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Related Concept Videos

Nomenclature of Alkynes02:39

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes


The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
Structure and Physical Properties of Alkynes02:37

Structure and Physical Properties of Alkynes

Introduction:
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
The simplest alkyne is ethyne, or...

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Related Experiment Video

Updated: Jun 17, 2026

Analysis of Raw and Processed Cyperi Rhizoma Samples Using Liquid Chromatography-Tandem Mass Spectrometry in Rats with Primary Dysmenorrhea
07:36

Analysis of Raw and Processed Cyperi Rhizoma Samples Using Liquid Chromatography-Tandem Mass Spectrometry in Rats with Primary Dysmenorrhea

Published on: December 23, 2022

Polyacetylenes from Bupleurum longiradiatum.

Hai-Qiang Huang1, Xi Zhang, Yun-Heng Shen

  • 1Department of Natural Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, People's Republic of China.

Journal of Natural Products
|December 10, 2009
PubMed
Summary

Researchers identified eight new polyacetylene compounds from Bupleurum longiradiatum. These natural products were evaluated for their potential to combat human leukemia (HL-60) cells.

Related Experiment Videos

Last Updated: Jun 17, 2026

Analysis of Raw and Processed Cyperi Rhizoma Samples Using Liquid Chromatography-Tandem Mass Spectrometry in Rats with Primary Dysmenorrhea
07:36

Analysis of Raw and Processed Cyperi Rhizoma Samples Using Liquid Chromatography-Tandem Mass Spectrometry in Rats with Primary Dysmenorrhea

Published on: December 23, 2022

Area of Science:

  • Natural Product Chemistry
  • Pharmacognosy
  • Medicinal Chemistry

Background:

  • Bupleurum longiradiatum is a plant species known for its traditional medicinal uses.
  • Polyacetylenes are a class of natural compounds with diverse biological activities.
  • Previous research has identified various compounds from the Bupleurum genus.

Purpose of the Study:

  • To isolate and characterize new polyacetylene compounds from Bupleurum longiradiatum.
  • To determine the structures and absolute configurations of these novel compounds.
  • To evaluate the cytotoxic activity of the isolated compounds against a human leukemia cell line.

Main Methods:

  • Extraction and isolation of compounds from the entire plant parts of Bupleurum longiradiatum.
  • Structure elucidation using comprehensive spectroscopic data interpretation (e.g., NMR, MS).
  • Determination of absolute configuration using the modified Mosher's method.
  • Cytotoxicity assays against the human leukemia cell line (HL-60).

Main Results:

  • Eight new polyacetylene compounds, designated 1-8, were successfully isolated and identified.
  • Six known polyacetylene compounds were also isolated.
  • The structures of the new compounds were confirmed through detailed spectroscopic analysis.
  • The absolute configuration of bupleurotoxin (9) was established.
  • All isolated compounds were tested for cytotoxicity against HL-60 cells, with results indicating varying degrees of activity.

Conclusions:

  • The study successfully identified novel polyacetylenes from Bupleurum longiradiatum, expanding the known chemical diversity of this plant.
  • The isolated compounds represent potential leads for the development of new anti-leukemia agents.
  • Further investigation into the structure-activity relationships and mechanisms of action is warranted.