Ten new cadinane-type sesquiterpenoids, named hibisceusins I-R (-), along with 14 known sesquiterpenoids (-), were acquired from the tainted stems of . Their structures were identified via spectroscopic analysis, one-dimensional (1D) and two-dimensional (2D) NMR, and computer-assisted structure elucidation techniques, including infrared (IR) and mass spectrometry (MS) data. Additionally, subsequent DP4/DP4+ probability methods were used to resolve 's relative configurations by comparing their experimental values to the predicted NMR data. The absolute configurations of compounds - were measured through electronic circular dichroism (ECD) spectra. The ability of all isolates to inhibit the growth of five phytopathogenic fungi (, Kleb., , Schltdl., and HK-27) was evaluated. Aldehydated sesquiterpenoids (, -, , , and ) and a known sesquiterpenoid quinine () exhibited significant inhibitory activities against , , , and HK-27 with minimum inhibitory concentration (MIC) values of 2.5-50 μg/mL, but all isolates remained inactive against . Moreover, the effects of the isolates on the mycelial morphology were watched through scanning electron microscopy. This study revealed that aldehydated cadinane-type sesquiterpenoids could be used as novel antifungal molecules to develop agrochemical fungicides in plant protection.
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http://dx.doi.org/10.1021/acs.jafc.3c08508 | DOI Listing |
Nat Prod Res
December 2024
Chemistry of Medicinal Plants Department, National Research Centre, Giza, Egypt.
A new cadinane-type sesquiterpene glucoside, 10-hydroxy, 1(H), 6(H), 7(H), 8(H)-cadinane-4-en-8-O--D-glucoside () as well as, 2 known analogues [sinaicin ()- linichlorinA ()], were isolated from the CHCl:MeOH organic extract of . Chemical structures of all isolated compounds were established depending upon the spectroscopic data including, 1D and 2D NMR and HRMS. Colo-205 (colorectal cancer), HepG2 (hepatocellular carcinoma) and MCF-7 (breast adenocarcinoma) and cancer cell lines were used to test the cytotoxic potential of the isolated compounds (-).
View Article and Find Full Text PDFJ Nat Prod
December 2024
School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa 920-1192, Japan.
Syzygioblanes A-C (-), isolated from the Indonesian traditional herbal medicine (), are meroterpenoids with a spiro ring formed through a [4 + 2] cycloaddition of the flavanone desmethoxymatteucinol with cyclic sesquiterpenoids. Our ongoing phytochemical investigation of resulted in the isolation of five additional spiro-meroterpenoids, syzygioblanes D-H (-), which are hybrids of the same flavanone with eudesmane/cadinane-type sesquiterpenoids. A possible biosynthetic pathway involves enzymatic dearomative hydroxylation of desmethoxymatteucinol followed by [4 + 2] cyclization of the resulting diene with a cyclic sesquiterpene containing an exocyclic methylene to form the unique spiro ring in the syzygioblane molecule.
View Article and Find Full Text PDFPhytochemistry
January 2025
School of Pharmacy, Jiangxi University of Chinese Medicine, Nanchang, 330004, PR China. Electronic address:
Fifteen undescribed sesquiterpenoid monomers, including six pairs of sesquiterpenoid enantiomers (1a/1b-3a/3b and 5a/5b-7a/7b) and three analogues (4, 8, and 9), together with two known sesquiterpenoid dimers (10 and 11) were isolated from the whole plant of Chloranthus henryi Hemsl. Their structures were characterized by spectroscopic data analysis, ECD calculations, and single crystal X-Ray diffractions. Compounds 1a and 1b were highly aromatic cadinane-type sesquiterpenoids.
View Article and Find Full Text PDFBiomolecules
March 2024
State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China.
, a traditional Chinese medicine with a wide range of pharmacological activities, is obtained from the dried rhizomes of VaL., S. G.
View Article and Find Full Text PDFJ Agric Food Chem
February 2024
Key Laboratory of Tropical Translational Medicine of Ministry of Education, Hainan Key Laboratory for Research and Development of Tropical Herbs, School of Pharmacy, Hainan Medical University, Haikou 571199, China.
Ten new cadinane-type sesquiterpenoids, named hibisceusins I-R (-), along with 14 known sesquiterpenoids (-), were acquired from the tainted stems of . Their structures were identified via spectroscopic analysis, one-dimensional (1D) and two-dimensional (2D) NMR, and computer-assisted structure elucidation techniques, including infrared (IR) and mass spectrometry (MS) data. Additionally, subsequent DP4/DP4+ probability methods were used to resolve 's relative configurations by comparing their experimental values to the predicted NMR data.
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