Acronyculatin P, A New Isoprenylated Acetophenone from the Stem Bark of<i>Acronychia pedunculata</i>

Tanjung, Mulyadi; Nurmalasari, Intan; Wilujeng, Aisyah Kanti; Saputri, Ratih Dewi; Rachmadiarti, Fida; Tjahjandarie, Tjitjik Srie

doi:10.20307/nps.2018.24.4.284

Cited by 8 publications

(7 citation statements)

References 12 publications

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“…Exhaustive purification of the crude EtOAc extract obtained after maceration of the roots of A. pedunculata led to the isolation of acrotrione B ( 1 ) and six known compounds, namely acronylin ( 2 ) 17 , 1-(2,4-dihydroxy-6-methoxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl)ethanone ( 3 ) 19 , acrovestone ( 4 ) 7 , 5′-prenylacrovestone ( 5 ) 3 , acropyrone ( 6 ) 7 , and acrofolione B ( 7 ) 7 . Their structures were solved by thorough analysis of NMR spectroscopic data and mass spectrometric data.…”

Section: Resultsmentioning

confidence: 99%

“…Members of this family include acrovestone and acrofolione A ( Fig. 1BS , Supporting Information) 7 , 9 . In such dimers, the formation of an ether linkage between C-4 and C-4‴, leading to a xanthene core, is relatively rare.…”

Section: Introductionmentioning

confidence: 99%

“…Extracts of its roots, stems, leaves, and fruit have been used as a treatment for diarrhea, cough, asthma, sores, ulcers, itchy skin, pain, rheumatism, and fever [6]. Previous phytochemical investigations of this plant report mostly isoprenylated acetophenones and their dimers, quinoline alkaloids, terpenoids, and coumarins as its secondary metabolites [7][8][9][10][11][12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

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Acrotrione B, a Prenylated and Highly Oxidized Xanthenoid with Antibacterial and Anti-proliferative Activities from the Roots of Acronychia pedunculata

et al. 2022

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A new prenylated xanthenoid with a highly oxidized core, acrotrione B (1), together with six previously reported acetophenones (2 – 7), were isolated from the roots of Acronychia pedunculata. The structures of the isolated compounds were elucidated by thorough analysis of their 1D and 2D NMR spectroscopic data. The relative and absolute configurations of acrotrione B were determined by electronic circular dichroism (ECD) calculations. Acrotrione B is an unusual, oxidized xanthenoid with a cyclohexadienone core that has not been previously reported. It thus represents a new skeletal type within the xanthenoid class. Acrotrione B (1) exhibited anti-proliferative activity against Hela (IC50 = 16.0 µM) and A549 (IC50 = 16.3 µM) cell lines. 5′-Prenylacrovestone (4) and acrovestone (5) were even more potent with IC50 values of 5.1 µM and 0.77 µM, respectively, against Hela cells and 11.8 µM and 1.13 µM, respectively, against A549 cells. Moreover, acrotrione B (1) displayed moderate antibacterial activities against Staphylococcus aureus, Bacillus cereus, and Bacillus subtilis, with MIC values in the range of 16 – 64 µg/mL. Finally, acropyrone (6) showed a significant suppression of lipopolysaccharide (LPS) induced NO production in murine macrophage J774.A1 cells (IC50 = 8.9 µM).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Acrotrione B, a Prenylated and Highly Oxidized Xanthenoid with Antibacterial and Anti-proliferative Activities from the Roots of Acronychia pedunculata

et al. 2022

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“…Scientists from universities in Indonesia, have been using artonin E as positive control when testing the cytotoxicity of compounds isolated from various plant species. The species included Macaranga gigantea, 45 Macaranga gigantifolia, 46 Corypha utan, 47 Melicope glabra, 48 Macaranga trichocarpa, 49 Acronychia pedunculata, 50 Calophyllum soulattri, 51 Willughbeia coriacea 52 The anti-cancer effects and mechanisms of artonin E have been reported in breast, lung, ovarian, colon and gastric cancer cells (Table 2). Effects include apoptosis, anoikis, anti-proliferation, cell cycle arrest, inhibition of migration and invasion, and overcoming tumor necrosis factorrelated apoptosis-inducing ligand (TRAIL) resistance.…”

