Euphorbia's chemistry and perspectives
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Euphorbia's chemistry and perspectives
News about latest developpements in Euphorbia's chemistry and ecochemistry and it's further perspectives
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Approach to the Tricyclic Core of the Tigliane–Daphnane Diterpenes. Concerning the Utility of Transannular Aldol Additions

Approach to the Tricyclic Core of the Tigliane–Daphnane Diterpenes. Concerning the Utility of Transannular Aldol Additions | Euphorbia's chemistry and perspectives | Scoop.it

Two transannular (TA) aldol reactions were used to assemble the tricyclic carbon skeleton found in the tigliane and daphnane classes of diterpene natural products.

 

Arthur J. Catino, Alexandra Sherlock, Peyton Shieh, Joseph S. Wzorek, and David A. EvansOrg. Lett., Article ASAPDOI: 10.1021/ol401367h 


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Cytotoxic Phorbol Esters of Croton tiglium

Cytotoxic Phorbol Esters of Croton tiglium | Euphorbia's chemistry and perspectives | Scoop.it

Chemical investigation of the seeds of Croton tiglium afforded eight new phorbol diesters (three phorbol diesters, 1–3, and five 4-deoxy-4α-phorbol diesters, 4–8), together with 11 known phorbol diesters (nine phorbol diesters, 9–17, and two 4-deoxy-4α-phorbol diesters, 18 and 19). The structures of compounds 1–8 were determined by spectroscopic data information and chemical degradation experiments. The cytotoxic activities of the phorbol diesters were evaluated against the SNU387 hepatic tumor cell line, and compound 3 exhibited the most potent activity (IC50 1.2 μM).

 

Xiao-Long Zhang†§, Lun Wang†§, Fu Li†, Kai Yu‡, and Ming-Kui Wang

J. Nat. Prod., Article ASAP

DOI: 10.1021/np300832n


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ChemDraw Magic 2 - More Tips and Tricks on ChemBioDraw13 (HD with subtitles)

Watch in HD: http://www.youtube.com/watch?v=SSZI8rh6sNY&fmt=22 PerkinElmer Informatics: http://www.perkinelmer.com/informatics Make sure you check out these ...

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Natural product isolation – how to get from biological material to pure compounds

Natural product isolation – how to get from biological material to pure compounds | Euphorbia's chemistry and perspectives | Scoop.it

Since the last comprehensive review by Otto Sticher on natural product isolation in NPR (O. Sticher, Nat. Prod. Rep., 2008, 25, 517), a plethora of new reports on isolation of secondary compounds from higher plants, marine organisms and microorganisms has been published. Although methods described earlier like the liquid-solid chromatographic techniques (VLC, FC, MPLC, HPLC) or partition chromatographic methods are still the major tools for isolating pure compounds, some developments like hydrophilic interaction chromatography (HILIC) have not been fully covered in previous reviews. Furthermore, examples of using different preparative solid-phase extraction (SPE) columns including molecular imprinting technology have been included. Special attention is given to chiral stationary phases in isolation of natural products. Methods for proper identification of plant material, problems of post-harvest changes in plant material, extraction methods including application of ionic liquids, de-replication procedures during natural product isolation are further issues to be discussed by the review. Selected work published between 2008 and mid-2012 is covered.

 

Franz Bucar ,  Abraham Wube and Martin Schmid Nat. Prod. Rep., 2013, Advance Article


DOI: 10.1039/C3NP20106F

 

 


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ENHANCING MACROCYCLIC DITERPENES AS MULTIDRUG-RESISTANCE REVERSERS: STRUCTURE-ACTIVITY STUDIES ON JOLKINOL D DERIVATIVES - Journal of Medicinal Chemistry (ACS Publications)

ENHANCING MACROCYCLIC DITERPENES AS MULTIDRUG-RESISTANCE REVERSERS: STRUCTURE-ACTIVITY STUDIES ON JOLKINOL D DERIVATIVES - Journal of Medicinal Chemistry (ACS Publications) | Euphorbia's chemistry and perspectives | Scoop.it
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Medicinal property, phytochemistry and pharmacology of several Jatropha species (Euphorbiaceae): A review

Medicinal property, phytochemistry and pharmacology of several Jatropha species (Euphorbiaceae): A review | Euphorbia's chemistry and perspectives | Scoop.it

The genus Jatropha (Euphorbiaceae) comprises of about 170 species of woody trees, shrubs, subshrubs or herbs in the seasonally dry tropics of the Old and the New World. They are used in medicinal folklore to cure various diseases of 80% of the human population in Africa, Asia and Latin America. Species from this genus have been popular to cure stomachache, toothache, swelling, inflammation, leprosy, dysentery, dyscrasia, vertigo, anemia, diabetis, as well as to treat HIV and tumor, opthalmia, ringworm, ulcers, malaria, skin diseases, bronchitis, asthma and as an aphrodisiac. They are also employed as ornamental plants and energy crops. Cyclic peptides alkaloids, diterpenes and miscellaneous compounds have been reported from this genus. Extracts and pure compounds of plants from this genus are reported for cytotoxicity, tumor-promoting, antimicrobial, antiprotozoal, anticoagulant, immunomodulating, anti-inflammatory, antioxidant, protoscolicidal, insecticidal, molluscicidal, inhibition AChE and toxicity activities.

