Seven new drimane-type sesquiterpenoids, namely the sporulositols A-D (1-4), 6-hydroxydiaporol (5), seco-sporulositol (6) and sporuloside (7) were isolated from the ethyl acetate extract of fermentation broth for a marine-derived fungus Paraconiothyrium sporulosum YK-03. Their structures were elucidated by analysis of extensive spectroscopic data, and the absolute configurations were established by crystal X-ray diffraction analysis and comparisons of circular dichroism data. Among them, sporulositols A-E (1-4) and seco-sporulositol (6) represent the first five examples of a unique class of drimanic mannitol derivatives, while compounds 6 and 7 may represent two new series of natural drimanes, possessing an aromatic ring with a rare 4,5-secodrimanic skeleton and an unusual CH3-15 rearranged drimanic α-D-glucopyranside, respectively. Furthermore, the origin of mannitol moiety was investigated by reliable HPLC and NMR analyses.
Paraconiothyrium sporulosum, Paraconiothyrium, drimane-type sesquiterpenoid, seco-sporulositol, sporuloside, sporulositol
NCBI PubMed ID: 31083454Publication DOI: 10.3390/molecules24091817Journal NLM ID: 100964009Publisher: Basel, Switzerland: MDPI
Correspondence: Zhang LH
; Chen G ; Wang HF ; Bai J ; Hua HM ; Sun Y ; Pei YH
Institutions: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing, China, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, China, Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing, China, Department of Medicinal Chemistry and Natural Medicine Chemistry, College of Pharmacy, Harbin Medical University, Harbin, China
Methods: 13C NMR, 1H NMR, NMR-2D, IR, DNA sequencing, X-ray, acid hydrolysis, HPLC, UV, extraction, optical rotation measurement, CD, CC, cell growth, HR-ESI-MS, cytotoxicity assay, LPLC
Found