Section: Anti-cancer Activities Of Artonin Ementioning

confidence: 99%

Artonin E: A Short Review of its Chemistry, Sources, Anti-Cancer Activities and Other Pharmacological Properties

2023

TJNPR

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Among the prenylated flavonoids is a group known as artonins. To date, 24 of such compounds (artonins A-Y) have been recorded. 6 Pharmacological properties of artonins include anti-plasmodial, anticancer and antibacterial activities. In this article, the chemistry, sources, anti-cancer and other medicinal properties of artonin E from Artocarpus species are reviewed for the first time. A brief account on other artonins is included. Some prospects and future research on artonin E and other artonins are suggested. Chemistry of Artonin EArtonin E or 5'-hydroxymorusin from Artocarpus species (Moraceae) is a prenylated flavonoid with a molecular formula of C25H24O7 and molecular weight of 436.5 g/mol. 6,7 The molecular structure of artonin E has three aromatic rings (A-C) with three OH groups at C2', C4' and C5' of ring B, and one OH group at C5 of ring A (Figure 1). There are two prenyl units, one isoprenoid substituent at C3 of oxygenated ring C and one forming a dimethylpyrane ring D at C7 and C8. The presence of a double bond between C2 and C3, and a carbonyl group at C4 are essential for the bioactivities of artonin E. Morusin has a similar molecular structure as artonin E except that it lacks the OH group at C5'. For this reason, artonin E is sometimes called 5'-hydroxymorusin. 6 The structure of artonin E is a 3-isoprenyl 2',4',5'-trioxygenated flavone. 5,7 Other compounds with the same structural type are artoindonesianins L and U. Prenylated flavonoids also include 3isoprenyl 2',4'-dioxygenated flavones such as artocarpin 8 and morusin. 9Sources of Artonin E Artonin E was first isolated from the bark Artocarpus altilis (syn. A. communis) 10 (Figure 2). Subsequently, artonin E was reported in other Artocarpus species that include A. chama, A. elasticus, A. gomezianus, A. kemando, A. lanceifolius, A. lowii, A. nobilis, A. rigida, A. rigidus (syn. A. rotunda), A. scortechnii and A. teysmannii (Table 1). Plant part most reported are the root and bark, with no reports on the leaf.

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“…The methyl proton from the ester is seen at δH 3.66 (3H, s, COCH3), and the methylene proton signals are separated at δH 2.72 (1H, dd, J = 13.7; 5.4 Hz, H-7a'), and 2.51 (1H, dd, J = 13.7; 10.3 Hz, H-7b'). The 13 The cytotoxic activity of compounds 1-2 against HeLa cells, showing moderate activity with an IC50 value of 10.1 and 12,.5 μM, respectively (Tanjung et al, 2021;2012;Saputri et al, 2021). (+)-Pinoresinol (1) is slightly more active than alyterinate A (2).…”

Section: Cytotoxic Activitymentioning

confidence: 99%

Isolation of Lignans from The Stem Bark of Willughbeia coriacea and Their Cytotoxic Activity

2023

TJNPR

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Willughbeia coricea Wall is a herbal medicine to treat diarrhea in Dayak People, Kalimantan, Indonesia. This study aims to determine the structure of the lignans and their anticancer activity against cervical cancer cells (HeLa). Two lignan derivatives, (+)-pinoresinol (1) and alyterinate A (2), were isolated from the roots of the W. coricea Wall. The structures of 1 and 2 were determined based on UV, IR, HRESIMS, 1D (1H and 13C), and 2D NMR (HMQC and HMBC) spectroscopic analysis. Compounds 1-2 showed moderate activity against HeLa cells with an IC50 value of 10.1 and 12.5 μM, respectively.

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Acronyculatin P, A New Isoprenylated Acetophenone from the Stem Bark ofAcronychia pedunculata

Cited by 8 publications

References 12 publications

Acrotrione B, a Prenylated and Highly Oxidized Xanthenoid with Antibacterial and Anti-proliferative Activities from the Roots of Acronychia pedunculata

Acrotrione B, a Prenylated and Highly Oxidized Xanthenoid with Antibacterial and Anti-proliferative Activities from the Roots of Acronychia pedunculata

Artonin E: A Short Review of its Chemistry, Sources, Anti-Cancer Activities and Other Pharmacological Properties

Isolation of Lignans from The Stem Bark of Willughbeia coriacea and Their Cytotoxic Activity

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