Neric acid derivatives produced by the honey bee fungal entomopathogen Ascosphaera apis

Gallardo, Gabriela L.; Peña, Nora I.; Cabrera, Gabriela M.

doi:10.1016/j.phytol.2008.07.008

Cited by 18 publications

(6 citation statements)

References 20 publications

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“…were present in its aqueous extract. The biologically active geraniol, grandisol (the boll weevil pheromone), neric acid (a pheromone), neophytadiene, n -hexadecanoic acid, phytol, octadecanoic acid (anti-inflammatory, antioxidant, anticancer), hexacosene, and nandrolone (anticancer) were observed in the investigated ethanolic extract of C. citratus while its aqueous extract contained cyclopentasiloxane (antioxidant), cis-linalool oxide (antifungal and antitermitic), trans-linalool oxide (pyranoid), pentasiloxane, hexadecanoic acid, , and hexasiloxane (antieczemic, anticoranary, antiantrogenic, and nematicide) .…”

Section: Resultsmentioning

confidence: 99%

“…The The values were the average of triplicate samples (n = 3) ± S.D., two-way analysis of variance (ANOVA) shows (P ≤ 0.05), so results are significant. biologically active geraniol, 59 grandisol (the boll weevil pheromone), 60 neric acid (a pheromone), 61 neophytadiene, 62 n-hexadecanoic acid, 63 phytol, 62 octadecanoic acid (antiinflammatory, antioxidant, anticancer), 64 hexacosene, 65 and nandrolone (anticancer) 66 were observed in the investigated ethanolic extract of C. citratus while its aqueous extract contained cyclopentasiloxane (antioxidant), 67 cis-linalool oxide (antifungal and antitermitic), 68 trans-linalool oxide (pyranoid), 69 pentasiloxane, 67 hexadecanoic acid, 63,67 and hexasiloxane (antieczemic, anticoranary, antiantrogenic, and nematicide). 70 Geraniol is the main bioactive component of C. citratus, 59 which shows a variety of activities including repellence to sand flies, mosquitoes, cattle ticks, 71 prevention of secondary complications in diabetes and reduction of hyperglycaemia, 72 anti-inflammatory and antioxidant properties, 73 antifungal activity, 74 activity against respiratory pathogens, skin and food-derived strains, potential against prostate/kidney/liver/bowel and skin cancer, 73 and antibacterial properties especially against B. subtilis (a pathogen of the bakery industry).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Synergistic Antibacterial Screening of Cymbopogon citratus and Azadirachta indica: Phytochemical Profiling and Antioxidant and Hemolytic Activities

et al. 2023

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Current studies were performed to investigate the phytochemistry, synergistic antibacterial, antioxidant, and hemolytic activities of ethanolic and aqueous extracts of Azadirachta indica (EA and WA) and Cymbopogon citratus (EC and WC) leaves. Fourier transform infrared data verified the existence of alcoholic, carboxylic, aldehydic, phenyl, and bromo moieties in plant leaves. The ethanolic extracts (EA and EC) were significantly richer in phenolics and flavonoids as compared to the aqueous extracts (WA and WC). The ethanolic extract of C. citratus (EC) contained higher concentrations of caffeic acid (1.432 mg/g), synapic acid (6.743 mg/g), and benzoic acid (7.431 mg/g) as compared to all other extracts, whereas chlorogenic acid (0.311 mg/g) was present only in the aqueous extract of A. indica (WA). Food preservative properties of C. citratus can be due to the presence of benzoic acid (7.431 mg/g). Gas chromatography–mass spectrometry analysis demonstrated the presence of 36 and 23 compounds in A. indica and C. citratus leaves, respectively. Inductively coupled plasma analysis was used to determine the concentration of 26 metals (Al, As, B, Ba, Ca, Cd, Co, Cr, Cu, Fe, K, Mg, Mn, Mo, Na, Ni, Pb, Sb, Se, Si, Sn, Sr, V, Zn, Zr, Ti); the metal concentrations were higher in aqueous extracts as compared to the ethanolic extracts. The extracts were generally richer in calcium (3000–7858 ppm), potassium (13662–53,750 ppm), and sodium (3181–8445 ppm) and hence can be used in food supplements as a source of these metals. Antioxidant potential (DDPH method) of C. citratus ethanolic extract was the highest (74.50 ± 0.66%), whereas it was the lowest (32.22 ± 0.28%) for the aqueous extract of A. indica. Synergistic inhibition of bacteria (Staphylococcus aureus and Escherichia coli) was observed when the aqueous extracts of both the plants were mixed together in certain ratios (v/v). The highest antibacterial potential was exhibited by the pure extract of C. citratus, which was even higher than that of the standard drug (ciprofloxacin). The plant extracts and their mixtures were more active against S. aureus as compared to E. coli. No toxic hemolytic effects were observed for the investigated extracts indicating their safe medicinal uses for human beings.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Synergistic Antibacterial Screening of Cymbopogon citratus and Azadirachta indica: Phytochemical Profiling and Antioxidant and Hemolytic Activities

et al. 2023

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“…As we know, ( Z )-3,7-dimethyl-2,6-octadienoic acid and ( 6R )-3,7-dimethyl-7-hydroxyl-2-octen-1,6-olide exhibited certain fungicidal activities [17,18]. The racemic 3,7-dimethyl-7-hydroxyl-2-octen-1,6-olide, the other seven-membered lactone derivatives and ( E )-3,7-dimethyl-2,6-octadienoic acid were synthesized and some of them were found to exhibit better fungicidal activities in our laboratory [19,20,21].…”

