Antibacterial and cytotoxic properties of isoprenoids from the red sea soft coral, &lt;i&gt;Lobophytum&lt;/i&gt; sp

Al-Footy, Khalid O.; Alarif, Walied M.; Zubair, Muhammad Sulaiman; Ghandourah, Mohamed A.; Aly, Magda M.

doi:10.4314/tjpr.v15i7.11

Cited by 15 publications

(15 citation statements)

References 30 publications

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“…The NMR data for compound 9 are presented in this paper. The other known compounds, which are piperine ( 10 ) [22], methyl piperate ( 11 ) [23], piperanine ( 12 ) [24], pipernonaline ( 13 ) [25], piperchabamide B ( 14 ) [9], piperolein-B ( 15 ) [22], 3-phenyl-1-(piperidin-1-yl)propan-1-one ( 16 ) [17] ( E )-3-phenyl-1-(piperidin-1-yl)prop-2-en-1-one ( 17 ) [17], trans -fagaramide ( 18 ) [26], pipercide ( 19 ) [27], guineensine ( 20 ) [27], dihydropiperlonguminine ( 21 ) [25], 5,6-dihydro-1 H -pyridin-2-one ( 22 ) [28], 3-chloro-4-hydroxy-2-piperidone ( 23 ) [29], octahydro-4-hydroxy-3 α -methyl-7-methylene- α -(1-methylethyl)-1 H -indene-1-methanol ( 24 ) [30], alismoxide ( 25 ) [31] (4 S, 4a S, 6 S, 8a S )-octahydro-4-hydroxy-4,8a-dimethyl-6-(1-methylethenyl)naphthalen-1( 2H )-one ( 26 ) [16], ent -4(15)-eudesmene-1 β ,6 α -diol ( 27 ) [32], methylsalicylate-2- O - β - d -glucopyranoside ( 28 ) [33], rozin ( 29 ) [19], piperchabaoside A ( 30 ) [20] (6 S ,9 R )-roseoside ( 31 ) [34], and 2′- O -methyluridine ( 32 ) [35], were identified by comparing their spectroscopic data with those in the literature.…”

Section: Resultsmentioning

confidence: 99%

New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum

Tang

Zhang

et al. 2019

Nat. Prod. Bioprospect.

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Two new amides ( E )- N -cinnamoyl-2-methoxypiperidine ( 1 ) and ( R )-1-(2-oxopyrrolidin-3-yl)-5,6-dihydropyridin-2(1 H )-one ( 2 ), four new amide glucosides, retrofractosides A–D ( 3 – 6 ), and two new phenylpropanoid glucosides, retrofractosides E ( 7 ) and F ( 8 ), together with 24 known compounds ( 9 – 32 ) were isolated from the fruits of Piper retrofractum . The chemical structures of these new compounds were elucidated based on extensive spectroscopic analysis. All of these isolates ( 1 – 32 ) were evaluated for inhibitory activity against mouse platelet aggregation induced by the peptide AYPGKF-NH 2 . ( E )- N -(Tetrahydro-2 H -pyran-2-yl)cinnamamide ( 9 ) showed a weak inhibitory effect, with an inhibition ratio of 52.0% at a concentration of 150 μM. Graphical Abstract Electronic supplementary material The online version of this article (10.1007/s13659-019-0208-z) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum

Tang

Zhang

et al. 2019

Nat. Prod. Bioprospect.

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“…Concerning the main constituents of the EO from the leaves of C. matourensis, some of them, e.g., β-caryophyllene, cembrene, p -cymene, and β-elemene, have been reported as cytotoxic agents [ 22 , 25 , 26 , 27 , 28 ], indicating that the mixture of them are associated with the cytotoxic and antitumor properties of this EO.…”

