Four Novel Phenanthrene Derivatives with α-Glucosidase Inhibitory Activity from Gastrochilus bellinus

San, Htoo Tint; Chatsumpun, Nutputsorn; Juengwatanatrakul, Thaweesak; Pornputtapong, Natapol; Likhitwitayawuid, Kittisak; Sritularak, Boonchoo

doi:10.3390/molecules26020418

Cited by 8 publications

(5 citation statements)

References 29 publications

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“…The roots of this plant have been used as traditional Thai medicine to alleviate liver dysfunction and nephropathy [ 2 , 8 ]. In our continuing studies on bioactive compounds from orchids [ 9 , 10 ], we have explored the chemical constituents from the aerial parts of C. ensifolium with no previous reports on the chemical investigation. In the present study, a methanolic extract prepared from the aerial parts of this plant exhibited a significant cytotoxic effect against various cancer cells.…”

Section: Introductionmentioning

confidence: 99%

Three New Dihydrophenanthrene Derivatives from Cymbidium ensifolium and Their Cytotoxicity against Cancer Cells

et al. 2022

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From the aerial parts of Cymbidium ensifolium, three new dihydrophenanthrene derivatives, namely, cymensifins A, B, and C (1–3) were isolated, together with two known compounds, cypripedin (4) and gigantol (5). Their structures were elucidated by analysis of their spectroscopic data. The anticancer potential against various types of human cancer cells, including lung, breast, and colon cancers as well as toxicity to normal dermal papilla cells were assessed via cell viability and nuclear staining assays. Despite lower cytotoxicity in lung cancer H460 cells, the higher % apoptosis and lower % cell viability were presented in breast cancer MCF7 and colon cancer CaCo2 cells treated with 50 µM cymensifin A (1) for 24 h compared with the treatment of 50 µM cisplatin, an available chemotherapeutic drug. Intriguingly, the half-maximum inhibitory concentration (IC50) of cymensifin A in dermal papilla cells at >200 µM suggested its selective anticancer activity. The obtained information supports the further development of a dihydrophenanthrene derivative from C. ensifolium as an effective chemotherapy with a high safety profile for the treatment of various cancers.

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Section: Introductionmentioning

confidence: 99%

Three New Dihydrophenanthrene Derivatives from Cymbidium ensifolium and Their Cytotoxicity against Cancer Cells

et al. 2022

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“…30 Syringaldehyde is abundantly present in lignocellulosic (Mori Folium, Apricot pits, Gastrochilus bellinus, etc.) [31][32][33][34][35] and has wide applications in biomedicine (monitoring of disease-related markers, modification activity of antimicrobial agents, etc.). [36][37][38][39] In this study, syringaldehyde was chosen as the raw material for the design and synthesis of S1 (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

“…Syringaldehyde is abundantly present in lignocellulosic (Mori Folium, Apricot pits, Gastrochilus bellinus , etc. ) 31–35 and has wide applications in biomedicine (monitoring of disease‐related markers, modification activity of antimicrobial agents, etc.) 36–39 .…”

Section: Introductionmentioning

confidence: 99%

Bifunctional free radical photoinitiator based on syringaldehyde

Wang

et al. 2022

Polymers for Advanced Techs

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Syringaldehyde, a natural compound, was chosen to design a novel acylphosphine oxide (S1). Maximum absorption at 337 nm with very high molar extinction coefficient (above 13,000 M À1 cm À1 ) was detected for S1. As a type I photoinitiator, S1 could initiate the photopolymerization of TMPTA and ca. 50% of the double bond conversion (DC) could be obtained upon irradiation of LED@385 nm or LED@420 nm for 300 s. As coinitiator in type II system, S1 could cooperate with DETX and exhibit higher performance (ca. 60% of DC) than typical pair of DETX and EDAB. Density functional theory (DFT) is used to study the characteristics of excited state and transition manners of S1 after light absorption. Orbital distributions of singlet and triplet electron clouds, transition energy levels, and oscillator strength are also predicted. Results suggest that after intersystem crossing (ISC) and internal conversion (IC), free radicals formed through α-cleavage (Norrish Type I reaction) or breakage of O-H bond in S1. All results indicate that S1 could act as a bifunctional photoinitiator. Based on the above results, the roles of S1 during photoinitiation are also proposed.

