Antimicrobial properties and metabolite profiling of the ethyl acetate fractions of Sinularia polydactyla and Cespitularia simplex surrounding Mauritius Island

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DEEYA JAHAJEEAH
VISHWAKALYAN BHOYROO
MALA RANGHOO-SANMUKHIYA

Abstract

Abstract. Jahajeeah D, Bhoyroo V, Ranghoo-Sanmukhiya M. 2023. Antimicrobial properties and metabolite profiling of the ethyl acetate fractions of Sinularia polydactyla and Cespitularia simplex surrounding Mauritius Island. Indo Pac J Ocean Life 7: 133-142. Soft corals form an integral part of the reef ecosystem. This study assessed the antibacterial activities of Mauritius Island's soft corals and their different natural compounds having important biological properties. Antimicrobial assays and GCMS-MS analysis were performed using ethyl acetate extracts of Sinularia polydactyla and Cespitularia simplex. The results for both species indicated significant activity against most clinically pathogenic bacterial strains tested. In addition, S. polydactyla and C. simplex extracts gave the most potent action spectra yielding the largest inhibition zone diameter, especially against the Gram-positive Staphylococcus aureus (8.73 ± 2.87 and 6.00 ± 1.20 mm), respectively. The MIC also confirmed that the Gram-positive Bacillus subtilis and S. aureus strains were the most susceptible bacteria when exposed to the soft coral extracts, while Pseudomonas aeruginosa and Escherichia coli were the most resistant Gram-negative strains. The biochemical profile of the extracts showed the presence of terpenoids, steroids, flavonoids, coumarins, and quinones. GCMS-MS analysis also identified 151 compounds in S. polydactyla and 91 compounds in C. simplex. Several previously published studies have shown the biological activities of different species of Cespitularia; however, this is the first study to demonstrate the antibacterial activity and compound profiling of C. simplex. Although studies have been carried out on S. polydactyla extracts, compounds such as 25-Hydroxycholesterol and spathulenol have not yet been reported. The results from the study suggest that both S. polydactyla and C. simplex are potential sources of novel antibiotics and possess a myriad of chemical compounds which may lend themselves to bioprospecting.

2017-01-01

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References
Abdelkarem FM, Desoky EK, Nafady AM, Allam AE, Mahdy A, Ashour A, Mohamed GA, Miyamoto T, Shimizu K. 2021. Two new polyhydroxylated steroids from Egyptian soft coral Heteroxenia fuscescens (Fam.; Xeniidae). J Nat Prod 35 (2): 236-243. DOI: 10.1080/14786419.2019.1624958.
Abubakar M, Majinda R. 2016. GC-MS Analysis and preliminary antimicrobial activity of Albizia adianthifolia (Schumach) and Pterocarpus angolensis (DC). Medicines 3 (1): 3. DOI: 10.3390/medicines3010003.
Afifi R, Abdel-Nabi IM, El-Shaikh K. 2016. Antibacterial activity from soft corals of the Red Sea, Saudi Arabia. J Taibah Univ Sci 10 (6): 887-895. DOI: 10.1016/j.jtusci.2016.03.006.
Aggarwal BB, Yuan W, Li S, Gupta SC. 2013. Curcumin-free turmeric exhibits anti-inflammatory and anticancer activities: Identification of novel components of turmeric. Mol Nutr Food Res 57 (9): 1529-42. DOI: 10.1002/mnfr.201200838.
Ahmed AF, Su JH, Shiue RT, Pan XJ, Dai CF, Kuo YH, Sheu JH. 2004. New beta-caryophyllene-derived terpenoids from the soft coral Sinularia nanolobata. J Nat Prod 67 (4): 592-597. DOI: 10.1021/np030286w.
Alotaibi AA, Bepari A, Bassiri RA. 2021. Saussurea Lappa exhibits anti-oncogenic effect in Hepatocellular Carcinoma, HepG2 Cancer Cell Line by Bcl-2 mediated apoptotic pathway and mitochondrial cytochrome C release. Curr Issues Mol Biol 43 (2): 1114-1132. DOI: 10.3390/cimb43020079.
Altameme H, Hameed I, Idan S. 2016. Artemisia annua: Biochemical products analysis of methanolic aerial parts extract and antimicrobial capacity. RJPBCS 7 (2): 1843-1868.
