Isolasi Pinostrobin Dari Rimpang Temu Kunci (Boesenbergia rotunda) Dan Sintesis Dua Senyawa Turunannya

Al-Fattah, Raihan Muhammad (2026) Isolasi Pinostrobin Dari Rimpang Temu Kunci (Boesenbergia rotunda) Dan Sintesis Dua Senyawa Turunannya. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Tuberkulosis (TB) merupakan salah satu penyakit infeksi paling mematikan di dunia, dengan Indonesia menempati posisi kedua negara beban TB tertinggi secara global. Resistensi terhadap obat lini pertama seperti isoniazid, rifampisin, dan pirazinamida mendorong perlunya pengembangan senyawa antituberkulosis baru melalui pendekatan modifikasi struktur molekul. Pinostrobin (5-hidroksi-7-metoksiflavanon) (6) merupakan flavonoid bioaktif utama pada rimpang temu kunci (Boesenbergia rotunda) yang memiliki spektrum aktivitas farmakologis luas, meliputi antiinflamasi, antikanker, antimikroba, dan antioksidan. Berdasarkan hal tersebut, penelitian ini bertujuan mengisolasi pinostrobin (6) dari rimpang temu kunci serta sintesis dua senyawa turunan N-asilhidrazonnya sebagai kandidat senyawa bioaktif baru. Pinostrobin (6) diisolasi melalui metode maserasi menggunakan pelarut n-heksana terhadap 500 gram serbuk rimpang kering, dilanjutkan pemekatan dan rekristalisasi dengan metanol. Sintesis senyawa turunan dilakukan melalui reaksi kondensasi pinostrobin (6) dengan pirazin-2-karbohidrazida (8a) dalam etanol dan dengan nikotinik hidrazida (8b) dalam isopropanol, keduanya menggunakan katalis asam sulfat pekat pada suhu 70°C selama 3 jam. Kemurnian senyawa dipantau menggunakan Kromatografi Lapis Tipis (KLT), sedangkan identifikasi struktur dikonfirmasi dengan spektroskopi FTIR, NMR 1H dan 13C, serta spektrometri massa resolusi tinggi (HRMS). Pinostrobin (6) berhasil diisolasi sebagai padatan putih kekuningan dengan rendemen 1,41% (b/b) dan titik leleh 114–115°C. Reaksi kondensasi pinostrobin (6) dengan pirazin-2-karbohidrazida (8a) menghasilkan senyawa (E)-N'-(5-hidroksi-7-metoksi-2-fenilkroman-4-iledena) pirazina-2-karbohidrazida (9a) berupa padatan putih dengan rendemen 98%, sedangkan reaksi dengan nikotinik hidrazida (8b) menghasilkan senyawa (E)-N'-(5-hidroksi-7-metoksi-2-fenilkroman-4-iledena) nikotinohidrazida (9b) dengan rendemen 91%. Struktur kedua senyawa telah dikonfirmasi melalui data spektroskopi yang konsisten. Kedua senyawa ini merupakan senyawa baru yang belum pernah dilaporkan sebelumnya dan berpotensi memperkaya basis data senyawa kimia global serta menjadi kandidat untuk uji bioaktivitas lebih lanjut.
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Tuberculosis (TB) is one of the deadliest infectious diseases in the world, with Indonesia ranking second among countries with the highest TB burden globally. Resistance to first-line drugs such as isoniazid, rifampicin, and pyrazinamide drives the need for the development of new antituberculosis compounds through a molecular structure modification approach. Pinostrobin (5-hydroxy-7-methoxyflavanone) (6) is the main bioactive flavonoid in fingerroot (Boesenbergia rotunda) rhizomes, which possesses a broad spectrum of pharmacological activities, including anti-inflammatory, anticancer, antimicrobial, and antioxidant properties. Based on this, this study aims to isolate pinostrobin (6) from fingerroot rhizomes and synthesize two of its N-acylhydrazone derivatives as new bioactive compound candidates. Pinostrobin (6) was isolated through a maceration method using n-hexane solvent on 500 grams of dried rhizome powder, followed by concentration and recrystallization with methanol. The synthesis of the derivative compounds was carried out through the condensation reaction of pinostrobin (6) with pyrazine-2-carbohydrazide (8a) in ethanol and with nicotinic hydrazide (8b) in isopropanol, both using concentrated sulfuric acid as a catalyst at 70°C for 3 hours. Compound purity was monitored using Thin Layer Chromatography (TLC), while structural identification was confirmed by FTIR spectroscopy, 1H and 13C NMR, and high-resolution mass spectrometry (HRMS). Pinostrobin (6) was successfully isolated as a yellowish-white solid with a yield of 1.41% (w/w) and a melting point of 114–115°C. The condensation reaction of pinostrobin (6) with pyrazine-2-carbohydrazide (8a) yielded the compound (E)-N'-(5-hydroxy-7-methoxy-2-phenylchroman-4-ylidene)pyrazine-2-carbohydrazide (9a) as a white solid with a 98% yield, while the reaction with nicotinic hydrazide (8b) yielded the compound (E)-N'-(5-hydroxy-7-methoxy-2-phenylchroman-4-ylidene) nicotinohydrazide (9b) with a 91% yield. The structures of both compounds were confirmed through consistent spectroscopic data. Both are novel compounds that have not been previously reported, potentially enriching the global chemical compound database and serving as candidates for further bioactivity assays.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	nikotinik hidrazida, pinostrobin, pirazin-2-karbihidrazida, temu kunci, fingerroot, nicotinic hydrazide, pinostrobin, pyrazine-2-carbohydrazide
Subjects:	Q Science Q Science > QD Chemistry Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry Q Science > QD Chemistry > QD471 Chemical compounds - Structure and formulas Q Science > QD Chemistry > QD63 Extraction
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Raihan Muhammad Al-fattah
Date Deposited:	04 Aug 2026 08:02
Last Modified:	04 Aug 2026 08:02
URI:	http://repository.its.ac.id/id/eprint/143728

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