Taxuspines E ∼ H and J, new taxoids from the Japanese yew Taxus cuspidata

Kobayashi, Jun’ichi; Inubushi, Akiko; Hosoyama, Hirokazu; Yoshida, Norinobu; Sasaki, Takuma; Shigemori, Hideyuki

doi:10.1016/0040-4020(95)00255-7

Cited by 49 publications

(27 citation statements)

References 18 publications

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“…9). Taxagifine (108) and taxinine M (111) represent two taxanes with a 12,16-epoxy ring, which showed modest cytotoxicities against KB cells, although there is no oxetane ring in the molecules which was regarded as an essential element [36]. The 1 H-NMR of this Fig.…”

Section: 144mentioning

confidence: 98%

“…1700-fold less cytotoxic against KB cells than taxol [102]. On the other hand, taxchinin B (13) containing an oxetane ring showed no cytotoxicity against KB cells [36].…”

Section: 2mentioning

confidence: 99%

“…Irradiation of the corresponding 13-oxotax-11-enes led to the bonding between C(3) and C(11); however, only a mixture of isomers was obtained ((Z)-and (E)-configured side-chains) [92], and the 3,11-bridge rendered the structure less flexible. Taxinine K (27) and taxinine L (28) are the first two 3,11-cyclotaxanes from T. cuspidata [40], while taxuspine H (30) is the sole 3,11-cyclotaxane with an alkaloid side chain at C(5) [36], and 34 is the first 3,11-cyclotaxane with a glycoside at C(5) [38] (see Fig. 3).…”

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Chemical Studies on Taxus cuspidata

Dong

Zhang

et al. 2010

Chemistry & Biodiversity

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Section: 144mentioning

confidence: 98%

“…1700-fold less cytotoxic against KB cells than taxol [102]. On the other hand, taxchinin B (13) containing an oxetane ring showed no cytotoxicity against KB cells [36].…”

Section: 2mentioning

confidence: 99%

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confidence: 99%

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Chemical Studies on Taxus cuspidata

Dong

Zhang

et al. 2010

Chemistry & Biodiversity

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“…Taxuspine N (13) was the first example of taxoids containing a 6/8/6-membered ring system with a 3-N,N-dimethylamino-3-phenylpropanoyl group at C-13 from Taxus species. Taxuspines H (8), N (13), P (15), and Z (25) contained a 3-N,N-dimethylamino-3-phenylpropanoyl group (Winterstein's acid). The absolute stereochemistry of this group was determined to be all R by chiral HPLC analysis (Sumichiral OA-5000) of the acid hydrolysates of taxuspines H (8), N (13), P (15), and Z (25).…”

Section: Taxanes (6/8/6-membered Ring System)mentioning

confidence: 99%

Bioactive taxoids from the Japanese yew Taxus cuspidata

Kobayashi

Shigemori

2002

Medicinal Research Reviews

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A series of new taxoids, named taxuspines A-H and J-Z (1-25) and taxezopidines A-H and J-L (26-36), have been isolated together with 37 known taxoids (37-73) including paclitaxel (53) from the Japanese yew, Taxus cuspidata Sieb. et Zucc. (Taxaceae). These new taxoids possess various skeletons containing 5/7/6, 6/10/6, 6/5/5/6, 6/8/6, or 6/12-membered ring systems. Among the new taxoids, some non-taxol-type compounds remarkably reduced CaCl(2)-induced depolymerization of microtubules, or increased cellular accumulation of vincristine in multidrug-resistant tumor cells as potent as verapamil. On the other hand, chemical derivatization of taxinine (37), one of major taxoids obtained from this yew, led to the discovery of unusual reactions of taxinine derivatives. Here we describe our recent results on the isolation, structure elucidation, and bioactivity of these new and known taxoids and the formation of unexpected products of the unusual reactions of taxinine.

