Furanasperterpenes A (1) and B (2) with a novel 6/6/6/6/5 pentacyclic skeleton and a new 11-acetoxy-terretonin E (3), were isolated from the marine-derived Aspergillus terreus GZU-31-1. Their structures were elucidated based on spectroscopic methods, and the absolute configurations were determined by X-ray diffraction and electronic circular dichroism (ECD) calculations. A possible biogenetic pathway was proposed. These compounds were evaluated for their lipid-lowering effects in 3T3-L1 adipocytes. Furanasperterpene A (1) showed the equivalent activity in reducing TG levels to positive control (berberine) at the concentration of 5 μM.
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http://dx.doi.org/10.1016/j.bioorg.2020.103968 | DOI Listing |
J Nat Prod
April 2024
Department of Chemistry, University of Aberdeen, Aberdeen AB24 3UE, Scotland, U.K.
Two novel polyketides, accraspiroketides A () and B (), which feature unprecedented [6 + 6+6 + 6] + [5 + 5] spiro chemical architectures, were isolated from sp. MA37 Δ mutant strain. Compounds - exhibit excellent activity against Gram-positive bacteria (MIC = 1.
View Article and Find Full Text PDFJ Org Chem
November 2022
Sate Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 211198, People's Republic of China.
Two highly oxygenated pentacyclic polyketides with two new carbon skeletons, trichopsistide A () and trichopsistide B (), were isolated from the plant endophyte WZ-196 derived from the leaf of Diels. The structures of these polyketides with full configurations were determined by comprehensive spectroscopic analysis, computer-assisted structure elucidation software, computational calculation, and X-ray crystal diffraction. Among them, represented the first example of an unprecedented 5/6/6/6/5 pentacyclic ketal-containing polyketide pyridine alkaloid, and possessed a novel 6/6/6/6/5 pentacyclic ketal-containing polyketide scaffold fused with an α-pyrone.
View Article and Find Full Text PDFPhytomedicine
November 2022
Centre for Cancer & Inflammation Research, School of Chinese Medicine, Hong Kong Baptist University, Hong Kong, China. Electronic address:
Background: Meroterpenoid furanasperterpene A (T2-3) with a novel 6/6/6/6/5 pentacyclic skeleton was isolated from the Aspergillus terreus GZU-31-1. Previously, we showed that T2-3 possessed significant lipid-lowering effects in 3T3-L1 adipocytes at 5 μM concentration. However, its therapeutic effect in metabolic disease and the underlying mechanisms of action remain unclear.
View Article and Find Full Text PDFOrg Lett
August 2021
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P. R. China.
Alstoscholarisine K, an indole alkaloid with eight chiral carbons and featuring a novel 6/5/6/6/6/6/6/5 octacyclic architecture, was found to be specific to the gall-infected leaves of . Its structure was elucidated by spectroscopy, computational analysis, and single-crystal X-ray diffraction. The unusual highly fused cage-like pyrrolo[1,2-]pyrimidine structure with an additional -CN unit is possibly derived from a combination of monoterpenoid indole and polyamine pathways.
View Article and Find Full Text PDFJ Org Chem
August 2021
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People's Republic of China.
Nine novel polyketide-terpenoid hybrids (-), characterized by a 1-alkylated-3,5-dihydroxyphenyl derivative coupled with a modified farnesyl pyrophosphate (FPP) unit, were isolated from a soil-derived fungus . Their structures were determined by comprehensive spectroscopic data, single-crystal X-ray diffraction analyses, and electronic circular dichroism calculations. Structurally, compounds , , , and possess a rare thiazole moiety; compounds and are the first examples of meroterpenoids featuring an undescribed 6/6/6/6/5 pentacyclic system and bearing a tetrahydrofuran ring fused to a polyketide and a sesquiterpenoid subunit; compounds and possess a rare 2-1,4-thiazin-3(4)-one moiety; and compound represents the first example of meroterpenoid having an unusual thiazol-2(3)-one moiety.
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