 

Carla W. Sabandar,Norizan Ahmat, Faridahanim Mohd Jaafar, I. Sahidin

Phytochemistry,In Press, Corrected Proof

Available online 12 November 2012

http://dx.doi.org/10.1016/j.phytochem.2012.10.009, How to Cite or Link Using DOI


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Jatrophane diterpenoids from the latex of Euphorbia dendroides and their anti-P-glycoprotein activity in human multi-drug resistant cancer cell lines

Jatrophane diterpenoids from the latex of Euphorbia dendroides and their anti-P-glycoprotein activity in human multi-drug resistant cancer cell lines | Euphorbia's chemistry and perspectives | Scoop.it

Thirteen jatrophane diterpenoids (1–10, 13–15), three previously isolated (11, 12, 16) and a known tigliane (17) were isolated from the latex of Euphorbia dendroides. The structures and relative configurations of compounds were elucidated by spectroscopic techniques. The P-glycoprotein (P-gp) inhibiting activities of the representative set of jatrophanes (1–6 and 11–16) have been assessed. Jatrophanes 2 and 5 demonstrated the most powerful inhibition of P-gp, higher than R(+)-verapamil and tariquidar in colorectal multi-drug resistant (MDR) cells (DLD1-TxR).

 

Phytochemistry

Available online 15 October 2012

http://dx.doi.org/10.1016/j.phytochem.2012.09.003


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Antiviral chlorinated daphnane diterpenoid orthoesters from the bark and wood of Trigonostemon cherrieri

Antiviral chlorinated daphnane diterpenoid orthoesters from the bark and wood of Trigonostemon cherrieri | Euphorbia's chemistry and perspectives | Scoop.it

The chemical study of the bark and the wood of Trigonostemon cherrieri, a rare endemic plant of New Caledonia, led to the isolation of a series of highly oxygenated daphnane diterpenoid orthoesters (DDO) bearing an uncommon chlorinated moiety: trigocherrins A–F and trigocherriolides A–D. Herein, we describe the isolation and structure elucidation of the DDO (trigocherrins B–F and trigocherriolides A–D). We also report the antiviral activity of trigocherrins A, B and F (1, 2 and 6) and trigocherriolides A, B and C (7–9) against various emerging pathogens: chikungunya virus (CHIKV), Sindbis virus (SINV), Semliki forest virus (SFV) and dengue virus (DENV).

 

Pierre-Marie Allard,Pieter Leyssen,Marie-Thérèse Martin,Mélanie Bourjot,Vincent Dumontet,Cécilia Eydoux,Jean-Claude Guillemot,Bruno Canard,Cyril Poullain,Françoise Guéritte,Marc Litaudon.

Phytochemistry, Available online 29 August 2012

http://dx.doi.org/10.1016/j.phytochem.2012.07.023


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Dreaded sap of Euphorbia can zap skin and eyes

Dreaded sap of Euphorbia can zap skin and eyes | Euphorbia's chemistry and perspectives | Scoop.it

Emergency rooms in California and Florida often run into cases of Euphorbia latex in the eyes. This caustic liquid can burn the cornea and damage vision either temporarily or permanently, so this is no laughing matter. Problems occur on the skin of sensitive individuals too. Reports of latex creating fire-like burns and blistering is not uncommon. Rashes can be painful and long-lasting unless you have the antidote.Clark learned long ago that the official antidote to the latex is Aeonium lindleyi, a small succulent plant.

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Bioactive components in the fruits of Ziziphus jujuba Mill. against the inflammatory irritant action of Euphorbia plants

Bioactive components in the fruits of Ziziphus jujuba Mill. against the inflammatory irritant action of Euphorbia plants | Euphorbia's chemistry and perspectives | Scoop.it

As a famous folk medicine, it is used as antidote in traditional Chinese formula, Shi Zao Decoction, to relieve the drastic inflammatory irritant nature of Euphorbia species. The irritant activities may cause serious adverse effects in clinical practices. This study aimed to investigate the active components of Z. jujuba through the inhibitory effects on the inflammatory cells activated by Euphorbia kansui and prostratin, a phorbol ester isolated from Euphorbia fischeriana.

