Discovery of anti-diabetic natural products from Erythrina subumbrans (Hassk) Merr, Garcinia cowa Roxb ex Choisy, and Garcinia nigrolineata Planch ex T anderson

Name: Piyaporn Phukhatmuen

keyword: Erythrina subumbrans

MeSH: Phytochemicals -- 300602

Classification :.DDC: e-Theses

; Garcinia cowa

MeSH: Diabetes -- 300603

MeSH: Natural products -- 300604

MeSH: Garcinia -- 300605

MeSH: Antibacterial agents -- 15735

LCSH: Phytochemicals -- 300602

LCSH: Diabetes -- 300603

LCSH: Natural products -- 300604

LCSH: Garcinia -- 300605

LCSH: Antibacterial agents -- 15735

Abstract: Phytochemical investigation of selected plants aimed to discover antidiabetic compounds from Erythrina subumbrans (Hassk.) Merr., Garcinia cowa Roxb. ex Choisy, and Garcinia nigrolineata Planch. ex T. Anderson led to the isolation and identification of total 58 compounds. A new pterocarpan (2.1) together with 27 known compounds (2.2-2.28) were isolated and identified from the twig and root extracts of E. subumbrans (Fabaceae). Their structures were characterized by spectroscopic methods. All isolated compounds were evaluated for their antidiabetic, antimicrobial, and anti-inflammatory properties. Eryvarin D (2.3), 1-methoxyerythrabyssin (2.8), erythrabyssin II (2.9) and 5-hydroxysophoranone (2.22) showed α-glucosidase inhibitory activity with IC50 values of 13.4 ± 0.05, 24.5 ± 0.13, 29.0 ± 0.05, and 12.8 ± 0.14 µM, respectively, while eryvarin E (2.2) showed α-amylase inhibitory activity with an IC50 value of 67.6 ± 1.12 µM. 5-Hydroxysophoranone (2.22) and 4′-hydroxy-6,3′,5′-triprenylisoflavanone (2.24) inhibited glycation activity with the IC50 values of 36.9 ± 0.62 and 40.5 ± 0.37 µM, respectively. From cell-based assays, 2,2-dimethyl-2H-chromene-6-carboxaldehyde (2.27) showed the highest ability to induce glucose consumption (IC50 29.1 ± 0.86 µM) and glucose uptake (2.8-fold), and to inhibit nitric oxide (NO) production (IC50 52.5 ± 0.56 µM) without cell toxicity. In addition, erythrabyssin II (2.9) showed antimicrobial activities against Gram-positive bacteria and fungi with MIC values ranging from 2-4 µg/mL. α-Glucosidase bioassay-guided investigation of EtOAc extract of G. cowa (Clusiaceae) resulted in the isolation and identification of a new decahydro-1H-xanthene derivative, garciniacowone K (3.1) together with 10 known compounds. Benzophenone (3.2), xanthones (3.3-3.7), biphenyl (3.8), and triterpenes (3.9-3.11) were isolated from fractions which showed good α-glucosidase inhibitory activity. All structures were characterized by NMR spectroscopic data. Among the α-glucosidase inhibitory activity tested compounds, guttiferone I (3.2) showed the most effective to inhibit α-glucosidase and promote glucose consumption activity in 3T3-L1 cells. A phytochemical investigation from latex and twig extracts of G. nigrolineata (Clusiaceae) led to the isolation and identification of a new geranylated xanthone, nigrolineaxanthone AA (4.1) along with 18 known compounds (4.2–4.19). All structures were characterized by NMR spectroscopic methods and compared with those literature data. Some of isolated compounds were evaluated for their antidiabetic activities and cytotoxicity against cancer cell lines. compounds 4.12 (IC50 value of 25.8 ± 0.2 µM), 4.16 (IC50 value of 124.8 ± 0.7 µM), and 4.17 (IC50 value of 44.4 ± 1.1 µM) exhibited the highest α-glucosidase inhibitory, α-amylase inhibitory, and glycation inhibition activities, respectively. Compound 4.11 showed glucose consumption and glucose uptake with IC50 values of 14.2 ± 0.8 µM and 3.1-fold. Compound 4.10 displayed cytotoxic activity against colon cancer (SW480) with an IC50 value of 4.3 ± 0.1 µM), while compound 4.2 showed cytotoxicity against leukemic cancer (K562) with IC50 value of 4.4 ± 0.3 µM.

Mae Fah Luang University. Learning Resources and Educational Media Center

Address: CHIANG RAI

Email: library@mfu.ac.th

Name: Surat Laphookhieo

Role: Advisor

Created: 2022

Modified: 2023-04-08

Issued: 2023-04-08

วิทยานิพนธ์/Thesis

application/pdf

CallNumber: e-Theses

eng

DegreeName: Doctor of Philosophy

Level: Doctoral Degree

Descipline: Applied Chemistry

Grantor: Mae Fah Luang University

©copyrights Mae Fah Luang University

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