Open Access Open Access  Restricted Access Subscription Access

In vitro Evaluation of Crude Extracts and Isolated Compounds from Goniothalamus rongklanus and Goniothalamus latestigma for Bioactive Properties


Affiliations
1 Laboratory of Natural Products, Center of Excellence for Innovation in Chemistry, Lampang Rajabhat University, 52100 Lampang, Thailand
2 The Forest Herbarium, Department of National Park, Wildlife and Plant Conservation, Ministry of Natural Resources and Environment, 10900 Bangkok, Thailand
 

The genus Goniothalamus belongs to the Annonaceae family. The pure compounds from Goniothalamus rongklanus and Goniothalamus latestigma were isolated by repeated column chromatography. The structures were recognized by NMR spectral methods. The chemical compounds of ethyl acetate extract (EtOAc) from the stems of G. rongklanus were identified as goniotriol (1) and stigmasterol glucoside (2). The EtOAc leaves extract of G. latestigma yielded a compound, which was identified as pinocembrin (3). The ethyl acetate (EtOAc) and methanol (MeOH) extract were tested for anti-HIV-1 RT and cytotoxic activities against P-388, KB, HT 29, MCF-7, A 549, ASK and CL cell lines. The EtOAc and MeOH extract of G. rongklanus showed evidence of anti-HIV-1 RT inhibition at 76.44 and 88.48 %, respectively. The EtOAc extract of G. rongklanus and G. latestigma showed cytotoxic activities on KB and HT 29 with an ED50 at <4 μg/mL. In addition, antibacterial study on extracts and isolated compounds was also performed. Antibacterial study was evaluated using nine strains (Staphylococcus aureus, Enterobacter aerogenes, Escherichia coli 0157: H7, Escherichia coli (ETEC), Escherichia coli (EPEC), Proteus mirabilis, Salmonella typhimuriam, Shigella flexneri and Vibrio cholera) by Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC) method. Goniotriol was the most effective antibacterial with a MIC in the range <0.16 - 0.6 mg/mL and MBC in the range 0.3 - >5 mg/mL. The antibacterial activity of goniotriol has been reported for the first time.

Keywords

Antibacterial Activity, Anti-HIV-1 RT, Cytotoxicity, Goniothalamus rongklanus, Goniothalamus lagestima.
Font Size

User

Notifications
JOURNAL COVERS
  

  • Saunders RM, Chalermglin P. A synopsis of Goniothalamus species (Annonaceae) in Thailand, with descriptions of three new species. Botanical Journal of the Linnean Society. 2008; 156(3):355–84. https://doi.org/10.1111/j.1095-8339.2007.00762.x
  • Jiang MM, Feng YF, Gao H, Zhang X, Tang JS, Yao XS. Three new bis styryllactones from Goniothalamus cheliensis. Fitoterapia. 2011; 82(4):524–7. https://doi.org/10.1016/j.fitote.2010.11.014. PMid:21075179
  • Li X, Chang CJ. Antitumor cytotoxicity and stereochemistry of polyketides from Goniothalamus amuyon. Natural Product Letters. 1996; 8(3):207–15. https://doi.org/10.1080/10575 639608044895
  • The National Identity Office. The National Identity Office, Endemic and Rare Plants of Thailand, Bangkok. 2000; 50-1.
  • Wattanapiromsakul C, Wangsintaweekul B, Sangprapan P, Itharat A, Keawpradub N. Goniothalamin, a cytotoxic compound, isolated from Goniothalamus macrophyllus (Blume) Hook. f. & Thomson var. macrophyllus. Songklanakarin Journal of Science and Technology. 2005; 27(2):479–87.
  • Abdullah N, Sahibul-Anwar H, Ideris S, Hasuda T, Hitotsuyanagi Y, Takeya K, Diederich M, Choo CY. Goniolandrene A and B from Goniothalamus macrophyllus. Fitoterapia. 2013; 88:1–6. https://doi.org/10.1016/j.fitote.2013.03.028. PMid:23570840
  • Wiart C. Goniothalamus species: a source of drugs for the treatment of cancers and bacterial infections. Evidence-based Complementary and Alternative Medicine. 2007; 4(3):299– 311. https://doi.org/10.1093/ecam/nem009. PMid:17965760. PMCid:PMC1978243
  • Choo CY, Abdullah N, Diederich M. Cytotoxic activity and mechanism of action of metabolites from the Goniothalamus genus. Phytochemistry Reviews. 2014; 13(4):835–51. https://doi.org/10.1007/s11101-014-9372-2
  • Iqbal E, Lim LB, Salim KA, Faizi S, Ahmed A, Mohamed AJ. Isolation and characterization of aristolactam alkaloids from the stem bark of Goniothalamus velutinus (Airy Shaw) and their biological activities. Journal of King Saud University-Science. 2018; 30(1):41–8. https://doi.org/10.1016/j.jksus.2016.12.008
  • Thanuphol P, Asami Y, Shiomi K, Wongnoppavich A, Tuchinda P, Soonthornchareonnon N. Marcanine G, a new cytotoxic 1-azaanthraquinone from the stem bark of Goniothalamus marcanii Craib. Natural product research. 2018; 32(14):1682–9. https://doi.org/10.1080/14786419.2017.1396588. PMid:29098873
  • Rasol NE, Ahmad FB, Lim XY, Chung FFL, Leong CO, Mai CW, Ismail NH. Cytotoxic lactam and naphthoquinone alkaloids from ischolar_mains of Goniothalamus lanceolatus Miq. Phytochemistry Letters. 2018; 24: 51–5. https://doi.org/10.1016/j.phytol.2018.01.009
  • Lekphrom R, Kanokmedhakul S, Kanokmedhakul K. Bioactive styryllactones and alkaloid from flowers of Goniothalamus laoticus. Journal of Ethnopharmacology. 2009; 125(1):47–50. https://doi.org/10.1016/j.jep.2009.06.023. PMid:19573585
  • Prawat U, Chaimanee S, Butsuri A, Salae AW, Tuntiwachwuttikul P. Bioactive styryllactones, two new naphthoquinones, and one new styryllactone, and other constituents from Goniothalamus scortechinii. Phytochemistry Letters. 2012; 5(3):529–34. https:// doi.org/10.1016/j.phytol.2012.05.007
  • Suchaichit N, Kanokmedhakul K, Panthama N, Poopasit K, Moosophon P, Kanokmedhakul S. A 2H-tetrahydropyran derivative and bioactive constituents from the bark of Goniothalamus elegants Ast. Fitoterapia. 2015; 103: 206–12. https://doi.org/10.1016/j.fitote.2015.04.005. PMid:25865074
  • Reutrakul V, Anantachoke N, Pohmakotr M, Jaipetch T, Sophasan S, Yoosook C, Kasisit J, Napaswat C, Santisuk T, Tuchinda P. Cytotoxic and anti-HIV-1 caged xanthones from the resin and fruits of Garcinia hanburyi. Planta Medica. 2007; 73(01):33–40. https://doi.org/10.1055/s-2006-951748. PMid:17117343
  • Chailungka A, Junpirom T, Pompimon W, Nuntasaen N, Meepowpan P. Two flavonoids first isolated from the seed of Syzygium nervosum and preliminary study of their anticancer and anti-HIV-1 reverse transcriptase activities. Maejo International Journal of Science and Technology. 2017; 11(01):58–67.
  • Thiplueang C, Punyanitya S, Udomputtimekakul P, Buayairaksa M, Nuntasaen N, Banjerdpongchai R, Wudtiwai B, Pompimon W. Sawtehtetronenin and its cytotoxicity from Goniothalamus sawtehii. Natural Products Communication. 2014; 9(12):1769– 71. https://doi.org/10.1177/1934578X1400901228
  • Nath K, Talukdar AD, Bhattacharya MK, Bhowmik D, Chetri S, Choudhury D, Mitra A, Bhattacharjee A. Antibacterial activity of certain ferns against multi drug resistant organisms. Journal of Natural Remedies. 2018; 17(4):144–53. https://doi.org/10.18311/jnr/2017/15758
  • Khatun M, Billah M, Quader MA. Sterols and sterol glucoside from Phyllanthus species. Dhaka University Journal of Science. 2012; 60(1):5–10. https://doi.org/10.3329/dujs.v60i1.10327
  • Abdullah A, Zakaria Z, Ahmad FB, Mat-Salleh K, Din LB. Chemical constituents from the fruit peel of goniothalamus scortechinii. Sains Malaysiana. 2009; 38(3):365–9.
  • Napal GND, Carpinella MC, Palacios SM. Antifeedant activity of ethanolic extract from Flourensia oolepis and isolation of pinocembrin as its active principle compound. Bioresource Technology. 2009; 100(14):3669–73. https://doi.org/10.1016/j.biortech.2009.02.050. PMid:19342224

