Макрокарпальный C

Description

Macrocarpal C (Macrocarpal C) is a formylated phloroglucinol compound with a sesquiterpene fragment of the aromatic dendran series, C28H38O5, CAS 142628-53-3. Isolated from fresh leaves of the globular eucalyptus Eucalyptus globulus Labill (in the Chinese tradition - “Lan An”). Systematic name: 5-[(1R)-1-[(1aR,4aR,7S,7aR,7bR)-decahydro-1,1,7-trimethyl-4-methylene-1H-cycloprop[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxy-1,3-benzenedicarbaldehyde. Synonyms: large-fruited C, (−)-large-fruited C, large-fruited G; additional registration number 145416-92-8. Catalog section - sesquiterpenes.

Basic Attributes

• CAS No.: 142628-53-3 (Additional No. 145416-92-8)
• Chemical formula: C28H38O5
• Molecular Weight: 454.607
• Exact weight: 454.60
• DSSTox ID: DTXSID50162107
• PSA Specifications: 94.8
• XLogP3: 10.79
• Density: 1.2 ± 0.1 g/cm³ (calculated value)
• Boiling point: 503.9 ± 50.0 °C at 760 mm Hg. Art. (calculated value)
• Flash point: 272.6 ± 26.6 °C (estimated value)
• Refractive index: 1.594

Structure

The terpene part of the molecule is built on a cyclopropazulene framework - a tricyclic system of the aromatic-dendran type with a cyclopropane ring, which distinguishes macrocarpal C from the eudesmane representatives of the group (macrocarpals E, K, L). The aromatic part is trihydroxybenzenedicarbaldehyde, that is, phloroglucinol with two aldehyde groups. There are five oxygen atoms in the molecule, not six, as in the eudesmane analogues: there is no tertiary hydroxyl in the terpene fragment. Hence the smaller polar surface (94.8 versus 115) and the highest lipophilicity in the series - XLogP3 10.79.

Biological activity studied

• antifungal effect on the dermatophyte Trichophyton mentagrophytes: minimum inhibitory concentration 1.95 μg/ml; In terms of potency in equal concentrations, the compound surpassed terbinafine and nystatin
• the mechanism of antifungal action includes three components: disruption of membrane permeability (increase in the absorption of SYTOX Green dye by 69.2% at a concentration of 1 × MIC, P = 0.0043), oxidative stress (increase in the level of reactive oxygen species by 144.3% after 3 hours, P = 0.0063) and DNA fragmentation with signs of apoptosis, increasing over time according to data TUNEL test
• inhibition of dipeptidyl peptidase-4 (DPP-4) - the effect is manifested in the aggregated form of the compound
• suppression of oral pathogens with minimum inhibitory concentrations of 0.20–6.25 μg/ml and inhibition of glucosyltransferase have been described for the group of macrocarpals from Eucalyptus globulus

Scope of application

• research on antifungal agents against dermatophytes
• work on DPP-4 inhibitors
• analytical standard for the control of Eucalyptus globulus extracts
• phytochemical studies of the genus Eucalyptus

Storage and handling

Tightly closed container, darkness, low temperature. Prepare solutions using organic solvents; when biological testing, take into account the compound’s tendency to aggregate, which determines the observed activity. GHS classification, transport codes and toxicological data are not included in the card; work with gloves and safety glasses.