Two new bicyclic sulfoxides from Welsh onion.
Toshihiro Nohara1, Yukio Fujiwara2, Tsuyoshi Ikeda3
1Faculty of Pharmaceutical Sciences, Sojo University, 22-1, 4-Chome, Nishi-ku, Ikeda, Kumamoto, 860-0082, Japan. none@ph.sojo-u.ac.jp.
Journal of Natural Medicines
|December 18, 2015
Summary
Newly discovered compounds, welsonins A1 and A2, from Welsh onions may fight cancer. Welsonin A1 suppresses tumor cell growth by impacting M2 macrophages, offering potential therapeutic applications.
Area of Science:
- Natural Product Chemistry
- Oncology
- Immunology
Background:
- Allium fistulosum (Welsh onion) bulbs are a source of bioactive compounds.
- Sulfoxides are sulfur-containing compounds with diverse biological activities.
- Macrophages play critical roles in tumor progression and immune response.
Purpose of the Study:
- To isolate and characterize novel bicyclic sulfoxides from Welsh onion bulbs.
- To investigate the anti-cancer properties of the isolated compounds, specifically welsonin A1.
- To elucidate the mechanism of action of welsonin A1 in tumor suppression.
Main Methods:
- Extraction of compounds from Allium fistulosum bulbs using acetone.
- Structure elucidation of isolated compounds (welsonins A1 and A2) using spectroscopic analysis.
- Assessment of welsonin A1's effect on tumor-cell proliferation and M2 macrophage polarization.
Main Results:
- Two new bicyclic sulfoxides, welsonins A1 and A2, were identified as tetrahydrothiophene-S-oxide derivatives.
- The structures suggest a biosynthetic origin from the coupling of 1-propenyl sulfenic acid and uronic acid.
- Welsonin A1 demonstrated the ability to inhibit M2 macrophage polarization, leading to suppressed tumor-cell proliferation.
Conclusions:
- Welsonins A1 and A2 are novel natural products isolated from Welsh onions.
- Welsonin A1 exhibits anti-cancer potential by modulating the tumor microenvironment through M2 macrophage inhibition.
- These findings highlight the therapeutic promise of Welsh onion-derived compounds in cancer treatment.
Related Concept Videos
02:26Preparation and Reactions of Sulfides
6.0K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
6.0K
01:16Cycloaddition Reactions: Overview
3.7K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
3.7K
01:27Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
3.0K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
3.0K
01:14Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
3.0K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
3.0K
01:20Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
2.7K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.7K
01:29Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
6.5K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
6.5K