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Koetsu Takahashi - One of the best experts on this subject based on the ideXlab platform.
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antifungal Abietane type diterpenes from the cones of taxodium distichum rich
Journal of Chemical Ecology, 2010Co-Authors: Norihisa Kusumoto, Tatsuya Ashitani, Tetsuya Murayama, Koichi Ogiyama, Koetsu TakahashiAbstract:The chemical composition of Taxodium distichum cones and the antifungal activities of twelve diterpenoids against two wood decay fungi, Trametes versicolor (white-rot) and Fomitopsis palustris (brown-rot) were examined. The chemical composition of the major extractive fraction, the n-C6H14 extract, was evaluated and its antifungal properties were identified. Twelve diterpenoids including ten Abietane-type components were isolated from the n-C6H14 extract: 6,7-dehydroferruginol (1), ferruginol (2), 6,7-dehydroroyleanone (3), sandaracopimaric acid (4), taxodione (5), taxodal (6), taxodone (7), sugiol (8), xanthoperol (9), salvinolone (10), 5,6-dehydrosugiol (11), and 14-deoxycoleon U (12). Compounds 5 and 12 were highly active against both wood-decay fungi. In particular, the activities of these compounds against F. palustris were potent. The results suggest that the position and the number of hydroxyl groups on Abietane-type structures may be related to antifungal activities against T. versicolor and F. palustris.
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Antitermitic Activities of Abietane-type Diterpenes from Taxodium distichum Cones
Journal of Chemical Ecology, 2009Co-Authors: Norihisa Kusumoto, Tatsuya Ashitani, Tetsuya Murayama, Koichi Ogiyama, Yuichi Hayasaka, Koetsu TakahashiAbstract:Eight known Abietane-type diterpenes were isolated from the weak acidic fraction of the n -hexane extract from cones of Taxodium distichum , one of the extant, living fossil conifers. They were identified as 6,7-dehydroroyleanone ( 1 ), taxodal ( 2 ), taxodione ( 3 ), salvinolone ( 4 ), 14-deoxycoleon U ( 5 ), 5,6-dehydrosugiol ( 6 ), sandaracopimaric acid ( 7 ), and xanthoperol ( 8 ). The structures of these compounds were determined by comparison of NMR spectral data with published data. The antitermitic (termicidal and antifeedant) activities of the compounds 1 – 8 against the subterranean termite, Reticulitermes speratus Kolbe, were evaluated. Compounds 1 and 3 showed potent termicidal activity, and 5 and 8 showed potent antifeedant activity. Compound 1 was found to be one of the representative bioactive compounds in the n -hexane extract of T. distichum cones. Compounds 1 – 8 , with the exception of 7 , were oxides of ferruginol ( 9 ). Therefore, the presence of various oxidation forms of the Abietane-type structure reflects their various bioactivities.
Jinfeng Hu - One of the best experts on this subject based on the ideXlab platform.
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trichotomone a new cytotoxic dimeric Abietane derived diterpene from clerodendrum trichotomum
Tetrahedron Letters, 2013Co-Authors: Juan Xiong, Zhilai Hong, Guoxun Yang, Wenxuan Wang, Ming Li, Yun Zhao, Ya Huang, Jinfeng HuAbstract:Abstract A novel dimeric diterpene (named trichotomone, 1 ) was isolated from the roots of the medicinal ornamental plant Clerodendrum trichotomum . Compound 1 is a rare phenolic ketal of a regular Abietane derivative cyrtophyllone B and a rearranged Abietane derivative containing a 17(15→16),18(4→3)- diabeo -Abietane framework related to uncinatone. The structure was elucidated by extensive spectroscopic methods. The absolute configuration was defined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Trichotomone ( 1 ) exhibited in vitro cytotoxicities against several human cancer cell lines (A549, Jurkat, BGC-823 and 293T WT) with IC 50 values ranged from 7.51 to 19.38 μM.
