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Antidiabetic and Cytotoxic Activities of Rotenoids and Isoflavonoids Isolated from Millettia pachycarpa Benth.

ABSTRACT: A phytochemical investigation of the root and leaf extracts of Millettia pachycarpa Benth resulted in the isolation and identification of 16 compounds, including six rotenoids (1-6) and 10 prenylated isoflavonoids (7-16). Compound 4 was isolated as a scalemic mixture, which was resolved by chiral HPLC to afford (-)-(6aS,12aS)-12a-hydroxy-α-toxicarol (4) and (+)-(6aR,12aR)-12a-hydroxy-α-toxicarol (4). (+)-(6aR,12aR)-Millettiapachycarpin (3) and (-)-(6aS,12aS)-12a-hydroxy-α-toxicarol (4) were isolated as new compounds. The absolute configuration of (-)-(6R)-pachycarotenoid (2), (+)-(6aR,12aR)-millettiapachycarpin (3), (-)-(6aS,12aS)-4 and (+)-(6aR,12aR)-12a-hydroxy-α-toxicarol (4), (+)-(6aS,12aS)-(5), and (-)-(6aS,12aS,2″R)-sumatrol (6) were identified by electronic circular dichroism (ECD) data. (-)-(6aS,12aS,2″R)-Sumatrol (6) was also confirmed by X-ray diffraction analysis using Cu-Kα radiation. Antidiabetic activities, including α-glucosidase and α-amylase inhibitory activities, and cytotoxicities against lung cancer A549, colorectal cancer SW480, and leukemic K562 cells of some isolated compounds were evaluated. Of these, isolupalbigenin (11) exhibited the highest α-glucosidase inhibitory activity, with an IC₅₀ value of 11.3 ± 0.2 μM, whereas the scalemic mixture of 12a-hydroxy-α-toxicarol (4) displayed the best α-amylase inhibitory activity, with an IC₅₀ value of 106.9 ± 0.2 μM. Euchrenone b10 (15) exhibited the highest cytotoxicity against lung cancer A549, colorectal cancer SW480, and leukemic K562 cells, with IC₅₀ values of 40.3, 39.1, and 15.1 μM, respectively. In addition, molecular docking simulations of α-glucosidase inhibition of the active compounds were studied.

SUBMITTER: Suthiphasilp V

PROVIDER: S-EPMC9301698 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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Antidiabetic and Cytotoxic Activities of Rotenoids and Isoflavonoids Isolated from Millettia pachycarpa Benth.

Suthiphasilp Virayu V Rujanapun Narawadee N Kumboonma Pakit P Chaiyosang Boonyanoot B Tontapha Sarawut S Maneerat Tharakorn T Patrick Brian O BO Andersen Raymond J RJ Duangyod Thidarat T Charoensup Rawiwan R Laphookhieo Surat S

ACS omega 20220706 28

A phytochemical investigation of the root and leaf extracts of Millettia pachycarpa Benth resulted in the isolation and identification of 16 compounds, including six rotenoids (1-6) and 10 prenylated isoflavonoids (7-16). Compound 4 was isolated as a scalemic mixture, which was resolved by chiral HPLC to afford (-)-(6aS,12aS)-12a-hydroxy-α-toxicarol (4) and (+)-(6aR,12aR)-12a-hydroxy-α-toxicarol (4). (+)-(6aR< ...[more]

PMID: 35874225

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Project description:Increasing prevalence of antimicrobial resistance (AMR) has posed a major health concern worldwide, and the addition of new antimicrobial agents is diminishing due to overexploitation of plants and microbial resources. Inevitably, alternative sources and new strategies are needed to find novel biomolecules to counter AMR and pandemic circumstances. The association of plants with microorganisms is one basic natural interaction that involves the exchange of biomolecules. Such a symbiotic relationship might affect the respective bio-chemical properties and production of secondary metabolites in the host and microbes. Furthermore, the discovery of taxol and taxane from an endophytic fungus, Taxomyces andreanae from Taxus wallachiana, has stimulated much research on endophytes from medicinal plants. A gram-positive endophytic bacterium, Paenibacillus peoriae IBSD35, was isolated from the stem of Millettia pachycarpa Benth. It is a rod-shaped, motile, gram-positive, and endospore-forming bacteria. It is neutralophilic as per Joint Genome Institute's (JGI) IMG system analysis. The plant was selected based on its ethnobotany history of traditional uses and highly insecticidal properties. Bioactive molecules were purified from P. peoriae IBSD35 culture broth using 70% ammonium sulfate and column chromatography techniques. The biomolecule was enriched to 151.72-fold and the yield percentage was 0.05. Peoriaerin II, a highly potent and broad-spectrum antimicrobial peptide against Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922, and Candida albicans ATCC 10231 was isolated. LC-MS sequencing revealed that its N-terminal is methionine. It has four negatively charged residues (Asp + Glu) and a total number of two positively charged residues (Arg + Lys). Its molecular weight is 4,685.13 Da. It is linked to an LC-MS/MS inferred biosynthetic gene cluster with accession number A0A2S6P0H9, and blastp has shown it is 82.4% similar to fusaricidin synthetase of Paenibacillus polymyxa SC2. The 3D structure conformation of the BGC and AMP were predicted using SWISS MODEL homology modeling. Therefore, combining both genomic and proteomic results obtained from P. peoriae IBSD35, associated with M. pachycarpa Benth., will substantially increase the understanding of antimicrobial peptides and assist to uncover novel biological agents.

Dataset Information

Antidiabetic and Cytotoxic Activities of Rotenoids and Isoflavonoids Isolated from Millettia pachycarpa Benth.

Publications

Antidiabetic and Cytotoxic Activities of Rotenoids and Isoflavonoids Isolated from <i>Millettia pachycarpa</i> Benth.

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