Aparna V, Dileep KV, Mandal PK, Karthe P, Sadasivan C, Haridas M. 2012. Anti-inflammatory property of n-hexadecanoic acid: structural evidence and kinetic assessment. Chem Biol Drug Des 80 (3): 434-439. DOI: 10.1111/j.1747-0285.2012.01418.x.
Arancibia LA, Naspi CV, Pucci GN, Arce ME, Colloca CB. 2016. Biological activity of 1-heneicosanol isolated from Senecio coluhuapiensis, an endemic species from Patagonia, Argentina. The Pharm Chem J 3 (4): 73-77.
Aratake S. Tomura T. Saitoh S. 2012. Soft coral Sarcophyton (Cnidaria: Anthozoa: Octocorallia) species diversity and chemotypes. PloS One 7 (1): e30410. DOI: 10.1371/journal.pone.0030410.
Beechan CM, Djerassi C, Eggert H. 1978. Terpenoids-LXXIV: The sesquiterpenoids from the soft coral Sinularia mayi. Tetrahedron Lett 34 (16): 2503-2508. DOI: 10.1016/0040-4020(78)88378-1.
Bernardini G, Minetti M, Polizzotto G, Biazzo M, Santucci A. 2018. Pro-apoptotic activity of french polynesian Padina pavonica extract on human osteosarcoma cells. Mar Drug 16 (12): 504. DOI: 10.3390/md16120504.
Blunt J, Copp B, Keyzers R, Munro M, Prinsep M. 2017. Marine natural products. Nat Prod Rep 34: 235-294. DOI: 10.1039/C6NP00124F.
Brahmachari G. 2017. Andrographolide: A molecule of antidiabetic promise. In: Brahmachari G (eds). Discovery and Development of Antidiabetic Agents from Natural Products. Elsevier. Amsterdam, Netherlands. DOI: 10.1016/B978-0-12-809450-1.00001-6.
Breijyeh Z, Jubeh B, Karaman R. 2020. Resistance of Gram-negative bacteria to current antibacterial agents and approaches to resolve it. Molecules 25 (6): 1340. DOI: 10.3390/molecules25061340.
Burgos RA, Alarcón P, Quiroga J, Manosalva C, Hancke J. 2020. Andrographolide, an anti-Inflammatory multitarget drug: all roads lead to cellular metabolism. Molecule 26 (1): 5. DOI: 10.3390/molecules26010005.
Cai DY, Gao X, Wu XH, Hong TT. 2013. Synergistic effect of beta-elemene injection combined paclitaxel injection on human breast cancer MB-468 cells: an in vitro study. Chin J Integr Med 33 (7): 978-982.
Carroll AR, Copp BR, Davis RA, Keyzers RA, Prinsep MR. 2020. Marine natural products. Nat Prod Rep 39: 1122-1171. DOI: 10.1039/D0NP00089B.
Carvalho AMS, Heimfarth L, Pereira EWM. 2020. Phytol, a chlorophyll component, produces anti-hyperalgesic, anti-inflammatory, and antiarthritic effects: possible NF?B pathway involvement and reduced levels of the proinflammatory cytokines TNF-? and IL-6. J Nat Prod 83 (4): 1107-1117. DOI: 10.1021/acs.jnatprod.9b01116.
Chan WK, Tan LT, Chan KG, Lee LH, Goh BH. 2016. Nerolidol: A sesquiterpene alcohol with multi-faceted pharmacological and biological activities. Molecules 21 (5): 529. DOI: 10.3390/molecules21050529.
Chang HT, Cheng YH, Wu CL, Chang ST, Chang TT, Su YC. 2008. Antifungal activity of essential oil and its constituents from Calocedrus macrolepis var. formosana Florin leaf against plant pathogenic fungi. Bioresour Technol 99 (14): 6266-6270. DOI: 10.1016/j.biortech.2007.12.005.
Chen S, Ahmed A, Dai CF, Lu CK, Hu W, Wang J, Shu JH. 2006. Sinugibberosides A?E, new terpenoids with cyclic peroxyhemiketal from the soft coral Sinularia gibberosa. Tetrahedron Lett 62 (29): 6802-6807. DOI: 10.1016/j.tet.2006.04.088.
Chen W, Li Y, Guo Y. 2012. Terpenoids of Sinularia soft corals: Chemistry and bioactivity. APSB 2 (3): 227-237. DOI: 10.1016/j.apsb.2012.04.004.
