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Newly synthesised oxime and lactone derivatives from Dipterocarpus alatus dipterocarpol as anti-diabetic inhibitors: experimental bioassay-based evidence and theoretical computation-based prediction

Phuong Thao, Tran Thi ; Bui, Thanh Q ; Thi Thanh Hai, Nguyen ; Huynh, Lam K ; Quy, Phan Tu ; Bao, Nguyen Chi ; Dung, Nguyen Thi ; Chi, Nguyen Linh ; Van Loc, Tran ; Smirnova, Irina E ; Petrova, Anastasiya V ; Ninh, Pham Thi ; Van Sung, Tran ; Nhung, Nguyen Thi Ai

RSC advances, 2021-11, Vol.11 (57), p.35765-35782 [Periódico revisado por pares]

England: Royal Society of Chemistry

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  • Título:
    Newly synthesised oxime and lactone derivatives from Dipterocarpus alatus dipterocarpol as anti-diabetic inhibitors: experimental bioassay-based evidence and theoretical computation-based prediction
  • Autor: Phuong Thao, Tran Thi ; Bui, Thanh Q ; Thi Thanh Hai, Nguyen ; Huynh, Lam K ; Quy, Phan Tu ; Bao, Nguyen Chi ; Dung, Nguyen Thi ; Chi, Nguyen Linh ; Van Loc, Tran ; Smirnova, Irina E ; Petrova, Anastasiya V ; Ninh, Pham Thi ; Van Sung, Tran ; Nhung, Nguyen Thi Ai
  • Assuntos: Chemistry ; Computation ; Coordination compounds ; Diabetes ; Esterification ; Esters ; Glucosidase ; Inhibitors ; Lactones ; Proteins
  • É parte de: RSC advances, 2021-11, Vol.11 (57), p.35765-35782
  • Notas: ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
    These authors contributed equally to this work.
  • Descrição: -derived products are expected to exhibit anti-diabetes properties. Natural dipterocarpol (1) was isolated from collected in Quang Nam province, Vietnam; afterwards, 20 derivatives including 13 oxime esters (2 and 3a-3m) and 7 lactones (4, 5, 6a-6e) were semi-synthesised. Their inhibitory effects towards diabetes-related proteins were investigated experimentally (α-glucosidase) and computationally (3W37, 3AJ7, and PTP1B). Except for compound 2, the other 19 compounds (3a-3m, 4, 5, and 6a-6d) are reported for the first time, which were modified at positions C-3, C-24 and C-25 of the dipterocarpol imidation, esterification, oxidative cleavage and lactonisation reactions. A framework based on docking-QSARIS combination was proposed to predict the inhibitory behaviour of the ligand-protein complexes. Enzyme assays revealed the most effective α-glucosidase inhibitors, which follow the order 5 (IC of 2.73 ± 0.05 μM) > 6c (IC of 4.62 ± 0.12 μM) > 6e (IC of 7.31 ± 0.11 μM), and the computation-based analysis confirmed this, , 5 (mass: 416.2 amu; polarisability: 52.4 Å ; DS: -14.9 kcal mol ) > 6c (mass: 490.1 amu; polarisability: 48.8 Å ; DS: -13.7 kcal mol ) > 6e (mass: 549.2 amu; polarisability: 51.6 Å ; DS: -15.2 kcal mol ). Further theoretical justifications predicted 5 and 6c as versatile anti-diabetic inhibitors. The experimental results encourage next stages for the development of anti-diabetic drugs and the computational strategy invites more relevant work for validation.
  • Editor: England: Royal Society of Chemistry
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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