Geranyl chalcone derivatives with antifungal and radical scavenging properties from the leaves of Artocarpus nobilis

Jayasinghe, Lalith; Balasooriya, B A I S; Padmini, W.Chintha; Hara, Noriyuki; Fujimoto, Yoshinori

doi:10.1016/j.phytochem.2004.03.033

Cited by 85 publications

(65 citation statements)

References 6 publications

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“…The 4'-methoxychalcones (8)(9)(10)(11)(12)(13)(14)(15) were obtained in order to evaluate the impact of compound structures, including electron donating and electron acceptor substituents at para position in ring B on antimicrobial activity of these compounds.…”

Section: Discussionmentioning

confidence: 99%

“…Jayasinghe et al [15] proved that plant geranylchalcones isolated from Artocarpus nobilis (Moraceae) have antifungal activity towards Cladosporium cladosporioides. López et al [16] suggested that electron-donating substituents (e.g.,´OCH 3 ) in ring B of chalcones decrease their antifungal activity towards human dermatophytes, while electron acceptor groups (e.g.,´NO 2 ) at the para position have the opposite effect and augment this activity.…”

Section: Introductionmentioning

confidence: 99%

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Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues

Stompor

Żarowska

2016

Molecules

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Abstract:The objective of this study was to evaluate the antimicrobial activity of structural analogues of xanthohumol 1, a flavonoid compound found in hops (Humulus lupulus). The agar-diffusion method using filter paper disks was applied. Biological tests performed for selected strains of Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria, fungi (Alternaria sp.), and yeasts (Rhodotorula rubra, Candida albicans) revealed that compounds with at least one hydroxyl group-all of them have it at the C-4 position-demonstrated good activity. Our research showed that the strain S. aureus was more sensitive to chalcones than to the isomers in which the heterocyclic ring C is closed (flavanones). The strain R. rubra was moderately sensitive to only one compound: 4-hydroxy-4'-methoxychalcone 8. Loss of the hydroxyl group in the B-ring of 4'-methoxychalcones or its replacement by a halogen atom (´Cl,´Br), nitro group (´NO 2 ), ethoxy group (´OCH 2 CH 3 ), or aliphatic substituent (´CH 3 ,´CH 2 CH 3 ) resulted in the loss of antimicrobial activity towards both R. rubra yeast and S. aureus bacteria. Xanthohumol 1, naringenin 5, and chalconaringenin 7 inhibited growth of S. aureus, whereas 4-hydroxy-4 1 -methoxychalcone 8 was active towards two strains: S. aureus and R. rubra.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues

Stompor

Żarowska

2016

Molecules

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“…Senyawa fenolik yang merupakan senyawa paling banyak ditemukan dalam genus Artocarpus adalah golongan senyawa flavonoid. Senyawa fenolik tersebut dilaporkan memiliki aktivitas sebagai anti bakteri [5], anti fungal [6], anti malaria [7] dan sitotoksik [8]. Flavonoid yang terdapat dalam genus Artocarpus terdiri dari calkon, flavanon, dan flavon.…”

Section: Pendahuluanunclassified

KECENDERUNGAN POLA OKSIDASI FLAVONOID PADA KULIT BATANG DAN KAYU BATANG Artocarpus scortechinii KING. (Moraceae)

Hakim¹

2009

J. Pijar MIPA

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Abstrak. Flavonoid yang terdapat dalam genus Artocarpus terdiri dari calkon, flavanon, flavon dan flavan-3-ol. Gugus prenil pada flavonoid tersebut ada pada posisi C-3 dan cincin B teroksigenasi pada posisi C-4' atau C-2', C-4' atau C-2', C-4', C-5'. Selain itu prenilasi juga dapat terjadi pada posisi C-6, C-8, dan C-3'. Pola yang demikian sangat jarang ditemukan pada famili tumbuhan selain Moraceae. Kajian lebih lanjut terhadap pola oksigenasi cincin B pada bagian kulit batang dan kayu batang menjadi sangat menarik karena ditemukan kecenderungan yang dapat mewakili kedua bagian tersebut. Dari data metabolit sekunder kulit batang A. scortechinii King memperlihatkan kecenderungan pola oksigenasi pada cincin B dari kerangka flavon pada posisi 2', 4' dan 5'. Perkecualian hanya terjadi pada flavon sederhana, dimana oksigenasi terdapat pada posisi 2' dan 4' sedangkan metabolit sekunder dari kayu batang A. scortechinii King memperlihatkan kecenderungan pola oksigenasi cincin B pada posisi 2', 4'.Kata Kunci: Artocarpus scortechinii King, prenilasi, dan flavonoid. PATTERN PREFERENCE OXIDATION OF THE FLAVONOID AT BARK AND HEART-WOOD OF ARTOCARPUS SCORTECHINII KING.(MORACEAE)Abstract. Flavonoid which is in gender Artocarpus consisted of the chalcon, flavanon, flavon and flavan-3-ol. Prenylated of the flavonoid on position C-3 and B ring oxigenation on C-4' or C-2', C-4' or C-2', C-4', C-5'. Others prenylated also can be on position C-6, C-8, and C-3'. Such pattern is very rare found at set of relatives of plant besides Moraceae. Furthermore study to pattern of oxigenation on B ring at bark and heartwood become very attractive because found a tendency which can deputize second of the shares. From data metabolite secunder of the bark A. scortechinii King show the preference of pattern oxigenation of B ring from framework flavon on course 2', 4' and 5'. Exception is only became of the simple flavon, where oxigenation of there are on course 2' and 4' while metabolite secunder from heartwood A. scortechinii King show the tendency of pattern of oxigenation of B ring on course 2', 4'.

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“…A few of them have shown antifungal and anti-oxidant activities. For instance, 2 ,4 ,4-trihydroxy-3 -[6-hydroxy-3,7-dimethyl-2(E), 7-octadienyl]chalcone and 2 ,4 ,4-trihydroxy-3 -[2-hydroxy-7-methyl-3-methylene-6-octaenyl]chalcone were reported to exhibit antifungal activity against Cladosporium cladosporioides and radical scavenging activity [3].…”

Section: Introductionmentioning

confidence: 99%

New Cycloartane-type Triterpenoids from Artocarpus nobilis

Zahid

Ata

Samarasekera

2007

Zeitschrift Für Naturforschung B

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Recent phytochemical studies on the ethanolic extract of Artocarpus nobilis, collected from Sri Lanka, have resulted in the isolation of two new cycloartane-type triterpenoids, artocarpuate A (1) and artocarpuate B (2). Structures of these new compounds were established with the aid of extensive NMR spectroscopic studies. Compounds 1 and 2 were found to exhibit weak acetylcholinesterase inhibitory activity.

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Geranyl chalcone derivatives with antifungal and radical scavenging properties from the leaves of Artocarpus nobilis

Cited by 85 publications

References 6 publications

Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues

Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues

KECENDERUNGAN POLA OKSIDASI FLAVONOID PADA KULIT BATANG DAN KAYU BATANG Artocarpus scortechinii KING. (Moraceae)

New Cycloartane-type Triterpenoids from Artocarpus nobilis

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