Isolation, identification and bioactivity of steroids compounds from red algae Eucheuma cottonii petroleum ether fraction

Fasya, Ahmad Ghanaim; Baderos, Ahmad; Madjid, Armeida Dwi Ridhowati; Amalia, Suci; Megawati, Dewi Sinta

doi:10.1063/1.5115629

Cited by 10 publications

(7 citation statements)

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“…Strychnos spinosa [25] Acanthophora spicifera [26] Cladophora fascicularis [27] Sargassum muticum [28] Antitrypanosomal [25] Anti-obesity, [28] a novel selective LXRb agonist, [29] and anticancer activities [30] b-sitosterol (4) Terrestrial plant Red macroalgae Green macroalgae Brown macroalgae Microalgae Synadenium glaucescens [31] Eucheuma cottonii [32] Ulva fasciata [33] Sargassum glaucescens [34] Nannochloropsis [35] Antimicrobial, [36] antiviral activity against hepatitis B virus, [37] antioxidant and anticancer activities [38] Glycoglycerolipids (5,9) Terrestrial plant Red macroalgae Brown macroalgae Cyanobacteria Soybean [39] Exophyllum wentii [40] Sargassum horneri [41] Phormidium sp. [42] Accumulation inhibition, [39] antitumor, antiviral, anti-inflammatory and anticancr activities [30,43] Kjellmanianone (6) Brown macroalgae Sargassum naozhouense [44] Antibacterial effect against E. coli and Bacillus subtilis [45] Loliolide 7Terrestrial plant Brown macroalgae…”

Section: Introductionmentioning

confidence: 99%

The inhibitory effect of some natural bioactive compounds against SARS-CoV-2 main protease: insights from molecular docking analysis and molecular dynamic simulation

Abdelrheem

Ahmed

El-Mageed

et al. 2020

Journal of Environmental Science and Health, Part A

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This work aimed at evaluating the inhibitory effect of ten natural bioactive compounds (1-10) as potential inhibitors of SARS-CoV-2-3CL main protease (PDB ID: 6LU7) and SARS-CoV main proteases (PDB IDs: 2GTB and 3TNT) by molecular docking analysis. The inhibitory effect of all studied compounds was studied with compared to some proposed antiviral drugs which currently used in COVID-19 treatment such as chloroquine, hydroxychloroquine, azithromycin, remdesivir, baloxvir, lopinavir, and favipiravir. Homology modeling and sequence alignment was computed to evaluate the similarity between the SARS-CoV-2-3CL main protease and other SARS-CoV receptors. ADMET properties of all studied compounds were computed and reported. Also, molecular dynamic (MD) simulation was performed on the compound which has the highest binding affinity inside 6LU7 obtained from molecular docking analysis to study it is stability inside receptor in explicit water solvent. Based on molecular docking analysis, we found that caulerpin has the highest binding affinity inside all studied receptors compared to other bioactive compounds and studied drugs. Our homology modeling and sequence alignment showed that SARS-CoV main protease (PDB ID: 3TNT) shares high similarity with 3CLpro (96.00%). Also, ADMET properties confirmed that caulerpin obeys Lipinski's rule and passes ADMET property, which make it a promising compound to act as a new safe natural drug against SARS-CoV-2-3CL main protease. Finally, MD simulation confirmed that the complex formed between caulerpin and 3CLpro is stable in water explicit and had no major effect on the flexibility of the protein throughout the simulations and provided a suitable basis for our study. Also, binding free energy between caulerpin and 6LU7 confirmed the efficacy of the caulerpin molecule against SARS-CoV-2 main protease. So, this study suggested that caulerpin could be used as a potential candidate in COVID-19 treatment.

