New Potential Inhibitors of Pheromonal Attractionin the Oriental Fruit Moth, Cydia molesta

1998 ◽  
Vol 63 (7) ◽  
pp. 1031-1044 ◽  
Author(s):  
Michal Hoskovec ◽  
Oldřich Hovorka ◽  
Blanka Kalinová ◽  
Bohumír Koutek ◽  
Aleš Svatoš ◽  
...  
Keyword(s):  
Biological Activities ◽  
Inhibitory Effect ◽  
Oriental Fruit Moth ◽  
Single Sensillum Recording ◽  
Wind Tunnel Experiments ◽  
Structural Modifications ◽  
Cydia Molesta ◽  
Single Sensillum ◽  
Behavioural Experiments ◽  
Potential Inhibitors

New analogues of (Z)-dodec-8-en-1-yl acetate (Z8-12:OAc, 1), the main sex pheromone component of the Oriental fruit moth, Cydia molesta, were designed by formally transferring the terminal propyl group from the C-9 to the C-7 position to form vinyl-branched (2, 3) or, after isomerization, ethylidene-branched (4) structures and by replacing the -CH=CH- grouping by the -S-CH2- moiety (5, 6). Their biological activities were studied both electrophysiologically and behaviourally (laboratory mating and wind tunnel experiments). All the structural modifications resulted in analogues whose electroantennographic activities were lower than that of 1 following the order 1 >> 6 ≈ 5 >> 2 ≈ 4 ≈ 3. The single sensillum recording activities indicated that all the analogues stimulate the same Z8-12:OAc receptor neurone. In behavioural experiments, the analogues were generally found to reduce the ability of males to find a pheromone source, however, to different degrees. The highest inhibitory effect (90%) was observed for the thia analogues 5 and 6. The results support the view that the inhibitory properties of the analogues should not be entirely associated with their pheromone-mimicking capabilities.

ChemInform Abstract: New Potential Inhibitors of Pheromonal Attraction in the Oriental Fruit Moth, Cydia molesta.

ChemInform ◽  
2010 ◽  
Vol 30 (7) ◽  
pp. no-no
Author(s):  
M. HOSKOVEC ◽  
O. HOVORKA ◽  
B. KALINOVA ◽  
B. KOUTEK ◽  
A. SVATOS ◽  
...  
Keyword(s):  
Oriental Fruit Moth ◽  
Cydia Molesta ◽  
Potential Inhibitors

Synthesis and biological properties of cholecystokinin heptapeptide analogues containing D- and L-forms of tert-leucine or neopentylglycine in position 5

1991 ◽  
Vol 56 (10) ◽  
pp. 2209-2217 ◽  
Author(s):  
Jan Hlaváček ◽  
Jana Pírková ◽  
Jan Pospíšek ◽  
Jiřina Slaninová ◽  
Lenka Maletínská
Keyword(s):  
Gall Bladder ◽  
Solid Phase ◽  
Biological Activities ◽  
Biological Properties ◽  
Phase Synthesis ◽  
Structural Modifications ◽  
Bladder Contraction ◽  
Anorectic Effect ◽  
Carboxy Terminal ◽  
Anorectic Activity

Using solution or solid-phase synthesis we prepared the cholecystokinin fragment Boc-CCK-7 (Boc-Tyr-(SO3-.Na+)-Met-Gly-Trp-Met-Asp-PheNH2) and its four analogues in which the methionine moiety (Met) in the carboxy-terminal part is replaced by tert-leucine (Tle) or neopentylglycine (Neo) residue or D-enantiomers of these non-coded amino acids. These structural modifications led to reduction of the studied biological activities (gall bladder contraction, anorectic activity, analgetic and sedation activity) of all prepared analogues except Boc[Neo5]-CCK-7 which, being less analgetically active, retains full gall bladder and sedation activity of CCK-8. Moreover, its anorectic activity is substantially higher (400%). This analogue is very interesting particularly for its selectively increased (4x) anorectic effect compared with that of CCK-8.

Effect of guaianolides in the meiosis reinitiation of amphibian oocytes

Zygote ◽  
2016 ◽  
Vol 25 (1) ◽  
pp. 10-16 ◽  
Author(s):  
J. Zapata-Martínez ◽  
G. Sánchez-Toranzo ◽  
F. Chaín ◽  
C.A.N. Catalán ◽  
M.I. Bühler
Keyword(s):  
Biological Activities ◽  
Wide Spectrum ◽  
Sesquiterpene Lactones ◽  
Inhibitory Effect ◽  
Biological Molecules ◽  
Plant Metabolites ◽  
Major Mechanism ◽  
Bufo Arenarum ◽  
Asteraceae Family

