Antioxidant activity-guided isolation of usnic acid and diffractaic acid compounds from lichen genus Usnea sp.

Maulidiyah, Maulidiyah; Darmawan, Akhmad; Erviana, Ahmad; Musdalifah, Andi; Wibowo, Dwiprayogo; Agus, Salim La Ode; Arham, Zul; Faizal, Mustapa; Adiba, Nurdin Ishmah Farah; Nurdin, Muhammad

doi:10.7324/japs.2021.110210

Cited by 7 publications

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“…[ 10 ]. Various lichen bioactivities are due to this compound, such as gastroprotective [ 15 ], cardioprotective [ 16 ], neuroprotective [ 17 ], cytoprotective [ 18 ], cytotoxic [ 19 ], anticancer [ 20 ], antimicrobial [ 21 ], antidiabetic [ 22 ], analgesic-antipyretic [ 23 ], and anti-inflammatory [ 24 ] properties, mainly through its antioxidant action, reducing oxidative damage [ 25 ]. Some of the other phenolic metabolites previously mentioned also display different biological effects.…”

Section: Introductionmentioning

confidence: 99%

Antioxidant, Cytotoxic, and Rheological Properties of Canola Oil Extract of Usnea barbata (L.) Weber ex F.H. Wigg from Călimani Mountains, Romania

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Usnea genus (Parmeliaceae, lichenized Ascomycetes) is a potent phytomedicine, due to phenolic secondary metabolites, with various pharmacological effects. Therefore, our study aimed to explore the antioxidant, cytotoxic, and rheological properties of Usnea barbata (L.) Weber ex F.H. Wigg (U. barbata) extract in canola oil (UBO) compared to cold-pressed canola seed oil (CNO), as a green solvent used for lichen extraction, which has phytoconstituents. The antiradical activity (AA) of UBO and CNO was investigated using UV-Vis spectrophotometry. Their cytotoxicity was examined in vivo through a brine shrimp lethality (BSL) test after Artemia salina (A. salina) larvae exposure for 6 h to previously emulsified UBO and CNO. The rheological properties of both oil samples (flow behavior, thixotropy, and temperature-dependent viscosity variation) were comparatively analyzed. The obtained results showed that UBO (IC50 = 0.942 ± 0.004 mg/mL) had a higher 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity than CNO (IC50 = 1.361 ± 0.008 mg/mL). Both UBO and CNO emulsions induced different and progressive morphological changes to A. salina larvae, incompatible with their survival; UBO cytotoxicity was higher than that of CNO. Finally, in the temperature range of 32–37 °C, the UBO and CNO viscosity and viscoelastic behavior indicated a clear weakening of the intermolecular bond when temperature increases, leading to a more liquid state, appropriate for possible pharmaceutical formulations. All quantified parameters were highly intercorrelated. Moreover, their significant correlation with trace/heavy minerals and phenolic compounds can be observed. All data obtained also suggest a possible synergism between lichen secondary metabolites, minerals, and canola oil phytoconstituents.

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Section: Introductionmentioning

confidence: 99%

Antioxidant, Cytotoxic, and Rheological Properties of Canola Oil Extract of Usnea barbata (L.) Weber ex F.H. Wigg from Călimani Mountains, Romania

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“…The spectrum shows the similarity of data from usnic acid compounds 8,35) . Based on a 1 H-NMR spectrum (Fig.…”

Section: Identi Cation Of Isolate Structurementioning

confidence: 54%

“…In the final stage, we compare results with the appropriate literature by Huneck and Yoshimura (1996) 35) and Maulidiyah et al (2021) 8) , it is assumed that the isolated compound from the ethyl acetate fraction is a usnic acid (C 18 H 16 O 7 ) ( Table 2) . Usnic acid is one of the main contents of lichen Usnea sp.…”

Section: Identi Cation Of Isolate Structurementioning

confidence: 99%

“…Lichen Usnea has diverse species, such as U. longissima, U. articulate, U. sternaii, U. vrieseana, U. blepharea, U. comosa, U. flexuosa, U. bayleyi, U. javanica, and U. dasypoga 5) . Isolation of secondary metabolites from lichen Usnea has been reported, such as atranorin 6) , thamnolic acid 7) , diffractic acid, and usnic acid 8) . Usnea sp.…”

