Isolasi dan Uji Bioaktivitas Senyawa dari Mangifera rufocostata dan Mangifera foetida

Mustikasari, Kamilia (2024) Isolasi dan Uji Bioaktivitas Senyawa dari Mangifera rufocostata dan Mangifera foetida. Doctoral thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Tumbuhan dari genus mangifera yaitu Mangifera rufocostata dan Mangifera foetida dimanfaatkan masyarakat Kalimantan Selatan. M. rufocostata dan M. foetida tumbuh di Kalimantan Selatan dengan nama lokal masing-masing adalah Asem Tanduy dan Hambawang. Eksplorasi pada kedua tanaman tersebut melalui metabolit profiling ekstrak metanol kedua tanaman dengan LC-MS/MS, mengetahui kandungan total fenolat (TPC) dan total flavonoid (TFC), uji bioaktivitas untuk mengetahui aktivitas antioksidan (ABTS, DPPH, FRAP) dan aktivitas penghambatan enzim α-glukosidase (in vitro dan in silico), serta aktivitas sitotoksik terhadap sel kanker HT-29, HeLa, dan MCF-7. Isolasi senyawa dengan metode ekstraksi, fraksinasi dan pemurnian menggunakan kromatografi, dilanjutkan penentuan struktur dengan spektrometer 1H-NMR, 13C-NMR, HMBC, dan COSY. Uji penghambatan isolat terhadap enzim α-glukosidase (in vitro dan in silico). Derivatisasi struktur senyawa hasil isolasi dengan metode esterifikasi, produknya diidentifikasi dengan LC-MS/MS dan diuji aktivitas penghambatannya terhadap enzim α-glukosidase (in vitro dan in silico). Hasil LC-MS/MS menunjukkan bahwa ekstrak metanol kulit batang M. rufocostata mengandung senyawa utama mangiferin (17,25%) dan asam kuinat (12,83%), sedangkan ekstrak metanol M. foetida mengandung senyawa utama asam 3,4-dihidroksimandelat (7,67%) dan mangiferin (6,16%). Ekstrak metanol kulit batang M. rufocostata mempunyai TPC dan TFC, antioksidan (ABTS, DPPH, FRAP), dan penghambatan enzim α-glukosidase secara in vitro lebih besar daripada ekstrak M. foetida. Beberapa fraksi polar dari ekstrak M. rufocostata dan M. foetida serta isolat mangiferin aktif menghambat enzim α-glukosidase secara in vitro. Mangiferin, irisanton, 7-Hidroksi-2-(4-hidroksifenil)-4-okso-3,4-dihidro-2H-kromen-5-il β-D-glukopiranosida dan kuersetin, berpotensi menghambat enzim α-glukosidase secara in silico. Hasil uji sitotoksisitas menunjukkan ekstrak metanol M. rufocostata bersifat sitotoksik terhadap sel kanker HT-29 dengan IC50 0,25 ± 2,74 µg/mL. Isolat yang diperoleh dari M. rufocostata adalah friedelin, 2-propilpentil galat, dan mangiferin, sedangkan yang diperoleh dari M. foetida adalah mangiferin. Isolat mangiferin aktif menghambat enzim α-glukosidase secara in vitro dengan IC50 22,82±5,87 µg/mL, sedangkan friedelin dan 2-propilpentil galat berturut-turut hanya menghambat sebesar 45,56±2,67 dan 42,71±3,36%. Isolat tersebut berpotensi menghambat enzim α-glukosidase secara in silico. Derivatisasi struktur mangiferin menghasilkan mangiferin pentapentanoat, mangiferin isopentanoat, dan mangiferin butaheksanoat dengan rendemen di bawah 10%. Senyawa derivatisasi tersebut berpotensi menghambat enzim α-glukosidase secara in silico.
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Plants from the mangifera genus such as Mangifera rufocostata and Mangifera foetida have been widely used by the people of South Kalimantan. M. rufocostata and M. foetida grow in South Kalimantan, locally known as Asem Tanduy and Hambawang respectively. This research explored the properties of the two plants through the metabolite profiles of the methanol extracts of the two plants using LC-MS/MS and to determine the total phenolic (TPC) and total flavonoid (TFC) content, bioactivity test was conducted to determine antioxidant activity (ABTS, DPPH, FRAP), and inhibitory activity of the α-glucosidase enzyme (in vitro and in silico), as well as cytotoxic activity against HT-29, Hela, and MCF-7 cancer cells. The compounds isolated through extraction, fractionation and purification methods using various chromatography techniques, followed by structure determination using 1H-NMR, 13C-NMR, HMBC and COSY spectrometers. Inhibition test of isolates against the α-glucosidase enzyme (in vitro and in silico). The structure of the isolated compound was modified using the esterification method, and identify the product using LC-MS/MS, as well as inhibition tests of modified products against the α-glucosidase enzyme (in vitro and in silico). The results of LC-MS/MS showed that the methanol stem extract of M. rufocostata bark contained the major compounds mangiferin (17.25%) and quinic acid (12.83%), while the methanol extract of M. foetida contained the major compound 3,4-Dihydroxymandelic acid (7.67 %) and mangiferin (6.16%). The methanol extract of M. rufocostata stem bark has greater TPC, TFC, antioxidant activity (ABTS, DPPH, FRAP) and inhibition of the α-glucosidase enzyme in vitro than M. foetida extract. Several polar fractions from M. rufocostata and M. foetida extracts as well as mangiferin isolates actively inhibit the α-glucosidase enzyme in vitro. Mangiferin, irisxhantone, 7-hydroxy-2-(4-hydroxyphenyl)-4-oxu-3,4-dihydro-2H-chromen-5-yl-D-glucopyranoside, and Kuersetin have the potential to inhibit the α-glucosidase enzyme in silico. The results of the cytotoxicity test showed that the methanol extract of M. rufocostata was cytotoxic to HT-29 cancer cells with an IC50 of 0.25 ± 2.74 µg/mL. The isolates obtained from M. rufocostata were friedelin, 2-propylpentyl gallate, and mangiferin, while those obtained from M. foetida were mangiferin. Mangiferin actively inhibits the α-glucosidase enzyme in vitro with an IC50 of 22.82 ± 5.87 µg/mL, while friedelin and 2-propylpentyl gallate only inhibit 45.56 ± 2.67 and 42.71 ± 3.36% respectively. This isolate has the potential to inhibit the α-glucosidase enzyme in silico. Modification of the mangiferin structure produces mangiferin pentapentanoate, mangiferin isopentanoate, and mangiferin butahexanoate with yields below 10%. This modified compound has the potential to inhibit the α-glucosidase enzyme in silico.

Item Type:	Thesis (Doctoral)
Uncontrolled Keywords:	isolasi, bioaktivitas, M. rufocostata, M. foetida, isolation, bioactivity
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47001-(S3) PhD Thesis
Depositing User:	Kamilia Mustikasari
Date Deposited:	23 Aug 2024 02:27
Last Modified:	23 Aug 2024 02:27
URI:	http://repository.its.ac.id/id/eprint/115509

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