SummarySesquiterpene lactones (STLs) are a large and structurally diverse group of plant metabolites generally found in the Asteraceae family. STLs exhibit a wide spectrum of biological activities and it is generally accepted that their major mechanism of action is the alkylation of the thiol groups of biological molecules. The guaianolides is one of various groups of STLs. Anti-tumour and anti-migraine effects, an allergenic agent, an inhibitor of smooth muscle cells and of meristematic cell proliferation are only a few of the most commonly reported activities of STLs. In amphibians, fully grown ovarian oocytes are arrested at the beginning of meiosis I. Under stimulus with progesterone, this meiotic arrest is released and meiosis progresses to metaphase II, a process known as oocyte maturation. There are previous records of the inhibitory effect of dehydroleucodin (DhL), a guaianolide lactone, on the progression of meiosis. It has been also shown that DhL and its 11,13-dihydroderivative (2H-DhL; a mixture of epimers at C-11) act as blockers of the resumption of meiosis in fully grown ovarian oocytes from the amphibian Rhinella arenarum (formerly classified as Bufo arenarum). The aim of this study was to analyze the effect of four closely related guaianolides, i.e., DhL, achillin, desacetoxymatricarin and estafietin as possible inhibitors of meiosis in oocytes of amphibians in vitro and discuss some structure–activity relationships. It was found that the inhibitory effect on meiosis resumption is greater when the lactone has two potentially reactive centres, either a α,β–α′,β′-diunsaturated cyclopentanone moiety or an epoxide group plus an exo-methylene-γ-lactone function.

scholarly journals A novel radiolytic rotenone derivative, rotenoisin A, displays potent anticarcinogenic activity in breast cancer cells

2021 ◽  
Author(s):  
Dong-ho Bak ◽  
Seong Hee Kang ◽  
Chul-hong Park ◽  
Byung Yeoup Chung ◽  
Hyoung-Woo Bai
Keyword(s):  
Breast Cancer ◽  
Adverse Effects ◽  
Cancer Cells ◽  
Breast Cancer Cells ◽  
Parent Compound ◽  
Inhibitory Effect ◽  
Chemotherapeutic Agents ◽  
Epidermal Keratinocytes ◽  
Functional Changes ◽  
Structural Modifications

Abstract Chemotherapy for cancer treatment has therapeutic limitations, such as drug resistance, excessive toxic effects and undesirable adverse effects. Therefore, efforts to improve the safety and efficacy of chemotherapeutic agents are essential. Ionizing radiation can improve physiological and pharmacological properties by transforming structural modifications of the drug. In this study, in order to reduce the adverse effects of rotenone and increase anticancer activity, a new radiolytic rotenone derivative called rotenoisin A was generated through radiolytic transformation. Our findings showed that rotenoisin A inhibited the proliferation of breast cancer cells and increased the rate of apoptosis, whereas it had no inhibitory effect on primary epidermal keratinocytes compared with rotenone. Moreover, rotenoisin A-induced DNA damage by increasing reactive oxygen species (ROS) accumulation. It was also confirmed not only to alter the composition ratio of mitochondrial proteins, but also to result in structural and functional changes. The anticancer effect and molecular signalling mechanisms of rotenoisin A were consistent with those of rotenone, as previously reported. Our study suggests that radiolytic transformation of highly toxic compounds may be an alternative strategy for maintaining anticancer effects and reducing the toxicity of the parent compound.

Tanshinone IIA: Pharmacology, total synthesis, and progress in structure-modifications

2021 ◽  
Vol 28 ◽  
Author(s):  
Xing Huang ◽  
Hao Deng ◽  
Qing-kun Shen ◽  
Zhe-Shan Quan
Keyword(s):  
Herbal Medicine ◽  
Total Synthesis ◽  
Chinese Herbal Medicine ◽  
Biological Activities ◽  
Structural Features ◽  
Tanshinone Iia ◽  
Structural Modifications ◽  
Chinese Herbal ◽  
Bioactive Constituent

: Tanshinone IIA, a major bioactive constituent of Danshen, a Chinese herbal medicine, has gained extensive exploration owing to its unique structural features and multiple promising biological activities. This review focuses on the pharmacology, total synthesis, and structural modifications of tanshinone IIA. We hope this review will contribute to a better understanding of the progress in the field and provide constructive suggestions for further study of tanshinone IIA.

scholarly journals The Natural Compound Hydrophobic Usnic Acid and Hydrophilic Potassium Usnate Derivative: Applications and Comparisons

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5995
Author(s):  
Hallysson Douglas Andrade de Araújo ◽  
Hianna Arely Milca Fagundes Silva ◽  
José Guedes da Silva Júnior ◽  
Mônica Camelo Pessoa de Azevedo Albuquerque ◽  
Luana Cassandra Breitenbach Barroso Coelho ◽  
...  
Keyword(s):  
Biological Activities ◽  
Structural Characteristics ◽  
Usnic Acid ◽  
Raw Material ◽  
Structural Modifications ◽  
Hydrophobic Molecule ◽  
Antiparasitic Agents ◽  
Toxic Molecule

Usnic acid is the best-studied lichen metabolite, presenting several biological activities, such as antibacterial, immunostimulating, antiviral, antifungal, anti-inflammatory, and antiparasitic agents; despite these relevant properties, it is a hydrophobic and toxic molecule. In this context, scientific research has driven the development of innovative alternatives, considering usnic acid as a source of raw material in obtaining new molecules, allowing structural modifications (syntheses) from it. The purpose is to optimize biological activities and toxicity, with less concentration and/or response time. This work presents a literature review with an analogy of the hydrophobic molecule of usnic acid with its hydrophilic derivative of potassium usnate, emphasizing the elucidation and structural characteristics, biological activities, and toxicological aspects of both molecules, and the advantages of using the promising derivative hydrophilic in different in vitro and in vivo assays when compared to usnic acid.