Abstract Views: 379

PDF Views: 140




  • In vitro Evaluation of Crude Extracts and Isolated Compounds from Goniothalamus rongklanus and Goniothalamus latestigma for Bioactive Properties

Abstract Views: 379  |  PDF Views: 140

Authors

Nutthapol Funnimid
Laboratory of Natural Products, Center of Excellence for Innovation in Chemistry, Lampang Rajabhat University, 52100 Lampang, Thailand
Wilart Pompimon
Laboratory of Natural Products, Center of Excellence for Innovation in Chemistry, Lampang Rajabhat University, 52100 Lampang, Thailand
Narong Nuntasaen
The Forest Herbarium, Department of National Park, Wildlife and Plant Conservation, Ministry of Natural Resources and Environment, 10900 Bangkok, Thailand

Abstract


The genus Goniothalamus belongs to the Annonaceae family. The pure compounds from Goniothalamus rongklanus and Goniothalamus latestigma were isolated by repeated column chromatography. The structures were recognized by NMR spectral methods. The chemical compounds of ethyl acetate extract (EtOAc) from the stems of G. rongklanus were identified as goniotriol (1) and stigmasterol glucoside (2). The EtOAc leaves extract of G. latestigma yielded a compound, which was identified as pinocembrin (3). The ethyl acetate (EtOAc) and methanol (MeOH) extract were tested for anti-HIV-1 RT and cytotoxic activities against P-388, KB, HT 29, MCF-7, A 549, ASK and CL cell lines. The EtOAc and MeOH extract of G. rongklanus showed evidence of anti-HIV-1 RT inhibition at 76.44 and 88.48 %, respectively. The EtOAc extract of G. rongklanus and G. latestigma showed cytotoxic activities on KB and HT 29 with an ED50 at <4 μg/mL. In addition, antibacterial study on extracts and isolated compounds was also performed. Antibacterial study was evaluated using nine strains (Staphylococcus aureus, Enterobacter aerogenes, Escherichia coli 0157: H7, Escherichia coli (ETEC), Escherichia coli (EPEC), Proteus mirabilis, Salmonella typhimuriam, Shigella flexneri and Vibrio cholera) by Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC) method. Goniotriol was the most effective antibacterial with a MIC in the range <0.16 - 0.6 mg/mL and MBC in the range 0.3 - >5 mg/mL. The antibacterial activity of goniotriol has been reported for the first time.

Keywords


Antibacterial Activity, Anti-HIV-1 RT, Cytotoxicity, Goniothalamus rongklanus, Goniothalamus lagestima.

References





DOI: https://doi.org/10.18311/jnr%2F2019%2F23766