|Year : 2022 | Volume
| Issue : 77 | Page : 188-192
Anti-inflammatory, antioxidant, cytotoxic activities, and sesquiterpenoid contents of Paralemnalia thyrsoides
Aya Ali Alassass1, Marwa S Abubakr2, Walied M Alarif3, Seif-Eldin N Ayyad4, Abd-Elsalam E Mohammed2
1 Department of Pharmacognosy, Faculty of Pharmacy, Al Azhar University, Cairo; Department of Pharmacognosy, Faculty of Pharmacy, Horus University, Damietta, Egypt
2 Department of Pharmacognosy, Faculty of Pharmacy, Al Azhar University, Cairo, Egypt
3 Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz University, Jeddah, Saudi Arabia
4 Department of Chemistry, Faculty of Science, Damietta University, Damietta, Egypt
|Date of Submission||19-May-2021|
|Date of Decision||12-Nov-2021|
|Date of Acceptance||04-Jan-2022|
|Date of Web Publication||28-Mar-2022|
Walied M Alarif
Department of Marine Chemistry, Faculty of Marine Sciences, King Abdelaziz University, Jeddah 21589
Source of Support: None, Conflict of Interest: None
| Abstract|| |
Background and Objectives: Paralemnalia thyrsoides is an octocoral species of the family Nephtheidae. It has established as platform for the production of a varied array of sesquiterpenoids such as africanane, nardosinane, and neolemnane -type compounds. Antiviral and cytotoxic effects of sesquiterpenes from P. thyrsoides were reported. Materials and Methods: The animal sample of P. thyrsoides was repeatedly extracted with organic solvents. Then, the animal extract was fractionated and purified employing different planar chromatographic methods. The chemical structures of all isolated metabolites were identified by employing spectroscopic tools (ultraviolet [UV], IR, and nuclear magnetic resonance) along with MS. The anti-inflammatory activity (membrane stabilization%), and histamine release inhibitory effect, the antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, along with cytotoxic activity against four-cancer cells: hepatocellular carcinoma (Hep G-2), colon (HCT-116), prostate (PC-3), and breast (MCF-7) cancers were evaluated. Results: Three new sesquiterpenoids along with two known ones and a gorgostane steroid. The three new sesquiterpenoids were identified as eudesma-1, 2, 15-trihydroxy-3-en-7-one (1), eudesma-1, 2, 15-trihydroxy-5-ene (2), and nardosinanol J (3). Whereas the known compounds were identified as lemnolin A (4) and gorgostane (5). The in-vitro assays results revealed that the total organic extract showed anti-inflammatory activity (membrane stabilization %) with IC50 of 88.3 ± 1.2 compared to positive control (indomethacin with IC50 of 17.02 ± 1.2 μg/ml) and strong histamine release inhibitory effect with IC50 of 17.94 ± 1.08 compared to a positive control (diclofenac with IC50 of 17.94 ± 1.26 μg/ml). It also showed that the total organic extract has antioxidant activity using DPPH assay with an IC50 of 157.5 ± 4.24μg/ml. Moreover, the total organic extract has strong inhibitory activities against Hep G-2 with an IC50 of 12.1 ± 1.1 μg/ml, HCT-116 with an IC50 of 13.4 ± 1.8 μg/ml, PC-3 with an IC50 of 28.6 ± 2.7 μg/ml, and good inhibitory activity against MCF-7 with an IC50 of 49.0 ± 3.9 μg/ml. Conclusion: The observed bioactivity and the variety of carbon skeletons isolated warrants further work on the constituents of P. thyrsoides.
Keywords: Alcyonacea, anti-inflammatory, chromatography, spectroscopy, nephtheidae, norsesquiterenoids
|How to cite this article:|
Alassass AA, Abubakr MS, Alarif WM, Ayyad SEN, Mohammed AEE. Anti-inflammatory, antioxidant, cytotoxic activities, and sesquiterpenoid contents of Paralemnalia thyrsoides. Phcog Mag 2022;18:188-92
|How to cite this URL:|
Alassass AA, Abubakr MS, Alarif WM, Ayyad SEN, Mohammed AEE. Anti-inflammatory, antioxidant, cytotoxic activities, and sesquiterpenoid contents of Paralemnalia thyrsoides. Phcog Mag [serial online] 2022 [cited 2022 Sep 27];18:188-92. Available from: http://www.phcog.com/text.asp?2022/18/77/188/341060
- A Red Sea specimen of the soft coral Paralemnalia thyrsoides was chemically explored. After extraction, fractionation, and purification, five secondary metabolites were isolated. The compounds isolated include four sesquiterpenes and a common marine sterol. The anti-inflammatory, cytotoxicity, and antioxidant activity were evaluated.
