An efficient synthesis of the octahydro-1H-2,4-methanoindene core of phragmalin-type limonoids, such as xyloccensins O and P, is reported. The success of the synthetic route is predicated on the use of network analysis in the retrosynthetic analysis and a Diels-Alder reaction for the synthesis of a key hydrindanone derivative.
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http://dx.doi.org/10.1021/ol300647k | DOI Listing |
Fitoterapia
January 2025
Guangdong Key Laboratory for Research and Development of Natural Drugs, The First Dongguan Affiliated Hospital, School of Pharmacy, Guangdong Medical University, Dongguan 523808, China; College of Pharmacy, Jinan University, #855Xingye Avenue, Guangzhou 510632, China; Dongguan Key Laboratory for Marine Innovative Drugs and Bioproducts, Guangdong Medical University, Dongguan 523808, China. Electronic address:
Ten new limonoids, named xylomolones E-N (1-10), and two new protolimonoids, named xylomolones O (11) and P (12), were isolated from seeds of the Thai mangrove Xylocarpus moluccensis, together with the known compound, hispidone acetonide (13). The structures of these compounds were established by extensive NMR spectroscopic data, single-crystal X-ray diffraction analysis, and comparison of experimental ECD spectra. The absolute configurations of xylomolones E (1) and L (8) were unambiguously determined by single-crystal X-ray diffraction analyses, conducted with Cu Kα radiation.
View Article and Find Full Text PDFPhytochemistry
June 2024
Department of Chemistry, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia. Electronic address:
Phytochemical study of the fruits of Chisocheton erythrocarpus (Hiern) allowed the identification of eight undescribed limonoids, namely erythrocarpines O - V (1-6, 7a and 7b), along with seven known compounds. The structures of these compounds were elucidated based on spectroscopic and HRMS data, along with electronic circular dichroism to configure the absolute configuration. Erythrocarpines O and P are γ-hydroxybutenolide analogs of mexicanolide-type limonoids while erythrocarpine Q - V are phragmalin-type limonoids possessing a 1,29-oxymethylene bridge with either benzoyl or cinnamoyl moiety in their structures.
View Article and Find Full Text PDFOrg Biomol Chem
March 2024
School of Pharmacy, Anhui University of Chinese Medicine, Hefei 230012, P.R. China.
Three novel phragmalin-type limonoids, swieteliacates S-U (1-3), were isolated from leaves, alongside four previously identified limonoids (4-7). The structures, encompassing absolute configurations, were delineated through 1D and 2D NMR analyses, high-resolution mass spectrometry (HR-MS), and NMR and ECD calculations. Swieteliacate S (1) is a distinctive cryptate comprising a tricyclo[4.
View Article and Find Full Text PDFFitoterapia
March 2024
Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia. Electronic address:
A phytochemical study on the bark of Chisocheton erythrocarpus Hiern (Meliaceae) has led to the isolation of six new phragmalin-type limonoids named erythrocarpines I - N (1-6) along with one known limonoid, erythrocarpine F (7). Their structures were fully characterized by spectroscopic methods. The pre-treatment of NG108-15 cells with 1-5, 7 (2 h) demonstrated low to good protective effects against HO exposure; 1 (83.
View Article and Find Full Text PDFMolecules
November 2023
Laboratory of Liquid Chromatography, Institute of Exact and Natural Sciences, Federal University of Pará, Belém 66075-110, Brazil.
King is a plant commonly known as Brazilian mahogany. The wood from its stem is highly prized for its exceptional quality, while its leaves are valued for their high content of phragmalin-type limonoids, a subclass of compounds known for their significant biological activities, including antimalarial, antitumor, antiviral, and anti-inflammatory properties. In this context, twelve isolated limonoids from leaves were employed as standards in mass spectrometry-based molecular networking to unveil new potential mass spectrometry signatures for phragmalin-type limonoids.
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