Anticancer mechanism of artonin E and related prenylated flavonoids from the medicinal plant Artocarpus elasticus

Bailly, Christian

doi:10.13057/biofar/f190202

Cited by 9 publications

(8 citation statements)

References 129 publications

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“…Artonin 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.…”

Section: Chemistry Of Artonin Ementioning

confidence: 99%

“…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.…”

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confidence: 99%

“…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.…”

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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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Section: Chemistry Of Artonin Ementioning

confidence: 99%

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confidence: 99%

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

2023

TJNPR

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“…These plants contain a large diversity of bioactive compounds, including many prenyl flavonoids and cyclized derivatives that have revealed interesting anticancer properties [ 18 , 19 ]. The most important compound in the series is artonin E, the subgroup of compounds designated artonins, with the derivative artonin E as a lead anticancer agent [ 20 ]. Artonin E belongs to the class of organic compounds known as xanthone prenylated flavonoids [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

Artonin F Induces the Ubiquitin-Proteasomal Degradation of c-Met and Decreases Akt-mTOR Signaling

et al. 2022

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Targeted therapies that selectively inhibit certain molecules in cancer cells have been considered promising for cancer treatment. In lung cancer, evidence has suggested that mesenchymal-epithelial transition factor (c-Met) oncoprotein drives cancer progression through its signaling transduction pathway. In this paper, we report the downregulation of c-Met by artonin F, a flavonoid isolated from Artocarpus gomezianus. Artonin F was found to be dominantly toxic to lung cancer cells by mediating apoptosis. With regard to its mechanism of action, artonin F downregulated c-Met expression, consequently suppressed the phosphatidylinositol-3 kinase/Akt/mammalian target of rapamycin signaling, increased Bax expression, decreased Bcl-2 expression, and activated caspase-3. The depletion of c-Met was mediated by ubiquitin-proteasomal degradation following co-treatment with artonin F, with the proteasome inhibitor MG132 reversing its c-Met-targeting effect. The immunoprecipitation analysis revealed that artonin F significantly promoted the formation of the c-Met–ubiquitin complex. Given that ubiquitin-specific protease 8 (USP8) prevents c-Met degradation by deubiquitination, we performed a preliminary in silico molecular docking and observed that artonin F blocked the catalytic site of USP8. In addition, artonin F interacted with the catalytic residues of palmitoylating enzymes. By acting as a competitive inhibitor, artonin F could reduce the degree of palmitoylation of c-Met, which affected its stability and activity. In conclusion, c-Met is critical for cancer cell survival and the failure of chemotherapeutic regimens. This novel information on the c-Met downregulating effect of artonin F will be beneficial for the development of efficient anticancer strategies or targeted therapies.

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“…Plants have played an important role in human civilization for a long time. Humans have recognized their reliance on plants since the beginning of time, primarily for food, construction materials to build houses (shelter), clothing, and the main ingredient of health care (medicine) (Geng et al 2017;Moallem et al 2017;Jima and Megersa 2018;Chhetri et al 2019;Purushothaman et al 2020;Bailly 2021). Aside from these basic human needs, the plants are deeply entwined with religions such as Buddhism and Hinduism.…”

Section: Introductionmentioning

confidence: 99%

An ethnobotanical study of plants used in socio-religious activities in Bhutan

JIGME

YANGCHEN²

2022

Asian J Ethnobiol

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Abstract. Jigme, Yangchen K. 2022. An ethnobotanical study of plants used in socio-religious activities in Bhutan. Asian J Ethnobiol 5: 44-51. Ethnobotany encompasses all elements of plants’ natural and direct interaction with humans. Plants have been linked to human civilization since antiquity. Like Hindu people, Buddhists worship plants or use their components in different ways to perform various socio-religious ceremonies. However, this indigenous knowledge is diminishing rapidly due to the disinterest shown by the younger generation. Therefore, there need to document this indigenous knowledge regarding the usage of religious plants. The present study was conducted in Kanglung Gewog under Trashigang Dzongkhag, Bhutan, to document the plant species used for religious purposes. The ethnobotanical data were collected through semi-structured telephone interviews. A total of 24 plant species belonging to 16 families and 22 genera used in religious practices were documented. Among the 16 families, the most utilized species belong to the family Poaceae (4 species), followed by the family Ericaceae and Cupressaceae (3 species each) and Pinaceae (2 species). Out of these, trees account for 58 percent of all plants reported, followed by herbs (25%), shrubs (13%), and climbers (4%). The tree's trunk's most utilized parts, followed by the leaves, whole plant, seeds, and fruits. The majority of the plants recorded (58%) are used for religious ceremonies, and 42 percent of the plants are used for making religious items. The people of Kanglung have extensive indigenous knowledge on using plants in socio-religious activities. Still, rapid socio-economic development and the disinterest of the younger generation have become a major threat to preserving this indigenous knowledge. Therefore, it is necessary to preserve this indigenous knowledge on using plants in socio-religious activities by proper documentation and identification of plant species used to save these plants from further loss and sustainable utilization.

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Anticancer mechanism of artonin E and related prenylated flavonoids from the medicinal plant Artocarpus elasticus

Cited by 9 publications

References 129 publications

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

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

Artonin F Induces the Ubiquitin-Proteasomal Degradation of c-Met and Decreases Akt-mTOR Signaling

An ethnobotanical study of plants used in socio-religious activities in Bhutan

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