Section: Discussionmentioning

confidence: 99%

Antitumor Effect of the Essential Oil from the Leaves of Croton matourensis Aubl. (Euphorbiaceae)

et al. 2018

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Croton matourensis Aubl. (synonym Croton lanjouwensis Jabl.), popularly known as “orelha de burro”, “maravuvuia”, and/or “sangrad’água”, is a medicinal plant used in Brazilian folk medicine as a depurative and in the treatment of infections, fractures, and colds. In this work, we investigated the chemical composition and in vitro cytotoxic and in vivo antitumor effects of the essential oil (EO) from the leaves of C. matourensis collected from the Amazon rainforest. The EO was obtained by hydrodistillation using a Clevenger-type apparatus and characterized qualitatively and quantitatively by gas chromatography coupled to mass spectrometry (GC–MS) and gas chromatography with flame ionization detection (GC–FID), respectively. In vitro cytotoxicity of the EO was assessed in cancer cell lines (MCF-7, HCT116, HepG2, and HL-60) and the non-cancer cell line (MRC-5) using the Alamar blue assay. Furthermore, annexin V-FITC/PI staining and the cell cycle distribution were evaluated with EO-treated HepG2 cells by flow cytometry. In vivo efficacy of the EO (40 and 80 mg/kg/day) was demonstrated in C.B-17 severe combined immunodeficient (SCID) mice with HepG2 cell xenografts. The EO included β-caryophyllene, thunbergol, cembrene, p-cymene, and β-elemene as major constituents. The EO exhibited promising cytotoxicity and was able to cause phosphatidylserine externalization and DNA fragmentation without loss of the cell membrane integrity in HepG2 cells. In vivo tumor mass inhibition rates of the EO were 34.6% to 55.9%. Altogether, these data indicate the anticancer potential effect of C. matourensis.

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“…These bioactive compounds showed various pharmacological activities such as antimicrobial, anti-inflammatory and cytotoxic (Putra et al, 2016). Previously, our study on soft corals of Sarcophyton trocheliphorum and lobophytum sp have found numerous secondary metabolites possessing antibacterial and antitumor activities Al Footy et al, 2016). In continuing our focus research on marine organism, particularly from Indonesian marine, our study now starting on soft corals collected off Togean Islands, located in Tojo Una-una, Central Sulawesi.…”

Section: Introductionmentioning

confidence: 92%

Screening of Antibacterial and Anticancer Activity of Soft Corals from Togean Islands, Indonesia

Zubair

Lallo

Rusmiyanti

et al. 2018

Indonesian J. Pharm.

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Soft corals (Octocorallia, Alcyonaceae) have been reported to possess diverse biological activities and unique structural chemistry. This study aims to screen the potential antibacterial and anticancer activity of some soft corals collected from Togean Islands, Central Sulawesi, Indonesia. They were Lobophytum sp, Sarcophyton sp, Sinularia sp 1, and Sinularia sp 2. All dried coral materials were extracted for 3 x 24 h by maceration method using methanol and then evaporated by rotary evaporator to obtain viscous extracts. The determination of antibacterial activity had been performed by well agar diffusion method against Staphylococcus aureus and Escherichia coli. Meanwhile, the cytotoxic activity was performed by MTT method, followed by apoptosis annexin V-FTIC assay. Identification for the presence of terpenoids was performed by p-anisaldehyde-sulphuric acid spraying reagent on thin layer chromatography (TLC). Sinularia sp 2 extract have strongly inhibited S. aureus and E.coli with the diameter of inhibition of 15.80 mm and 15.73 mm, respectively. Moreover, Sinularia sp 2 extract possessed also cytotoxic activity against human breast adenocarcinoma (MCF-7) and colorectal carcinoma (HCT-116) with the IC50 of 46.807 and 47.186 μg/mL, respectively. Extract Sinularia sp 1 was found to have strongest cytotoxicity on human colon colorectal carcinoma (HCT-116) with the IC50 of < 1.505 μg/mL. Annexin V-FTIC assay clearly exhibited that the apoptosis mechanism is proposed by the extracts of Sinularia sp 1 and Sinularia sp 2. Terpenoids were identified on both extracts suggesting for further purification and isolation for the bioactive terpenoid compounds.

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Antibacterial and cytotoxic properties of isoprenoids from the red sea soft coral, <i>Lobophytum</i> sp

Abstract: (IZD,(7)(8)(9)(10)(11) MIC ≥ 30 μg/mL). In addition, only diterpene compound (4)

Cited by 15 publications

References 30 publications

New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum

New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum

Antitumor Effect of the Essential Oil from the Leaves of Croton matourensis Aubl. (Euphorbiaceae)

Screening of Antibacterial and Anticancer Activity of Soft Corals from Togean Islands, Indonesia

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