Сульфокостулид В

Description

Sulfocostulide B (sulfocostunolide B) is a sesquiterpene lactone with a sulfonic acid group, isolated from the roots of Saussurea lappa (Saussurea burdock, costus; the modern accepted name of the species is Saussurea costus, family Asteraceae). The compound is described together with sulfocostunolide A in the article “Two New Sesquiterpene Lactones with the Sulfonic Acid Group from Saussurea lappa”, Chemical and Pharmaceutical Bulletin, 2005, vol. 53, no. 7, p. 841. In that work, the structure of the substance was established as 13-sulfo-dihydroreynosine, a derivative of reynosine eudesmanolide with a sulfo group at C-13.

Basic Attributes

• CAS No: 1059671-65-6
• Chemical formula: C15H20O5S
• English name: Sulfocostulide B (Sulfocostunolide B)
• Molecular Weight: 312.38
• Exact weight: 312.103
• DSSTox ID: DTXSID40780091, DTXSID00780092

Characteristics

• PSA: 89
• XLogP3: 1.1

An XLogP3 value of about one in the presence of an ionizable sulfo group indicates a moderate polarity of the molecule: it dissolves well in methanol and water-alcohol mixtures, which is taken into account when preparing samples and selecting the mobile phase.

Structure and origin

The basis of the molecule is a eudesmanolide sesquiterpene framework with a γ-lactone ring. The sulfonic group at C-13 is attached to the exocyclic methylene group of the lactone: it arises from the addition of a sulfite ion at the activated double bond of the α-methylene-γ-lactone. This combination of a terpenoid skeleton and a strongly acidic sulfo group is rare among natural compounds, which explains the interest in this substance in phytochemistry.

The source of excretion is the roots of Saussurea lappa. Costus roots are traditionally used in India, China and Japan; Costunolide, dehydrocostus lactone and other sesquiterpene lactones are isolated from the same raw materials.

Scope of application

• Analytical Standard for Control of Identity and Quantification in Saussurea lappa Extracts
• Reference compound for phytochemical profiling of costus roots
• Object of research in the chemistry of natural sesquiterpene lactones

Storage and handling

The hazard class, transport codes and storage mode are not given in the original product card. Handling corresponds to the practice of working with standard samples of natural compounds: sealed containers, protection from light and moisture, preparation of working solutions immediately before analysis. There is no data on melting point, density, solubility and toxicity in the card, so these items are not given.

Synonyms

• Sulfocostulide B
• Sulfocostunolide B
• Sulfocostunolide B
• 13-Sulfo-dihydroreynosine (as originally described)