­^¤åºK­n The search for potential anti-tumor agents among taxane diterpenes is becoming an interesting and essential issue in the last two deades. Interest in Taxol was also around strongly when Taxol was discovered as effective clinical anti-cancer drug. In order to discover new Taxol derivatives, the twigs and leaves of the Formosan Taxus sumatrana (Miq) de Laub. growing in the forest of Kaohsiung Liukuei area was collected for phytochemical and anti-tumor investigation. The structures of these taxane diterpenes and their derivatives were established primarily on the basis of their spectral analysis and chemical derivatization. The application of NMR techniques included 1H NMR, 13C NMR, DEPT, COSY, HMQC, HMBC, NOESY and another physical methods which include MS, UV, IR and optical rotation. In this experiment, we have identified as taxinine M (67)¡B 2£\,5£\-dihydroxy-7£],9£\,10£],13-tetraacetoxy-4(20),11-taxadiene (68) ¡B 2£\-deacetyl-5£\-decinnamoyl-taxagifine (69) ¡Bwalifoliol (70) ¡B10-deacetyl-baccatin III (71) ¡B10,13-deacetyl-abeo-baccatin IV (72) ¡B 10-deacetyl-13-oxo-baccatin III (73) ¡B 19-hydroxy-13-oxo-baccatin III (74) ¡A 19-hydroxy-10-deacetyl-baccatin III (75) ¡B19-hydroxy- baccatin III (76) ¡B taxayuntin G (77) ¡B 10-deacetyl-10- oxo-baccatin III (78) ¡B tasumatrol E (79) ¡B tasumatrol F (80) and tasumatrol G (81), among them, compounds 79¡B80¡Band 81 were new compounds from natural source. All of these compounds were sent to medical science research institute in Taiwan for anti-tumor in vitro test. The investigation of their structures and activity relationship is now in progress.

ABSTRACT To search for practical sources of potential useful taxoids and study the structure and activity relationship of taxoids, the leaves of Formosan Taxus mairei was extracted with n-hexane, ethanol, acetone and methanol, respectively. Extensive column and preparative thin layer chromatography by bioassay-directed screening resulted in the isolation of 8 taxoids. Their structures were identified as 2-deacetoxy taxinine J ¡]77¡^ ¡B1£]-hydroxy-5£\-deacetyl baccatin I¡]78¡^¡Btaxumairol Z¡]79¡^¡Btaxayuntin G¡]80¡^¡Btaxuspine F¡]81¡^¡B wallifoliol¡]82¡^¡Btaxumairol Q ¡]83¡^¡B1-deacetyl baccatin III¡]84¡^. The compound 82-containg fraction from another batch of material was acylated to yield a series of derivatives and their structures were identified as 7, 13-diacetylwallifoliol¡]85¡^¡B9, 13 - diacetyltaxumairol W¡]86¡^¡B7, 13-dibenzoylwallifoliol¡]87¡^¡B10, 13 - dibenzoyltaxacustin¡]88¡^¡B7, 9-dibenzoyl taxumairol P¡]89¡^ primarily on the basis of 1- and 2-D NMR techniques including DEPT, COSY and HMBC experiments as well as chemical correlation with know compounds. Among them, compound 79 ¡B83 was first isolated in nature, compounds 78 and 80-82 were first isolated from T. mairei and compounds 85-89 were new derivatives. All of these compounds were sent to National Research Institute of Chinese Medicine for antitumor test in vitro. The investigation of their structure and activity relationship is now in progress.

No description available.

