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In Vitro Evaluation of Crude Extracts and Isolated Compounds from Goniothalamus Rongklanus and Goniothalamus Latestigma for Bioactive Properties

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In Vitro Evaluation of Crude Extracts and Isolated Compounds from Goniothalamus Rongklanus and Goniothalamus Latestigma for Bioactive Properties JOURNAL OF NATURAL REMEDIES RESEARCH ARTICLE DOI:10.18311/jnr/2019/23766 In vitro Evaluation of Crude Extracts and Isolated Compounds from Goniothalamus rongklanus and Goniothalamus latestigma for Bioactive Properties Nutthapol Funnimid1, Wilart Pompimon1* and Narong Nuntasaen2 1Faculty of Science, Laboratory of Natural Products, Center of Excellence for Innovation in Chemistry, Lampang Rajabhat University, 52100 Lampang, Thailand; [email protected], [email protected] 2The 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 as goniotriol (1) and stigmasterol glucoside (2). The EtOAc leaves extract of G. latestigma yielded a compound, which was 3). The ethyl acetate (EtOAc) and methanol (MeOH) extract were tested for anti-HIV-1 were identified 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 showedidentified evidence as pinocembrin 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 - time. 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 Keywords: Antibacterial Activity, Anti-HIV-1 RT, Cytotoxicity, Goniothalamus rongklanus, Goniothalamus lagestima 1. Introduction G. macrophyllus has been used in the treatment of colds, fever, malaria, cholera, to stimulate blood flow The genus Goniothalamus (Annonaceae) include about in the body and after childbirth5,6. This genus has been 1 185 species, of which 25 species are found in Thailand . previously reported for styryl lactones, flavonoids, This genus is widely distributed in the tropical forests naphthoquinones, azaanthraquinones, alkaloids, of Southeast Asia and are used in traditional medicine. and acetogenins7 – 11. Compounds isolated from Root barks of G. cheliensis and seeds of G. amuyon are Goniothalamus genus has generally shown cytotoxicity, 2, 3 used in the treatment of edema and arthritis . The antimycobacterial, antimalarial, antiinflammatory, 4 stem bark of G. laoticus has been applied as roborant . antitumor, antiviral, anti-larvicidal, anti-biofilm and *Author for correspondence Article Received on: 29.05.2019 Accepted on: 16.08.2019 Nutthapol Funnimid et al. 147 antiplasmodial activity7, 9, 12, 13. Styryl lactone compounds Q mass spectrometer at 70 eV (probe) and EIMS were are the most isolated compounds from this genus for measured by a BrÜker Esquire apparatus. Infrared example, goniothalamin, goniotriol, cardiobutanolide, spectra (IR) were recorded at potassium bromide (KBr) goniofufurone, altholactone, goniopypyrone, goniodiol, solid with a Shimadzu 8900 FT-IR spectrophotometer and goniothalamin oxide. Goniothalamin has shown and major bands (λmax) were noted in wave number cytotoxicity in oral cavity, breast, small cell lung, and (cm-1). The Column Chromatography (CC) were used vero cell lines14. silica gel 60 H from E. Merck. 70-230 mesh ASTM, G. rongklanus is a member of this genus, locally cat. No. 7734 and Sephadex LH-20 (20–150 µm) for known as ‘Pa-Nan-Rong-Kla’ in Thai. This species absorbents. Thin layer chromatography (TLC) technique is distributed in the Northern and North-Eastern was proceeded on silica gel 60 PF254 at aluminium Thailand. G. latestigma is locally known as ‘Sa-Lao- sheets and isolated compounds were described below Ton’ and distributed around Peninsular Thailand. These ultraviolet light. Melting points were defined by a Büchi species are small trees upto 8 m tall and slender, featured 322 micro melting point apparatus and records in degree by flowers with whorl of three sepals and two whorls of Celsius (˚C). three petals each, the inside petals are connivant and forming a distinctive dome over the stamens1. 