Choudhary A, Naughton LM, Montánchez I, Dobson A, Rai DK. 2017. Current status and future prospects of marine natural products (MNPs) as antimicrobials. Mar Drugs 15 (9): 272. DOI: 10.3390/md15090272.
CLSI. 2018. Performance standards for antimicrobial disk and dilution susceptibility tests for bacteria isolated from animals. In: Clinical and Laboratory Standards Institute, 4th edn VET08. Wayne, PA.
Coll JC, Bowden BF, Tapiolas DM, Willis RH, Djura P, Streamer M, Trott L. 1985. Studies of Australian soft corals—XXXV: The terpenoid chemistry of soft corals and its implications. Tetrahedron Lett 41 (6): 1085-1092. DOI: 10.1016/S0040-4020(01)96476-2.
Da Silva TBC, Alves VL, Mendonça LVH, Conserva LM, da Rocha EMM, Andrade EHA, Lemos RPL. 2004. Chemical constituents and preliminary antimalarial activity of Humiria balsamifera. Pharm Biol 42 (2): 94-97. DOI: 10.1080/13880200490510702.
Dahham SS, Tabana YM, Iqbal MA, Ahamed MB, Ezzat MO, Majid AS, Majid A. 2015. The anticancer, antioxidant and antimicrobial properties of the sesquiterpene ?-caryophyllene from the essential oil of Aquilaria crassna. Molecules 20 (7): 11808-11829. DOI: 10.3390/molecules200711808.
Deyab M, Elkatony T, Ward F. 2016. Qualitative and quantitative analysis of phytochemical studies on brown seaweed, Dictyota dichotoma. Intl J Eng Dev Res 4: 674-678.
Dineshkumar G, Karthik M, Rajakumar R. 2018. GC-MS analysis of bioactive compounds from ethanolic leaves extract of Eichhornia crassipes (Mart) Solms. and their pharmacological activities. J Pharm Innov 7: 459-462.
Eloff JN. 1998. A sensitive and quick microplate method to determine the minimal inhibitory concentration of plant extracts for bacteria. Planta Med 64 (8): 711-713. DOI: 10.1055/s-2006-957563.
Ermolenko EV, Imbs AB, Gloriozova TA, Poroikov VV, Sikorskaya TV, Dembitsky VM. 2020. Chemical diversity of soft coral steroids and their pharmacological activities. Mar Drugs18 (12): 613. DOI: 10.3390/md18120613.
Fidyt K, Fiedorowicz A, Strz?da?a L, Szumny A. 2016. ?-caryophyllene and ?-caryophyllene oxide-natural compounds of anticancer and analgesic properties. Cancer Med 5 (10): 3007-3017. DOI: 10.1002/cam4.816.
Girish C, Pradhan SC. 2017. Herbal drugs on the liver. In: Muriel P (eds). Liver Pathophysiology: Therapies and Antioxidants. Academic Press, Boston, MA, USA. DOI: 10.1016/B978-0-12-804274-8.00044-8.
Godin PJ, Stevenson JH, Sawicki RM. 1965. The insecticidal activity of jasmolin II and its isolation from pyrethrum (Chrysanthemum cinerariaefolium Vis.). J Econ Entomol 58 (3): 548-551. DOI: 10.1093/jee/58.3.548.
Goud T, Reddy N, Krishnaiah P, Venkateswarlu Y. 2002. Spathulenol: A rare sesquiterpene from soft coral Sinularia kavarattiensis. Biochem Syst Ecol 30 (5): 493-495. DOI: 10.1016/S0305-1978(01)00094-1.
Gumgumjee NM, Hajar AS. 2015. Antibacterial activities and GC-MS analysis of phytocomponents of Ehretia abyssinica R. Br. ex Fresen. Intl J Appl biol 6 (2): 236-241.
Hameed I, Mohammad G, Jawad M. 2016. In vitro antibacterial, antifungal and phytochemical analysis of methanolic fruit extract of Cassia fistula. Orient J Chem 32 (3): 1-18. DOI: 10.13005/ojc/320307.
Hassan A, Mohammad R, Hetta M, Mohamed T, El-Gendy O, Sleim A. 2016. Biological and chemical investigation of the soft coral Lobophytum pauciflorum collected from the egyptian Red Sea. Intl J Pharmacogn Phytochem Res 8 (6): 906-911.
