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Related Concept Videos

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Stereoisomerism of Cyclic Compounds

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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Updated: Jun 19, 2025

Histological Quantification to Determine Lung Fungal Burden in Experimental Aspergillosis
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Ten ring-B aromatized ergosterols from Aspergillus spectabilis.

Mengsha Wei1, Weiguang Sun1, Linlin Liu1

  • 1Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.

Chinese Journal of Natural Medicines
|July 26, 2024
PubMed
Summary

Ten new aromatic ergosterols were isolated from Aspergillus spectabilis. One compound, ergosterol 8, demonstrated significant neuroprotective effects by reducing cell apoptosis and preserving mitochondrial function.

Keywords:
Aromatic ergosterolsAspergillus spectabilisNeuroprotective activitiesSteroidsStructure elucidation

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Area of Science:

  • Natural Product Chemistry
  • Medicinal Chemistry
  • Mycology

Background:

  • Aspergillus species are a rich source of bioactive natural products.
  • Ergosterols with unique structural features are of interest for their biological activities.
  • The exploration of fungal metabolites can lead to the discovery of novel therapeutic agents.

Purpose of the Study:

  • To isolate and characterize novel ergosterols from Aspergillus spectabilis.
  • To investigate the neuroprotective potential of these newly discovered compounds.

Main Methods:

  • Isolation and purification of compounds using chromatographic techniques.
  • Structure elucidation employing high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) and nuclear magnetic resonance (NMR) spectroscopy.
  • Determination of absolute configurations via single-crystal X-ray diffraction and electronic circular dichroism (ECD) calculations.
  • In vitro assessment of neuroprotective activity using glutamate-induced SH-SY5Y cell models.

Main Results:

  • Ten ergosterols, Spectasterols F-O, with an aromatized B ring were identified.
  • Compound 4 exhibited an unusual C23 ergosterol structure with a truncated side chain.
  • Compound 8 displayed significant dose-dependent neuroprotective effects, reducing apoptosis and enhancing mitochondrial function in SH-SY5Y cells.

Conclusions:

  • Aspergillus spectabilis produces a diverse array of aromatic ergosterols.
  • Compound 8 represents a promising lead compound for developing neuroprotective therapies.
  • Further research into the mechanism of action of compound 8 is warranted.