Plant sesterterpenoids are an extremely rare family of natural products that generally possess novel chemical structures and diverse biological activities. Herein, we report the discovery of an unprecedented group of minor plant sesterterpenoids, gracilisoids B-E (2-5), which feature two types of highly functionalized bicyclo[3.2.0]heptane carbon skeletons, along with their biogenetically related precursor gracilisoid A (1), from a Lamiaceae ethnomedicinal plant, Eurysolen gracilis. To confirm their structures and obtain adequate materials for biological research, the asymmetric total syntheses of gracilisoids A-E (1-5) and four new biogenetically-related congeners gracilisoids F-I (6-9) were achieved from commercially available (-)-citronellal by a bioinspired approach that involves a Norrish-Yang photocyclization/α-hydroxy ketone rearrangement tandem reaction and a late-stage biomimetic photooxidation as key steps. Biological investigations revealed that gracilisoids A-I (1-9) significantly inhibited IFN-γ production and/or T cell proliferation probably through inhibition of the STAT pathway. The findings herald the potential of these gracilisoids as novel immunosuppressive agents, and efficient synthetic approaches will facilitate a comprehensive evaluation of their value in future drug development.
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http://dx.doi.org/10.1002/anie.202421497 | DOI Listing |
J Agric Food Chem
January 2025
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Characteristic Plant Extraction Laboratory, Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091, People's Republic of China.
One new azaphilone derivative () from in ordinary medium, one new phthalide derivative (), a microbial transformation product of ingredients by , a pair of new austdiol enantiomers (+)- and (-)-, one new epsilon-caprolactone derivative (), and one new ophiobolin-type sesterterpenoid () from the in host medium were reported. The structures were determined by spectroscopic analysis and single-crystal X-ray diffraction. Compounds - could completely inhibit the germination of rice seeds at 50 μg/mL, which is higher than that of the positive control.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
State Key Laboratory of Phytochemistry and Natural Medicines, and Yunnan, Key Laboratory of Natural Medicinal Chemistry Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P. R. China.
Plant sesterterpenoids are an extremely rare family of natural products that generally possess novel chemical structures and diverse biological activities. Herein, we report the discovery of an unprecedented group of minor plant sesterterpenoids, gracilisoids B-E (2-5), which feature two types of highly functionalized bicyclo[3.2.
View Article and Find Full Text PDFNat Prod Res
December 2024
School of Pharmaceutical Sciences (Shenzhen), Shenzhen Campus of Sun Yat-sen University, Shenzhen, P. R. China.
ABSTACTChemical investigation of an endophytic fungus, sp. J019, isolated from the plant species R. Br.
View Article and Find Full Text PDFStud Health Technol Inform
November 2024
Department of Informatics, Bioengineering, Robotics and System Engineering (DIBRIS), University of Genoa, Genoa, Italy.
Sesterterpenoids, a subset of the terpene family, exhibit notable biological activities. These natural compounds are present in a variety of organisms such as plants, fungi, bacteria, insects and marine life. The therapeutic potential and structural diversity of sesterterpenoids have attracted considerable interest in pharmacological and chemical research.
View Article and Find Full Text PDFPhytochemistry
January 2025
State Key Laboratory of Southwestern Chinese Medicine Resources, and Innovative Institute of Chinese Medicine and Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, 611137, PR China; State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, PR China. Electronic address:
Ten undescribed leucosceptrane-type sesterterpenoids with antipodal cyclopentenone moieties were isolated from the leaves of Leucosceptrum canum. Their structures including absolute configurations were elucidated by comprehensive spectroscopic analyses (including 1D and 2D NMR, and HRMS) and ECD calculations. In vitro immunosuppressive effects of these sesterterpenoids against the proliferation of T cells and the secretion of cytokine IFN-γ were evaluated.
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