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rearranged Abietane diterpenoids from the roots of clerodendrum trichotomum and their cytotoxicities against human tumor cells
Phytochemistry, 2013Co-Authors: Wenxuan Wang, Juan Xiong, Guoxun Yang, Yu Tang, Ming Li, Yun Zhao, Jinfeng HuAbstract:Abstract The roots of the medicinal ornamental plant Clerodendrum trichotomum yielded a series of rearranged Abietane diterpenoids, including three 17(15 → 16)-abeo-Abietane (1–3) and three 17(15 → 16),18(4 → 3)-diabeo-Abietane (4–6) derivatives. Their structures were elucidated by means of spectroscopic methods. The absolute configuration of (10R,16R)-12,16-epoxy-11,14,17-trihydroxy-6-methoxy-17(15 → 16)-abieta-5,8,11,13-tetraene-7-one (1) was deduced by a combination of single crystal X-ray diffraction analysis and the observed Cotton effects in its circular dichroism (CD) spectrum. All isolates were tested for their cytotoxicities against five human cancer cell lines (BGC-823, Huh-7, KB, KE-97, and Jurkat). Among them, compounds 4, 6, 9, 10, 12, and 14, each possessing a common 17(15 → 16),18(4 → 3)-diabeo-Abietane framework, were found to have remarkable cytotoxic effects with IC50 values ranging from 0.83 to 50.99 μM.
Irmgard Merfort - One of the best experts on this subject based on the ideXlab platform.
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Abietane diterpenes induce cytotoxic effects in human pancreatic cancer cell line mia paca 2 through different modes of action
Phytochemistry, 2012Co-Authors: Marcio Fronza, Berta Maria Heinzmann, Stefan Laufer, Evelyn Lamy, Stefan Gunther, Irmgard MerfortAbstract:Abstract Abietane diterpenes, especially those containing quinone moieties, are often reported to have cytotoxic effects on cancer cell lines. They deserve greater attention because several cancer chemotherapeutic agents also possess the quinone structural feature. To date, very little is known about their cytotoxic molecular modes of action. In the present study, five diterpenes, 7 alpha-acetoxyroyleanone, horminone, royleanone, 7-ketoroyleanone and sugiol which have been previously isolated from the medicinal plant Peltodon longipes were shown to possess cytotoxic activity against the human pancreatic cancer cell line MIA PaCa-2. 7 alpha-Acetoxyroyleanone, horminone and royleanone were demonstrated to possess alkylating properties using the nucleophile 4-(4-nitrobenzyl)pyridine. However, no clear correlation between the alkylating properties and cytotoxicity of these diterpenes was observed. Furthermore, the relaxation activity of human DNA topoisomerases I and II was found to be influenced by these compounds, with 7-ketoroyleanone and sugiol being the most active. These two diterpenes preferentially inhibited topoisomerase I and exhibited lower IC50 values than the classical topoisomerase I inhibitor camptothecin. Molecular docking studies revealed possible interactions of diterpenes with topoisomerase I, indicating that these compounds do not form the drug–enzyme–DNA covalent ternary complex as observed with camptothecin. A binding pocket located at the surface of the DNA-interaction site was proposed. Moreover, the ability of the five diterpenes to generate DNA-strand breaks in single cells was confirmed using the alkaline comet assay. As expected, these diterpenes also influenced cell cycle progression and arrested cells in different phases of the cell cycle, primarily the G1/G0 and S-phases. Interestingly, the diterpenes only exhibited a slight ability to induce apoptotic cell death and failed to generate intracellular reactive oxygen species. These results provide additional understanding of the cytotoxic effects of Abietane diterpenes. Depending on their functional groups, we propose that Abietane diterpenes utilise different mechanisms to induce cell death.
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in vitro cytotoxic activity of Abietane diterpenes from peltodon longipes as well as salvia miltiorrhiza and salvia sahendica
Bioorganic & Medicinal Chemistry, 2011Co-Authors: Marcio Fronza, Renato Murillo, S ślusarczyk, Michael Adams, Matthias Hamburger, Berta Maria Heinzmann, Stefan Laufer, Irmgard MerfortAbstract:Phytochemical investigations of the n -hexane extract from the roots of Peltodon longipes (Lamiaceae) resulted in the isolation of 12 known Abietane diterpenes ( 1–12 ). Structures were established on the basis of one and two dimensional nuclear magnetic resonance spectroscopic data ( 1 H and 13 C, COSY, HSQC and HMBC), electron ionization mass spectrometric analysis (EIMS) as well as comparison with data from literature. These compounds, as well as eight known diterpenes ( 13–19 ) from Salvia miltiorrhiza , and two from Salvia sahendica ( 20 and 21) were evaluated for their cytotoxic effects in human pancreatic (MIAPaCa-2) and melanoma (MV-3) tumor cell lines using the MTT assay. Tanshinone IIa ( 13 ), 7α-acetoxyroyleanone ( 1 ), 1,2-dihydrotanshinone ( 16 ) and cryptotanshinone ( 14 ) had the highest cytotoxic effects in MIAPaCa-2, displaying IC 50 of 1.9, 4.7, 5.6, and 5.8 μM, respectively. Structure–activity relationships of Abietane diterpenoid quinones are discussed.
