Isolation of 2,4-Di-tert-butylphenol and Butyrospermol 3-?-O-palmitate from Syzygium aqueum stem bark

Kristanti, Alfinda Novi; Aung, Ei Ei; Aminah, Nanik Siti; Takaya, Yoshiaki; Ramadhan, Rico

doi:10.15406/mojes.2020.05.00193

Cited by 4 publications

(1 citation statement)

References 16 publications

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“…The structure characterisation of these compounds was carried out through spectral analysis. The compounds were characterized as botryosphaeridione (1) [26] and 3-(3,5-di-tert-butyl-4-hydroxy) phenylpropionic acid (2), [27] variabilone (3), [28] 2,4-ditert-butylphenol (4), [29] indole-3-carboxylic acid (5), [30] tyrosol ( 6), [31,32] ethyl ferulate (7) and a new lignan (8). The structures of these compounds were determined by comparison of the 1 H and 13 C-NMR data with reported values.…”

Section: Chemical Constituents Of Eeppmentioning

confidence: 99%

A New Lignan (Polonilignan) and Inhibitors of Nitric Oxide Production from Penicillium polonicum, an Endophytic Fungi of Piper nigrum

Pal

Begum

et al. 2023

Chemistry & Biodiversity

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Inhibiting nitric oxide (NO) or its production is found to be of therapeutic benefit. To discover natural small molecule inhibitors of NO production, a bioassay-and LC/MS-guided chemical investigation was done on the metabolites of endophytic fungus isolated from fresh Piper nigrum fruits. The isolated pure strain was identified as Penicillium polonicum by 16S rDNA sequence comparison. The culture broth extract of P. polonicum (EEPP) exhibited a significant reduction of NO production (Griess method) in LPS-stimulated RAW 264.7 cells (P < 0.0001). To understand the chemical constituents of bioactive EEPP, column chromatography and p-TLC studies were carried out, which yielded eight pure compounds. They were characterised as botryosphaeridione (1), 3-(3,5-di-tert-butyl-4-hydroxy)phenylpropionic acid (2), variabilone (3), 2,4-di-tert-butylphenol (4), indole-3-carboxylic acid (5), tyrosol (6), ethyl ferulate (7) and a new lignan (8) based on the spectral analysis. The structure elucidation of the new lignan, named polonilignan (8), was based on HR-MS, 1 H-& 13 C-NMR, HÀ H COSY, HSQC and HMBC spectra. Compounds 2, 4, 5 and 6 showed a significant decrease (P < 0.0001) in the production of NO in LPS-induced RAW 264.7 cells. Tyrosol (6) and indole-3-carboxylic acid (5) controlled nitrite release with IC 50 values of 22.84 and 55.01 μM, respectively. This is the first report of (i) P. polonicum as an endophytic fungus of pepper fruits, (ii) isolation of compounds 1 -8 except 6 from P. polonicum culture broth extract and (iii) NO inhibition effect of 2, 4, 5 and 6.

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Section: Chemical Constituents Of Eeppmentioning

confidence: 99%

A New Lignan (Polonilignan) and Inhibitors of Nitric Oxide Production from Penicillium polonicum, an Endophytic Fungi of Piper nigrum

Pal

Begum

et al. 2023

Chemistry & Biodiversity

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Characterization, Pharmacology and In-silico study of 2,4 Ditertiary Butylphenol Isolated from the leaves of Ficus auriculata Lour.

Russell.S

Kumari.J

2023

Orient. J. Chem

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Ficus auriculata belongs to the family of dicotyledonous plant. The general phytochemical screening for Ethanol, Hexane, Chloroform and Water extracts are done. Since ethanol shows the presence of maximum compounds, it is subjected to the isolation of phenolic compounds by TLC and Column Chromatography. On repeating this process, a white crystalline solid results, which on the basis of UV-Vis, FT-IR, GC-MS, 1H NMR, confirms that the isolated compound is 2,4 Ditertiary Butyl Phenol (2,4 DTBP). The isolated compound is further studied for its solvent effect and subjected to anti-microbial and Cytotoxicity studies with AGS cancer cell line and HIEC-6 (Human Normal Intestinal Epithelial cell line). Docking studies is carried out using Patch Dock server, with 2,4DTBP as guest and Occluding, which is a Tight Junction Protein (TJP) as host. The resulted structure is further subjected to Lipinski Rule of five. The present study concludes that 2,4 DTBP shows intermediate resistance against gram positive and gram negative bacteria like S. aureus, E. coli, Klebsiela pneumonia, strongly resistant to fungi Candida sps. According to cytotoxic and in silico studies, the isolated compound has excellent anticancer properties and is thus used in the treatment of gastric cancer. From the Lipinski rule, it is confirmed that the drug can be administered orally.

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Bioactive triterpenoids from Indonesian medicinal plant Syzygium aqueum

et al. 2022

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A large common species, Syzygium aqueum, belonging to the genus Syzygium possesses numerous bioactive phytochemical constituents. Moreover, the different parts of this species have been used as folk medicine since centuries ago. In this study, a phytochemical exploration was carried out on the plant’s stem bark. Isolation of the compounds was carried out through the extraction step with some organic solvents, followed by separation and purification using chromatography techniques until the two triterpenoids were isolated from nonpolar and semipolar extracts. Structure elucidation was done using spectroscopic methods. These compounds were identified as alphitolic acid and arjunolic acid. Subsequently, these two compounds were used in anticancer tests against human cancer cells HeLa, T47D, and A549 using colorimetric assay. The result showed that both compounds showed more inhibition of the growth of HeLa and T47D than A549 cancer cells, with the highest activity shown by arjunolic acid against HeLa cell lines.

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Isolation of 2,4-Di-tert-butylphenol and Butyrospermol 3-?-O-palmitate from Syzygium aqueum stem bark

Cited by 4 publications

References 16 publications

A New Lignan (Polonilignan) and Inhibitors of Nitric Oxide Production from Penicillium polonicum, an Endophytic Fungi of Piper nigrum

A New Lignan (Polonilignan) and Inhibitors of Nitric Oxide Production from Penicillium polonicum, an Endophytic Fungi of Piper nigrum

Characterization, Pharmacology and In-silico study of 2,4 Ditertiary Butylphenol Isolated from the leaves of Ficus auriculata Lour.

Bioactive triterpenoids from Indonesian medicinal plant Syzygium aqueum

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