Abbreviations used: COSY: Homonuclear Correlation Spectroscopy; DEPT: Distortionless enhancement by polarization transfer; HepG-2: Hepatocellular carcinoma; HMBC: Heteronuclear multiple-bond correlation spectroscopy; HSQC: Heteronuclear single-quantum correlation spectroscopy; HCT-1116: Human colon cancer cell line; IR: Infrared; MS: Mass spectroscopy; MCF-7: Breast cancer; NMR: Nuclear magnetic resonance; NOESY: Nuclear Overhauser effect spectroscopy; PC-3: Prostate adenocarcinoma; PTLC: Preparative thin layer chromatography; DPPH: 2,2-diphenyl-1-picrylhydrazyl; TLC: Thin Layer Chromatography; UV: Ultraviolet.
| Introduction|| |
Seventy years have passed since the first successful attempts to separate natural compounds from marine creatures, and since that time marine organisms have continued to provide us with diverse organic compounds that possess remarkable prospects on the medical and environmental levels., Soft corals (coelenterata, Octocorallia, and Alcyonacea) are fleshy benthic marine animals capable of producing secondary compounds that enable these animals to defend themselves against the high level of predation present in the marine environment.
Members of the genus Paralemnalia have established as platform for the production of a varied array of natural bioactive sesquiterpenoids such as africanane, nardosinane, neolemnane -type compounds,,,,,,,,,,,,,, in addition to norsesquiterpenoids of nardosinane-type skeleton.,,, Several reported bioassay results on the secondary natural compounds from the genus Paralemnalia had displayed diverse biological applications such as antiviral ,, and cytotoxic.,,,,,,,,,,,,, Our ongoing project focuses on the exploration of the secondary content of marine organisms from the Red Sea environment. In addition, the cytotoxic activity of the isolated compounds is assessed. In the current work, a specimen of the alcyonacean Paralemnalia thyrsoides was collected, extracted, and chromatographed for pure compounds. Eudesma-1, 2, 15-trihydroxy-3-en-7-one (1), eudesma-1, 2, 15-trihydroxy-5-ene, (2) and nardosinanol J (3) are three previously unreported sesquiterpenes, in addition to the known sesquiterpene lemnolin A (4) and the cyclopropane-containing steroid gorgostane (5) were isolated.
| Materials and Methods|| |
Nuclear magnetic resonance (NMR) analyses were conducted at Mansoura University (NMR Unit Center, Faculty of Science) using Bruker Avance III (400 Hz).
In June 2019, a specimen of P. thyrsoides was collected from the Red Sea (Jeddah, Saudi Arabia). A voucher specimen (PLT19-01) was deposited at the Marine biology department, Faculty of Marine Sciences, KAU.
Extraction and isolation
The freeze-dried P. thyrsoides (500 g) specimen was extracted with 2 × 3 L of CHCl3/MeOH (1:1, v/v; 3 times; 24 h/patch; rt). The extract was completely dried to provide 16.3 g of viscous oil. 9.0 g of the obtained oil was well mixed with silica gel and prepared for chromatographic fractionation (normal phase Si gel column). The column fractionation started with petroleum ether and the polarity was increased gradually by adding increased percentages of chloroform in pet. ether and the EtOAc in pet. ether. A total of 552 fractions (50 ml each) were obtained. Normal phase Si gel TLC and visualizing reagents (UV254 and p-anisaldehyde) aided the process of fractions categorization. Promising fractions were further purified using Si gel preparative thin-layer chromatography (PTLC). Fraction A eluted which had eluted with CHCl3: EtOAc (9: 1) was further purified on PTLC and pet. ether: EtOAc (9:1; greenish color with p-anisaldehyde reagent, Rf 0.25) to give compound 5. Fraction B which had eluted with CHCl3: EtOAc (7: 3) was further purified on PTLC and pet. ether: EtOAc (1:1; purple color with p-anisaldehyde reagent, Rf 0.44) to give compound 4. Fraction C which had eluted with CHCl3: EtOAc (1:1) was initially purified on Sephadex LH-20 column and methanol and finally on PTLC and pet. ether: EtOAc (6:4; blue color with p-anisaldehyde reagent, Rf 0.61) to give compound 3. Fraction D which had eluted with CHCl3: EtOAc (2:8) was initially purified on sephadex LH-20 column and methanol and finally on PTLC and CHCl3: MeOH (9.7:0.3; grey color with p-anisaldehyde reagent, Rf 0.41) to give compound 2. Fraction E which had eluted with CHCl3: EtOAc (1:98) was purified on sephadex LH-20 column and methanol and finally on PTLC and CH2Cl2: EtOAc (9.8:0.2; purple color with p-anisaldehyde reagent, Rf 0.40) to give compound 1.