Section: Resultsmentioning

confidence: 99%

“…In agricultural chemicals, a lot of novel amide derivatives have been synthesized, some of them showed good fungicidal or insecticidal activities, and the mode of action on amide fungicides has been reviewed recently [8,9,10,11,12,13,14,15,16]. 2,6-Dimethyl-6-hydroxy-2 E ,4 E -hepta-2, 4-diene acid and ( 6R )-3,7-dimethyl-7-hydroxyl-2-octen-1,6-olide were isolated from the fruit of Litsea cubeba in Tibet, and they were evaluated to have good fungicidal activities in our laboratory [17,18]. Based on these results, some of the seven-membered lactone derivatives were synthesized and confirmed to exhibit moderate to excellent fungicidal activities [19,20,21].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Fungicidal Activities of (Z/E)-3,7-Dimethyl-2,6-octadienamide and Its 6,7-Epoxy Analogues

et al. 2015

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Abstract:In order to find new lead compounds with high fungicidal activity, (Z/E)-3,7-dimethyl-2,6-octadienoic acids were synthesized via selective two-step oxidation using the commercially available geraniol/nerol as raw materials. Twenty-eight different (Z/E)-3,7-dimethyl-2,6-octadienamide derivatives were prepared by reactions of (Z/E)-carboxylic acid with various aromatic and aliphatic amines, followed by oxidation of peroxyacetic acid to afford their 6,7-epoxy analogues. All of the compounds were characterized by HR-ESI-MS and 1 H-NMR spectral data. The preliminary bioassays showed that some of these compounds exhibited good fungicidal activities against Rhizoctonia solani (R. solani) at a concentration of 50 µg/mL. For example, 5C, 5I and 6b had 94.0%, 93.4% and 91.5% inhibition rates against R. solani, respectively. Compound 5f displayed EC 50 values of 4.3 and 9.7 µM against Fusahum graminearum and R. Solani, respectively.

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“…Four of them were characterized as (6 R )-3,7-dimethyl-7-hydroxy-2-octen-6-olide ( 2 ) [12,13], vanillic acid ( 3 ) [14], trans -3,4,5-trimethoxyl-cinnamyl alcohol ( 4 ) [15], and aporphine alkaloid oxonantenine ( 5 ) [16] by m.p., [α] D , MS, 1 H-NMR and 13 C-NMR spectral data.…”

Section: Resultsmentioning

confidence: 99%

The Fungicidal Terpenoids and Essential Oil from Litsea cubeba in Tibet

Jiazheng

Qimei

et al. 2010

Molecules

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A new C9 monoterpenoid acid (litseacubebic acid, 1) and a known monoterpene lactone (6R)-3,7-dimethyl-7-hydroxy-2-octen-6-olide (2), along with three known compounds – vanillic acid (3), trans-3,4,5-trimethoxylcinnamyl alcohol (4), and oxonantenine (5) – were isolated with bioassay-guided purification from the fruit extract of Litsea cubeba collected in Tibet. The structure of 1 was elucidated by MS, 1H-NMR, 13C-NMR, COSY, HSQC, HMBC, NOE spectral data as 2,6-dimethyl-6-hydroxy-2E,4E-hepta-2,4-diene acid. Additionally 33 compounds were identified from the essential oil of L. cubeba. The preliminary bioassay results showed that 1 and 2 have good fungicidal activities against Sclerotinia sclerotiorum, Thanatephorus cucumeris, Pseudocer-cospora musae and Colletotrichum gloeosporioides at the concentration of 588 and 272 μM, and the essential oil has good fungicidal activities against T. cucumeris and S. sclerotiorum, with IC50 values of 115.58 and 151.25 μg/mL, repectively.

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Neric acid derivatives produced by the honey bee fungal entomopathogen Ascosphaera apis

Cited by 18 publications

References 20 publications

Synergistic Antibacterial Screening of Cymbopogon citratus and Azadirachta indica: Phytochemical Profiling and Antioxidant and Hemolytic Activities

Synergistic Antibacterial Screening of Cymbopogon citratus and Azadirachta indica: Phytochemical Profiling and Antioxidant and Hemolytic Activities

Synthesis and Fungicidal Activities of (Z/E)-3,7-Dimethyl-2,6-octadienamide and Its 6,7-Epoxy Analogues

The Fungicidal Terpenoids and Essential Oil from Litsea cubeba in Tibet

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