Onionin A (1), a new, stable, sulfur-containing compound, was isolated from acetone extracts of bulbs of onion (Allium cepa), and its structure was characterized as 3,4-dimethyl-5-(1E-propenyl)-tetrahydrothiophen-2-sulfoxide-S-oxide, on the basis of the results of spectroscopic analysis. This compound showed the potential to suppress tumor-cell proliferation by inhibiting the polarization of M2 alternatively activated macrophages.
Fucoidans are marine sulfated biopolysaccharides that have heterogenous and complicated chemical structures. Various sugar monomers, glycosidic linkages, molecular masses, branching sites, and sulfate ester pattern and content are involved within their backbones. Additionally, sources, downstream processes, and geographical and seasonal factors show potential effects on fucoidan structural characteristics. These characteristics are documented to be highly related to fucoidan potential activities. Therefore, numerous chemical qualitative and quantitative determinations and structural elucidation methods are conducted to characterize fucoidans regarding their physicochemical and chemical features. Characterization of fucoidan polymers is considered a bottleneck for further biological and industrial applications. Consequently, the obtained results may be related to different activities, which could be improved afterward by further functional modifications. The current article highlights the different spectrometric and nonspectrometric methods applied for the characterization of native fucoidans, including degree of purity, sugar monomeric composition, sulfation pattern and content, molecular mass, and glycosidic linkages.
Esculeoside A (2), a spirosolane steroidal glycoside, is a major constituent isolated from Solanum lycopersicum, a commercial strain of mini tomatoes. The content variability of esculeoside A (2) was examined in mini, midi, and Momotaro tomatoes and various processed tomato products. In the green immature tomato fruit, tomatine (1) is oxidized at C-23 and C-27 to produce esculeoside A (2) in the ripe fruit. Further, esculeoside A (2) is partly converted to 3β-hydroxy-5α-pregn-16-en-20-one 3-O-β-lycotetraoside (6), a pregnane glycoside, in the overripe fruit. Esculeogenin A (3), the sapogenol of 2, is easily converted into 3β,16β-dihydroxy-5α-pregn-20-one (17). Metabolic studies showed excretion of androstane derivatives in the urine of human volunteer subjects after tomato consumption. Esculeogenin A (3) inhibited the accumulation of cholesterol esters in macrophages through its effects on acyl-CoA:cholesterol acyl transferase (ACAT). Oral administration of esculeoside A (2) to apoE-deficient mice significantly reduced serum levels of cholesterol, triglycerides, and LDL-cholesterol and ameliorated the severity of atherosclerotic lesions.
Garlic, Allium sativum L. (Liliaceae) occupies the top spot of the National Cancer Institute list of designer foods that protect cancer. The various biological activities of these foods are classified into roughly 2 functions: cardiovascular disease prevention and cancer prevention. Cholesterol synthesis, platelet aggregation, and arterial smooth muscle proliferation inhibition as well as anti-inflammatory, anti-oxidant, and hydrogen sulfide-mediated vasodilatory activities are included in the former category. Effects on carcinogen metabolism (enhanced cellular glutathione synthesis and induced cell cycle arrest and apoptosis), Helicobacter pylori infection, gastric cancer, and colorectal cancer make up the latter category.1-3) The chemistry of garlic sulfides is summarized in the text book editted by Block; 3,4) that is, S-allyl L-cysteine is oxidized to S-allyl L-cysteine sulfoxide (alliin), which is further decomposed into allyl sulfenic acid and amino acrylic acid. The former is hydrolyzed into diallyl thiosulfinate (allicin), which is then transformed into 2-vinyl-4H-1,3-dithiin and 3-vinyl-4H-1,2-dithiin via thioacrolein.On the other hand, allicin also produces diallyl disulfide, diallyl trisulfide, and (E ) and (Z )-ajoene 4) (Chart 1). We previously isoalted a novel stable sulfide, 3,4-dimethyl-5-(1-propenyl)-tetrahydrothiophene-2-sulfoxide-S-oxide, from the acetone extract of Allium cepa L. that we named onionin A, which inhibited macrophage activation. 5)A sulfer-containing substance from an acetone-soluble extract of A. sativum L. has been isolated and characterized in order to develop natural, healthy foods that potentially prevent and combat disease.Chinese garlic was roughly chopped and blended in a mixer along with acetone; subsequently, the mixture was soaked in acetone for 3 d at room temperature. The filtrate was evaporated at 40°C in vacuo to obtain a residue that was then subjected to polystyrene gel (Diaion HP-20) column Aso, Kumamoto 869-1404, Japan: d Faculty of Pharmaceutical Sciences, Fukuoka University; 8-19-1 Jyounan-ku, Nanakuma, Fukuoka 814-0180, Japan: and e Faculty of Pharmaceutical Sciences, Sojo University; 4-22-1 Ikeda, Kumamoto 860-0082, Japan. Received June 2, 2011; accepted August 17, 2011; published online August 22, 2011 Garlicnin A (1), a new stable, sulfur-containing compound isolated from a fraction of the acetone extracts of Allium sativum L. garlic bulbs, showed the potential to suppress tumor cell proliferation by inhibiting the polarization of M2 alternatively activated macrophages, and its structure was characterized as 3,4-dimethyl-5-(4,5-dithia-1E,7-octadiene)-tetrahydrothiophene-2-sulfoxide-S-oxide, on the basis of the results of spectroscopic analysis results.
