Lipovelutibols A-D: Cytotoxic Lipopeptaibols from the Himalayan Cold Habitat Fungus Trichoderma velutinum

  • J Nat Prod. 2018 Feb 23;81(2):219-226. doi: 10.1021/acs.jnatprod.6b00873.
Varun Pratap Singh  1  2 ,  Nalli Yedukondalu  3  4 ,  Vandana Sharma  5 ,  Manoj Kushwaha  5 ,  Richa Sharma  3  6 ,  Asha Chaubey  3  6 ,  Anil Kumar  2 ,  Deepika Singh  1  3  5 ,  Ram A Vishwakarma  1  3
Affiliations
  • 1. Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine , Canal Road, Jammu 180 001, India.
  • 2. Department of Biotechnology, Faculty of Sciences, Shri Mata Vaishno Devi University , Katra, Jammu and Kashmir 182320, India.
  • 3. Academy of Scientific and Innovative Research , Jammu 180 001, India.
  • 4. Natural Product Chemistry Division, CSIR-Indian Institute of Integrative Medicine , Canal Road, Jammu 180 001, India.
  • 5. Quality Control and Quality Assurance, CSIR-Indian Institute of Integrative Medicine , Canal Road, Jammu 180 001, India.
  • 6. Fermentation Technology Division, CSIR-Indian Institute of Integrative Medicine , Canal Road, Jammu 180 001, India.
PMID: 29373791 DOI: 10.1021/acs.jnatprod.6b00873
Abstract

Four novel lipovelutibols A (1), B (2), C (3), and D (4) containing six amino acid residues with leucinol at the C-terminus and a fatty acyl moiety (n-octanoyl) at its N-terminus were isolated from the psychrotrophic fungus Trichoderma velutinum collected from the Himalayan cold habitat. The structures (1-4) were determined by NMR and MS/MS, and the stereochemistry of Amino acids by Marfey's method. Lipopeptaibols 2 and 4 were found to contain d-isovaline, a nonproteinogenic amino acid, but lacked α-aminoisobutyric acid, characteristic of peptaibols. Cytotoxic activity of 2 and 4 was observed against HL-60, LS180, MDA-MB-231, and A549 Cancer cell lines.