Hooijerink D, Schilt R, Hoogenboom R, Huveneers-Oorsprong M. 1999. Identification of metabolites of the anabolic steroid methandienone formed by bovine hepatocytes in vitro. Analyst 123 (12): 2637-2641. DOI: 10.1039/A805132A.
Huong NT, Ngoc NT, Hanh TTH, Quang TH, Cuong,NX, Nam NH, Van Minh C. 2019. Chemical constituents from the soft coral Sinularia digitata. VJCH 57 (5): 636-640. DOI: 10.1002/vjch.201900112.
Jahajeeah D, Bhoyroo V, Ranghoo-Sanmukhiya M. 2021. An assessment of soft coral community (Octocorallia; Alcyonacea) around Mauritius and Rodrigues Islands — New records of soft corals. Reg Stud Mar Sci 47: 101976. DOI: 10.1016/j.rsma.2021.101976.
Jenecius A, Uthayakumari F, Mohan V. 2012. Gc-ms determination of bioactive components of Sauropus Bacciformis blume (Euphorbiaceae). J Chem Pharm Sci 2 (4): 347-358.
Jiang Z, Jacob JA, Loganathachetti DS, Nainangu P, Chen B. 2017. ?-Elemene: Mechanistic studies on cancer cell interaction and its chemosensitization effect. Front Pharmacol 9 (8): 105. DOI: 10.3389/fphar.2017.00105.
Joshi A, Krishnan GS, Kaushik V. 2020. Molecular docking and simulation investigation: Effect of beta-sesquiphellandrene with ionic integration on SARS-CoV2 and SFTS viruses. J Genet Eng Biotechnol 18: 78. DOI: 10.1186/s43141-020-00095-x.
Junwei L, Juntao C, Changyu N, Peng W. 2018. Molecules and functions of rosewood: Pterocarpus cambodianus. Arab J Chem 11 (6): 763-770. DOI: 10.1016/j.arabjc.2017.12.030.
Kamatou GP, Viljoen A. 2009. A review of the application and pharmacological properties of ?-bisabolol and ?-bisabolol-rich oils. J Am Oil Chem Soc 87: 1-7. DOI: 10.1007/s11746-009-1483-3.
Kav?i? S, Knez Ž, Leitgeb M. 2013. Antimicrobial activity of n-butyl lactate obtained via enzymatic esterification of lactic acid with n-butanol in supercritical trifluoromethane. J Supercrit Fluids 85: 143-150. DOI: 10.1016/j.supflu.2013.11.003.
Khalesi MK, Beeftink RH, Wijffels RH. 2008. The soft corals Sinularia flexibilis: potential for the drug development. In: Leewis RJ, Janse M (eds). Advances in coral Husbandry in Public Aquariums. Arnhem, Netherlands.
Kim DH, Park MH, Choi YJ. 2013. Molecular study of dietary heptadecane for the anti-inflammatory modulation of NF-kB in the aged kidney. PloS One 8 (3): e59316. DOI: 10.1371/journal.pone.0059316.
Kohlmeier M. 2013. Chapter 5 - How does nutrigenetics influence long-term health? In: Kohlmeier M (eds). Nutrigenetics. Academic Press, San Diego. DOI: 10.1016/B978-0-12-385900-6.00005-8.
Kusmita L, Nuryadi H, Widyananto PA, Muchlissin S, Sabdono A, Trianto A, Radjasa OK. 2021. Bioactivity of carotenoid produced by soft coral symbiotic microorganisms from Panjang and Karimunjawa Island, Central Java, Indonesia. Biodiversitas 22: 732-740. 10.13057/biodiv/d220226.
Lee GH, Hyun KY. 2018. 2-nonadecanone alleviates depression through inflammation relief in sd rat. Biomed Sci Letters 24: 206-212. DOI: 10.15616/BSL.2018.24.3.206.
Legault J, Côté PA, Ouellet S, Simard S, Pichette A. 2013. Iso-caryophyllene cytotoxicity induced by lipid peroxidation and membrane permeabilization in L-929 cells. J App Pharm Sci 3 (8): 25-31. DOI: 10.7324/JAPS.2013.3805.
