Terpenoids from the Chinese liverwort Heteroscyphus coalitus and their anti-virulence activity against Candida albicans

• Published in: Phytochemistry (Oxford) Vol. 174; pp. 112324 - 112334
• Main Authors: Wang, Xue, Jin, Xue-Yang, Zhou, Jin-Chuan, Zhu, Rong-Xiu, Qiao, Ya-Nan, Zhang, Jiao-Zhen, Li, Yi, Zhang, Chun-Yang, Chen, Wang, Chang, Wen-Qiang, Lou, Hong-Xiang
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.06.2020; Elsevier
• Subjects: acids; active ingredients; Anti-virulence; Biochemistry & Molecular Biology; biofilm; Candida albicans; circular dichroism spectroscopy; Diterpenes, Clerodane; fungi; genes; Geocalycaceae; Hepatophyta; Heteroscyphus coalitus (Hook.) Schiffner; hyphae; labdane; Life Sciences & Biomedicine; Liverwort; mosses and liverworts; nuclear magnetic resonance spectroscopy; Plant Sciences; Science & Technology; Sesquiterpenes; sesquiterpenoids; Terpenes; Terpenoids; transcription (genetics); X-ray diffraction; Candida albicans; Geocalycaceae; Anti-virulence; Liverwort; Heteroscyphus coalitus (Hook.) Schiffner; Terpenoids; BRYOPHYTES; DITERPENOIDS; CONSTITUENTS
• ISSN: 0031-9422; 1873-3700; 1873-3700
• DOI: 10.1016/j.phytochem.2020.112324

In this study, 14 previously undescribed terpenoids were isolated from the Chinese liverwort Heteroscyphus coalitus (Hook.) Schiffner, including a rare harziane type diterpenoid, heteroscyphsic acid A; eight ent-clerodane diterpenoids, heteroscyphsic acids B–I; four labdane diterpenoids, heteroscyphins A–D; and one guaiane sesquiterpene, heteroscyphin E; as well as a known ent-junceic acid. Their structures were determined by a combination of MS, NMR spectroscopy, electronic circular dichroism (ECD) and single crystal X-ray diffraction analyses. The anti-virulence activity of the isolated compounds against Candida albicans DSY654 demonstrated that most of them could block hyphal growth at concentrations ranging from 4–32 μg/ml. Further investigation of the most active compound, heteroscyphin D, revealed that it could suppress the ability of C. albicans DSY654 to adhere to A549 cells and form biofilms, and modulate the transcription of related genes in this fungus. Fourteen previously undescribed terpenoids were isolated from H. coalitus. Heteroscyphin D displayed anti-virulence activity against C. albicans. [Display omitted] •Fourteen previously undescribed terpenoids were isolated from H. coalitus.•Structures were determined by extensive spectroscopic analyses.•Heteroscyphin D displayed anti-virulence activity against C. albicans.