Total synthesis of the potent anti-inflammatory natural product solomonamide A along with structural revision and biological activity evaluation

2018 ◽  
Vol 16 (47) ◽  
pp. 9138-9142 ◽  
Author(s):  
Gorakhnath R. Jachak ◽  
Paresh R. Athawale ◽  
Heena Agarwal ◽  
Manoj Kumar Barthwal ◽  
Gianluigi Lauro ◽  
...  
Keyword(s):  
Biological Activity ◽  
Total Synthesis ◽  
Natural Product ◽  
Structural Revision ◽  
Activity Evaluation ◽  
Anti Inflammatory ◽  
First Time

Herein, we report the total synthesis of solomonamide A along with its structural revision for the first time.

STEROIDS PRESENT IN THE FOLLICULAR FLUID OF THE MARE

1960 ◽  
Vol 20 (2) ◽  
pp. 147-156 ◽  
Author(s):  
R. V. SHORT
Keyword(s):  
Biological Activity ◽  
Natural Product ◽  
Follicular Fluid ◽  
Physiological Significance ◽  
Chromatographic Techniques ◽  
First Time

SUMMARY Using paper chromatographic techniques, it has been possible to identify the following steroids in the follicular fluid of the mare (results expressed as μg/1.): oestradiol-17β, 460 μg; oestrone, 34 μg; cortisol, 12 μg; progesterone, 124 μg; 17α-hydroxyprogesterone, 66 μg; epitestosterone, 24 μg; androstenedione, 136 μg. In addition to these seven compounds, 136 μg of an unidentified oestrogen-like substance and 52 μg of an unidentified 17-ketosteroid were also present. This is the first time that epitestosterone has been identified as a natural product, and the possible significance of this compound is discussed. 19-Hydroxyandrostenedione, the postulated intermediate in the formation of oestrone from androstenedione, was not detected in this study, and some doubt is therefore cast on the theory that it is an essential intermediate in the biosynthesis of the ovarian oestrogens. The presence of relatively large amounts of an unidentified polar oestrogen in follicular fluid suggests that it may be of some physiological significance, although at the present time no information is available on the biological activity of this compound.

Isolation, Biological Activity Evaluation, Structure Elucidation, and Total Synthesis of Eliamid: A Novel Complex I Inhibitor

2012 ◽  
Vol 18 (36) ◽  
pp. 11362-11370 ◽  
Author(s):  
Gerhard Höfle ◽  
Klaus Gerth ◽  
Hans Reichenbach ◽  
Brigitte Kunze ◽  
Florenz Sasse ◽  
...  
Keyword(s):  
Biological Activity ◽  
Total Synthesis ◽  
Complex I ◽  
Structure Elucidation ◽  
Activity Evaluation ◽  
Novel Complex

Bioinspired total synthesis and structural revision of yuremamine, an alkaloid from the entheogenic plant Mimosa tenuiflora

2015 ◽  
Vol 51 (28) ◽  
pp. 6202-6205 ◽  
Author(s):  
Matthew B. Calvert ◽  
Jonathan Sperry
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Synthetic Approach ◽  
Structural Revision ◽  
True Structure ◽  
Mimosa Tenuiflora

A bioinspired synthetic approach to nominal yuremamine has uncovered the true structure of the natural product to be a flavonoidal indole.

Synthesis of α-exo-Methylene-γ-butyrolactone: Recent Developments and Applications in Natural Product Synthesis

Synthesis ◽  
2021 ◽  
Author(s):  
Weilong Liu ◽  
Nicolas Winssinger
Keyword(s):  
Natural Products ◽  
Biological Activity ◽  
Total Synthesis ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Vast Array ◽  
The Past ◽  
New Approaches ◽  
Recent Developments

The α-exo-methylene-γ-butyrolactone moiety is present in a vast array of structurally diverse natural products and is often central to their biological activity. In this review, we summarize new approaches to α-exo-methylene-γ-butyrolactones developed over the past decade as well as their applications in total synthesis.

Total synthesis and structural revision of an isopanepoxydone analog isolated from Lentinus strigellus

2018 ◽  
Vol 16 (27) ◽  
pp. 5043-5049 ◽  
Author(s):  
Yi Man ◽  
Shaomin Fu ◽  
Juan Chen ◽  
Bo Liu
Keyword(s):  
Molecular Structure ◽  
Total Synthesis ◽  
Natural Product ◽  
Asymmetric Total Synthesis ◽  
Structural Revision

Asymmetric total synthesis of compound 1, as a proposed molecular structure of a natural product, in 11 steps is described. The inconsistency of the characterization data prompted us to propose a different structure as compound 2 and accordingly accomplish total synthesis in 9 steps and confirm the structural revision of this natural product.