Eudesma-1, 2, 15-trihydroxy-3-en-7-one (1)
Colorless oil, (0.9 mg, 0.00016%); IR ʋmax (film) cm−1: 3513, 3497, 2923, 2853, 1691, 1661, 1372, 1366; NMR data were recorded in CDCl3(1H, 400 MHz; 13C, 100 MHz): [Table 1]; HRESIMS (positive mode) m/z = 269.1746 [M + H]+ (Calculated m/z = 269.1753 for C15H25O4).
|Table 1: 1H and 13CNMR spectral data for compounds 1a, 2 and 3 (400 MHz)|
Click here to view
Eudesma-1, 2, 15-trihydroxy-5-en (2)
Colorless oil, (0.7 mg, 0.00014%); IR ʋmax (film) cm−1: 3482, 3385, 2920, 1664, 1374, 1367; NMR data were recorded in CDCl3(1H, 400 MHz; 13C, 100 MHz): [Table 1]; HRESIMS (positive mode) m/z = 255.1953 [M + H]+ (Calculated m/z = 255.1960 for C15H27O3).
Nardosinanol J (3)
Colorless oil, (0.8 mg, 0.00015%); IR ʋmax (film) cm−1: 2960, 2854, 1723, 1697, 1166, 1037; NMR data were recorded in CDCl3(1H, 400 MHz; 13C, 100 MHz): [Table 1]; HRESIMS (positive mode) m/z = 295.1537 [M + H]+ (Calculated m/z = 295.1545 for C16H23O5).
Calculation of the membrane stabilization (percentage inhibition of hemolysis) was calculated as described by Shinde et al.
Histamine release assay
The histamine release was estimated as shown by Venkata et al. 2012.
| Mammalian cell lines|| |
All employed cancer cells were obtained from VACSERA Tissue Culture Unit.
| Cell line propagation|| |
Cytotoxic assay experiment was conducted as demonstrated by Mosmann (1983).
| Antioxidant assay|| |
By using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assay the antioxidant activity of the extract was determined at Al- Azhar University (the Regional Center for Mycology and Biotechnology RCMB).
| 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity|| |
Antioxidant assay experiment was conducted according to Yen and Duh, 1994.
| Results and Discussion|| |
Compound 1 was isolated as oily material. The molecular formula C15H24O4 was indicated from HRESIMS, requiring four degrees of unsaturation.13C NMR spectrum displayed fifteen carbon atoms. The DEPT experiments aided the classification of carbons into 3 CH3, 3 CH2, 6 CH, and 3 nonprotonated carbons. The IR spectrum displayed absorption bands at 3513, 3497 (OH function), 2923, 2853 (CH stretching), 1691 (carbonyl function), 1661 (carbon-carbon double bond), and 1372 and 1366 (gem-dimethyl) cm−1. 1H, 13C NMR, and HSQC spectral data clarified the existence of two secondary methyls resonating at δH/δC 1.03/18.8 and 0.71/14.4 ppm, one tertiary methyl signal at δC 19.6, a carbinol function (a primary alcohol) at δH/δC 4.11 and 3.30/61.9, two oxygenated methine groups at 4.02/73.7 and 4.15/69.5, a trisubstituted carbon-carbon double bond 5.70/111.3 and 156.7, along with carbonyl function at 211.7 ppm.