Li G, Li P, Tang X. 2019. Natural products from corals. In: Li Z (eds). Symbiotic Microbiomes of Coral Reefs Sponges and Corals. Springer, Dordrecht, The Netherlands. DOI: 10.1007/978-94-024-1612-1.
Madigan MT, Martinko JM, Parker J, Brock TD. 2000. Biology of Microorganisms. Prentice-Hall, Inc, New Jersey, USA.
Malarvili T,Velavan S, Parthasarathy R. 2015. GC-MS analysis of bioactive compounds in Bryonopsis laciniosa fruit extract. Intl J Pharm Sci 6 (8): 3375-3379. DOI: 10.13040/IJPSR.0975-8232.
Miti? ZS, Jovanovi? B, Jovanovi? S?, Stojanovi?-Radi? ZZ, Mihajilov-Krstev T, Jovanovi? NM, Stojanovi? GS. 2019. Essential oils of Pinus halepensis and P. heldreichii: Chemical composition, antimicrobial and insect larvicidal activity. Ind Crops Prod 140 (1): 111702. DOI: 10.1016/j.indcrop.2019.111702.
MNAP. 2017. Republic of Mauritius National Action Plan on Antimicrobial Resistance 2017-2021. Ministry of Health and Quality of Life, Mauritius.
Mohammad G. Omran AM, Hussein H. 2016. Antibacterial and phytochemical analysis of Piper nigrum using gas chromatography – mass spectrum and fourier-transform infrared spectroscopy. Intl J Pharmacogn Phytochem Res 8 (6): 977-996.
Mukda J, Mansuang W, Wandee G. 2013. Antidermatophytic properties of ar-turmerone, turmeric oil, and curcuma longa preparations. Intl Sch Res Notices 2013: 250597. DOI: 10.1155/2013/250597
Narayanasamy RR, Ramalakshmi S, Muthuchelian K. 2011. GC-MS analysis of bioactive components from the ethanolic leaf extract of Canthium dicoccum (gaertn.) Teijsm & binn. J Chem Pharm Res 3 (3): 792-798.
Nurrachma MY, Sakaraga D, Nugraha AY. 2021. Cembranoids of soft corals: Recent updates and their biological activities. Nat Prod Bioprospect 11: 243-306. DOI: 10.1007/s13659-021-00303-2.
Olaoye SB, Olukayode SA, Ayansola JA. 2017. Hexahydrofarnesyl acetone-rich extractives from Hildegardia barteri. J Herbs Spices Med Plants 23 (4): 393-400. DOI: 10.1080/10496475.2017.1350614.
Pavithra PS, Mehta A, Verma R. 2018. Aromadendrene oxide 2, induces apoptosis in skin epidermoid cancer cells through ROS mediated mitochondrial pathway. Life Sci 197: 19-29. DOI: 10.1016/j.lfs.2018.01.029.
Pechère M, Pechère J, Siegenthaler G, Germanier L, Saurat JH. 1999. Antibacterial activity of retinaldehyde against propionibacterium acnes. J. Dermatol 205 (2): 153-158. DOI: 10.1159/000051375.
Peng Z, Wang Y, Fan J. 2017. Costunolide and dehydrocostuslactone combination treatment inhibit breast cancer by inducing cell cycle arrest and apoptosis through c-Myc/p53 and AKT/14-3-3 pathway. Sci Rep 7: 41254. DOI: 10.1038/srep41254.
Rahman MM, Ahmad SH, Mohamed MT, Ab Rahman MZ. 2014. Antimicrobial compounds from leaf extracts of Jatropha curcas, Psidium guajava, and Andrographis paniculata. Sci World J 2014: 635240. DOI: 10.1155/2014/635240.
Rodríguez-Chaves D, Bagnarello-Madrigal V, Alpizar-Cordero J. 2018. Actividad in vitro anti-leishmania (Trypanosomatidae) del epóxido trans-Z-?-bisaboleno y del Safrol, en frutos de Piper auritum (Piperaceae). Rev Biol Trop 66 (2): 826-835. DOI: 10.15517/rbt.v66i2.33412.
Rosselli S, Maggio A, Formisano C, Napolitano F, Senatore F, Spadaro V, Bruno M. 2007. Chemical composition and antibacterial activity of extracts of Helleborus bocconei Ten. subsp. intermedius. Nat Prod Commun 2 (6): 675-679. DOI: 10.1177/1934578X0700200611.
