Six unusual meroterpenoids, psidiguajadiol A-J (-), and three known meroterpenoids (-) were isolated from the leaves of L. Compounds - represent the first examples of 6/8-formyl-5,7-dihydroxy-4-phenylchromane-coupled sesquiterpenoids. The structures of the undescribed compounds, including their absolute configurations, were elucidated by spectroscopic analyses, X-ray diffraction, and computational calculations. Compounds , , and exhibited inhibitory activities against PTP1B with IC values of 9.83, 18.52, and 16.87 μM, respectively. In light of these findings, we performed molecular docking studies to predict their inhibition mechanisms at the atomic level.
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http://dx.doi.org/10.1021/acs.jafc.1c08089 | DOI Listing |
J Org Chem
January 2025
Department of Pharmacy, The First Affiliated Hospital, Jinan University, Guangzhou 510630, China.
Nine new structurally diverse filicinic acid-based meroterpenoids (-) with four kinds of carbon skeletons were isolated from the rhizomes of . Their structures, including the absolute configurations, were elucidated by comprehensive analysis of spectroscopic data, quantum chemical calculations, and single-crystal X-ray diffraction. Structurally, compounds - feature an unprecedented 6/6/5/6/6/6 hexacyclic system with a rare oxaspiro[4.
View Article and Find Full Text PDFMar Drugs
October 2024
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, China.
J Med Chem
August 2024
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China.
Cisplatin is a widely used drug for the clinical treatment of tumors. However, nephrotoxicity limits its widespread use. A series of compounds including eight analogs () and 40 simplifiers () were synthesized based on the total synthesis of Psiguamer A and B, which were novel meroterpenoids with unusual skeletons from the leaves of .
View Article and Find Full Text PDFBioorg Chem
October 2024
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China. Electronic address:
Ten new B-ring aromatized 6/6/6-tricyclic dearomatized benzocogeijerene-based meroterpenoids with unusual methyl 1,2-shift or demethylation (2-9b), and two new geranylquinol derivatives (1 and 10), together with two known compounds (11 and 12), were isolated from the roots of Arnebia euchroma. Their structures were elucidated by extensive spectroscopic methods, X-ray diffraction crystallography, and ECD calculations. The plausible biosynthetic pathways including the unusual methyl 1,2-shfit and demethylation for B-ring aromatized 6/6/6-tricyclic meroterpenoids were discussed.
View Article and Find Full Text PDFOrg Lett
July 2024
Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, United States.
Halogenated phenazine meroterpenoids are a structurally unusual family of marine actinobacterial natural products that exhibit antibiotic, antibiofilm, and cytotoxic bioactivities. Despite a lack of established phenazine halogenation biochemistry, genomic analysis of sp. CNZ-289, a prolific lavanducyanin and C2-halogenated derivative producer, suggested the involvement of vanadium-dependent haloperoxidases.
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