The presence of several methyl groups included in the fifteen-carbon atom skeleton suggested that compound 1 belongs to the sesquiterpenes. Moreover, compound 1 is entirely a bicyclic sesquiterpene owing to the presence of a carbonyl function, a carbon-carbon double bond in a four- unsaturation sites skeleton. The presence of eudesmane-type sesquiterpene has proved after examining the methylation pattern in 1H, 13C NMR, DEPT, and HSQC spectra which showed a gem-dimethyl, a tertiary methyl, and the methyl group equivalent (i.e., the carbinol function). Though compound 1 has eudesmane-sesquiterpene carbon skeleton, which is decorated with alkyl substitution at positions 4, 7, and 10 however, the locations of three hydroxyls, a carbonyl, and a carbon-carbon double bond are still not accounted. The presence of an unsubstituted isopropyl function and a tertiary methyl (angular methyl) emphasized the presence of hydroxylation at Me-15 [Figure 1]. 1H-1H COSY spectrum established the presence of two methyl sequences, in addition to two isolated methylenes and the angular methyl. The first sequence started with the proton signal that appeared at δH 5.7 (H-3) which is correlated δH 4.15 (H-2), the latter proton is correlated with that resonating at chemical shift 4.02 (H-1). The second sequence started with the signal due to the CH proton resonating at 1.42 which is correlated with the CH2 signals that appeared at 1.66 and 1.53 (H-6), the latter proton signals are correlated with the CH proton at 2.04 (H-7). The later proton signal is correlated with H-11 resonating at δH 2.31, which in turn is correlated with two methyl-proton signals resonating at 1.03 and 0.71 ppm [Figure 2]. The previous extensive investigation of the COSY spectrum along with the detected heteronuclear multiple-bond correlation spectroscopy (HMBC) correlations between the angular methyl proton signals appeared at δH 0.91 with the CH2 carbon signal at δC 36.4 (C-1), the CH carbon signal at δC 36.3 (C-6), and the signal at 73.7, and the correlation observed between H-7 and the carbonyl at δC 211.7 (C-8) and C-6 confirmed the location of the carbonyl group at C-8, the hydroxyl functions at C-1, C-2 and C-15 and the carbon-carbon double bond at C-3-C-4 [Figure 2]. Hence, compound 1 can be identified as eudesma-1, 2,15-trihydroxy-3-en-8-one [Figure 1].
|Figure 2: Selected H-H COSY and heteronuclear multiple-bond correlation spectroscopy correlation of the compounds 1–3|
Click here to view
Compound 2 was isolated as colorless oily substance. The molecular formula was calculated as C15H26O3, determined by HRESIMS, requiring four degrees of unsaturation. 13C NMR spectrum displayed fifteen carbon atoms those were classified by DEPT procedures into three CH3, four CH2, six CH, and two non-protonated carbons. The IR spectrum displayed absorption bands at 3482, 3385 (OH function), 2920, 2816 (CH stretching), 1664 (carbon-carbon double bond), and 1374 and 1367 (gem-dimethyl) cm−1. 1H, 13C NMR, and HSQC spectral data clarified the existence of two secondary methyls that appeared at δH/δC 0.89/22.8 and at 0.86/22.7 ppm, one tertiary methyl signal at 0.90/21.8, a carbinol function (a primary alcohol) at 4.32 and 4.20/62.8, two oxygenated methine groups at 3.50/71.8 and 3.40/68.9, and a trisubstituted carbon-carbon double bond at 5.40/114.1 and 121.0 ppm. The presence of several methyl groups included in the fifteen-carbon atom skeleton suggested that compound 2 belongs to the sesquiterpenes. Moreover, compound 2 is entirely a bicyclic sesquiterpene owing to the presence of a carbon-carbon double bond in a three-unsaturation sites structure. The presence of eudesmane-type sesquiterpene has proved after examining the methylation pattern in 1H, 13C NMR, DEPT and HSQC spectra which showed a gem-dimethyl, a tertiary methyl, and the methyl group equivalent (i.e., the carbinol function). Though compound 2 has eudesmane-sesquiterpene carbon skeleton, which is decorated with alkyl substitution at positions 4, 7, and 10 however, the locations of three hydroxyls, and a carbon-carbon double bond are still not accounted. A similar treatment to the 2D NMR spectral data (1H-1H COSY and HMBC) revealed a similar compound to that of [Figure 2]. Two differences have been observed, for compound 2, no carbonyl function and the location of the double bond is in position 5. Therefore, compound 2 can be identified as eudesma-1, 2, 15-trihydroxy-5-en [Figure 1].