Rozirwan R, Bengen DG, Zamani NP, Effendi H, Chaidir C. 2014. Screening on the potential bioactive compounds of antibacterial activity in soft coral collected from South Bangka Island Waters and Lampung Bay. JITKT 6 (2): 83-295. DOI: 10.29244/jitkt.v6i2.9005.
Russo EB, Marcu J. 2017. Cannabis Pharmacology: The usual suspects and a few promising leads. Adv Pharmacol 80: 67-134. DOI: 10.1016/bs.apha.2017.03.004.
Saga Y, Hatakenaka Y, Matsumoto M, Yoshioka Y, Matsumura S, Zaima N, Konishi Y. 2020. Neuroprotective effects of aromatic turmerone on activity deprivation-induced apoptosis in cerebellar granule neurons. NeuroRep 1 (18): 1302-1307. DOI: 10.1097/WNR.0000000000001551.
Sain S, Naoghare PK, Devi SS, Daiwile A, Krishnamurthi K, Arrigo P, Chakrabarti T. 2014. Beta caryophyllene and caryophyllene oxide, isolated from Aegle marmelos, as the potent anti-inflammatory agents against lymphoma and neuroblastoma cells. Antiallergy Agents Med Chem 13 (1): 45-55. DOI: 10.2174/18715230113129990016.
Saleem M. 2009. Lupeol, a novel anti-inflammatory and anticancer dietary triterpene. Cancer Lett 285 (2): 109-115. DOI: 10.1016/j.canlet.2009.04.033.
Salem MZM, Ali HM, Basalah MO. 2014. Essential oils from wood, bark, and needles of Pinus roxburghii Sarg. From Alexandria, Egypt: antibacterial and antioxidant activities. BioResour 9 (4): 7454-7466. DOI: 10.15376/biores.9.4.7454-7466.
Sammarco PW, Coll JC. 1992. Chemical adaptations in the Octocorallia: Evolutionary considerations. Mar Ecol Prog Ser 88: 93-104. DOI: 10.3354/meps088093.
Saravanan R, Raja K, Shanthi D. 2021. GC-MS analysis, molecular docking and pharmacokinetic properties of phytocompounds from Solanum torvum unripe fruits and its effect on breast cancer target protein. Appl Biochem Biotechnol 194 (1): 529-555. DOI: 10.1007/s12010-021-03698-3.
Shaaban M, Shaaban K, Ghani M. 2013. Hurgadacin: A new steroid from Sinularia polydactyla. Steroids 78 (9): 866-873. DOI: 10.1016/j.steroids.2013.05.006.
Shareef H, Haidar J, Hussein H, Hameed I. 2016. Antibacterial effect of ginger (Zingiber officinale) roscoe and bioactive chemical analysis using gas chromatography mass spectrum. Orient J Chem 32 (2): 817-837. DOI: 10.13005/ojc/320207.
Soares GM, Figueiredo LC, Faveri M, Cortelli SC, Duarte PM, Feres M. 2012. Mechanisms of action of systemic antibiotics used in periodontal treatment and mechanisms of bacterial resistance to these drugs. J Appl Oral Sci 20 (3): 295-309. DOI: 10.1590/s1678-77572012000300002.
Tammam MA, Rárová L, Kvasnicová M. 2020. Bioactive steroids from the red sea soft coral Sinularia polydactyla. Mar Drugs 18 (12): 632. DOI: 10.3390/md18120632.
Tan N, Satana D, Sem B, Tan E, Altan HB, Demirci B. 2016. Antimycobacterial and antifungal activities of selected four Salvia species. Rec Nat Prod 10 (5): 593-603.
Tanod W, Aristawati A, Putra M, Muliadin M. 2018. Soft coral (Sinularia sp.) extracts with antibacterial activity. Omni-Akuatika 14 (1): 108-117. DOI: 10.20884/1.oa.2018.14.1.375.
Tanod W, Dewanto D, Ndobe S, Riyadi P, Putra M. 2019. Screening of antibacterial and Antioxidant activity of soft corals Sinularia sp. and Sarcophyton sp. from Palu Bay Central Sulawesi, Indonesia. Squalen Bull Mar Fish Postharvest Biotech 14 (2): 73-83. DOI: 10.15578/squalen.v14i2.394.