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Section: Introductionmentioning

confidence: 99%

The inhibitory effect of some natural bioactive compounds against SARS-CoV-2 main protease: insights from molecular docking analysis and molecular dynamic simulation

Abdelrheem

Ahmed

El-Mageed

et al. 2020

Journal of Environmental Science and Health, Part A

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“…Pemisahan yang lebih spesifik dapat dilakukan dengan cara hidrolisis untuk memutuskan ikatan antara glikon dan steroid [17]. Senyawa sterol yang merupakan salah satu jenis steroid ditemukan pada tumbuhan dalam keadaan berikatan dengan glikosida [18].…”

Section: Pendahuluanunclassified

Aktivitas Antioksidan Isolat Steroid Hasil Kromatografi Lapis Tipis dari Fraksi n-Heksana Hydrilla verticillata

Fasya

Purwantoro

Ulya

et al. 2020

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Hydrilla verticillata is one of Allah SWT creations that potential as an antioxidant. This study’s objectives were to determine antioxidant activity and identify steroid isolates of n-hexane fraction of H. verticillata. The steroid compounds were extracted using methanol solvent. The methanol extract was hydrolyzed with HCl 2 N and partitioned using n-hexane. The n-hexane fraction was tested phytochemically and separated using thin-layer chromatography (TLC). The steroids compounds were identified using UV-Vis spectrophotometer, FTIR, and LC-MS/MS. The result showed that maceration extraction produced 5.14% yield, whereas n-hexane fraction produce 47.95% yield. Steroid separation through analytical TLC revealed that n-hexane: ethyl acetate (4:1) as the best eluant with 12 spots, while separation using preparative TLC yielded 19 spots. Steroid isolate from TLC preparative has antioxidant activity with EC50 of 5.109 ppm. Identification of steroid compounds using UV-Vis produced maximum wavelengths at 203.9 and 276 nm, while using FTIR indicated the presence of O-H group, geminal dimethyl, C=O, C=C, secondary C-OH, and =C-H (alkene) which might contain steroid compounds. The result of LC-MS/MS showed the presence of β-sitosterol. Hydrilla verticillata merupakan salah satu ciptaan Allah SWT yang memiliki potensi sebagai antioksidan. Penelitian ini bertujuan mengetahui aktivitas antioksidan dan mengidentifikasi senyawa steroid pada isolat hasil pemisahan fraksi n-heksana H. verticillata. Senyawa steroid diekstraksi menggunakan pelarut metanol. Ekstrak pekat metanol dihidrolisis dengan HCl 2 N dan dipartisi dengan n-heksana. Fraksi n-heksana hasil partisi diuji fitokimia dan dipisahkan senyawanya menggunakan KLT (Kromatografi Lapis Tipis). Identifikasi dilakukan menggunakan UV-Vis, FTIR, dan LC-MS/MS. Hasil penelitian menunjukkan ekstraksi maserasi menghasilkan rendemen 5,14%, sedangkan rendemen partisi n-heksana sebesar 47,95%. Pemisahan steroid menggunakan KLT analitik menunjukkan bahwa variasi eluen terbaik adalah n-heksana: etil asetat (4:1) dengan 12 noda, sedangkan pemisahan KLT preparatif menghasilkan 19 noda. Isolat steroid hasil KLT preparatif memiliki aktivitas antioksidan dengan EC50 5,109 ppm. Identifikasi senyawa steroid menggunakan UV-Vis menunjukkan bahwa panjang gelombang maksimum sebesar 203,9 dan 276 nm, sedangkan untuk identifikasi isolat steroid menggunakan FTIR menunjukkan gugus fungsi O-H, geminal dimetil, C=O, C=C, C-OH sekunder dan =C-H (alkena) yang diduga merupakan senyawa steroid. Hasil LC-MS/MS menunjukkan adanya senyawa steroid β-sitosterol.

