2. Academic Validation
  3. Indole Diterpenoids from an Endophytic Penicillium sp

Indole Diterpenoids from an Endophytic Penicillium sp

  • J Nat Prod. 2019 Jun 28;82(6):1412-1423. doi: 10.1021/acs.jnatprod.8b00723.
Ni P Ariantari 1 2,  Elena Ancheeva 1,  Chenyin Wang 3,  Attila Mándi 4,  Tim-O Knedel 5,  Tibor Kurtán 4,  Chaidir Chaidir 6,  Werner E G Müller 7,  Matthias U Kassack 3,  Christoph Janiak 5,  Georgios Daletos 1,  Peter Proksch 1
Affiliations

Affiliations

  • 1 Institute of Pharmaceutical Biology and Biotechnology , Heinrich Heine University Düsseldorf , Universitätsstrasse 1 , 40225 Düsseldorf , Germany.
  • 2 Department of Pharmacy, Faculty of Mathematic and Natural Sciences , Udayana University , 80361 Bali , Indonesia.
  • 3 Institute of Pharmaceutical and Medicinal Chemistry , Heinrich Heine University Düsseldorf , Universitätsstrasse 1 , 40225 Düsseldorf , Germany.
  • 4 Department of Organic Chemistry , University of Debrecen , P.O.B. 400, 4002 Debrecen , Hungary.
  • 5 Institute of Inorganic Chemistry and Structural Chemistry , Heinrich Heine University Düsseldorf , Universitätsstraße 1 , 40225 Düsseldorf , Germany.
  • 6 Center for Pharmaceutical and Medical Technology , Agency for the Assessment and Application Technology , 10340 Jakarta , Indonesia.
  • 7 Institute of Physiological Chemistry , Universitätsmedizin der Johannes Gutenberg-Universität Mainz , Duesbergweg 6 , 55128 Mainz , Germany.
PMID: 31117519 DOI: 10.1021/acs.jnatprod.8b00723
Abstract

A chemical investigation of the endophyte Penicillium sp. (strain ZO-R1-1), isolated from roots of the medicinal plant Zingiber officinale, yielded nine new indole Diterpenoids (1-9), together with 13 known congeners (10-22). The structures of the new compounds were elucidated by 1D and 2D NMR analysis in combination with HRESIMS data. The absolute configuration of the new natural products 1, 3, and 7 was determined using the TDDFT-ECD approach and confirmed for 1 by single-crystal X-ray determination through anomalous dispersion. The isolated compounds were tested for cytotoxicity against L5178Y, A2780, J82, and HEK-293 cell lines. Compound 1 was the most active metabolite toward L5178Y cells, with an IC50 value of 3.6 μM, and an IC50 against A2780 cells of 8.7 μM. Interestingly, 1 features a new type of indole diterpenoid scaffold with a rare 6/5/6/6/6/6/5 heterocyclic system bearing an aromatic ring C, which is suggested to be important for the cytotoxic activity of this natural product against L5278Y and A2780 cells.

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