Thao NP. Thanh NV, Nam NH, Cuong NX, Kim YH. Kiem PV, Minh CV. 2015. Steroid constituents from Lobophytum crassum. VJOC 53 (2e): 1-4. DOI: 10.15625/0866-7144.2015-2e-001.
Trevizan L, Nascimento K, Santos JA. 2016. Anti-inflammatory, Antioxidant and anti-Mycobacterium tuberculosis activity of viridiflorol: The major constituent of Allophylus edulis (A. St.-Hil., A. Juss. & Cambess.) Radlk. J Ethnopharmacol 192: 510-515. DOI: 10.1016/j.jep.2016.08.053.
Tsai YC, Hsu HC, Yang WC, Tsai WJ, Chen CC, Watanabe T. 2007. Alpha-bulnesene, a PAF inhibitor isolated from the essential oil of Pogostemon cablin. Fitoterapia 78 (1): 7-11. DOI: 10.1016/j.fitote.2006.09.016.
Venkata Raman B, La S, Pardha Saradhi M, Narashimha Rao B, Naga Vamsi Krishna A, Sudhakar M, Radhakrishna TM. 2012. Antibacterial, Antioxidant activity and GC-MS analysis of Eupatorium odoratum. Asian J Pharm Clin Res 5 (2): 99-106.
Willie P, Uyoh EA, Aikpokpodion PO. 2021. Gas Chromatography-Mass Spectrometry (GC-MS) assay of bio-active compounds and phytochemical analyses in three species of Apocynaceae. Pharmacog J 13 (2): 383-392. DOI: 10.5530/pj.2021.13.49.
Xia B, Tong Y, Xia C, Chen C, Shan X. 2020. ?-Cyperone confers antidepressant-like effects in mice via neuroplasticity enhancement by sirt3/ros mediated nlrp3 inflammasome deactivation. Front Pharmacol 11: 577062. DOI: 10.3389/fphar.2020.577062.
Xie Q, Li F, Fang L, Liu W, Gu C. 2020. The antitumor efficacy of ?-elemene by changing tumor inflammatory environment and tumor microenvironment. Biomed Res Intl 2020: 6892961. DOI: 10.1155/2020/6892961.
Yan X, Liu J, Leng X, Ouyang H. 2021. Chemical diversity and biological activity of secondary metabolites from soft coral genus Sinularia since 2013. Mar Drugs 19 (6): 335. DOI: 10.3390/md19060335.
Yeo SK, Ali AY, Hayward OA, Turnham D, Jackson T, Bowen I D, Clarkson R. 2016. ?-Bisabolene, a sesquiterpene from the essential oil extract of opoponax (Commiphora guidottii), exhibits cytotoxicity in breast cancer cell lines. Phytotherapy 30 (3): 418-425. DOI: 10.1002/ptr.5543.
Yu Z, Wang R, Xu L, Xie S, Dong J, Jing Y. 2011. ?-elemene piperazine derivatives induce apoptosis in human leukemia cells through downregulation of c-FLIP and generation of ROS. PLoS One 6 (1): e15843. DOI: 10.1371/journal.pone.0015843.
Yuan L, Zhang F, Shen M, Jia S, Xie J. 2019. Phytosterols suppress phagocytosis and inhibit inflammatory mediators via ERK pathway on LPS-triggered inflammatory responses in RAW264.7 macrophages and the correlation with their structure. Foods 8 (11): 582. DOI: 10.3390/foods8110582.
Zhu TZ, Li XM, Luo LH, Xu YH, Cao P, Liu Y. 2014. beta-Elemene inhibits proliferation through crosstalk between glia maturation factor beta and extracellular signal regulated kinase 1/2 and impairs drug resistance to temozolomide in glioblastoma cells. Mol Med Rep 10 (2): 1122-1128. DOI: 10.3892/mmr.2014.2273.
Ziaei A, Ramezani M, Wright L, Paetz C, Schneider B, Amirghofran Z. 2011. Identification of spathulenol in Salvia mirzayanii and the immunomodulatory effects. Phytother Res 25 (4): 557-62. DOI: 10.1002/ptr.3289.
Zu S, Deng YQ, Zhou C. 2020. 25-Hydroxycholesterol is a potent SARS-CoV-2 inhibitor. Cell Res 30 (11): 1043-1045. DOI: 10.1038/s41422-020-00398-1.