Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2014 Mar 8;70(Pt 4):o408-9.
doi: 10.1107/S1600536814004632. eCollection 2014 Apr 1.

Trichodermaerin: a diterpene lactone from Trichoderma asperellum

Suchada Chantrapromma  1 , Chotika Jeerapong  2 , Worrapong Phupong  2 , Ching Kheng Quah  3 , Hoong-Kun Fun  3
Affiliations

Trichodermaerin: a diterpene lactone from Trichoderma asperellum

Suchada Chantrapromma et al. Acta Crystallogr Sect E Struct Rep Online. .

Abstract

The title compound, C20H28O3, known as 'trichodermaerin' [systematic name: (4E)-4,9,15,16,16-penta-methyl-6-oxa-tetra-cyclo-[10.3.1.0(1,10).0(5,9)]hexa-dec-4-ene-7,13-dione], is a diterpene lactone which was isolated from Trichoderma asperellum. The structure has a tetra-cycic 6-5-7-5 ring system, with the cyclo-hexa-none ring adopting a twisted half-chair conformation and the cyclo-pentane ring adopting a half-chair conformation, whereas the cyclo-heptene and tetra-hydro-furan-anone rings are in chair and envelope (with the methyl-substituted C atom as the flap) conformations, respectively. The three-dimensional architecture is stabilized by C-H⋯O inter-actions.

PubMed Disclaimer

Figures

Fig. 1.
Fig. 1.
The molecular structure of the title compound, showing 40% probability displacement ellipsoids.
Fig. 2.
Fig. 2.
The crystal packing of the title compound viewed along the a axis, showing screw chains. Only H atoms involved in hydrogen bonds were shown for clarity. Hydrogen bonds are shown as dashed lines.
Fig. 3.
Fig. 3.
Showing the connection of the adjacent screw chains by C—H···O weak interactions. Only H atoms involved in hydrogen bonds were shown for clarity. Hydrogen bonds are shown as dashed lines.
See this image and copyright information in PMC

References

    1. Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
    1. Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
    1. Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.
    1. Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.
    1. De los Santos-Villalobos, S., Guzmán-Ortiz, D. A., De-Folter, S., Gómez-Lim, M. A., Délano-Frier, J. P., De-Folter, S., Sánchez-García, P. & Peña-Cabriales, J. J. (2011). Biol. Control 2, 221–234.