Chemistry of Chinese yew, Taxus chinensis var. mairei

Li, Cunfang; Huo, Changhong; Zhang, Manli; Shi, Qing

doi:10.1016/j.bse.2007.08.002

Cited by 42 publications

(26 citation statements)

References 67 publications

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“…Fr. B-6 (2.3 g) was subjected to Sephadex LH-20, further purification by NP-HPLC using hexane/CH 2 ; calc. 591.2417).…”

Section: Taiwantaxin C (3)mentioning

confidence: 99%

“…The demand for this promising anticancer agent and new important intermediates from a new source led to isolation of various taxoids [2]. Diterpenes with different taxane skeletons are commonly found in this genus [2]. A normal taxane contains an eight-membered ring, sandwiched between two six-membered rings, but there are numerous compounds, which have rearranged taxane skeletons.…”

mentioning

confidence: 99%

“…The chemical constituents of different Taxus species have been studied for several decades. The demand for this promising anticancer agent and new important intermediates from a new source led to isolation of various taxoids [2]. Diterpenes with different taxane skeletons are commonly found in this genus [2].…”

mentioning

confidence: 99%

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abeo‐Taxane Diterpenoids from the Taiwanese Yew Taxus sumatrana

Wang

El‐Razek²,

Chen

et al. 2009

Chemistry & Biodiversity

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Chemical investigation of the acetonic extract of the leaves and twigs of Taxus sumatrana (Taxaceae) led to the isolation of four new taxane diterpene esters, taiwantaxins A-D (1-4, resp.). Their structures were determined primarily on the basis of 1D- and 2D-NMR techniques as well as MS. Compound 1 is a rearranged taxane diterpenoid possessing an opened oxetane ring moiety containing C(4), C(5), and C(20). The metabolites 2 and 3 belong to a 5/6/6 taxene system having a rare five-membered gamma-lactone ring comprising C(8), C(9), C(10), and C(19). Compound 4 is an example of a taxane diterpene containing a 6/8/6 ring system with a tetrahydrofuran ring comprising C(2), C(3), C(4), and C(20). The 11(15-->1)abeo-taxane diterpenoids, taiwantaxins A-C (1-3, resp.) are lacking an O-bearing functionality at either C(13) or C(14). Compound 2 showed significant cytotoxic activity against human PC-3 tumor cells.

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“…Fr. B-6 (2.3 g) was subjected to Sephadex LH-20, further purification by NP-HPLC using hexane/CH 2 ; calc. 591.2417).…”

Section: Taiwantaxin C (3)mentioning

confidence: 99%

mentioning

confidence: 99%

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abeo‐Taxane Diterpenoids from the Taiwanese Yew Taxus sumatrana

Wang

El‐Razek²,

Chen

et al. 2009

Chemistry & Biodiversity

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“…Taxol, the representative composition, showed significant antitumour effect mainly due to its unique mechanism (Schiff et al 1979). Since taxanes have been an important target for cancer therapy agents for a long time, many other important compounds such as flavonoids, lignans, steroids, phenolic acids, sesquiterpenes, nontaxane diterpenoids and inositol ethers (Li et al 2008) have been isolated from T. chinensis var. mairei.…”

Section: Introductionmentioning

confidence: 99%

A new taxane diterpenoid fromTaxus chinensisvar.mairei

Zhou

Liu

et al. 2014

Natural Product Research

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Taxadiene (3), a new taxane diterpenoid with an unusual hydroxy substituting at C-17, and six known compounds including two taxane diterpenoids (1 and 2) and four flavonoids (4-7) were isolated from the whole seedling of the Taxus chinensis var. mairei. Among them, compound 7 was isolated from T. chinensis var. mairei for the first time. Structures of these compounds were elucidated on the basis of spectroscopic data and by comparison with reported literature data.

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“…9)-di-abeo-taxanes, the 2(3 ! 20)-abeotaxanes (6/10/6-membered ring system), transannular taxanes, 3,11-cyclotaxanes, and 3,8-seco-taxanes (bicyclic taxanes 6/12-membered ring system) [2]. Current interest in the genus Taxus due to the presence of promising anticancer compounds in different parts of the plant focuses on obtaining diterpenes having complex tricyclic systems commonly referred to as taxanes [3].…”

mentioning

confidence: 99%

Tri‐ and Bicyclic Taxoids from the Taiwanese Yew Taxus sumatrana

Luh

El‐Razek

Liaw

et al. 2009

Helvetica Chimica Acta

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Five new taxoids, including a new 2(3 ! 20)-abeo-taxane with a 6/10/6-membered ring system and four 3,8-seco-taxanes having a 6/12-membered ring system, were isolated from an acetone extract of the leaves and twigs of the Taiwanese yew (Taxus sumatrana, Taxaceae). The structures were established as 2a,7b,10a-triacetoxy-5a-hydroxy-2(3 ! 20)-abeo-taxa-4(20),11-dien-9,13-dione (1), (3E,8E)-2a,9,10b, 13a,20-pentaacetoxy-7b-hydroxy-3,8-secotaxa-3,8,11-trien-5-one (2), (3E,8E)-2a,9,10b,13a,20-pentaacetoxy-5a,7b-dihydroxy-3,8-secotaxa-3,8,11-triene (3), (3E,8E)-9,10b,13a-triacetoxy-2a,7b,20-trihydroxy-5a-[(2E)-cinnamoyloxy]-3,8-secotaxa-3,8,11-triene (4), and (3E,8E)-2a, 5a,7b,9,10b,13a-hexaacetoxy-20-hydroxy-3,8-secotaxa-3,8,11-triene (5), respectively, on the basis 1D-and 2D-NMR spectral analyses. The in vitro cytotoxic activity of compounds 1 -5 against four human tumor cell lines, including HeLa (cervical epitheloid), WiDr (colon), Daoy (medulloblastoma), and Hep2 (liver carcinoma) tumor cells was evaluated. Whereas compounds 1 -3 were inactive, the novel taxanes 4 and 5 showed significant cytotoxicity.

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Chemistry of Chinese yew, Taxus chinensis var. mairei

Cited by 42 publications

References 67 publications

abeo‐Taxane Diterpenoids from the Taiwanese Yew Taxus sumatrana

abeo‐Taxane Diterpenoids from the Taiwanese Yew Taxus sumatrana

A new taxane diterpenoid fromTaxus chinensisvar.mairei

Tri‐ and Bicyclic Taxoids from the Taiwanese Yew Taxus sumatrana

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