Three new guaiane sesquiterpene lactones (4S)-4-hydroxy-gweicurculactone (1), zedoalactone G (2), and (1R, 4R, 5S, 10S)-zedoalactone B (3), and three known guaiane sesquiterpene lactones, including zedoarolide B (4), zedoalactone B (5), and a new natural product (+)-zedoalactone A (6), were isolated from the rhizomes of Curcuma wenyujin Y.H. Chen et C. Ling. The structures were elucidated by spectroscopic methods including 1D and 2D NMR and HR-ESI-MS. The absolute configuration of 2 was determined via the calculated electronic circular dichroism (ECD), whereas the absolute configurations of 1 and 3 were determined via the ECD data of the [Rh2(OCOCF3)4] complex and [Mo2(OAc)4] complex, respectively. The inhibitory effects of compounds 1-6 on nitric oxide production in lipopolysaccharide-activated macrophages were evaluated. All of them exhibited weak anti-inflammatory activity.

Download full-text PDF

Source
http://dx.doi.org/10.1080/10286020.2013.796936DOI Listing

Publication Analysis

Top Keywords

three guaiane
12
guaiane sesquiterpene
12
sesquiterpene lactones
12
rhizomes curcuma
8
curcuma wenyujin
8
lactones rhizomes
4
wenyujin three
4
lactones 4s-4-hydroxy-gweicurculactone
4
4s-4-hydroxy-gweicurculactone zedoalactone
4
zedoalactone 10s-zedoalactone
4

Similar Publications

Hypoglycemic activity and metabolite diversity of Archangium sp. UTMC 4535 with the first report on magnodelavin biosynthesis by bacteria.

Bioorg Chem

January 2025

Pharmaceutical Biotechnology Lab, School of Biology and Center of Excellence in Phylogeny of Living Organisms, College of Science, University of Tehran, 14155-6455 Tehran, Iran. Electronic address:

Diabetes has been declared an epidemy by the World Health Organization and represents a significant metabolic comorbidity. Given the promising pharmaceutical activities of myxobacterial secondary metabolites, we investigated the inhibitory potential of compounds from the soil myxobacterium Archangium sp. UTMC4535, leading to the identification of magnodelavin C, a guaiane sesquiterpene lactone.

View Article and Find Full Text PDF

Two heterocyclic sesquiterpenoid oligomers (1, 2) and four previously undescribed seco-pseudoguaianolide derivatives (3-6) were isolated from the inflorescence of Ambrosia artemisiifolia. Ambrosiadimer A (1) is an unprecedented dimer featuring a hexahydropyrrolizine core scaffold and two pseudoguaianolide units. Ambrosiatrimer A (2) is a trimer formed from three pseudoguaianolide units via a pyrrolidine ring.

View Article and Find Full Text PDF
Article Synopsis
  • - The study examined the chemical diversity of the SWUF15-40 fungus grown in a yeast-malt extract medium, shifting from the previous PDB medium using the OSMACs strategy, which resulted in discovering numerous bioactive compounds.
  • - Detailed analysis using IR, NMR, MS, and XRD techniques led to the identification of two new isopimarane derivatives, three guaiane derivatives, and four known compounds.
  • - A cyclic pentapeptide from the fungus showed promising anti-cancer activity against several cell lines and inhibited nitric oxide production, indicating that adjusting growth conditions can enhance the discovery of bioactive compounds in fungi.
View Article and Find Full Text PDF

Eudesmane-guaiane sesquiterpenoid dimers from Aucklandia costus trigger paraptosis-like cell death via ROS accumulation and MAPK hyperactivation.

Chin J Nat Med

November 2024

State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; Yunnan Characteristic Plant Extraction Laboratory, Kunming 650106, China. Electronic address:

Article Synopsis
  • Three novel compounds, auckcostusolides A-C, were extracted from Aucklandia costus leaves and their structures were analyzed using advanced spectroscopic techniques and X-ray diffraction.
  • Compounds 1 and 2 have the same basic structure but different configurations, a result of distinct chemical processes during their formation.
  • The study found that these compounds have toxic effects on various cancer cell lines, inducing a specific type of cell death called paraptosis, which is linked to processes like increased oxidative stress and ER stress.
View Article and Find Full Text PDF
Article Synopsis
  • * Their chemical structures were determined using advanced techniques like spectroscopy and mass spectrometry, with absolute configurations confirmed through electronic circular dichroism calculations.
  • * The new compounds were tested for their ability to kill cancer cells, showing that one compound was effective against three types of cancer cells (HT-29, A-549, and MCF-7), while the other was effective against only two (HT-29 and MCF-7).
View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!