Isolasi Pinostrobin dan Sintesis Turunan Hidrazon Pinostrobin

Nurhasan, Moch (2026) Isolasi Pinostrobin dan Sintesis Turunan Hidrazon Pinostrobin. Masters thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Tuberkulosis merupakan penyakit infeksi utama penyebab kematian, dan Indonesia menempati posisi kedua dalam jumlah kasus tuberkulosis terbanyak di dunia. Senyawa pinostrobin (6) dari rimpang temu kunci telah menunjukkan aktivitas antituberkulosis dengan MIC 12,5 µg/mL, sehingga terdapat potensi untuk ditingkatkan bioaktivitasnya melalui hibridisasi molekul. Penelitian ini telah berhasil mengisolasi senyawa pinostrobin (6) dengan metode maserasi menggunakan pelarut n-heksana dilanjutkan rekristalisasi menggunakan metanol. Senyawa pinostrobin (6) diperoleh dengan rendemen 1,41% (b/b kering), dan strukturnya diidentifikasi dengan spektrometer NMR (1H) dan spektrofotometer FTIR. Hibridisasi molekul senyawa pinostrobin (6) dilakukan dengan menerapkan reaksi adisi nukleofilik pada gugus karbonil dengan nukleofil berupa empat jenis hidrazida sehingga diperoleh empat molekul hibrid baru (10a-d). Reaksi dilakukan dalam pelarut etanol dengan katalis asam sulfat pekat, dan kemajuan reaksi dipantau dengan kromatografi lapis tipis. Struktur hidrazon pinostrobin (10a-d) diidentifikasi dengan HRMS, spektrometer NMR (1H, 13C), dan spektrofotometer FTIR. Senyawa (E)-N’-(5-hidroksi-7-metoksi-2-fenilkroman-4-iledena)iso-nikotinohidrazida (10a) telah berhasil didapatkan dengan rendemen sebesar 74%, senyawa (E)-N’-(5-hidroksi-7-metoksi-2-fenilkroman-4-iledena)furan-2-karbo-hidrazida (10b) dengan rendemen sebesar 50%, senyawa (E)-N’-(5-hidroksi-7-metoksi-2-fenilkroman-4-iledena)tiofen-2-karbohidrazida (10c) dengan rendemen sebesar 16%, dan senyawa (E)-N’-(5-hidroksi-7-metoksi-2-fenilkroman-4-iledena)hidrazina-1-karbotioamida (10d) dengan rendemen sebesar 76%.
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Tuberculosis is a major infectious disease and a leading cause of mortality, and Indonesia ranks second worldwide in terms of the number of tuberculosis cases. The pinostrobin (6) compound isolated from the rhizome of temu kunci has exhibited antituberculosis activity with a minimum inhibitory concentration (MIC) of 12.5 µg/mL, indicating the potential to further enhance its bioactivity through molecular hybridization. In this study, pinostrobin (6) compound was successfully isolated by maceration using n-hexane as the solvent, followed by recrystallization with methanol, affording a yield of 1.41% (w/w dry), and its structure was identified using (1H) NMR spectrometer and FTIR spectrophotometer. Molecular hybridization of pinostrobin (6) compound was carried out via a nucleophilic addition reaction at the carbonyl group using four different hydrazides as nucleophiles to afford four new hybrid molecules (10a–d), with the reaction performed in ethanol as the solvent and concentrated sulfuric acid as the catalyst, and the progress monitored by thin-layer chromatography. The structures of the pinostrobin hydrazones (10a–d) were elucidated using HRMS, (1H, 13C) NMR spectrometer, and FTIR spectrophotometer. The (E)-N’-(5-hydroxy-7-methoxy-2-phenylchroman-4-ylidene)isonicotinohydrazide (10a) compound was obtained in 74% yield, (E)-N’-(5-hydroxy-7-methoxy-2-phenylchroman-4-ylidene)furan-2-carbohydrazide (10b) compound in 50% yield, (E)-N’-(5-hydroxy-7-methoxy-2-phenylchroman-4-ylidene)thiophene-2-carbohydrazide (10c) compound in 16% yield, and (E)-N’-(5-hydroxy-7-methoxy-2-phenylchroman-4-ylidene)hydrazine-1-carbothioamide (10d) compound in 76% yield.

Item Type:	Thesis (Masters)
Uncontrolled Keywords:	Tuberkulosis, Pinostrobin, Hidrazon, Isolasi, Sintesis; Tuberculosis, Pinostrobin, Hydrazone, Isolation, Synthesis
Subjects:	Q Science > QD Chemistry
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47101-(S2) Master Thesis
Depositing User:	Moch. Nur hasan
Date Deposited:	05 Feb 2026 03:09
Last Modified:	05 Feb 2026 03:09
URI:	http://repository.its.ac.id/id/eprint/132166

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