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
. 2021 Sep:189:112830.
doi: 10.1016/j.phytochem.2021.112830. Epub 2021 Jun 20.

Three diketomorpholines from a Penicillium sp. (strain G1071)

Zeinab Y Al Subeh  1 , Huzefa A Raja  1 , Joanna E Burdette  2 , Joseph O Falkinham 3rd  3 , Scott E Hemby  4 , Nicholas H Oberlies  5
Affiliations

Three diketomorpholines from a Penicillium sp. (strain G1071)

Zeinab Y Al Subeh et al. Phytochemistry. 2021 Sep.

Abstract

Three previously undescribed diketomorpholine natural products, along with the known phenalenones, herqueinone and norherqueinone, were isolated from the mycoparasitic fungal strain G1071, which was identified as a Penicillium sp. in the section Sclerotiora. The structures were established by analyzing NMR data and mass spectrometry fragmentation patterns. The absolute configurations of deacetyl-javanicunine A, javanicunine C, and javanicunine D, were assigned by examining ECD spectra and Marfey's analysis. The structural diversity generated by this fungal strain was interesting, as only a few diketomorpholines (~17) have been reported from nature.

Keywords: Diketomorpholine; Javanicunine; Penicillium; Phenalenones; Pyrrolidinoindoline.

PubMed Disclaimer

Conflict of interest statement

Declaration of interests

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Figures

Fig. 1.
Fig. 1.
Structures of compounds 1–6.
Fig. 2.
Fig. 2.
Key COSY and HMBC correlations of 1–3.
Fig. 3.
Fig. 3.
Key NOESY correlations of compounds 1–3.
Fig. 4.
Fig. 4.
ECD spectra of compounds 1–4 in CH3CN.
Fig. 5.
Fig. 5.
(+)-HRESIMS fragmentation patterns of 1–3.
Fig. 6.
Fig. 6.
Proposed methanolysis products of 1–4. The R1 and R2 groups for compounds 1–4 are as noted in Fig. 5.
See this image and copyright information in PMC

References

    1. Afiyatullov SS, Kalinovskii AI, Pivkin MV, Dmitrenok PS, Kuznetsova TA, 2004. Fumitremorgins from the marine isolate of the fungus Aspergillus fumigatus. Chem. Nat. Compd 40, 615–617. DOI: 10.1007/s10600-005-0058-2. - DOI
    1. Al Subeh ZY, Raja HA, Maldonado A, Burdette JE, Pearce CJ, Oberlies NH, 2021. Thielavins: tuned biosynthesis and LR-HSQMBC for structure elucidation. J. Antibiot 74, 300–306. DOI: 10.1038/s41429-021-00405-6. - DOI - PMC - PubMed
    1. Aparicio-Cuevas MA, Rivero-Cruz I, Sánchez-Castellanos M, Menéndez D, Raja HA, Joseph-Nathan P, González M. d. C., Figueroa M, 2017. Dioxomorpholines and derivatives from a marine-facultative Aspergillus species. J. Nat. Prod 80, 2311–2318. DOI: 10.1021/acs.jnatprod.7b00331. - DOI - PubMed
    1. Arai K, Kimura K, Mushiroda T, Yamamoto Y, 1989. Structures of fructigenines A and B, new alkaloids isolated from Penicillium fructigenum Takeuchi. Chem. Pharm. Bull 37, 2937–2939. DOI: 10.1248/cpb.37.2937. - DOI
    1. Ayers S, Ehrmann BM, Adcock AF, Kroll DJ, Carcache de Blanco EJ, Shen Q, Swanson SM, Falkinham JO 3rd, Wani MC, Mitchell SM, Pearce CJ, Oberlies NH, 2012. Peptaibols from two unidentified fungi of the order Hypocreales with cytotoxic, antibiotic, and anthelmintic activities. J. Pept. Sci 18, 500–510. DOI: 10.1002/psc.2425. - DOI - PMC - PubMed

LinkOut - more resources