Uvarialuridols A-C, three new polyoxygenated cyclohexenes from the twig and leaf extracts of Uvaria lurida

Suthiphasilp, Virayu; Maneerat, Wisanu; Andersen, Raymond J.; Patrick, Brian O.; Phukhatmuen, Piyaporn; Pyne, Stephen G.; Laphookhieo, Surat

doi:10.1016/j.fitote.2019.104340

Cited by 14 publications

(10 citation statements)

References 30 publications

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“…Two new compounds 1 and 2 were obtained from the leaf extract, while three new compounds 3-5 were obtained from the flower extract. The known compounds were characterized by the comparison of their physical properties and spectroscopic data with the previous reports and identified as flexuvarin B (6) (Hsu et al, 2016), flexuvarin C (7) (Hsu et al, 2016), flexuvarin D (8) (Hsu et al, 2016), chrysin (9) (Meesakul et al, 2017), 5-hydroxy-7-methoxyflavone (tectochrysin) (10) (Righi et al, 2010), pinocembrin (11) (Meesakul et al, 2017), pinocembrin 7-O-benzoate (12) (Hoeneisen et al, 1993), 2 0 -hydroxy-4 0 ,6 0 -dibenzyloxychalcone (13) (Drewes and van Vuuren, 2008), zeylenone (14) (Suthiphasilp et al, 2019), 1R,6S-cherrevenol A (15) (Auranwiwat et al, 2019), and (À)-(5R)-desmoscochinoxepinone B (16) (Meesakul et al, 2019) (Figure 2).…”

Section: Glucose Uptake Assaysupporting

confidence: 84%

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Polyoxygenated seco-cyclohexenes derivatives from flower and leaf extracts of Desmos cochinchinensis and their α-glucosidase inhibitory activity

Suthiphasilp

Maneerat

Duangyod

et al. 2020

Heliyon

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Phytochemical investigations from the flower and leaf extracts of D. cochinchinensis resulted in the isolation and structural elucidation of five new polyoxygenated seco -cyclohexene derivatives, desmoscochinchinenes A-E ( 1 – 5 ), together with 11 known compounds ( 6 – 16 ). The structures on the new compounds were elucidated from their spectroscopic data, including UV, IR, NMR, and HRESITOFMS. Some of the isolated compounds were evaluated for their α -glucosidase inhibitory activities. Chrysin ( 9 ), pinocembrin 7- O -benzoate ( 12 ), and (−)-(5 R )-desmoscochinoxepinone B ( 16 ) inhibited α -glucosidase better than the standard control (acarbose, IC 50 = 83.5 μM) with IC 50 values of 5.7, 33.8, 53.3 μM, respectively.

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Section: Glucose Uptake Assaysupporting

confidence: 84%

“…The biosynthetic pathway of polyoxygenated cyclohexene and secocyclohexene were proposed from the shikimic acid pathway (Hsu et al, 2016;Macabeo et al, 2017;Suthiphasilp et al, 2019). The primary intermediate A as shown in Figure 4, is proposed as a forerunner based on our results.…”

Section: Discussionmentioning

confidence: 65%

Polyoxygenated seco-cyclohexenes derivatives from flower and leaf extracts of Desmos cochinchinensis and their α-glucosidase inhibitory activity

Suthiphasilp

Maneerat

Duangyod

et al. 2020

Heliyon

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“…A colorimetric α-glucosidase assay was performed according to the previously described method [4,5]. Briefly, the samples were dissolved in DMSO and further diluted with KH 2 PO 4 buffer (c 100 mM, pH 6.8) to make the final concentration of 10% DMSO.…”

Section: α-Glucosidase Inhibitory Activitymentioning

confidence: 99%

“…Multiple complications can arise, including both macro and microvascular dysfunctions [2], where complete treatment with insulin and oral hypoglycemic agents without side effects is difficult [3]. In the recent literature, many phenolic compounds isolated from Annonaceae plants have been recommended to treat diabetes mellitus alone or in combination with hypoglycemic agents [4,5].…”

Section: Introductionmentioning

confidence: 99%

α-Glucosidase inhibitory activity of compounds isolated from the twig and leaf extracts of Desmos dumosus

Suthiphasilp

Maneerat

Andersen

et al. 2021

Heliyon

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Four new compounds, (þ)-(2S)-desmosdumosone (1), (þ)-(2R)-7,8-dimethoxy-5-hydroxyflavanone (7), (þ)-(2R)-7-methoxychamanetin (9), and (þ)-(1ˊR,2ˊR)-phebalosin (18), and 25 known compounds were isolated from the twig and leaf extracts of Desmos dumosus. Compounds (AE)-7 and (AE)-9 were isolated as racemates and their enantiomers were separated by chiral HPLC. Their structures were elucidated by spectroscopic methods as well as comparisons made from the literature. The absolute configuration of (þ)-(1ʹR,2ʹR)-18 was established by X-ray diffraction analysis using Cu Kα radiation and electronic circular dichroism (ECD) spectoscopy. In contrast, the absolute configuration of compounds (þ)-(2S)-1, (þ)-(2R)-7, and (þ)-(2R)-9 were identified by comparing their ECD spectra and specific rotations with those of reported known compounds. Compounds 9, 11, 13, 14, 22, 25, and 28 showed α-glucosidase inhibitory activities with IC 50 values ranging from 5.3-52.7 μM, much better than that of standard control (acarbose, IC 50 value 83.5 μM). Compound 13 was the most active with an IC 50 value of 5.3 μM.

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“…Most of the Uvaria plants grown in Thailand are climbing shrubs and small trees. The fruits have deep orange, yellow, or rich red color, are usually aggregated, and are edible in some species [2]. Based on ethnopharmacological investigation, several species are used as folk medicine for treatment of several diseases.…”

Section: Introductionmentioning

confidence: 99%

Antioxidant and antimicrobial alkaloids isolated from twigs of Uvaria grandiflora Roxb.

Kongkum¹,

Thanasansurapong²,

Surapanich³

et al. 2021

ScienceAsia

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Phytochemical investigation of the MeOH-EtOAc (1:1 v/v) soluble fraction partitioned from the MeOH extract of twigs of Uvaria grandiflora Roxb. led to the isolation of six known compounds including aristolactam AII (1), aristolactam BI (2), velutinam (3), griffithinam (4), isoursuline (5), and sinactine (6). Their structures were determined on the basis of spectroscopic analysis and comparison with the literature data. Described in this work is the first report of isoursuline (5), an azafluorene derivative, and sinactine (6), a tetrahydroepiberberine, being isolated from plants in the Uvaria genus. Antioxidant and antimicrobial activities of some isolated compounds were evaluated. Among screened compounds, velutinam (3) showed antioxidant activity in the DPPH radical scavenging assay.

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Uvarialuridols A-C, three new polyoxygenated cyclohexenes from the twig and leaf extracts of Uvaria lurida

Cited by 14 publications

References 30 publications

Polyoxygenated seco-cyclohexenes derivatives from flower and leaf extracts of Desmos cochinchinensis and their α-glucosidase inhibitory activity

Polyoxygenated seco-cyclohexenes derivatives from flower and leaf extracts of Desmos cochinchinensis and their α-glucosidase inhibitory activity

α-Glucosidase inhibitory activity of compounds isolated from the twig and leaf extracts of Desmos dumosus

Antioxidant and antimicrobial alkaloids isolated from twigs of Uvaria grandiflora Roxb.

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