9. ^ a b Norihisa Kusumoto, Tatsuya Ashitani, Yuichi Hayasaka, Tetsuya Murayama, Koichi Ogiyama and Koetsu Takahashi (2009). "Antitermitic Activities of Abietane-type Diterpenes from Taxodium distichum Cones". Journal of Chemical Ecology. 35 (6): 635–642. doi:10.1007/s10886-009-9646-0. PMID 19475449.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  10. ^ M. C. Ballesta-Acosta1, M. J. Pascual-Villalobos and B. Rodríguez (2008). "Short communication. The antifeedant activity of natural plant products towards the larvae of Spodoptera littoralis". Spanish Journal of Agricultural Research. 6 (1): 85–91. doi:10.5424/sjar/2008061-304.{{cite journal}}: CS1 maint: numeric names: authors list (link)
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  12. ^ Hanson, R. C.; Lardy, H. A.; Kupchan, S. M. (1970). "Inhibition of phosphofructokinase by quinone methide and alpha-methylene lactone tumor inhibitors". Science. 168 (3929): 378–380. Bibcode:1970Sci...168..378H. doi:10.1126/science.168.3929.378. PMID 4244949.
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  73. ^ E. Alvarez-Manzaneda, R. Chahboun, E. Cabrera, E. Alvarez, R. Alvarez-Manzaneda, M. Lachkar and I. Messouri (2007). "First synthesis of picealactone C. A new route toward taxodione-related terpenoids from abietic acid". Tetrahedron Lett. 48 (6): 989–992. doi:10.1016/j.tetlet.2006.12.009.{{cite journal}}: CS1 maint: multiple names: authors list (link)

See also


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