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“…for C 31 H 38 O 7 K requires 561.2255). The 1 H-and 13 C-NMR, COSY and HMBC spectra tabulated in Table 2 indicated compound 2 to have a 3,11-cyclotaxane skeleton 3,6,11) with one acetoxy, one cinnamoyloxy, one keto and two hydroxy groups. The HMBC spectrum showed that the acetoxy and the cinnamoyloxy groups were respectively located at the 2-and 5-positions.…”

Section: )mentioning

confidence: 99%

New 2(3→20)Abeotaxane and 3,11-Cyclotaxane from Needles ofTaxus cuspidata

Shi

Zhao

et al. 2004

Bioscience, Biotechnology, and Biochemistry

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Two new taxoid metabolites, 2; 7; 10-triacetoxy-5,13-dihydroxy-2(3 ! 20)abeotaxa-4(20),11-dien-9-one (1) and 2-acetoxy-5-cinnamoyloxy-9,10-dihydroxy-3,11-cyclotax-4(20)-en-13-one (2), were isolated from the methanol extract of needles of the Japanese yew, Taxus cuspidata.Key words: Taxus cuspidata; Taxaceae; needles; 2(3 ! 20)abeotaxane; 3,11-cyclotaxane Yew trees are a rich source of biologically active taxane diterpenoids such as taxol Ò (paclitaxel), one of the most important drugs for ovarian and breast cancer currently on the market.1,2) Its unique mechanism of action, limited solubility and shortage have generated worldwide interest, and extensive chemical studies have been carried out.1-4) In a continuation of our studies on taxanes, 5,6) two new compounds were isolated from needles of the Japanese yew, Taxus cuspidata.Compound 1 was isolated from a methanolic extract of needles of Taxus cuspidata as white powder {½ D 22 ¼ À40 (c 0.06, CHCl 3 )} and its HR-FABMS analysis revealed the molecular formula as C 26 H 36 O 9 (m=z 531.1998 [MþK] þ , calcd. for C 26 H 36 O 9 K requires 531.1996). A combined analysis by 1-D and 2-D NMR (Table 1) revealed that 1 had a 2(3 ! 20)abeotaxane skeleton 3,5-10) with one keto, two hydroxy and three acetoxy groups. The positions of these functionalities was established by the HMBC spectrum. The relative configuration and proposed conformation of 1 were estimated from the results of an NOESY experiment (Table 1 and Fig. 1), enabling compound 1 to be unambiguously characterized as 2; 7; 10-triacetoxy-5,13-dihydroxy-2(3 ! 20)abeotaxa-4(20),11-dien-9-one. This was the 2-O-acetyl derivative of the compound previously isolated by us from the Chinese yew, Taxus mairei. 10)Compound 2 was isolated as a colorless gummy substance {½ D 22 ¼ þ19 (c 0.11, CHCl 3 )}. Its quasimolecular ion at m=z 561.2256 (MþK) þ generated by HR-FABMS revealed that the molecular formula of 2 was putatively C 31 H 38 O 7 (calcd. for C 31 H 38 O 7 K requires 561.2255). The 1 H-and 13 C-NMR, COSY and HMBC spectra tabulated in Table 2 indicated compound 2 to have a 3,11-cyclotaxane skeleton 3,6,11) with one acetoxy, one cinnamoyloxy, one keto and two hydroxy groups. The HMBC spectrum showed that the acetoxy and the cinnamoyloxy groups were respectively located at the 2-and 5-positions. The relative configuration was determined by an NOESY experiment, and the conformation is proposed to be that shown in Fig. 1. The structure of 2 was characterized as 2-acetoxy-5-cinnamoyloxy-9,10-dihydroxy-3,11-cyclotax-4(20)-en-13-one. This is the 10-O-deacetyl derivative of taxane isolated from seeds of the Chinese yew, Taxus yunnanensis. Biosci. Biotechnol. Biochem., 68 (7), [1584][1585][1586][1587] 2004 Note preparative column (22 Â 500 mm). Plant material. Needles of Taxus cuspidata, which were identified by Prof. Takashi Oritani of Toyama Prefectural University (Japan), were collected in the autumn of 2000 at Tsutsuzigaoka Park (Sendai, Japan).Extraction and isolation. Air-dried needles of Taxus cuspidata were ground...

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Taxuspines E ∼ H and J, new taxoids from the Japanese yew Taxus cuspidata

Cited by 49 publications

References 18 publications

Chemical Studies on Taxus cuspidata

Chemical Studies on Taxus cuspidata

Bioactive taxoids from the Japanese yew Taxus cuspidata

New 2(3→20)Abeotaxane and 3,11-Cyclotaxane from Needles ofTaxus cuspidata

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