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. 2024 Mar 14;25(6):3311.
doi: 10.3390/ijms25063311.

Labdane-Type Diterpenoids from Streptomyces griseorubens and Their Antimicrobial and Cytotoxic Activities

Chang-Su Heo  1   2 , Jong Soon Kang  3 , Jeong-Wook Yang  3 , Min Ah Lee  1   4 , Hwa-Sun Lee  1   4 , Hee Jae Shin  1   2
Affiliations

Labdane-Type Diterpenoids from Streptomyces griseorubens and Their Antimicrobial and Cytotoxic Activities

Chang-Su Heo et al. Int J Mol Sci. .

Abstract

Chemical investigation of the ethyl acetate (EtOAc) extract from a marine-derived actinomycete, Streptomyces griseorubens, resulted in the discovery of five new labdane-type diterpenoids: chlorolabdans A-C (1-3), epoxylabdans A and B (4 and 5), along with one known analog (6). The structures of the new compounds were determined by spectroscopic analysis (HR-ESIMS, 1D, and 2D NMR) and by comparing their experimental data with those in the literature. The new compounds were evaluated for their antimicrobial activity, and 2 displayed significant activity against Gram-positive bacteria, with minimum inhibitory concentration (MIC) values ranging from 4 to 8 µg/mL. Additionally, 1, 2, and 4 were tested for their cytotoxicity against seven blood cancer cell lines by CellTiter-Glo (CTG) assay and six solid cancer cell lines by sulforhodamine B (SRB) assay; 1, 2, and 4 exhibited cytotoxic activities against some blood cancer cell lines, with concentration causing 50% cell growth inhibition (IC50) values ranging from 1.2 to 22.5 µM.

Keywords: Streptomyces griseorubens; antimicrobial; chlorolabdan; cytotoxicity; diterpenoids; epoxylabdan; labdane.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
Structures of 1–6 isolated from S. griseorubens 2210JJ-087.
Figure 2
Figure 2
Schematic diagram of experimental procedures.
Figure 3
Figure 3
Key COSY, HMBC, and NOESY correlations of 1–3.
Figure 4
Figure 4
ΔδH values (in ppm) = δS − δR obtained for (S)- and (R)-MTPA esters of 1 and 2.
Figure 5
Figure 5
Key COSY, HMBC, and NOESY correlations of 4 and 5.
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