Comparative metabolomic analysis reveals the variations in taxoids and flavonoids among three Taxus species

Abstract Background Trees of the genus Taxus are highly valuable medicinal plants with multiple pharmacological effects on various cancer treatments. Paclitaxel from Taxus trees is an efficient and widely used anticancer drug, however, the accumulation of taxoids and other active ingredients can vary greatly among Taxus species. In our study, the metabolomes of three Taxus species have been investigated. Results A total of 2246 metabolites assigned to various primary and secondary metabolic pathways were identified using an untargeted approach. Analysis of differentially accumulated metabolites identified 358 T. media-, 220 T. cuspidata-, and 169 T. mairei-specific accumulated metabolites, respectively. By searching the metabolite pool, 7 MEP pathway precursors, 11 intermediates, side chain products and derivatives of paclitaxel, and paclitaxel itself were detected. Most precursors, initiated intermediates were highly accumulated in T. mairei, and most intermediate products approaching the end point of taxol biosynthesis pathway were primarily accumulated in T. cuspidata and T. media. Our data suggested that there were higher-efficiency pathways to paclitaxel in T. cuspidata and T. media compared with in T. mairei. As an important class of active ingredients in Taxus trees, a majority of flavonoids were predominantly accumulated in T. mairei rather than T. media and T. cuspidata. The variations in several selected taxoids and flavonoids were confirmed using a targeted approach. Conclusions Systematic correlativity analysis identifies a number of metabolites associated with paclitaxel biosynthesis, suggesting a potential negative correlation between flavonoid metabolism and taxoid accumulation. Investigation of the variations in taxoids and other active ingredients will provide us with a deeper understanding of the interspecific differential accumulation of taxoids and an opportunity to accelerate the highest-yielding species breeding and resource utilization.

Download Full-text

Comparative metabolomic analysis reveals the variations in taxoids and flavonoids among three Taxus species

10.21203/rs.2.10715/v1 ◽

2019 ◽

Author(s):

Ting Zhou ◽

Xiujun Luo ◽

Chengchao Zhang ◽

Xinyun Xu ◽

Chunna Yu ◽

...

Keyword(s):

Metabolic Pathways ◽

Side Chain ◽

Biosynthesis Pathway ◽

Metabolomic Analysis ◽

Active Ingredients ◽

Cancer Treatments ◽

Taxol Biosynthesis ◽

Metabolite Pool ◽

Derivatives Of ◽

Targeted Approach

Abstract Background Trees of the genus Taxus are highly valuable medicinal plants with multiple pharmacological effects on various cancer treatments. Paclitaxel from Taxus trees is an efficient and widely used anticancer drug, however, the accumulation of taxoids and other active ingredients can vary greatly among Taxus species. In our study, the metabolomes of three Taxus species have been investigated. Results A total of 2,246 metabolites assigning to various primary and secondary metabolic pathways were identified using a untargeted approach. Analysis of differential accumulated metabolites identified 358 T. media-, 220 T. cuspidata-, and 169 T. mairei-specific accumulated metabolites, respectively. By searching the metabolite pool, 7 MEP pathway precursors, 11 intermediates, side chain products and derivatives of paclitaxel, and paclitaxel itself were detected. Most precursors, initiated intermediates were highly accumulated in T. mairei, and most intermediate products approaching the end point of taxol biosynthesis pathway were primarily accumulated in T. cuspidata and T. media. Our data suggested that there were higher-efficiency pathways to paclitaxel in T. cuspidata and T. media compared with in T. mairei. As an important class of active ingredients in Taxus trees, a majority of flavonoids were predominantly accumulated in T. mairei rather than T. media and T. cuspidata. The variations in several selected taxoids and flavonoids were confirmed using a targeted approach. Conclusions Systematic correlativity analysis identifies a number of metabolites associated with paclitaxel biosynthesis, suggesting a potential negative correlation between flavonoid metabolism and taxoid accumulation. Investigation of the variations in taxoids and other active ingredients will provide us a deeper understanding of the interspecific differential accumulation of taxoids and an opportunity to accelerate the highest-yielding species breeding and resource utilization.

Download Full-text

Comparative metabolomic analysis reveals the variations in taxoids and flavonoids among three Taxus species

10.21203/rs.2.10715/v2 ◽

2019 ◽

Author(s):

Ting Zhou ◽

Xiujun Luo ◽

Chengchao Zhang ◽

Xinyun Xu ◽

Chunna Yu ◽

...

