REVIEW: SINTESIS TURUNAN ANDROGRAFOLID PADA GUGUS HIDROKSIL C-3 DAN C-19

Sri Indrayani, Sandra Megantara, Febrina Amelia Saputri

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


Keywords


Andrografolid; Andrographis paniculata; gugus hidroksil

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References


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DOI: http://dx.doi.org/10.20527/jps.v7i2.8495

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