Isolation of Artonin E from the root bark of Artocarpus rigida, synthesis of Artonin E acetate and evaluation of anticancer activity

Suhartati, Tati; Hernawan, Hernawan; Suwandi, Jhons Fatriyadi; Yandri, Yandri; Hadi, Sutopo

doi:10.20450/mjcce.2018.1406

Cited by 12 publications

(5 citation statements)

References 8 publications

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“…These features of the spectrum confirm that esterification of artocarpin involves two hydroxyl groups of the A ring on C2' and 4'. This finding is in agreement with the result of esterification of artonin E with acetic anhydride, which shows that the hydroxyl groups experiencing esterification are those attached to the A ring [39].…”

Section: -1-nmr Characterizationsupporting

confidence: 91%

Anticancer Activity Study of Modified Artocarpin Compound from Pudau Plant (Artocarpus kemando Miq.)

et al. 2023

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This research is a continuation of the successful isolation of artocarpin from the root of Artocarpus kemando Miq reported in our previous study. In the previous study, the artocarpin was characterized with UV-Vis and FTIR techniques. In this follow-up investigation, the artocarpin was subjected to a transesterification reaction using acetic anhydride and pyridine as catalysts, and the product of the reaction was specified as compound 1. The compound 1 was further characterized with different techniques to gain more complete data and then tested for anticancer activity test against P-388 murine leukemia cells. Characterizations of the compound 1 using 1H-NMR and 13C-NMR techniques suggest that the modification reaction resulted in the conversion of the -OH groups at C2' and 4' at the artocarpin molecule to -OOCH3, and based on the MS analysis, the compound was proposed to have the molecular formula of C30H32O8. Another important feature of compound 1 that should be noted is the significant improvement in stability compared to the unmodified artocarpin. Anticancer activity tests against P-388 murine leukemia cells revealed that compound 1 has an IC50of 2.35 g/mL, confirming that the compound is categorized as an active anticancer agent and suggesting that the compound has promising potential that deserves further investigations. Doi: 10.28991/ESJ-2023-07-03-05 Full Text: PDF

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Section: -1-nmr Characterizationsupporting

confidence: 91%

Anticancer Activity Study of Modified Artocarpin Compound from Pudau Plant (Artocarpus kemando Miq.)

et al. 2023

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“…34,37 Inhibition by artonin E acetate (IC50 = 2.79 µg/mL) was not as strong but was more stable than artonin E during storage. 38 Against MCF-7 breast, MDA-MB-231 breast, HepG2 liver and WRL68 liver cancer cells, inhibition by artonin E was 2.6, 13.5, 33.8 and 29.6 µg/mL. 19 A recent study reported that artonin E inhibited the growth of SKOV-3 ovarian cancer cells in 2D and 3D cultures, with IC50 values of 6 and 25 μg/mL at 72 h, respectively.…”

Section: Anti-cancer Activities Of Artonin Ementioning

confidence: 96%

“…11 Against murine P388 leukemia cells, inhibition by artonin E was very strong with IC50 value was 0.06 µg/mL. 34,37 Inhibition by artonin E acetate (IC50 = 2.79 µg/mL) was not as strong but was more stable than artonin E during storage. 38 Against MCF-7 breast, MDA-MB-231 breast, HepG2 liver and WRL68 liver cancer cells, inhibition by artonin E was 2.6, 13.5, 33.8 and 29.6 µg/mL.…”

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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“…Artoindonesianin V has shown cytotoxic effects against murine leukaemia P38 cells (Hakim et al, 2006). The artonin (art) M has been reported to be present in A. altilis (Hano et al, 1990) and A. rotunda (Suhartati et al, 2008). No studies have recorded specific medicinal effects/actions against human cell lines (Bailly, 2021).…”

Section: Receptor-ligand Complexmentioning

confidence: 99%

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2022

JST

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Coronavirus Disease 2019 (COVID-19) caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) is a global health threat. Traditional herbals and dietary plants with medicinal values have a long antiviral history and, thus, are extensively studied in COVID-19 therapeutics development. Breadfruit (Artocarpus altilis) is a food crop with rich nutrient composition. This study screened selected breadfruit prenylated flavonoids for their potential inhibitory activities against the SARS-CoV family receptors using molecular docking and molecular dynamics (MD) simulation. The A. altilis prenylated flavonoids were selected as target ligands (artocarpin, artoindonesianin V, artonin M, cudraflavone

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Isolation of Artonin E from the root bark of Artocarpus rigida, synthesis of Artonin E acetate and evaluation of anticancer activity

Cited by 12 publications

References 8 publications

Anticancer Activity Study of Modified Artocarpin Compound from Pudau Plant (Artocarpus kemando Miq.)

Anticancer Activity Study of Modified Artocarpin Compound from Pudau Plant (Artocarpus kemando Miq.)

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

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