Taxanes from Taxus baccata

Appendino, Giovanni; Gariboldi, Pierluigi; Pisetta, Angelo; Bombardelli, Ezio; Gabetta, Bruno

doi:10.1016/0031-9422(92)80454-m

Cited by 64 publications

(47 citation statements)

References 11 publications

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“…It is known that the carbonyl of the five-membered A ring enone typically resonates further downfield (δ 208-210) 17,18 than that of the corresponding six-membered A ring enone in taxinines (δ 198-200). 19 The 13 C NMR spectrum of enone 8 showed a single peak at δ 207, which suggests a fivemembered enone and, thus, an 11(15f1)-abeo-taxane structure. To verify that there had not been any skeletal rearrangement of 2 induced by PCC, which is an acidic reagent, another oxidation of 2 was carried out under neutral conditions 20 with tetrapropylammonium perruthenate (TPAP) and N-methylmorpholine N-oxide (NMO) as catalyst and co-oxidant, respectively.…”

Section: Resultsmentioning

confidence: 99%

Characterization of an abeo-Taxane: Brevifoliol and Derivatives

et al. 2004

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Brevifoliol is a natural diterpene isolated from Taxus baccata Nutt. A series of brevifoliol 1 derivatives, 2-8 and 10, were prepared for characterization and semisynthesis purposes and included the introduction of acetyl, Troc, and TES groups at C-5 and C-13. Derivatives 16-20 of 5-acetylbrevifoliol 2 were obtained via esterification with cinnamic acid, with both 2S-(-)- and 2R-(+)-3-phenyllactic acid, and with N-benzoyl-(2'R,3'S)-3'-phenylisoserine at C-13. Brevifoliol compounds 12, 13, and 15 with either 2S-(-)-phenyllactate moieties at C-5 and C-13 or an N-benzoyl-(2'R,3'S)-3'-phenylisoserinyl at C-13 were also prepared. An abeo-taxane structure for 1 was clearly defined from the (13)C NMR analysis of the 5-acetyl-13-oxo derivative 8 and from the conversion of 1 into 10, a conformationally restrained compound having a C-13, C-15 oxygen bridge. The biological activity of each of these derivatives is being studied.

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Section: Resultsmentioning

confidence: 99%

Characterization of an abeo-Taxane: Brevifoliol and Derivatives

et al. 2004

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“…This is due to the isolation of an antitumor compound Taxol (Paclitaxel) isolated from the bark of Taxus brevifolia (Cragg et al, 1995;Schiff et al, 1979). Appendino et al, (1992) have identified two constituents taxine A (30%) and taxine B (2%) from an amorphous basic fraction known as taxine from the needles of T. wallichiana. Further, an impressive array of taxanes and other analogues, 10-deacetyl-baccatin III, 10-deacetyl-taxol, cephalomannine, 10-deacetyl-cephalomannine, 19-hydroxy-baccatin III were also identified and these are being used as intermediates for the semi-synthesis of Taxol (Appendino et al, 1993;Miller 1980;Mclaughlin et al, 1981).…”

Section: Abies Spectabilismentioning

confidence: 99%

Comparative Pharmacognostic Studies on the Leaves of Abies spectabilis and Taxus wallichiana

Rawat

Mehrotra

Shome

1996

International Journal of Pharmacognosy

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Pharmacognostic studies on the leaves of Abies spectabilis (D. Don) Spach. and Taxus wallichiana Zucc., implicated as 'Talispatra' -an important herbal drug of indigenous systems of medicine, have been performed. Epidermal characters, scanning electron microscopical features along with the fluorescence characters of powder and thin layer chromatography of the hexane extract have been found to be valuable parameters for the identification of these species and for the authentication of marketed drug 'Talispatra'.

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“…These compounds have thus been used in the semisynthesis of 7-deoxy-10-acetyldocetaxel [17], 7-deoxypaclitaxel [18] and their analogues [19]. Other 7-deoxy-9-dihydropaclitaxel analogues bearing acyl groups at C-9 have been synthesized from 5-cinnamoyltriacetyltaxicin-I [20].…”

Section: Investigation Of the Widespread Canadian Yewmentioning

confidence: 99%

General and Recent Aspects of the Chemistry and Structure Activity Relationships of Taxoids

Guéritte

2001

CPD

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The antimitotic agents of the Taxoid series are important substances as anticancer drugs. The efficacy of paclitaxel (Taxol) and docetaxel (Taxotere) has been well demonstrated in the treatment of breast, ovarian and lung cancers. Although these drugs have brought benefits in cancer chemotherapy, they unfortunately possess some disadvantages due to their inefficacy on certain resistant cancers, and due to their toxic side effects. For these reasons, the synthesis of new taxoids with improved biological activity is still an important research area. This review while covering general aspects of taxoid chemistry focuses on recent developments in this area especially those contributing to the improved availability of antimitotic taxoids. Studies of structure-activity relationships are also described.

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Taxanes from Taxus baccata

Cited by 64 publications

References 11 publications

Characterization of an abeo-Taxane: Brevifoliol and Derivatives

Characterization of an abeo-Taxane: Brevifoliol and Derivatives

Comparative Pharmacognostic Studies on the Leaves of Abies spectabilis and Taxus wallichiana

General and Recent Aspects of the Chemistry and Structure Activity Relationships of Taxoids

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