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“…Senyawa metabolit sekunder yang terkandung E. cottonii adalah steroid dan triterpenoid [8]. Senyawa steroid tersebut memiliki toksisitas terhadap Artemia salina [9] dan berpotensi sebagai antioksidan [2] serta antimikroba [5]. Adapun senyawa triterpenoid memiliki kemampuan sebagai zat yang mampu meningkatkan aktivitas rifampisin (antibiotik) dalam menghambat pertumbuhan bakteri Mycobacterium tuberculosis [10].…”

Section: Pendahuluanunclassified

Variasi Komposisi Eluen pada Isolasi Steroid dan Triterpenoid Alga Merah Eucheuma cottonii dengan Kromatografi Kolom Basah

Madjid

Rahmawati

Fasya

2020

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Steroid and triterpenoid compounds in petroleum ether fractions of red algae Eucheuma cottonii were isolated by slurry column chromatography. Isolation was started with maceration extraction using methanol solvent. The methanol extract was hydrolyzed with HCl 2 N and partitioned using petroleum ether solvent. The presence of steroid and triterpenoid was determined by phytochemical test using Lieberman Burchard reagent. Petroleum ether fraction was separated by slurry column chromatography with the variation of eluent composition n-hexane: ethyl acetate 16:4; 17:3; 18:2. The isolates were monitored by analytical thin-layer chromatography (TLC) and the best result was identified using FTIR. Percent yields of methanol extract and petroleum ether fraction were 11.866% and 8.03%, respectively. The optimum eluent composition in column chromatography for separation was n-hexane : ethyl acetate (18:2) obtained 2 steroid and 3 triterpenoid fractions. FTIR analysis gives information about functional groups of –OH, C=C, C-O, CH2, -C(CH3)2forsteroids and functional groups of –OH, C=O, C=C, CH2, -C(CH3)2 for triterpenoid.Keywords: Eucheuma cottonii, column chromatography, steroid, triterpenoid, variation of eluent composition Senyawa steroid dan triterpenoid dalam fraksi petroleum eter alga merah Eucheuma cottonii telah diisolasi menggunakan kromatografi kolom basah. Isolasi dilakukan dengan cara ekstraksi maserasi menggunakan pelarut metanol. Ekstrak pekat metanol dihidrolisis dengan HCl 2 N dan dipartisi menggunakan pelarut petroleum eter. Senyawa steroid dan triterpenoid diuji fitokimia menggunakan reagen Lieberman Burchard. Fraksi petroleum eter dipisahkan menggunakan kromatografi kolom basah variasi komposisi eluen n-heksana:etil asetat dengan perbandingan 16:4; 17:3; dan 18:2. Hasil isolasi dimonitoring menggunakan kromatografi lapis tipis (KLT) analitik. Hasil monitoring yang terbaik diidentifikasi gugus fungsinya menggunakan FTIR. Hasil penelitian menunjukkan rendemen ekstrak metanol dan fraksi petroleum eter masing-masing sebesar 11,866% dan 8,03%. Pemisahan kolom dengan variasi komposisi eluen n-heksana:etil asetat terbaik adalah 18:2 dengan diperoleh 2 kelompok fraksi steroid dan 3 kelompok fraksi triterpenoid. Hasil analisis FTIR pada isolat steroid memberikan informasi gugus –OH, C=C, C-O, CH2, -C(CH3)2, sedangkan isolat triterpenoid memberikan informasi gugus –OH, C=O, C=C, CH2,-C(CH3)2. Gugus gem dimetil (-C(CH3)2)merupakan ciri khas rantai samping steroid ataupun triterpenoid.Kata kunci: Eucheuma cottonii, kromatografi kolom, steroid, triterpenoid, variasi komposisi eluen

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Isolation, identification and bioactivity of steroids compounds from red algae Eucheuma cottonii petroleum ether fraction

Abstract: The production of cinnamic acid secondary metabolites through in vitro culture of callus Camellia sinensis L with the elicitor of cobalt metal ions

Cited by 10 publications

References 10 publications

The inhibitory effect of some natural bioactive compounds against SARS-CoV-2 main protease: insights from molecular docking analysis and molecular dynamic simulation

The inhibitory effect of some natural bioactive compounds against SARS-CoV-2 main protease: insights from molecular docking analysis and molecular dynamic simulation

Aktivitas Antioksidan Isolat Steroid Hasil Kromatografi Lapis Tipis dari Fraksi n-Heksana Hydrilla verticillata

Variasi Komposisi Eluen pada Isolasi Steroid dan Triterpenoid Alga Merah Eucheuma cottonii dengan Kromatografi Kolom Basah

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