­^ ¤å ºK ­n Nearly 400 taxane diterpenoids have been isolated and identified¡C Taxol is a diterpene amide natural product isolated from Taxus brevifolia. The clinical formulation of Taxol has received US FDA approval for treatment of chemotherapy refractory metastatic breast and ovarian cancers, and the drug has shown activity against other cancers in clinical trials. In order to discover new taxoid derivatives, the twigs and leaves of the Formosan Taxus sumatrana (Miq) de Laub. growing in the forest of Kaohsiung Liukuei area was collected for phytochemical and anti-tumor investigation. This investigation has resulted in the isolation of nineteen taxoids, which were identified as tasumatrol H (1)¡Btasumatrol I (2)¡Btasumatrol J (3)¡Btasumatrol K (4)¡Btasumatrol L (5)¡B10-deacetyl- 13-oxo baccatin III (6) ¡B 10- deacetyl baccatin III (7) 20-acetoxy-2£\-benzyloxy-4£\,5£\,7£\,9£\,13£\-pentahydroxy-11(15-1)11(10-9)bisabeotax-11-eno-10,15- lactone (8) ¡B5£\-hydroxy-2£\,7£],9£\,10£],13£\-tetraacetoxy 4(20) 11¡Vtaxadine (9)¡Btaxuspine F (10) ¡Bbaccatin IV (11)¡Bwalifoliol (12)¡B20-deacetyl texachitriene A (13)¡Btaxinin M (14)¡B7-epi-10 deacetyl taxol (15)¡BTaxol (16)¡Bbaccatin III (17)¡Btaxacin (18) ¡Byunnanxane (19).Among them, compounds 1¡B2¡B3¡B4¡B5 are new compounds from natural source. All structures were established primarily on the basis of 1D and 2D NMR techniques, including DEPT, COSY, HMBC and NOESY experiments. Tasumatrols I¡BJ and K (2-4) exhibited cytotoxicities against human Hepa59T/VGH¡BNCI¡BHela¡BDLD-1 and Med tumor cell lines.

Taxol is a complex polyoxygenated diterpene isolated from Pacific yew (Taxus brevifolia). The structures of Taxoids are diversified with species, season and growth environment and the clinical effectiveness of Taxol as a microtubule-stabilizing therapeutic agent for treatment of several malignancies has motivated many scientists to isolate new taxoids and investigate their anti-tumor activities. In this continuing search for new and bioactive natural taxoids, reinvestigation of the acetone extract of the twigs, needles and branches of Taxus sumatrana (Taxaceae) afforded thirty-seven taxane diterpenes esters, including sumataxins sumataxin A (1)¡Bsumataxin B (2)¡Bsumataxin C (3)¡Bsumataxin D (4)¡Btaxuyunnanine C (5)¡B5a,7B,9a,10B,13a-petaacetoxy-4(20),11-taxadiene (6)¡B2a,5a,9a,10B,14B-pentaacetoxytaxa-4(20),11-taxadiene (7)¡B14B-hydroxytaxusin (8)¡B2a-deacetoxytaxinine J (9)¡Btaxa-4-(20),11-diene-2a,5a,7B,9a,10B,13a-hexaol hexaacetate (10)¡B1-dehydroxy baccatin VI (11)¡B7B,9a,10B,13a,20-pentaacetoxy-2a-benzoyloxy-4a,5a-dihydroxytax-11-ene (12)¡Btaxacin (13)¡Bbaccatin VI (14)¡Btaxuspinanane J (15)¡B2-deacetoxy-5-decinnamoyltaxinine J (16)¡BN-Methyl taxol C (17)¡B10-deacetyl yunnanaxane (18)¡Btaxumairol B (19)¡Btaxinine M (20)¡Bbaccatin III (21)¡Btaxuspinanane I (22)¡Btaxumairol K (23)¡Bwallifoliol (24)¡B13-oxo-baccatin III (25)¡Btaxol (26)¡B7-epi-10-deacetyl taxol (27)¡B10-deacetyl-13-oxo-baccatin III (28)¡B19-hydroxybaccatin III (29)¡B10-deacetyl taxol (30)¡B10-deacetyl-baccatin III (31)¡B13-acetyl-13-decinamoyltaxachinin B (32)¡B5-deacetyltaxachitriene B (33)¡B5-epicanadensene (34)¡Btaxezopidine F (35)¡B13a,7B-diacetoxy-2a,5a,10B-trihydroxy-9-keto-2(3¡÷20)abeotaxane (36)¡B2-deacetyl taxine B (37). The structures of new compounds were established on the basis of their spectroscopic analyses. Among them, compounds 1, 2, 3 and 4 are new compounds from natural source, 2a-deacetoxytaxinine J (9)¡Btaxuspinanane J (15) had effects on PBMC (Peripheral Blood Mononuclear Cells) proliferation, and sumataxin A¡BD (1¡B4) had light exhibitedactivity of HSV-1.