2.3 Extraction and Isolation There are no reports related to isolation of 2.3.1 Isolation of Chemical Constituents from compounds from G. rongklanus and G. latestigma and G. rongklanus Extracts their bioactive evaluation. Hence, the study was planned The air-dried milled stems of G. rongklanus (1.772 to extract, isolate, characterize the compounds from G. kg) was extracted with EtOAc (6 × 5 L) (ethyl acetate) rongklanus and G. latestigma and to evaluate them for and MeOH (6 × 5 L) (methanol) at room temperature Anti-HIV-1 RT (Reverse Transcriptase), cytotoxicity for three days to yield EtOAc extract (47.98 g) and and antibacterial activity. MeOH extract (103.86 g) after solvent removal by rotary evaporator. The EtOAc extract was isolated to pure compounds 2. Materials and Methods by CC with gradient mixtures of Hexane: EtOAc (100:0–0:100) followed by mixtures EtOAc: MeOH 2.1 Plant Materials (100:0–0:100) to give 8 fractions (A1-A8) which was characterized by TLC. Fraction A7 (8.04 g) was The stems of G. rongklanus (BKF. 152884) were collected further subjected to CC to furnish 5 subfraction from Phuhin Rongkhla National Park, Amphoe (B1-B5). Subfraction B3 (0.48 g) was crystallized by Nakhonthai, Phitsanulok Province, Northern Thailand 95% ethanol to yield yellow needles of compound in 2017. The leaves ofG. latestigma (BKF. 163333) 1 (0.3 g). were collected from Surat Thani provinces, Thailand in Subfraction B (1.70 g) was separated on CC 2017. The plant materials were authenticated by Narong 4 by eluting with gradient mixtures of Hexane: Nantasean, The Forest Herbarium, Ministry of Natural EtOAc (100:0–0:100) followed by mixtures EtOAc: Resources and Environment, Bangkok. MeOH (100:0–0:100) to provide 4 fractions 2.2 General Procedures (C1–C4). Subfraction C3 and C4 showed similar TLC characteristic therefore it was combined and then 1H (500 MHz), 13C (125 MHz) and 2D NMR spectra were further purified by flash column chromatography noted on a BrÜker AV-500 spectrometer in deuterated (FCC) with gradient mixtures of Hexane: EtOAc chloroform (CDCl3) and deuterated methanol (CD3OD) (100:0–0:100) followed by mixtures EtOAc: MeOH solutions. The tetramethylsilane (TMS) was internal (100:0–0:100) to give 3 fractions (D1-D3) followed by standard of chemical shifts (δ) in ppm. The mass crystallization of D2 in MeOH : CH2Cl2 (1:1) to yield spectra were recorded on a Thermo Finnigan Polaris compound 2 (0.02 g) as white solid. Journal of Natural Remedies | ISSN: 2320-3358 http://www.informaticsjournals.com/index.php/jnr | Vol 19 (3) | July 2019 148 In vitro Evaluation of Crude Extracts and Isolated Compounds from Goniothalamus rongklanus and Goniothalamus latestigma for Bioactive Properties 2.3.2 Isolation of Chemical Constituents from positive control15, 17. The concentration of the samples was G. latestigma Extracts 20 - 0.16 µg/mL in 0.5 % DMSO. The cancer cell lines used were Murine lymphocytic leukemia (P-388), Human oral The air-dried milled leaves ofG. latestigma (1.035 cavity carcinoma (KB), Human colon adenocarcinoma kg) was extracted with EtOAc (6 × 5 L) and MeOH (HT 29), Human breast adenocarcinoma (MCF-7), (6 × 5 L) at room temperature for three days to yield Human lung, adenocarcinoma (A 549), Rat glioma cell EtOAc extract (46.55 g) and MeOH extract (60.69 g) (ASK) and Chang liver (CL). MEM (minimum essential after solvent removal by rotary evaporator. medium with Earles salt and L-glutamine) in 10% FBS The EtOAc extract was separated by CC with gradient were used for culturing of cell lines. The cell lines were mixtures of Hexane: EtOAc (100:0–0:100) followed by maintained t 37 °C for 72 hours (48 hours for P-388) mixtures EtOAc: MeOH (100:0–0:100) to yield 7 fractions in 5% CO and 100% relative humidity, followed by (E –E ) which was characterized by TLC. Fraction E 2 1 7 3 stabilizing with 20% trichloroacetic acid at 4 °C for 60 (9.09 g) was further subjected to column chromatography min and then stained for 30 min by 0.4 % SRB in 1% to give 5 subfraction (F -F ). Subfraction F (0.72 g) was 1 5 2 acetic acid at room temperature. The unbound dye was subjected to CC by eluting with Hexane: EtOAc (100:0– washed by 1% acetic acid, already dried stain was mixed 0:100) and then with mixtures EtOAc : MeOH (100:0– with 10 mM Tris base with pH = 10. The absorbance was 0:100) to obtain 3 fractions (G -G ). The G (0.57 g) 1 3 2 read at 510 nm on a microplate reader and 50% effective was recrystallized by 95% ethanol to yield compound 3 dose (ED ) was calculated. (0.44 g) as pale needles. 50 2.6 Bacterial Strains 2.4 Anti-HIV-1 RT (Reverse Transcriptase) Assay In vitro antibacterial studies were carried out against nine strains (Staphylococcus aureus ATCC 25923 DMST The extracts of G. rongklanus and G. latestigma were tested 8840, Enterobacter aerogenes ATCC13048 DMST 8841, for anti-HIV-1 RT assay and cytotoxicity at the Service Escherichia coli 0157 : H7 DMST 12743, Escherichia Centre of Department of Microbiology, Mahidol University, coli (Enterotoxigenic, ETEC) DMST 30543, Escherichia Thailand.
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