First total synthesis of marine derived anti-inflammatory natural product (-)-Herdmanine-D enabled by Steglich esterification

Synlett ◽  
2021 ◽  
Author(s):  
Pankaj Sharma ◽  
Nutan Sharma ◽  
Gunjan Kashyap ◽  
Sunita Bhagat
Keyword(s):  
Carboxylic Acid ◽  
Drug Development ◽  
Total Synthesis ◽  
Natural Product ◽  
Optical Activity ◽  
Marine Natural Product ◽  
Current Strategy ◽  
Synthetic Strategy ◽  
Steglich Esterification ◽  
Anti Inflammatory

An efficient and regioselective route for the first total synthesis of anti-inflammatory marine natural product (-)-Herdmanine-D has been described with an excellent overall yield of 18%. The key feature of the synthetic strategy includes Steglich esterification of regioselectively constructed 6-bromo-5-methoxy-1H-indole-3-carboxylic acid and L-Tyrosine. L-isomer was confirmed through measurement of optical activity. The current strategy paves the way for construction of diverse analogues of the title natural product for drug development.

Total Synthesis and Structural Revision of a Harziane Diterpenoid

2019 ◽  
Author(s):  
Moritz Honig ◽  
Erick Carreira
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Spectral Characteristics ◽  
Tertiary Alcohol ◽  
Carbon Skeleton ◽  
Structural Revision ◽  
Stereochemical Analysis ◽  
Quaternary Stereocenter

The first total synthesis of nominal harziane diterpenoid is disclosed, whose spectral characteristics did not match those of the reported natural product. Stereochemical analysis and subsequent synthesis of the epimeric tertiary alcohol led to reassignment of configuration of the natural product. At the heart of the synthesis is an enyne cycloisomerization that sets a key quaternary stereocenter within a cyclobutane with high diastereocontrol. The route features strategies for the synthesis of the highly congested 6–5–7–4 carbon skeleton characteristic of the caged harziane diterpenoids.

Two Atropisomeric N-Methyldioncophyllines A and N-Methylphylline, their Naphthalene-Free Heterocyclic Moiety, from Ancistrocladus barteri

2003 ◽  
Vol 58 (6) ◽  
pp. 577-584 ◽  
Author(s):  
Gerhard Bringmann ◽  
Christoph Schneider ◽  
Ulrike Möhler ◽  
Robert-Michael Pfeifer ◽  
Roland Götz ◽  
...  
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis ◽  
Natural Product ◽  
West African ◽  
The West ◽  
Naphthylisoquinoline Alkaloids ◽  
Crude Extracts ◽  
First Time ◽  
Heterocyclic Moiety

The West African plant Ancistrocladus barteri (Ancistrocladaceae) was investigated chemically for the first time. Besides the known naphthylisoquinoline alkaloids N-methyldioncophylline A and 7-epi-N-methyldioncophylline A (i.e. its atropo-diastereomer), a new naphthalene-free alkaloid, belonging to the ‘Dioncophyllaceae type’, was isolated. Its structure was elucidated by spectroscopic and degradative methods and confirmed by total synthesis. The new compound, named N-methylphylline, is exactly the isoquinoline “half” of both, N-methyldioncophylline A and its atropisomer. Furthermore, the related tetrahydroisoquinoline O,N-dimethylphylline, an intermediate in the chemical synthesis of N-methylphylline, was detected as a new natural product in crude extracts of A. barteri.

Total synthesis, structural elucidation and anti-inflammatory activity evaluation of 2-deoxy-3,6-anhydro hexofuranoside derivatives isolated from Sauropus rostratus

2016 ◽  
Vol 14 (46) ◽  
pp. 10906-10913 ◽  
Author(s):  
Chenxi Zhang ◽  
Chengcheng Wang ◽  
Zihao Wang ◽  
Genzoh Tanabe ◽  
Osamu Muraoka ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Structural Elucidation ◽  
Inflammatory Activity ◽  
Activity Evaluation ◽  
Anti Inflammatory

The first total synthesis of four 2-deoxy-3,6-anhydro hexofuranoside derivatives isolated from Genus Sauropus rostratus was accomplished.

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