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All Journal Farmaka Indonesian Journal of Applied Sciences Jurnal Farmasi Sains dan Terapan (Journal of Pharmacy Science and Practice) Indonesian Journal of Cancer Chemoprevention Dharmakarya : Jurnal Aplikasi Ipteks Untuk Masyarakat Indonesian Journal of Pharmaceutical Science and Technology Indonesian Journal of Science and Technology Pharmascience The Indonesian Biomedical Journal IDJP (Indonesian Journal of Pharmaceutics) Indonesian Journal of Chemistry Majalah Farmasi dan Farmakologi (Trends in Pharmacy and Pharmaceutical Sciences) Pharmacology and Clinical Pharmacy Research Majalah Farmasetika Kumawula: Jurnal Pengabdian Kepada Masyarakat Jurnal Ilmiah Farmako Bahari Journal of Community Development Journal of Global Pharma Technology Jurnal Mahasiswa Ilmu Kesehatan Jurnal Farmasi Galenika Jurnal Farmasi Sains dan Terapan (Journal of Pharmacy Science and Practice)
MEGANTARA, SANDRA
Universitas Padjadjaran
Agriculture, Biological Sciences & Forestry Arts Humanities Biochemistry, Genetics & Molecular Biology Chemical Engineering, Chemistry & Bioengineering Chemistry Computer Science & IT Decision Sciences, Operations Research & Management Economics, Econometrics & Finance Engineering Environmental Science Health Professions Immunology & microbiology Languange, Linguistic, Communication & Media Materials Science & Nanotechnology Medicine & Pharmacology Nursing Public Health Social Sciences

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Journal : Pharmascience

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REVIEW: SINTESIS TURUNAN ANDROGRAFOLID PADA GUGUS HIDROKSIL C-3 DAN C-19 Sri Indrayani; Sandra Megantara; Febrina Amelia Saputri
Jurnal Pharmascience Vol 7, No 2 (2020): Jurnal Pharmascience
Publisher : Program Studi Farmasi FMIPA Universitas Lambung Mangkurat