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Isolation, Structure Determination, and Anti-HIV Evaluation of Tigliane-Type Diterpenes and Biflavonoid from Stellera chamaejasme

Isolation, Structure Determination, and Anti-HIV Evaluation of Tigliane-Type Diterpenes and Biflavonoid from Stellera chamaejasme | Euphorbia's chemistry and perspectives | Scoop.it

Five novel tigliane-type diterpenes, stelleracins A–E (3–7), a novel flavanone dimer, chamaeflavone A (8), and six known compounds were isolated from the roots of Stellera chamaejasme. Their structures were elucidated by extensive spectroscopic analyses. The isolated compounds were evaluated for anti-HIV activity in MT4 cells. New compounds 3–5 showed potent anti-HIV activity (EC90 0.00056–0.0068 μM) and relatively low or no cytotoxicity (IC50 4.4–17.2 μM). These new compounds represent promising new leads for development into anti-AIDS clinical trial candidates.

 

Yoshihisa Asada*†, Aya Sukemori‡, Takashi Watanabe§, Kuber J. Malla, Takafumi Yoshikawa‡, Wei Li*, Xinzhu Kuang, Kazuo Koike, Chin-Ho Chen, Toshiyuki Akiyama#, Keduo Qian#, Kyoko Nakagawa-Goto#, Susan L. Morris-Natschke#, Yan Lu#, and Kuo-Hsiung Lee

J. Nat. Prod., Article ASAP

DOI: 10.1021/np300815t

Publication Date (Web): April 23, 2013


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Concepts and technologies for tracking bioactive compounds in natural product extracts: generation of libraries, and hyphenation of analytical processes with bioassays

Concepts and technologies for tracking bioactive compounds in natural product extracts: generation of libraries, and hyphenation of analytical processes with bioassays | Euphorbia's chemistry and perspectives | Scoop.it

Since the advent of high-throughput screening (HTS) in the early 1990s, a wealth of innovative technologies have been proposed and implemented for the effective localization and characterization of bioactive constituents in complex matrices. The latest developments in this field are reviewed under the perspective of their applicability to natural product-based drug discovery. The approaches discussed here include TLC-based bioautography, HPLC-based assays with on-line, at-line and off-line detection, as well as affinity-based methods, such as frontal affinity chromatography, pulsed ultrafiltration mass spectrometry, imprinted polymers, and affinity capillary electrophoresis. Selected practical examples are given to illustrate the strengths and limitations of these approaches in contemporary natural product lead discovery. In addition, compatibility issues of natural product extracts and HTS are addressed, and selected protocols for the generation of high quality libraries are presented.

 

Olivier Potterat and Matthias Hamburger Nat. Prod. Rep., 2013, Advance Article

DOI: 10.1039/C3NP20094A


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Natural product isolation – how to get from biological material to pure compounds

Natural product isolation – how to get from biological material to pure compounds | Euphorbia's chemistry and perspectives | Scoop.it

Since the last comprehensive review by Otto Sticher on natural product isolation in NPR (O. Sticher, Nat. Prod. Rep., 2008, 25, 517), a plethora of new reports on isolation of secondary compounds from higher plants, marine organisms and microorganisms has been published. Although methods described earlier like the liquid-solid chromatographic techniques (VLC, FC, MPLC, HPLC) or partition chromatographic methods are still the major tools for isolating pure compounds, some developments like hydrophilic interaction chromatography (HILIC) have not been fully covered in previous reviews. Furthermore, examples of using different preparative solid-phase extraction (SPE) columns including molecular imprinting technology have been included. Special attention is given to chiral stationary phases in isolation of natural products. Methods for proper identification of plant material, problems of post-harvest changes in plant material, extraction methods including application of ionic liquids, de-replication procedures during natural product isolation are further issues to be discussed by the review. Selected work published between 2008 and mid-2012 is covered.

 

Franz Bucar ,  Abraham Wube and Martin Schmid Nat. Prod. Rep., 2013, Advance Article


DOI: 10.1039/C3NP20106F

 

 


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Trends in Plant Science - Plant chemical defense: at what cost?

Trends in Plant Science - Plant chemical defense: at what cost? | Euphorbia's chemistry and perspectives | Scoop.it

Just how costl are specialized metabolites? Maybe not very - this opinion article suggests that "secondary metabolites serve auxiliary roles, including functions associated with primary metabolism. ..The costs of plant chemical defense can be offset by multifunctional biosynthesis and the optimization of primary metabolism. These additional benefits may negate the trade-off between primary and secondary metabolism,"


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The Seven Sins in Academic Behavior in the Natural Sciences

The Seven Sins in Academic Behavior in the Natural Sciences | Euphorbia's chemistry and perspectives | Scoop.it

“Seven deadly sins” in modern academic research and publishing can be condensed into a list ranging from poorly described experimental or computational setups to falsification of data. This Essay describes these sins and their ramifications, and serves as a code of best practice for researchers in their quest for scientific truth.