In recent years, many marine invertebrates were studied in the world, and many compounds were discovered from soft corals (for example: sesquiterpenoids, diterpenoids, steroids and so on). From the previous studies on marine nature products, we found that verticillenes of soft corals have similar structures to taxoid diterpenoids of Taxus sp. This prompted us to study Taxus sp., thus we may indirectly understand the correlation of verticillienes of Taxus with verticilliene diterpenes of the soft corals. In order to discover new taxoid derivatives, the twigs and leaves of the Formosan T. sumatrana growing in Taiwan were investigated. Chromatographic separations of acetone extract of the leaves and twigs of this species yielded taxoid-enrich extracts. Fractionation of T. sumatrana has resulted in the isolation of four new compounds 1- 4. All structures were established primarily on the basis of 1D and 2D NMR experiments and other physical methods, such as mass spectroscopy, infrared, ultraviolet and optical rotation. The compound 1 is a taxoid 6/10/6 ring skeleton. The compounds, 2~4, are the verticillene skeleton, but the functional groups are different.

This dissertation mainly discussed the investigation of two different Formosan soft corals, Junceella juncea and Cespitularia taeniata, as well as twigs and needles of Taxus sumatrana (Taxaceae). Their EtOAc extracts were investigated by intensive chromatography. Twenty-seven new natural products were isolated and parts of their biological activities were studied. Three new briarane-type natural products, Juncenolides I-K¡]1-3¡^, were isolated from Junceella juncea. In the research of soft coral Cespitularia taeniata, eleven new compounds inculding two new skeleton natural products ¡]4-5¡^of 6/13 bicyclic, one cespitularane-type diterpene (6), four verticillane-type diterpenes (7-10), one 10, 11-seco verticillane-type diterpene (11), three sesquiterpenes (12-14) were purified. Chemical investigation of Taxus sumatrana (Taxaceae) resulted in isolation of thirteen new taxane diterpenes, including tasumatrols R-U, W, Z ¡]15-18, 20, 23¡^, six wallifoliol-type diterpenes, tasumatrols V, Y¡]19, 22¡^ and 11(15¡÷1), 11(10¡÷9) diabeotaxane diterpenes , taiwantaxins B-C ¡]25-26¡^ ; 2(3¡÷20) abeotaxane diterpene, tasumatrol X ( 21¡^; one 11(15¡÷1) abeotaxane diterpene, taiwantaxin A¡]24¡^; one 6/8/6 ring system diterpene, taiwantaxin D¡]27¡^,. All the structures of above compounds were elucidated by physical and spectroscopic analyses (IR, mass, UV, optical rotation and NMR), and also by comparisions with the published data. Cytotoxicity and in vitro anti-inflammatory activities were measured by Dr. Kuo Yao-Haur, respectively. The biological activities of compounds 1-14 against MCF-7 (Human breast adenocarcinoma), Doay (Human medulloblastoma), WiDr (Human colon adenocarcinoma), Hela (Human cervical epitheloid carcinoma) , compounds 12 and 14 showd weak cytotoxicity. Tasumatrol Y (22) exhibited mild cytotoxicity against human liver carcinoma (Hepa2) with ED50 at 3.5 £gg/mL. Taiwantaxin B (25) showed marked cytotoxicity against human prostate cancer (PC-3) cell lines with an IC50 of 5.02 +0.6 £gg/mL (8.96 +0.34 £gM).

Thesis (Ph. D.)--University of Chicago, 1916. / "Private edition, distributed by the University of Chicago libraries, Chicago, Illinois." "Contributions from the Hull botanical laboratory 234." "Reprinted from the Botanical gazette, vol. LXIV, no. 2, August 1917." "Literature cited": p. 132-133.

Proefschrift Universiteit van Amsterdam. / Met bibliogr., lit. opg. - Met samenvatting in het Nederlands.

Abstract In recent years, Taxus species have attracted a great interest because Paclitaxel, an anticancer agent, was isolated from T.brevifolia. Since the discovery of Paclitaxel many new taxane diterpenes from various Taxus species were isolated. In order to discover new taxoids, twigs and leaves of Taxus sumatrana (Miq.) de Laub. Growing in Taiwan were employed. Chromatographic separation of acetone extract of the leaves and twigs of the plant has yielded four taxane diterpenes and one derivative, designated tasumatrol M (1), tasumatrol N (2), tasumatrol O (3) and 7-deacetyl-canadensene (4). All structures were established primarily on the basis of 1D and 2D NMR techniques, including DEPT, COSY, HMBC and NOESY experiments. Compound 1, 2 and 3 were inactive as tested against human KB, Hepa59T, Hela, DLD-1 and WiDr tumor cell lines. Compounds 1 and 2, possessing a bicyclic skeleton, together with compounds 3 were new compounds from natural source. The possible biosynthetic pathway of compounds 1 and 2 were derived from geranylgeranyl pyrophosphate and verticillene.