| Project/Area Number |
09556020
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 展開研究 |
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| Research Field |
Bioproduction chemistry/Bioorganic chemistry
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| Research Institution | TOHOKU UNIVERSITY |
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Principal Investigator |
ORITANI Takayuki Graduate School of Agricultural Science, Tohoku University, Professor, 大学院・農学研究科, 教授 (20005630)
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| Co-Investigator(Kenkyū-buntansha) |
ORITANI Takashi Toyama Prefectural University, Professor, 教授 (80088997)
KIYOTA Hiromasa Graduate School of Agricultural Science, Tohoku University, Assistant, 大学院・農学研究科, 助手 (30234397)
杉山 長美 東北大学, 農学部, 助教授 (10125586)
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| Project Period (FY) |
1997 – 1999
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| Project Status |
Completed (Fiscal Year 1999)
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| Budget Amount *help |
¥12,400,000 (Direct Cost: ¥12,400,000)
Fiscal Year 1999: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1998: ¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 1997: ¥6,900,000 (Direct Cost: ¥6,900,000)
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| Keywords | yew / Taxus cuspidata / Taxus mairei / Taxus yunnanensis / taxane diterpenoid / 2(3→20)-abeotaxane / bicyclic taxane diterpenoid / タキサンジテルペノイド / 1-hydroxy-taxuspineC / secotaxatriene-2,3-diol / secotaxa-3,7,11-trien-9-one / 11(15→1)-abeotax-11-enetetraol / taxachitriene / canadensene / 単離 / 構造解析 |
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| Research Abstract |
1. Three kinds of yew trees, Japanese yew Taxus cuspidata (needles and seeds) and Chinese yews T. mairei (sees, bark, and needles) and T. yunnanensis (seeds), were investigated, and about 200 compounds including taxoids, flavonoids, ligananes, ecdysteroids, abietanes, 9(10→20)-abeo abietanes, vomifoliol and its derivatives were isolated.
2. More than 70 new taxoids including almost all the structural types were isolated form above three kinds of yew trees, and their structures were established through spectroscopic methods including 1D and 2D NMR techniques.
3. 2(3→20)-Abeotaxanes and bicyclic taxoids were rare in the nature. Among more than 300 taxoids only eight 2(3→20)-abeotaxanes and six bicyclic taxoids were reported in the past researching. In this work, besides six known bicyclic taxoids and six out of eight known 2(3→20)-abeotaxanes, nineteen new bicyclic taxoids and ten new 2(3→20)-abeotaxanes were added to these two smaller groups.
4. Several crucial intermediates were isolated from yew trees for the first time, especially taxoid with 4(5),11-diene and bicyclic taxoid with a 7-en-9-one structural unit (a verticillene skeleton) has never been isolated from Taxus species in the past studies. Accordingly, the isolation of these two kinds of compounds from yew trees may shed light on the biosynthesis of taxane diterpenoids, and also afford new clues for the total synthesis of paclitaxel and related compounds.
5. It was found that T. cuspidata distributed in Shikoku area contained a relatively high level of taxol in the leaves, and that a bicyclic taxane diterpenoids showed the anticancer activity.
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