 

Picture: Detail from “The Seven Deadly Sins” by Hieronymus Bosch.

 

 

Prof. Dr. Wilfred F. van Gunsteren

ngewandte Chemie International Edition

Article first published online: 3 DEC 2012

DOI: 10.1002/anie.201204076

 


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Ingenane-type diterpenes with a modulatory effect on IFN-γ production from the roots of Euphorbia kansui

Ingenane-type diterpenes with a modulatory effect on IFN-γ production from the roots of Euphorbia kansui | Euphorbia's chemistry and perspectives | Scoop.it

A new ingenane-type diterpene, (3S,5R)5-O-(2,3-dimethylbutanoyl)-13-O-dodecanoyl-20-O-deoxyingenol (1), and six known compounds,3-O-(2,3-dimethylbutanoyl)-13-O-dodecanoyl-20-O-deoxyingenol (2), 20-O-decanoylingenol (3), 20-O-acetylingenol-3-O-(2′E,4′Z) decadienoate (4), kansuiphorin A (5), 3-O-(2,3-dimethylbutanoyl)-13-O-dodecanoylingenol (6), and kansuinin F (7) were isolated and evaluated for their effect on IFN-γ production in NK92 cells. Interestingly, subjection to compounds 4 and 6 (10 nM) displayed the most significant response in IFN-γ production, comparable to that produced by the same dose of phorbol 12-myistate 13-acetate (PMA). High doses of compounds 3 (100 nM), 1 (1. 25 μM) and 5 (5.0 μM) have also been shown to activate the IFN-γ production.

 

Archives of Pharmacal Research, Volume 35, Number 9 - SpringerLink

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Wound healing activity of latex of Euphorbia caducifolia

Wound healing activity of latex of Euphorbia caducifolia | Euphorbia's chemistry and perspectives | Scoop.it

Euphorbia caducifolia is a Euphorbiaceae species native to Thar Desert of India, where latex of E. caducifolia (ECL) is used by the local inhabitants for treatment of bleeding wound, cutaneous eruption and other skin diseases.

Looking to the medicinal importance of the plant, it was considered worthwhile to scientifically evaluate the ECL for the wound healing activity.

 

ScienceDirect.com - Journal of Ethnopharmacology

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Diterpenes from European Euphorbia Species Serving as Prototypes for Natural-Product-Based Drug Discovery

Diterpenes from European Euphorbia Species Serving as Prototypes for Natural-Product-Based Drug Discovery | Euphorbia's chemistry and perspectives | Scoop.it

Diterpenes occurring in plants of the Euphorbiaceae family are of considerable interest in the context of natural product drug discovery programs because of their wide range of potentially valuable biological activities and their broad structural diversity due to their different polycyclic and macrocyclic skeletons and the various aliphatic and aromatic ester groups. Euphorbia species have provided many lead compounds (resiniferatoxin, prostratin, jatrophane and pepluane esters) for drug development, some of which are currently involved in preclinical or clinical studies, but the importance of natural products of this type can be demonstrated primarily by the recent approval of ingenol 3-angelate (ingenol mebutate) by the FDA for the treatment of actinic keratosis. An appreciable time has passed since a new plant chemotype – a natural product without structural modification – has been introduced into clinical practice. Ingenol 3-angelate, a Euphorbia peplus metabolite, serves as a new prototype for natural product-based drug discovery. The aim of this paper is to provide an overview of the chemical and pharmacological potential of European Euphorbia species. Besides the main aspects of the development of ingenol 3-angelate as a drug, screening methods, isolation strategies, the chemical characteristics of Euphorbia diterpenes and the results of pharmacological investigations are surveyed.


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De novo assembly of Euphorbia fischeriana root transcriptome identifies prostratin pathway related genes

De novo assembly of Euphorbia fischeriana root transcriptome identifies prostratin pathway related genes | Euphorbia's chemistry and perspectives | Scoop.it

Euphorbia fischeriana is an important medicinal plant found in Northeast China. The plant roots contain many medicinal compounds including 12-deoxyphorbol-13-acetate, commonly known as prostratin that is a phorbol ester from the tigliane diterpene series. Prostratin is a protein kinase C activator and is effective in the treatment of Human Immunodeficiency Virus (HIV) by acting as a latent HIV activator. Latent HIV is currently the biggest limitation for viral eradication. The aim of this study was to sequence, assemble and annotate the E. fischeriana transcriptome to better understand the potential biochemical pathways leading to the synthesis of prostratin and other related diterpene compounds.

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Journal of Cancer Research and Clinical Oncology, Volume 127, Number 1 - SpringerLink

Journal of Cancer Research and Clinical Oncology, Volume 127, Number 1 - SpringerLink | Euphorbia's chemistry and perspectives | Scoop.it
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