Compound 3 was isolated as colorless oily substance. The molecular formula was calculated as C16H22O5, determined by HRESIMS, requiring six unsaturation. The IR spectrum revealed bands at 1733 (carbonyl ester), 1697 (carbonyl), 2960, 2854 (CH stretching), and 1166 and 1037 (epoxy) cm−1. 13C NMR spectrum displayed sixteen carbon atoms those were classified with the aid of DEPT procedures into four CH3, three CH2, four CH, and five nonprotonated carbons. 1H, 13C and HSQC NMR displayed signals due to two carbonyl functions resonating at δC206.8 and 202.3, an ester function at δH/δC 2.22/21.2 and 174.0 ppm, two quaternary methyls δH/δC 2.29/31.4, and 1.04/18.2, a secondary methyl at 0.87/16.2, and resonances due to oxirane ring δH/δC 3.20/62.1 and 63.3 ppm. Taking into consideration six degrees of unsaturation, three carbonyl functions, together with the absence of any absorption due to carbon-carbon unsaturation, compound 3 is a fourteen-carbon atoms tricyclic-sesquiterpenoid. The nature of the sesquiterpenoids has been assigned as a nornardosinane- type, based on the methylation pattern and comparison with similar published compounds. 1H-1H COSY spectrum exhibited two proton sequences, the first started with the oxirane proton resonating at 3.20 (H-1) and ended by the methyl protons resonating at 0.87 (H-14) [Figure 2] and [Table 2], the second sequence started with the CH proton appeared at 5.37 (H-7) and ended by the CH2 protons resonating at 2.28 and 2.12 (H-9). Investigation of the HMBC spectrum established the location of oxirane ring through the correlations of H-1 with C-2, C-5, and C-9, the esterification position through the correlation of H-8 with C-6, C-7, and C-10, and the location of the acetyl group through the correlation between H-12 with C-5 and C-6. Compound 3 was identified as nardosinanol J [Figure 1].
In addition to the three new compound, two known compounds were isolated and identified as lemnolin A (4) and gorgosterol (5).
The in vitro assays results revealed that the total organic extract of P. thyrsoides showed anti-inflammatory activity (membrane stabilization%) with IC50 of 88.3 ± 1.2 compared to positive control (indomethacin with IC50 of 17.02 ± 1.2 μg/ml) and strong histamine release inhibitory effect with IC50 of 17.94 ± 1.08 compared to a positive control (diclofenac with IC50 of 17.94 ± 1.26 μg/ml).
It also showed that the total organic extract of P. thyrsoides has antioxidant activity using DPPH assay with IC50 of 157.5 ± 4.24μg/ml compared to a positive control (ascorbic acid with IC50 of 14.2 ± 0.24μg/ml). Results also showed that the total organic extract has strong inhibitory activities against HepG-2 with an IC50 of 12.1 ± 1.1 μg/ml, colon cancer IC50 of 13.4 ± 1.8 μg/ml, PC-3 with an IC50 of 28.6 ± 2.7 μg/ml, and good inhibitory activity against MCF-7 with IC50 of 49.0 ± 3.9 μg/ml. Vinblastine sulfate was employed as a positive control with IC50 values of 2.93 ± 1.05, 3.5 ± 6.36, 42.2 ± 1.10, and 5.9 ± 0.9 for HepG-2, HCT-116, PC-3, and MCF-7, respectively.
| Conclusion|| |
The Red Sea soft coral P. thyrsoides, was found to be a source of different sesquiterpenoids and norsesquiterpenoid carbon skeletons. The obtained in vitro assays results clarified that the total organic extract of P. thyrsoides showed strong anti-inflammatory activity (membrane stabilization %) and strong histamine release inhibitory effect. Furthermore, it exhibited antioxidant activity and significant cytotoxic effects against HepG-2 and colon cancer cell lines.
The authors would like to thank the marine biologist Mr. Kamal Al-dahoody, faculty of Maritime studies, KAU, for sample collection and identification.
Financial support and sponsorship
Conflicts of interest
There are no conflicts of interest.
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[Figure 1], [Figure 2]