Keyword(s):

Metabolic Pathways ◽

Side Chain ◽

Biosynthesis Pathway ◽

Pharmacological Effects ◽

Metabolomic Analysis ◽

Active Ingredients ◽

Cancer Treatments ◽

Taxol Biosynthesis ◽

Metabolite Pool ◽

Derivatives Of

Abstract Background Trees of the genus Taxus are highly valuable medicinal plants with multiple pharmacological effects on various cancer treatments. Paclitaxel from Taxus trees is an efficient and widely used anticancer drug, however, the accumulation of taxoids and other active ingredients can vary greatly among Taxus species. In our study, the metabolomes of three Taxus species have been investigated.Results A total of 2,246 metabolites assigned to various primary and secondary metabolic pathways were identified using an untargeted approach. Analysis of differentially accumulated metabolites identified 358 T. media -, 220 T. cuspidata -, and 169 T. mairei -specific accumulated metabolites, respectively. By searching the metabolite pool, 7 MEP pathway precursors, 11 intermediates, side chain products and derivatives of paclitaxel, and paclitaxel itself were detected. Most precursors, initiated intermediates were highly accumulated in T. mairei , and most intermediate products approaching the end point of taxol biosynthesis pathway were primarily accumulated in T. cuspidata and T. media . Our data suggested that there were higher-efficiency pathways to paclitaxel in T. cuspidata and T. media compared with in T. mairei . As an important class of active ingredients in Taxus trees, a majority of flavonoids were predominantly accumulated in T. mairei rather than T. media and T. cuspidata . The variations in several selected taxoids and flavonoids were confirmed using a targeted approach.Conclusions Systematic correlativity analysis identifies a number of metabolites associated with paclitaxel biosynthesis, suggesting a potential negative correlation between flavonoid metabolism and taxoid accumulation. Investigation of the variations in taxoids and other active ingredients will provide us with a deeper understanding of the interspecific differential accumulation of taxoids and an opportunity to accelerate the highest-yielding species breeding and resource utilization.

Download Full-text

Comparative metabolomic analysis reveals the variations in taxoids and flavonoids among three Taxus species

10.21203/rs.2.10715/v3 ◽

2019 ◽

Author(s):

Ting Zhou ◽

Xiujun Luo ◽

Chengchao Zhang ◽

Xinyun Xu ◽

Chunna Yu ◽

...

Keyword(s):

Metabolic Pathways ◽

Side Chain ◽

Biosynthesis Pathway ◽

Pharmacological Effects ◽

Metabolomic Analysis ◽

Active Ingredients ◽

Cancer Treatments ◽

Taxol Biosynthesis ◽

Metabolite Pool ◽

Derivatives Of

Abstract Background Trees of the genus Taxus are highly valuable medicinal plants with multiple pharmacological effects on various cancer treatments. Paclitaxel from Taxus trees is an efficient and widely used anticancer drug, however, the accumulation of taxoids and other active ingredients can vary greatly among Taxus species. In our study, the metabolomes of three Taxus species have been investigated.Results A total of 2,246 metabolites assigned to various primary and secondary metabolic pathways were identified using an untargeted approach. Analysis of differentially accumulated metabolites identified 358 T. media -, 220 T. cuspidata -, and 169 T. mairei -specific accumulated metabolites, respectively. By searching the metabolite pool, 7 MEP pathway precursors, 11 intermediates, side chain products and derivatives of paclitaxel, and paclitaxel itself were detected. Most precursors, initiated intermediates were highly accumulated in T. mairei , and most intermediate products approaching the end point of taxol biosynthesis pathway were primarily accumulated in T. cuspidata and T. media . Our data suggested that there were higher-efficiency pathways to paclitaxel in T. cuspidata and T. media compared with in T. mairei . As an important class of active ingredients in Taxus trees, a majority of flavonoids were predominantly accumulated in T. mairei rather than T. media and T. cuspidata . The variations in several selected taxoids and flavonoids were confirmed using a targeted approach.Conclusions Systematic correlativity analysis identifies a number of metabolites associated with paclitaxel biosynthesis, suggesting a potential negative correlation between flavonoid metabolism and taxoid accumulation. Investigation of the variations in taxoids and other active ingredients will provide us with a deeper understanding of the interspecific differential accumulation of taxoids and an opportunity to accelerate the highest-yielding species breeding and resource utilization.

Download Full-text

Absolute configuration at C(20) of the derivatives of 21-nor-5α-cholane-20,24-diol

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19802443 ◽

1980 ◽

Vol 45 (9) ◽

pp. 2443-2451

Author(s):

Vladimír Pouzar ◽

Miroslav Havel

Keyword(s):

Absolute Configuration ◽

Side Chain ◽

Chemical Correlation ◽

The Absolute ◽

Derivatives Of

Derivatives of 21-nor-5α-cholane-20,24-diol XI and XIX were prepared by stepwise construction of the side-chain in the position 17β. Their absolute configuration at C(20) was determined on the basis of chemical correlation with the derivatives of 21-nor-5α-cholan-20-ol, XVI and XXIV. The absolute configuration of alcohols XVI and XXIV was determined from the ratio of the yields in which they are formed during the reduction of ketone X and using the benzoate rule. To compounds XI-XVIII the configuration 20R and to compounds XIX-XXVI the configuration 20S has been assigned.