Pseudomonas aeruginosa is an opportunistic bacterium causing several health problems and having many virulence factors like biofilm formation on different surfaces. There is a significant need to develop new antimicrobials due to the spreading resistance to the commonly used antibiotics, partly attributed to biofilm formation. Consequently, this study aimed to investigate the anti-biofilm and anti-quorum sensing activities of Dioon spinulosum, Dyer Ex Eichler extract (DSE), against Pseudomonas aeruginosa clinical isolates. DSE exhibited a reduction in the biofilm formation by P. aeruginosa isolates both in vitro and in vivo rat models. It also resulted in a decrease in cell surface hydrophobicity and exopolysaccharide quantity of P. aeruginosa isolates. Both bright field and scanning electron microscopes provided evidence for the inhibiting ability of DSE on biofilm formation. Moreover, it reduced violacein production by Chromobacterium violaceum (ATCC 12,472). It decreased the relative expression of 4 quorum sensing genes (lasI, lasR, rhlI, rhlR) and the biofilm gene (ndvB) using qRT-PCR. Furthermore, DSE presented a cytotoxic activity with IC50 of 4.36 ± 0.52 µg/ml against human skin fibroblast cell lines. For the first time, this study reports that DSE is a promising resource of anti-biofilm and anti-quorum sensing agents.
It has been shown that commercial tomato juice packaged in 900 g plastic bottles contains rare, naturally occurring steroidal solanocapsine-type tomato glycosides in which the saponins consist of esculeosides B-1 (2) and B-2 (3) in 0.041% as major components lacking esculeoside A. We suggest that these saponins are derived from esculeoside A (1) when the juice in plastic bottles is prepared by treatment with boiling water, similar to the process used in preparing canned tomatoes. Herein, the obtained tomato saponins (2) and (3) provided sapogenols esculeogenin B 1 (4) and B 2 (5), respectively, by acid hydrolysis. The former was identical to esculeogenin B previously reported, and the latter was a new sapogenol characterized to be (5α,22S,23S,25S)-22,26-epimino-16β,23-epoxy-3β,23,27-trihydroxycholestane.
Given the lack of adequate research on (Dioon spinulosum) Dyer Ex Eichler, this study was conducted focusing on different biological activities and phytochemical investigation of D. spinulosum for the first time. D. spinulosum showed strong protective activity against DNA damage and potent activity against VERO cell line. It also presented antimicrobial and hepatoprotective activity. Phytochemical investigation of the leaves resulted in isolation of two new flavonoids, apigenin 7-O-α-D-glucopyranoside (15) and amentoflavone 7-O-α-Lrhamnopyranoside (16) were isolated from Dioon spinulosum leaves in addition to fifteen known compounds: phytone (1), trans-phytol (2), β-sitosterol (3), stigmasterol (4), oliveriflavone (5), 7,4′,7″,4″′-tetramethylamentoflavone (6), 7,4',7''-trimethylamentoflavone (7), scaidopitysin (8), bilobetin (9), isoginkgetin (10), aromadendrin (11), sotusflavone (12), engeletin (14) and eriocitrin (17) for the first time together with amentoflavone (13). Compounds (11) and (13) displayed very strong cytotoxic activity and showed the highest protective activity against DNA damage.
We examined the sulfides in onion (Allium cepa L.), Welsh onion (A. fistulosum L.), and garlic (A. sativum L.), and obtained three new thiolane-type sulfides (onionins A 1 -A 3 ) from onion; two new thiabicyclic-type sulfides (welsonins A 1 , A 2 ), together with onionins A 1 -A 3 , from Welsh onion; and six new acyclic-type sulfides (garlicnins L-1-L-4, E, and F), ten new thiolane-type sulfides (garlicnins A, B 1 -B 4 , C 1 -C 3 , K 1 , and K 2 ), and three new atypical cyclic-type sulfides (garlicnins G, I, and J) from garlic. Acetone extracts showed the potential of these sulfides in inhibiting the polarization of M2 activated macrophages that are capable of suppressing tumor-cell proliferation. The effect of the thiolane-type sulfide of a major component, onionin A 1 , on tumor progression and metastasis in both osteosarcoma and ovarian cancer-bearing mouse models was then examined. Tumor proliferation was depressed, and tumor metastasis was controlled by regulating macrophage activation. These results showed that onionin A 1 is an effective agent for controlling tumors in both in vitro and in vivo models, and that the antitumor effects observed in vivo are likely caused by reversing the antitumor immune system. Activation of the antitumor immune system by onionin A 1 might be an effective adjuvant therapy for patients with osteosarcoma, ovarian cancer and other malignant tumors. Based on these findings, pharmacological investigations will be conducted in the future to develop natural and healthy foods and anti-cancer agents that can prevent or combat disease.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.