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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated benzene...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

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Related Experiment Video

Updated: Jul 3, 2026

High-resolution Tandem Mass Spectrometry for Studying Chemical Constituents of Gynura bicolor DC
07:16

High-resolution Tandem Mass Spectrometry for Studying Chemical Constituents of Gynura bicolor DC

Published on: February 2, 2024

Sesquiterpenoids from Hedyosmum orientale.

Zu-Shang Su1, Sheng Yin, Zhi-Wang Zhou

  • 1State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai, 201203, People's Republic of China.

Journal of Natural Products
|July 25, 2008
PubMed
Summary

Researchers isolated five new guaiane-type sesquiterpenoids, hedyosumins A-E, from Hedyosmum orientale. One compound, 9alpha-hydroxyasterolide, demonstrated moderate activity against lung and leukemia tumor cell lines.

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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
07:59

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

Published on: October 4, 2019

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Last Updated: Jul 3, 2026

High-resolution Tandem Mass Spectrometry for Studying Chemical Constituents of Gynura bicolor DC
07:16

High-resolution Tandem Mass Spectrometry for Studying Chemical Constituents of Gynura bicolor DC

Published on: February 2, 2024

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
07:59

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

Published on: October 4, 2019

Area of Science:

  • Natural Product Chemistry
  • Phytochemistry
  • Organic Chemistry

Background:

  • Hedyosmum orientale is a plant species known to produce diverse secondary metabolites.
  • Sesquiterpenoids, a class of natural products, often exhibit significant biological activities.
  • Investigating the chemical constituents of Hedyosmum orientale can lead to the discovery of novel compounds with therapeutic potential.

Purpose of the Study:

  • To isolate and characterize new guaiane-type sesquiterpenoids from the aerial parts of Hedyosmum orientale.
  • To identify known sesquiterpenoids that have not been previously reported as natural products.
  • To evaluate the cytotoxic activities of the isolated compounds against selected human tumor cell lines.

Main Methods:

  • Phytochemical investigation involving extraction and chromatographic separation techniques (e.g., column chromatography, HPLC).
  • Structure elucidation of isolated compounds using comprehensive spectroscopic methods (e.g., NMR, MS, IR).
  • In vitro cytotoxic activity assays against A-549 (lung carcinoma) and HL-60 (promyelocytic leukemia) cell lines.

Main Results:

  • Five new guaiane-type sesquiterpenoids, designated hedyosumins A-E (1-5), were successfully isolated.
  • Five known sesquiterpenoids (6-10) were also identified, including two compounds obtained as natural products for the first time: 10alpha-hydroxy-1,5alpha H-guaia-3,7(11)-dien-8alpha,12-olide and 9alpha-hydroxyasterolide.
  • 9alpha-Hydroxyasterolide (7) exhibited moderate cytotoxic activity against A-549 and HL-60 cell lines, with IC50 values of 3.1 and 8.8 microM, respectively.

Conclusions:

  • The study successfully identified novel guaiane-type sesquiterpenoids from Hedyosmum orientale.
  • The isolation of previously unreported natural products expands the known chemical diversity of this plant genus.
  • 9alpha-Hydroxyasterolide shows potential as an anticancer agent, warranting further investigation.