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Related Concept Videos

Stereoisomers02:32

Stereoisomers

On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to restricted...
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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,...
Isomerism02:43

Isomerism

Isomers are molecules with the same molecular formula but different structural arrangements. Isomers can be further classified into constitutional isomers and stereoisomers. Constitutional isomers differ in the connectivity of their constituent atoms. For example, 2-butanol and diethyl ether are constitutional isomers, as they have the same chemical formula, C4H10O, but differ in the connectivity of the carbon and oxygen atoms. Constitutional isomers have different physical and chemical...
Stereoisomerism02:52

Stereoisomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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).
Green Algae01:21

Green Algae

Green algae, also referred to as chlorophytes, are different from red algae in having the chloroplasts containing chlorophylls a and b, which give them their distinct green hue. However, they lack phycobiliproteins, preventing them from developing the red or blue-green pigmentation seen in red algae. In terms of photosynthetic pigment composition, green algae closely resemble plants and share a close evolutionary relationship with them. Taxonomically Green algae belong to Phylum Chlorophyta in...

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A new isocoumarin from Hypericum annulatum.

Paraskev T Nedialkov1, Dimitrina Zheleva-Dimitrova, Ulrich Girreser

  • 1Department of Pharmacognosy, Faculty of Pharmacy, Medical University of Sofia, Sofia, Bulgaria. pnedialkov@pharmfac.net

Natural Product Research
|September 14, 2007
PubMed
Summary

Researchers discovered a new isocoumarin, annulatomarin, from Hypericum annulatum. This compound showed modest growth-inhibitory effects against human chronic myeloid leukemia cells in vitro.

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Area of Science:

  • Natural Product Chemistry
  • Pharmacology
  • Medicinal Chemistry

Background:

  • The plant Hypericum annulatum is a source of bioactive natural products.
  • Isocoumarins are a class of compounds with diverse biological activities.
  • Leukemia remains a significant health challenge, necessitating the search for novel therapeutics.

Purpose of the Study:

  • To isolate and characterize new compounds from Hypericum annulatum.
  • To evaluate the in vitro cytotoxic activity of isolated compounds against cancer cell lines.

Main Methods:

  • Aerial parts of Hypericum annulatum were extracted and subjected to chromatographic separation.
  • The structure of the new compound was elucidated using detailed spectroscopic analysis (NMR, MS).
  • In vitro cytotoxic activity was assessed against human chronic myeloid leukemia LAMA-84 cells.

Main Results:

  • A new isocoumarin, annulatomarin (1), was isolated and structurally characterized.
  • Physcion and beta-sitosterol were also identified as known compounds.
  • Annulatomarin demonstrated a modest inhibitory effect on LAMA-84 cell growth with an IC(50) of 111 microM.

Conclusions:

  • Annulatomarin is a novel isocoumarin isolated from Hypericum annulatum.
  • The compound exhibits preliminary cytotoxic activity against chronic myeloid leukemia cells.
  • Further investigation into annulatomarin's mechanism of action and therapeutic potential is warranted.