Rui Zhang - One of the best experts on this subject based on the ideXlab platform.
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Three new Abietane-type diterpene glycosides from the roots of Tripterygium wilfordii.
Fitoterapia, 2017Co-Authors: Qiushan Wu, Rui ZhangAbstract:Abstract Three new Abietane-type diterpene glycosides named as tripterycoside A (1), tripterycoside B (2), tripterycoside C (3), along with two known ones, 11-O-β- d -glucopyranosyl-neotritophenolide (4), wilfordoside A (5), and nine other known compounds, 5-hydroxymethylmellein (6),1,2-bis-(3-methoxy-4-hydroxyphenyl)-1,3-propanediol (7), leptolepisol C (8), icariol A2 (9), tripfordine A (10), 16α-hydroxy-ent-kauran-19-oic acid (11),wilforine (12), wilfordine (13), 3-acetyloleanolic acid (14),were isolated from the roots of Tripterygium wilfordii. Their structures have been elucidated on the basis of NMR and MS data. To the best of our knowledge, Abietane-type diterpene glycosides were rarely reported natural products, especially Abietane-type diterpene glycoside containing 7-oxo group (compound 3) was reported here for the first time. Furthermore, compounds 6, 7, 8 and 14 were isolated from this plant for the first time. Compounds 1–5 showed statistically significant inhibitory effects on IL-1β secretion in LPS-induced rat primary synovial fibroblasts at 10 μM.
Wenxuan Wang - One of the best experts on this subject based on the ideXlab platform.
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trichotomone a new cytotoxic dimeric Abietane derived diterpene from clerodendrum trichotomum
Tetrahedron Letters, 2013Co-Authors: Juan Xiong, Zhilai Hong, Guoxun Yang, Wenxuan Wang, Ming Li, Yun Zhao, Ya Huang, Jinfeng HuAbstract:Abstract A novel dimeric diterpene (named trichotomone, 1 ) was isolated from the roots of the medicinal ornamental plant Clerodendrum trichotomum . Compound 1 is a rare phenolic ketal of a regular Abietane derivative cyrtophyllone B and a rearranged Abietane derivative containing a 17(15→16),18(4→3)- diabeo -Abietane framework related to uncinatone. The structure was elucidated by extensive spectroscopic methods. The absolute configuration was defined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Trichotomone ( 1 ) exhibited in vitro cytotoxicities against several human cancer cell lines (A549, Jurkat, BGC-823 and 293T WT) with IC 50 values ranged from 7.51 to 19.38 μM.
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rearranged Abietane diterpenoids from the roots of clerodendrum trichotomum and their cytotoxicities against human tumor cells
Phytochemistry, 2013Co-Authors: Wenxuan Wang, Juan Xiong, Guoxun Yang, Yu Tang, Ming Li, Yun Zhao, Jinfeng HuAbstract:Abstract The roots of the medicinal ornamental plant Clerodendrum trichotomum yielded a series of rearranged Abietane diterpenoids, including three 17(15 → 16)-abeo-Abietane (1–3) and three 17(15 → 16),18(4 → 3)-diabeo-Abietane (4–6) derivatives. Their structures were elucidated by means of spectroscopic methods. The absolute configuration of (10R,16R)-12,16-epoxy-11,14,17-trihydroxy-6-methoxy-17(15 → 16)-abieta-5,8,11,13-tetraene-7-one (1) was deduced by a combination of single crystal X-ray diffraction analysis and the observed Cotton effects in its circular dichroism (CD) spectrum. All isolates were tested for their cytotoxicities against five human cancer cell lines (BGC-823, Huh-7, KB, KE-97, and Jurkat). Among them, compounds 4, 6, 9, 10, 12, and 14, each possessing a common 17(15 → 16),18(4 → 3)-diabeo-Abietane framework, were found to have remarkable cytotoxic effects with IC50 values ranging from 0.83 to 50.99 μM.
