Spiroleiferthione A and Oleiferthione A: Two Unusual Isothiocyanate-Derived Thioketone Alkaloids from Moringa oleifera Lam. Seeds

Pharmaceuticals · 7 authors, 3 centres

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TL;DR

One compound, Spiroleiferthione A, showed moderate, dose-dependent inhibition of human kidney cell proliferation induced by high glucose in an in vitro assay.

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Their structures were elucidated using spectroscopic data, NMR calculations, electronic circular dichroism, and X-ray diffraction. Spiroleiferthione A was identified as a rare 2-thiohydantoin with a novel spirocyclic structure. Bioactivity testing focused on a single in vitro assay, where Spiroleiferthione A demonstrated moderate, dosage-dependent inhibitory activity against high glucose-induced proliferation of human renal mesangial cells. The study's limitations include the restriction to in vitro testing, the lack of investigation into in vivo efficacy or mechanism for the diabetic nephropathy model, and the evaluation of only two compounds.

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other

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preclinical research

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ORIGINAL PAPER

PMC10054748

Spiroleiferthione A and Oleiferthione A: Two Unusual Isothiocyanate-Derived Thioketone Alkaloids from Moringa oleifera Lam. Seeds

Pharmaceuticals

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ABSTRACT

Abstract Spiroleiferthione A ( 1 ), with a 2-thiohydantoin a heterocyclic spiro skeleton, and oleiferthione A ( 2 ), an imidazole-2-thione derivative, were isolated from the aqueous extract of Moringa oleifera Lam. seeds. The unprecedented structures of 1 and 2 were elucidated by extensive spectroscopic data, X-ray diffraction, and gauge-independent atomic orbital (GIAO) NMR calculation, as well as electronic circular dichroism (ECD) calculation. The structures of 1 and 2 were determined to be (5 R ,7 R ,8 S )-8-hydroxy-3-(4′-hydroxybenzyl)-7-methyl-2-thioxo-6-oxa-1, 3-diazaspiro [4.4] nonan-4-one, and 1-(4′-hydroxybenzyl)-4,5-dimethyl-1,3-dihydro-2 H -imidazole-2-thione, respectively. Biosynthetic pathways for 1 and 2 have been proposed. Compounds 1 and 2 are considered to have originated from isothiocyanate and then undergone a series of oxidation and cyclization reactions to form 1 and 2 . Compounds 1 and 2 demonstrated weak inhibition rates of NO production, 42.81 ± 1.56% and 33.53 ± 2.34%, respectively, at a concentration of 50 μM. Additionally, Spiroleiferthione A demonstrated moderate inhibitory activity against high glucose-induced human renal mesangial cell proliferation in a dosage-dependent manner. A wider range of biological activities, and the diabetic nephropathy protective activity of Compound 1 in vivo and its mechanism of action, need further investigation after the sufficient enrichment of Compound 1 or total synthesis. Keywords: Moringa oleifera Lam. seeds, thioketone alkaloids, isolation, structure elucidation

CITATION EXPORT

Yueping Jiang, Rong Liu, Ling Huang et al.. Spiroleiferthione A and Oleiferthione A: Two Unusual Isothiocyanate-Derived Thioketone Alkaloids from Moringa oleifera Lam. Seeds. Pharmaceuticals. (2023). https://doi.org/10.3390/ph16030452

AUTHORS

7 · 3 CENTRES

Yueping Jiang, Rong Liu, Ling Huang, Qi Huang, Min Liu, Shao Liu, Jing Li

1Department of Pharmacy, Xiangya Hospital, Central South University, Changsha 410008, China; [email protected] (Y.J.);
2National Clinical Research Center for Geriatric Disorders, Institute for Rational and Safe Medication Practices, Xiangya Hospital, Central South University, Changsha 410008, China
3College of Pharmacy, Dali University, Dali 671000, China