Morelsins A–F, six sesquiterpenoids from the liquid culture of Morchella importuna

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Highlights

  • Six new sesquiterpenoids, morelsin A-F were isolated from ethyl acetate extract of liquid culture of Morchella. Importuna.

  • The structures were illustrated by extensive spectroscopic data and X-ray crystallography analyses.

  • Compounds 9 and 10 exhibited pancreatic lipase inhibiting activity.

Abstract

Morchella is a genus of edible mushrooms possessing high medicinal value. Morchella importuna is the major selected species for artificial cultivation in China. Six new sesquiterpenoids, morelsins A–F (16) and four known compounds (710) were isolated from ethyl acetate extract of liquid culture of M. importuna. The structures were solved by extensive spectroscopic data and X-ray crystallography analyses. The pancreatic lipase inhibitory activites of compounds were screened. Compounds 9 and 10 exhibited pancreatic lipase inhibiting activity.

Introduction

True Morchella (Morchella, Morchellaceae, Pezizales, Pezizomycetes, Ascomycota), edible and medicinal mushrooms, are famous for their delicate taste, and they show medicinal value [1]. Morchella are distributed worldwide and have long been sought for their unique and savory flavor and unique appearance with high ecological and economic values. Thus, Morchella were extensively traded because of their high price [2]. In China and some other Asian countries, morels have been used in Traditional Chinese Medicine for thousands of years [3]. Many biologically active constituents, such as triterpenoids, alkaloids, β-glucan, tremellastin and lentinan KS-2 were found from fruiting bodies, mycelia and fermented broth [[4], [5], [6], [7]].

As early as the 1960s, morels were approved by the US Food and Drug Administration and recorded in “Compendium of Materia Medica” written by Shizhen Li during the Ming Dynasty of China [8,9]. M. importuna, one of the major cultivated species, showed extensive pharmacological activity based on its biological substances. The aqueous extract of M. importuna showed anti-Leishmania activity [10] and neuroprotective effect on nervous diseases [11,12]. In addition, one new polysaccharide (MIPW50-1), isolated from M. importuna, exhibited an immune-potentiating effect [13]. Though M. importuna became increasingly valuable as a functional food and natural medicine, its chemical components remain unclear. In our previous studies, new compounds (herierin V, 1-O-β-d-ribofuranose-morelin) were isolated from Morchella sp. YDJ-ZY-1 and Morchella conica [14,15].

Therefore, in this paper, a systematic investigation of the chemical components of M. importuna was carried out and in vitro pancreatic lipase inhibition activity was evaluated. Six new sesquiterpenoids (morelsins A–F) and four known compounds [2-(1-oxo-2-hydroxyethyl)furan (7), 2-(d-glycerol-1,2-dihydroxyethyl)furan (8), (22E,24S)-24-methyl-5α-choleata-7,22-diene-3β,5β,6β-triol (9), ergosta-4,6,8 (14),22-tetraene-3-one (10)] were isolated from liquid fermentation of M. importuna. In addition, compounds 9 and 10 showed pancreatic lipase inhibitory activity. Our findings provide data to clarify the chemical constituents of M. importuna, and for healthy and functional food production.

Section snippets

Structural elucidation of morelsins A–F (1–6)

From the liquid fermentation, ten compounds, including six new sesquiterpenoids, were isolated from the culture broth of M. importuna by various chromatographic techniques and their structures were mainly determined using NMR spectra, HR-MS and single-crystal diffraction experiments. New secondary metabolites were identified as morelsins A–F (16) (Fig. 1). Known secondary metabolites were identified as 2-(1-oxo-2-hydroxyethyl)furan (7), 2-(d-glycerol-1,2-dihydroxyethyl)furan (8), (22E,24S

Conclusion

In summary, chemical compositions of EtOAc extraction via liquid fermentation of M. importuna were investigated and 10 compounds were isolated, including six new sesquiterpenoids, two aromatic compounds and two sterol compounds. Eight compounds were isolated from the genus Morchella for the first time. Compounds 9 and 10 showed pancreatic lipase inhibitory activity.

General method

1D and 2D NMR spectroscopic data were recorded on an Agilent DD2400-MR 400 MHz spectrometer (Agilent Technologies, Santa Clara, CA), using TMS as an internal standard. A Bruker maXis quadrupole-time-of-flight mass spectrometer was used to obtain the HR-ESI-MS data. Single-crystal X-ray diffraction data were collected at 100 K on a Rigaku Oxford Diffraction Supernova Dual Source, equipped with an Atlas S2 CCD using Cu Kα radiation. The absorbance for biological activities was obtained on a

Declaration of competing interest

No conflict of interest exits in the submission of this manuscript, and manuscript is approved by all authors for publication. I would like to declare on behalf of my co-authors that the work described was original research that has not been published previously, and not under consideration for publication elsewhere, in whole or in part. All the authors listed have approved the manuscript that is enclosed.

Acknowledgments

This work was supported by the National Natural Science Foundation of China, Grant/Award Number: 21462057 and the Undergraduate Innovation and Entrepreneurship Training Program (201751105, 201710661037).

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