Section: Introductionmentioning

confidence: 99%

“…Based on our previous study, the lichen Usnea sp. contains secondary metabolites such as 2'-hydroxy-1'-(4-hydroxyl-5-methoxy-2-methyl-phenyl) -etone 30) , 3-［1'-(2",3"-dihydroxyphenyl) -propyl］ -7-hydroxy-chroman-4-one 31) , (5E,6E) 5-ethylidene-7-formyl-6,7-hydroxymethylhept-6-enoate 32) , eumitrin A1 33) , atranorin 6) , and diffractaic acid 8) . Isolation, structural elucidation, and inhibition test of the α-glucosidase enzyme of a usnic acid compound from lichen genus Usnea sp.…”

Section: Introductionmentioning

confidence: 99%

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Potential of Usnic Acid Compound from Lichen Genus <i>Usnea</i> sp. as Antidiabetic Agents

et al. 2022

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There are still few reports of secondary metabolites from lichens Usnea sp. as an antidiabetic agent. Based on data from the International Diabetes Federation 15) , the prevalence of global diabetes is expected to increase by 552 million by 2030. Data from the World Health Organization (WHO) 16) also reports that diabetes mellitus is the seventhlargest cause of death. One of the essential therapeutic methods for reducing plasma glucose levels is to inhibit α-glucosidase activity 17−19) . Several previous studies have reported the potential of lichen exploration as a good antidiabetic agent. The α-amylase inhibition test which has shown a positive potency there are 22 types of lichen, such us Ramalina conduplicans,

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Usnic Acid Isolated from Lichen Usnea sp. from Ciwidey, West Java

et al. 2023

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Indonesia is a tropical country that has a variety of plants. Plants are one potential source of medicine. One of them is Lichen Usnea sp., which is used by the community to treat several diseases, so further research is needed to study the chemical composition contained and other potentials of this plant. Research on the chemical constituent of Lichen Usnea sp. consists of various stages: sample preparation, maceration using methanol, fractionation by Vacum Liquid Chromatography (VLC) and radial chromatography guided by Thin Layer Chromatography (TLC) eluting with n-hexane, chloroform and ethyl acetate obtaining an isolated compound. The isolated compound was analyzed by various spectroscopic data (UV-Vis, FT-IR, 1H-NMR and 13C-NMR). Based on the spectra, the isolated compound was usnic acid.Keywords: Usnic acid; Lichen; Usnea sp.ABSTRAKIsolat Asam Usnat dari Lichen Usnea sp. Asal Ciwidey, Jawa BaratIndonesia adalah negara tropis dengan banyaknya spesies tumbuhan. Tumbuhan adalah salah satu sumber bahan baku yang potensial untuk obat–obatan. Salah satunya Lichen Usnea sp. yang digunakan masyarakat dalam pengobatan beberapa penyakit, sehingga diperlukan penelitian lebih lanjut untuk mengetahui senyawa kimia yang terkandung dan potensi lainnya dari tanaman ini. Penelitian kandungan kimia dari Lichen Usnea sp. asal Ciwidey, Jawa Barat, terdiri dari berbagai tahapan, yaitu, persiapan sampel, maserasi dengan pelarut metanol, fraksinasi dan pemurnian dengan metode Kromatografi Cair Vakum (KCV) dan kromatografi radial yang dipandu dengan Kromatografi Lapis Tipis (KLT) dengan eluen n-heksana, kloroform dan etil asetat dan menghasilkan satu senyawa. Senyawa yang diperoleh tersebut dianalisis dengan berbagai data spektroskopi (UV, IR, 1H-NMR, dan 13C-NMR). Hasil karakterisasi menunjukkan bahwa senyawa tersebut adalah asam usnat.Kata kunci: Asam usnat; Lichen; Usnea sp.

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Antioxidant activity-guided isolation of usnic acid and diffractaic acid compounds from lichen genus Usnea sp.

Cited by 7 publications

References 3 publications

Antioxidant, Cytotoxic, and Rheological Properties of Canola Oil Extract of Usnea barbata (L.) Weber ex F.H. Wigg from Călimani Mountains, Romania

Antioxidant, Cytotoxic, and Rheological Properties of Canola Oil Extract of Usnea barbata (L.) Weber ex F.H. Wigg from Călimani Mountains, Romania

Potential of Usnic Acid Compound from Lichen Genus <i>Usnea</i> sp. as Antidiabetic Agents

Usnic Acid Isolated from Lichen Usnea sp. from Ciwidey, West Java

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