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20527/jps.v7i2.8495

Abstract

Andrografolid merupakan senyawa diterpenoid utama dari tanaman Andrographis paniculata dan telah dikenal memiliki berbagai aktivitas farmakologi. Andrografolid memiliki struktur menarik yang terdiri dari α-alkiliden γ-butirolakton, dua ikatan olefin pada C-8 and C-12 dan tiga gugus hidroksil. Dari ketiga gugus hidroksil tersebut, salah satunya adalah gugus hidroksil alilik pada C-14 dan yang lainnya adalah gugus hidroksil sekunder dan primer pada C-3 dan C-19. Gugus hidroksil C-3 dan C-19 merupakan gugus yang potensial untuk dimodifikasi. Review ini menjelaskan tentang pentingnya gugus hidroksil andrografolid pada C-3 dan C-19 dan pengaruhnya terhadap aktivitas biologis yang ditimbulkannya. Modifikasi andrografolid pada gugus tersebut dengan menambahkan gugus hidroksibenzaldehid dapat meningkatkan efek farmakologis sebagai anti-HIV. Esterifikasi yang terjadi pada C-3 dan C-19 dapat meningkatkan aktivitas sebagai antitumor. Penambahan ester aromatik baik di C-3 dan C-19 dapat mengurangi aktivitas senyawa sebagai antitumor. Modifikasi pada gugus tersebut dapat dilakukan dengan mekanisme reaksi substitusi nukleofilik dengan penambahakn katalis dan pemanasan. Pemanasan dengan metode iradiasi microwave memberikan hasil sintesis dengan nilai rendemen yang paling tinggi.  Andrographolide is a diterpenoid lactone isolated from the herb of Andrographis paniculata and known for its multiple pharmacological activities. Andrographolide has an interesting architecture consisting of an α-alkylidene γ-butyrolactone moiety, two olefin bond (C-8 and C-12), and three hydroxyls groups. Of the three hydroxyl groups, one is allylic at C-14, and the others are secondary and primary at C-3 and C-19, respectively. Hydroxyl groups C-3 and C-19 are the potential groups to be modified. The review describes the importance of the hydroxyl groups of andrographolide located at C-3 and C-19 and its effect toward its biological activity. Modification by adding hydroxyl-benzaldehyde moiety to the hydroxyl groups could increase the activity of the compound as anti-HIV. Esterification at C-3 and C-19 could also enhance the activity of the compund as antitumor. The addition of aromatic esters both at C-3 and C-19 could lose the compound’s activity as antitumor. Modification of the hydroxyl groups of andrographolide located at C-3 and C-19 could be carried out by the mechanism of nucleophilic substitution reactions with the addition of catalysts and heating. Heating by using microwave irradiation method gives the highest synthesis yield.Keywords: Andrographolide, Andrographis paniculata, hydroxyl groups
Co-Authors Ade Zuhrotun Adira Rahmawaty Aeni, Wida Nur Alifia Syifa Pebriani Annisa Ayu Ningtyas Carolina Sitepu ARNANDA, QUINZHEILLA PUTRI ASRI SAVITRI Atusholihah, Annisa Auliya AS, Nisa Nurul Baihaqi, Achmad Al Batari A. Larasati Bawono, Lidya Cahyo Dede Jihan Oktaviani Dede Jihan Oktaviani Dhania Novitasari Diah Siti Fatimah DIAH SITI FATIMAH Eli Halimah, Eli Ella Fazila Elsa Noor Hapitria Ester Uli Elisabeth Simanjuntak Fadhilah, Ersa FAJRA DINDA CRENDHUTY Fatharan, Rahma Haniyyah FATIMAH, DIAH SITI Fauzia Rahma Cahyani Fauziyyah, Ganis Fitria Febrina Amelia Saputri Febrina Amelia Saputri, Febrina Amelia Filza Yulina Ade Ganendra Akbar Hadiyanto Gin Gin Ginanjar, Gin Gin Gofarana Wilar Gracia Anastasya Hanna Goeanawan HARTONO, ADI Holis Abdul Holik, Holis Abdul Hutabarat, Rismauli Ruth Natasari Ida Musfiroh -, Ida Musfiroh Isman, Hasna Siti Munifah Iyan Sopyan Jiranusornkul, Supat Jutti Levita Khairinisa, Miski Aghnia Maknun, Shofiyah Durin Maryam Hasymia Ishmatullah Mochamad Rizal Muchtaridi Muchtaridi Muhammad Afif Muhammad Ikhsan Muhammad Syahid Abdillah Mutakin Mutakin Nabila Alivia Yasmin NADIATUL KHAIRA. Y Nasrul Wathoni Nisa Safitri Norisca Aliza Putriana Nova Sylviana Nurdiani Adiningsih Nurdiani Adiningsih OKTAVIANI, DEDE JIHAN Prayoga, Randy Rassi Quinzheilla Putri Arnanda Quinzheilla Putri Arnanda RAMADHAN, SAQILA ALIFA Rania Talinta L Ray, Hamidie Ronald Daniel Rejeki, Purwo Sri Ridwan, Hanna Salwa Rina Wijayanti Rini Hendriani Ronny Lesmana Rusdin, Agus Sabila, Rusydina Salim, Prayoga Drajat Pangestu Salsabilla, Bunga Indra Saqila Alifa Ramadhan Saqila Alifa Ramadhan Shella - Widiyastuti Shella Widiyastuti Shella Widiyastuti Shinta Lestari SHINTA LESTARI Shinta Lestari, Shinta Silvia, Nurfianti Siska Sari Marvita Sitti Faza Karima Slamet Ibrahim - SOLEH SOLEH SOLEH Sri Adi Sumiwi Sri Indrayani Suhandi, Cecep Suhendi, Cece Susianti Susianti Trie Oktaviani Unang Supratman Vita Murniati Tarawan Widiyastuti, Shella Yasmiwar Susilawati Yogiyanto Yogiyanto Yuni Susanti Pratiwi