Neobeguea mahafalensis is used as a medicinal plant in Madagascar. A decoction of the stem bark of this species is reported to treat back pain. Recently, it was reported that a decoction of the root bark, containing two novel phragmalin limonoids as identified active constituents, exhibited an extraordinarily high potency and remarkably long duration in augmenting sexual activity in male rodents.From the dichloromethane extract of the root barks of N. mahafalensis, nine phragmalin limonoids were isolated, of which eight were novel compounds. The structures were established mainly by extensive use of 2D NMR spectroscopic techniques and high-resolution mass spectrometry. One of the new compounds named dodoguin displayed sleep-inducing activity in Swiss albino mice. The amount of 3-10 mg/kg of this compound induced sleep 18-22 min after its administration with a duration of 16-18 min.
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http://dx.doi.org/10.1055/s-0042-108741 | DOI Listing |
J Am Chem Soc
January 2025
Department of Chemistry, Zhejiang University, Hangzhou 310058, China.
The asymmetric and divergent total syntheses of two phragmalin (moluccensins G and H) and two khayanolide-type (krishnolide F and khayseneganin F) limonoids were disclosed, which employed a torquoselective interrupted Nazarov cyclization as the key step. Taken together with a Liebeskind-Srogl coupling, a benzoin condensation, and bidirectional acyloin rearrangements, our strategy would simplify the synthetic design of both phragmalin and khayanolide-type limonoids and facilitate their modular syntheses. Moreover, the described approach also provides additional insights into the biosynthetic relationships between these two distinct skeletons.
View Article and Find Full Text PDFFitoterapia
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 PDFInt J Mol Sci
July 2024
State Key Laboratory of Green Pesticide, South China Agricultural University, Guangzhou 510642, China.
Plants of the Meliaceae family have long attracted researchers' interest due to their various insecticidal activities, with triterpenes being the main active ingredients. In this paper, we discuss triterpenoids with insecticidal activity from insecticidal plant species of genera (, , , , , , , , , , , , , , and ) in the family Meliaceae. Among these genera, deserves further research, with twelve species possessing insecticidal activity.
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.
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