scholarly journals Response of female Cydia molesta (Lepidoptera: Tortricidae) to plant derived volatiles

2003 ◽  
Vol 93 (4) ◽  
pp. 335-342 ◽  
Author(s):  
D. Natale ◽  
L. Mattiacci ◽  
A. Hern ◽  
E. Pasqualini ◽  
S. Dorn
Keyword(s):  
Host Plant ◽  
Green Leaf Volatiles ◽  
Oriental Fruit Moth ◽  
Gas Chromatography Mass Spectrometry ◽  
Headspace Volatiles ◽  
Component Mixture ◽  
Leaf Volatiles ◽  
Cydia Molesta ◽  
Bioactive Fraction ◽  
A Chain

AbstractPeach shoot volatiles were attractive to mated female oriental fruit moth, Cydia molesta (Busck), in a dual choice arena. No preference was observed between leaf odours from the principle host plant, peach, and the secondary host plant, apple. Twenty-two compounds were identified in headspace volatiles of peach shoots using gas chromatography–mass spectrometry. Green leaf volatiles accounted for more than 50% of the total emitted volatiles. A bioassay-assisted fractionation using different sorbent polymers indicated an attractant effect of compounds with a chain length of 6–8 carbon atoms. The major compounds of this fraction were tested either singly or in combinations for behavioural response of females. Significant bioactivity was found for a three-component mixture of (Z)-3-hexen-1-yl acetate, (Z)-3-hexen-1-ol and benzaldehyde in a 4:1:1 ratio. This synthetic mixture elicited a similar attractant effect as the full natural blend from peach shoots as well as the bioactive fraction.

Cydia molesta. [Distribution map].

1967 ◽  
Author(s):  
Keyword(s):  
North America ◽  
South America ◽  
Host Plants ◽  
Pacific Islands ◽  
Fruit Trees ◽  
Oriental Fruit Moth ◽  
Distribution Map ◽  
Cydia Molesta ◽  
New Distribution ◽  
Distribution In Europe

Abstract A new distribution map is provided for Cydia molesta[Grapholita molesta] (Busck) (Lep., Tortricidae) (Oriental Fruit Moth). Host Plants: Peach and many other fruit trees, etc. Information is given on the geographical distribution in EUROPE, France, Germany, Greece, Hungary, Italy, Malta, Switzerland, Yugoslavia, ASIA, China, Hong Kong, Japan, Korea, Taiwan, Turkey, AFRICA, Morocco, AUSTRALASIA and PACIFIC ISLANDS, Australia, NORTH AMERICA, Canada, Mexico, U.S.A., SOUTH AMERICA, Argentina, Brazil, Uruguay.

Discovery of a Novel Small-Molecule Interleukin-6 Inhibitor through Virtual Screening Using Artificial Intelligence

2021 ◽  
Vol 18 ◽  
Author(s):  
Yoshiaki Sato ◽  
Ikuo Kashiwakura ◽  
Masaru Yamaguchi ◽  
Hironori Yoshino ◽  
Takeshi Tanaka ◽  
...  
Keyword(s):  
Artificial Intelligence ◽  
Small Molecule ◽  
Interleukin 6 ◽  
Inflammatory Diseases ◽  
Biological Activities ◽  
Inhibitory Effect ◽  
Dependent Manner ◽  
Cell Functions ◽  
Dependent Cell ◽  
Dose Dependent

Background: Interleukin-6 (IL-6) is a multifunctional cytokine involved in various cell functions and diseases. Thus far, several IL-6 inhibitors, such as, humanized monoclonal antibody have been used to block excessive IL-6 signaling causing autoimmune and inflammatory diseases. However, anti-IL-6 and anti-IL-6 receptor monoclonal antibodies have some clinical disadvantages, such as a high cost, unfavorable injection route, and tendency to mask infectious diseases. While a small-molecule IL-6 inhibitor would help mitigate these issues, none are currently available. Objective: The present study evaluated the biological activities of identified compounds on IL-6 stimulus. Methods: We virtually screened potential IL-6 binders from a compound library using INTerprotein’s Engine for New Drug Design (INTENDD®) followed by the identification of more potent IL-6 binders with artificial intelligence (AI)-guided INTENDD®. The biological activities of the identified compounds were assessed with the IL-6-dependent cell line 7TD1. Results: The compounds showed the suppression of IL-6-dependent cell growth in a dose-dependent manner. Furthermore, the identified compound inhibited expression of IL-6-induced phosphorylation of signal transducer and activator of transcription 3 in a dose-dependent manner. Conclusion: Our screening compound demonstrated an inhibitory effect on IL-6 stimulus. These findings may serve as a basis for the further development of small-molecule IL-6 inhibitors.

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