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“…Previous studies revealed that orchids produce various classes of secondary metabolites, such as stilbenoids, anthraquinones, flavonoids, terpenoids, steroids, and alkaloids (Nongdam, 2014). So far, the AGIs obtained from Orchidaceae can be chemically classified into 7 major groups: (i) bibenzyl derivatives, for example, 4,5-dihydroxy-3,4-dimethoxybibenzyl and dendrofalconerol A from Dendrobium tortile, gigantol from Dendrobium devonianum, batatasin III and dendrosinen B from Dendrobium infundibulum, and dendroscabrol B from Dendrobium scabrilingue (Limpanit et al, 2016a;Na Ranong et al, 2019;Sarakulwattana et al, 2020;Sun et al, 2014); (ii) phenanthrene-related compounds, for example, 4,5-dihydroxy-2-methoxy-9,10-dihydrophenanthrene from Dendrobium christyanum, lusianthridin, and coelonin from Dendrobium scabrilingue (San et al, 2020;Sarakulwattana et al, 2020), bobulretin A from Bulbophyllum retusiusculum (Sun et al, 2018), gastrobellinol C from Gastrochilus bellinus (San et al, 2021), and 5-methoxy-7-hydroxy-9,10-dihydro-1,4-phenanthrenequinone from Dendrobium formosum (Inthongkaew et al, 2017); (iii) flavonoids, for example, rutin from Pholida chinensis, naringenin from Dendrobium densiflorum, and 5-hydroxy-3-…”

Section: Chapter I Introductionmentioning

confidence: 99%

“…(v) lignans, for example, syringaresinol-4-O-D-glucopyranoside from Flickingeria fimbriata (Chen et al, 2018); (vi) phenylpropanoids, for example, coniferyl aldehyde from Gastrochilus bellinus (San et al, 2021); and (vii) benzylmalate glycosides, for example, arundinoside D from Arundina graminifolia (Auberon et al, 2019). These are illustrated in Table 1 and Figure 1.…”

Section: Chapter I Introductionmentioning

confidence: 99%

?-glucosidase inhibitors from dendrobium delacourii, dendrobium gibsonii and aerides multiflora

Thant

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In this study, three plants from the Orchidaceae family, i.e., Dendrobium delacourii, Dendrobium gibsonii, and Aerides multiflora, were investigated for their chemical constituents and ?-glucosidase inhibitory activities. A total of thirty compounds were isolated and structurally characterized. Eleven known compounds were identified from Dendrobium delacourii, including hircinol, ephemeranthoquinone, densiflorol B, moscatin, 4,9-dimethoxy-2,5-phenanthrenediol, gigantol, batatasin III, lusianthridin, 4,4',7,7'-tetrahydroxy-2,2'-dimethoxy-9,9',10,10'-tetrahydro-1,1'-biphenanthrene, phoyunnanin E, and phoyunnanin C. Two new compounds, i.e., dihydrodengibsinin and dendrogibsol, were isolated from Dendrobium gibsonii, along with seven known compounds including ephemeranthol A, dengibsinin, nobilone, aloifol I, lusianthridin, denchrysan A, and 4-methoxy-9H-fluorene-2,5,9-triol. Four new compounds, i.e., aerimultins A-C and dihydrosinapyl dihydroferulate, and six known compounds, which include methoxycoelonin, gigantol, imbricatin, agrostonin, dihydroconiferyl dihydro-p-coumarate and 5-methoxy-9,10-dihydrophenanthrene-2,3,7-triol, were obtained from Aerides multiflora. All the isolated compounds were evaluated for ?-glucosidase inhibitory activity. When compared with the drug acarbose (IC50 value 514.4 ? 9.2 ?M), eight dimeric compounds showed potent activity: 4,4',7,7'-tetrahydroxy-2,2'-dimethoxy-9,9',10,10'-tetrahydro-1,1'-biphenanthrene, phoyunnanin E, phoyunnanin C, dendrogibsol, aerimultins A-C and agrostonin) (IC50 values 5.2 77.0 ?M). Seven monomeric compounds exhibited moderate activity: moscatin, gigantol, lusianthridin, 6-methoxycoelonin, imbricatin, dihydroconiferyl dihydro-p-coumarate, and 5-methoxy-9,10-dihydrophenanthrene-2,3,7-triol (IC50 values 115.2 - 390.1 ?M). The other compounds displayed no activity, including hircinol, ephemeranthoquinone, densiflorol B, 4,9-dimethoxy-2,5-phenanthrenediol, batatasin III, dihydrodengibsinin, ephemeranthol A, dengibsinin, nobilone, aloifol I, dechrysan A, 4-methoxy-9H-fluorene 2,5,9-triol, and dihydrosinapyl dihydroferulate (less than 50 % inhibition at 100 ?g/ml). The kinetic studies on the most potent compounds, i.e., phoyunnanin C, phoyunnanin E, dendrogibsol, and aerimultin C revealed that all were non-competitive inhibitors with a higher affinity to the ?-glucosidase enzyme than the drug acarbose.

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Four Novel Phenanthrene Derivatives with α-Glucosidase Inhibitory Activity from Gastrochilus bellinus

Cited by 8 publications

References 29 publications

Three New Dihydrophenanthrene Derivatives from Cymbidium ensifolium and Their Cytotoxicity against Cancer Cells

Three New Dihydrophenanthrene Derivatives from Cymbidium ensifolium and Their Cytotoxicity against Cancer Cells

Bifunctional free radical photoinitiator based on syringaldehyde

?-glucosidase inhibitors from dendrobium delacourii, dendrobium gibsonii and aerides multiflora

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