Download Full-text

Synthesis of New Derivatives of BEDT-TTF: Installation of Alkyl, Ethynyl, and Metal-Binding Side Chains and Formation of Tris(BEDT-TTF) Systems

Magnetochemistry ◽

10.3390/magnetochemistry7080110 ◽

2021 ◽

Vol 7 (8) ◽

pp. 110

Author(s):

Songjie Yang ◽

Matteo Zecchini ◽

Andrew Brooks ◽

Sara Krivickas ◽

Desiree Dalligos ◽

...

Keyword(s):

Metal Binding ◽

Tricarboxylic Acid ◽

Metal Salts ◽

Side Chain ◽

Side Chains ◽

Ethynyl Group ◽

X Ray ◽

Transition Metal Salts ◽

Alkyl Side Chains ◽

Derivatives Of

The syntheses of new BEDT-TTF derivatives are described. These comprise BEDT-TTF with one ethynyl group (HC≡C-), with two (n-heptyl) or four (n-butyl) alkyl side chains, with two trans acetal (-CH(OMe)2) groups, with two trans aminomethyl (-CH2NH2) groups, and with an iminodiacetate (-CH2N(CH2CO2−)2 side chain. Three transition metal salts have been prepared from the latter donor, and their magnetic properties are reported. Three tris-donor systems are reported bearing three BEDT-TTF derivatives with ester links to a core derived from benzene-1,3,5-tricarboxylic acid. The stereochemistry and molecular structure of the donors are discussed. X-ray crystal structures of two BEDT-TTF donors are reported: one with two CH(OMe)2 groups and with one a -CH2N(CH2CO2Me)2 side chain.

Download Full-text

ChemInform Abstract: CYCLIC UNSATURATED COMPOUNDS. LXII. DERIVATIVES OF CYCLOPENTADIENE CONTAINING G AN ETHOXYCARBONYL GROUP IN THE SIDE CHAIN

Chemischer Informationsdienst ◽

10.1002/chin.197823136 ◽

1978 ◽

Vol 9 (23) ◽

Author(s):

V. A. MIRONOV ◽

S. A. YANKOVSKII ◽

V. T. LUK'YANOV

Keyword(s):

Side Chain ◽

Unsaturated Compounds ◽

Derivatives Of

Download Full-text

ChemInform Abstract: A GENERAL SYNTHESIS OF SIDE CHAIN DERIVATIVES OF Δ9-THC

Chemischer Informationsdienst ◽

10.1002/chin.197812366 ◽

1978 ◽

Vol 9 (12) ◽

Author(s):

C. G. PITT ◽

H. H. SELTZMAN ◽

Y. SAYED ◽

C. E. JUN. TWINE ◽

D. L. WILLIAMS

Keyword(s):

Side Chain ◽

Derivatives Of ◽

General Synthesis

Download Full-text

New 4-Hydroxypyridine and 4-Hydroxyquinoline Derivatives as Inhibitors of NADH-ubiquinone Reductase in the Respiratory Chain

Zeitschrift für Naturforschung C ◽

10.1515/znc-1989-7-811 ◽

1989 ◽

Vol 44 (7-8) ◽

pp. 609-616 ◽

Cited By ~ 22

Author(s):

Kun Hoe Chung ◽

Kwang Yun Cho ◽

Yasuko Asami ◽

Nobutaka Takahashi ◽

Shigeo Yoshida

Keyword(s):

Electron Transport ◽

Respiratory Chain ◽

Side Chain ◽

Pyridine Derivatives ◽

Transport Function ◽

Optimal Length ◽

Structure Activity ◽

Membrane Effect ◽

Relationship Of ◽

Derivatives Of

Many derivatives of 2,3-dim ethoxy-4-hydroxypyridine, which were designed from examination of the structure-activity relationship of piericidins, were tested for inhibition of NADH-UQ reductase. The lipophilic side chain of those compounds was indicated to be a key part for activity and its optimal length was conjectured. By the use of two different phases of assay material, intact mitochondria and submitochondria, the size of a membrane effect was shown to depend on the structure of the side chain. 4-Hydroxyquinoline derivatives were also tested for an analogous role in relation to the electron transport function of menaquinone, and they were proven to be inhibitors of NADH-UQ reductase as good as the pyridine derivatives.

Download Full-text