Antimicrobial efficacy, antioxidant profile and nine alternative active constituents from petroleum ether and ethyl acetate extract of Entada spiralis

• Main Authors: Harun, Aiza, Abdul Aziz, Noorshilawati, Mohd Azenan, Nor Shazleen, Muhammad Kamarazzaman, NurFarah Farini, Mat So'ad, Siti Zaiton
• Format: Article
• Language: English; English
• Published: Malaysian Analytical Sciences Society 2020
• Subjects: QD Chemistry
• Online Access: http://irep.iium.edu.my/83656/1/Aiza_24_5_8forIREPIIUM.pdf; http://irep.iium.edu.my/83656/7/83656_Antimicrobial%20efficacy%2C%20antioxidant%20profile_scopus.pdf; http://irep.iium.edu.my/83656/; https://mjas.analis.com.my/mjas/v24_n5/pdf/Aiza_24_5_8.pdf

This study aimed to investigate the antimicrobial activity of petroleum ether extracts and the identification of alternative antimicrobial and antioxidative constituents from petroleum ether extract and ethyl acetate extract of Entada spiralis stem. Antimicrobial activity was evaluated through disc diffusion method on five human superficial skin disease-caused microbes such as Staphylococcus aureus, Staphylococcus epidermidis, Microsporum gypseum, Trichophyton mentagrophytes, Trychophyton tonsurans and one plant pathogen namely Erwinia chrysanthemi. The presence of antioxidants was determined from thin layer chromatography (TLC) sprayed with 2,2-diphenyl-1 picrylhydrazyl. The isolation of antioxidant and antimicrobial compounds was performed through preparative TLC. The structure of isolated compounds was determined from gas chromatography mass spectrometry (GCMS) and liquid chromatography mass spectrometry (LCMS) equipped with Wiley Library matching individually. The petroleum ether extract successfully inhibited the growth of all bacteria and dermatophytes in a concentration dependent manner whereby S. epidermis was highly susceptible towards the extract with inhibition zone of 16.0 mm at concentration of 400mg/mL as well as M. gypseum. Most of the components from petroleum ether extract and ethyl acetate extract developed on TLC were antioxidative which was seen as yellow spots against purple background after spraying with DPPH reagent. Four antioxidative constituents were successfully isolated and tentatively identified as 18,19-Secoyohimban-19-oic acid,16,17,20,21-tetradehydro16-(hydroxymethyl)-methylester (1), Oxiraneoctanoic acid (2), 9,12-Octadecadienoic acid (3), and 11-O-p- Coumarylnepeticin(4). Five antimicrobial constituents were successfully isolated and tentatively identified as 4-benzyloxy-4-[2,2,-dimethyl-4- dioxolanyl]Butylaldehyde, (5), Isobutyl octadecyl benzoate ester (6), 3',8,8'-Trimethoxy-3-piperidyl-2,2'-binaphthalene-1,1',4,4'-tetrone (7), 1,2,4,5-tetramethylbenzene (8) and Hordatine B (9). Thus, E. spiralis is seen to be a promising source of bioactive ingredients which is very important as the basis of scientific information for the development of natural antimicrobial and antioxidant agents. ********************************************************************** Kajian ini memfokuskan kepada kajian sifat antimikrob ekstrak petroleum eter dan pencarian komponen aktif antimikrob dan antioksida dari ekstrak petroleum eter dan etil asetat dari batang pokok Entada spiralis. Aktiviti antimikrob dinilai menggunakan kaedah penyerakan cakera terhadap lima jenis mikrob penyakit kulit iaitu Staphylococcus aureus, Staphylococcus epidermis, Microsporum gypseum, Trichophyton mentagrophytes, Trychophyton tonsurans dan satu jenis mikrob tumbuhan iaitu Erwinia chrysanthemi. Ciri antioksidan ekstrak komponen yang telah dipisahkan di atas kromatografi lapisan nipis (KLN) telah dianalisa menggunakan kaedah penyemburan dengan bahan 2,2-difenil-1-pikrilhidrazil (DPPH) di atas KLN. Pemisahan komponen aktif antioksida dan antimikrob telah dijalankan dengan menggunakan KLN. Spektrometer jisim kromatografi gas dan spektrometer jisim kromatografi cecair dengan data Wiley telah digunakan untuk menganalisa dan mengenalpasti struktur bahan aktif. Ekstrak petroleum eter berkesan dalam menyekat pertumbuhan bakteria dan kulat di mana bakteria S. epidermis dan kulat M. gypseum paling kuat disekat pertumbuhannya oleh ekstrak dengan zon perencatan 16.0 mm pada kepekatan 400 mg/mL. Kebanyakan komponen dalam ekstrak petroleum eter dan etil asetat yg telah dipisahkan di atas KLN bersifat antioksida dengan memberikan kesan tompokan kuning setelah disembur dengan larutan DPPH. Sebanyak empat komponen antioksida berjaya dipisahkan dan dikenalpasti sebagai Asid 18,19-Sekoyohimban-19,16,17,20,21-tetradihidro-16-(hidroksimetil)-metilester (1), Asid okzairanoktanoik (2), Asid 9,12-Oktadekadienoik (3), dan 11-O-p- Koumarilnepetisin (4). Sebanyak lima jenis komponen antimikrob berjaya dipisahkan dan dikenali sebagai, 4-benziloksi-4-[2,2,-dimetil-4-dioksolanil]Butilaldehid(5), Isobutil oktadesil benzoat ester(6), 3',8,8'-Trimetoksi-3-piperidil-2,2'-binaftalin-1,1',4,4'-tetron (7), 1,2,4,5-tetramethylbenzene (8) dan Hordatin B (9). Maka, E. spiralis dilihat sebagai pokok yang berpotensi untuk mendapatkan bahan bioaktif semulajadi di mana bahan ini penting sebagai maklumat asas bagi kajian penghasilan bahan antioksida dan antimikrob semulajadi.