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Volatile Profiling Aided in the Isolation of Anti-Proliferative Lupeol from The processes Article Volatile Profiling Aided in the Isolation of Anti-Proliferative Lupeol from the Roots of Clinacanthus nutans (Burm. f.) Lindau Angelina Ying Fang Cheng 1, Peik Lin Teoh 1 , Lalith Jayasinghe 2 and Bo Eng Cheong 1,* 1 Biotechnology Research Institute, Universiti Malaysia Sabah, Jalan UMS, Kota Kinabalu 88400, Malaysia; [email protected] (A.Y.F.C.); [email protected] (P.L.T.) 2 National Institute of Fundamental Studies, Hantana Road, Kandy 20000, Sri Lanka; [email protected] * Correspondence: [email protected]; Tel.: +60-88-320000 (ext. 8530) Abstract: Isolation of anti-proliferative compounds from plants is always hindered by the complexi- ties of the plant’s nature and tedious processes. Clinacanthus nutans (Burm. f.) Lindau is a medicinal plant with reported anti-proliferative activities. Our study aimed to isolate potential anti-proliferative compounds present in C. nutans plant. To start with, for our study, we came up with a strategy by first profiling the volatile compounds present in the leaf, stem and root of C. nutans using GC-MS. Comparing the plant’s volatile profiles greatly narrowed down our target of study. We decided to start with the isolation and characterization of a pentacyclic terpenoid, i.e., lupeol from the roots of C. nutans, as this compound was found to present abundantly in the roots compared to the leaf or stem. We developed a simple maceration and re-crystallization method, without the necessity to go through the fractionation or column chromatography for the isolation of lupeol. Characterizations of the isolated compound identified the compound as lupeol. The anti-proliferative activity of the isolated lupeol was further investigated against the MCF-7 cell line, which showed comparable anti-proliferative activity with the authentic lupeol and camptothecin. Our strategy to profile every Citation: Cheng, A.Y.F.; Teoh, P.L.; part of the plant first, followed by selection of the most suitable plant part and targeted compound Jayasinghe, L.; Cheong, B.E. Volatile proved useful for further isolation and characterization bioactive compound from C. nutans. Profiling Aided in the Isolation of Anti-Proliferative Lupeol from the Keywords: Clinacanthus nutans; profiling; root; GC-MS; lupeol; anti-proliferative; MCF-7 cells Roots of Clinacanthus nutans (Burm. f.) Lindau. Processes 2021, 9, 1383. https://doi.org/10.3390/pr9081383 1. Introduction Academic Editor: Zongbi Bao Clinacanthus nutans (Burm. f.) Lindau from the Acanthaceae family is a small shrub which is naturally found in tropical and subtropical Asian countries, including Malaysia, Received: 29 June 2021 Thailand, Indonesia, Vietnam, and China [1]. In Malaysia, the plant is commonly known as Accepted: 30 July 2021 Published: 9 August 2021 Belalai Gajah and Sabah snake grass [2]. The aerial part of this plant, i.e., the leaf (Figure1 ) has been shown to possess a vast spectrum of pharmacological activities, in which the anti- Publisher’s Note: MDPI stays neutral proliferative activities on various human cancer cell lines have been extensively studied. with regard to jurisdictional claims in For instance, C. nutans leaf extracted with chloroform, methanol, and water has been published maps and institutional affil- reported to demonstrate anti-proliferative effects against various human cancer cell lines, iations. such as the liver hepatocellular carcinoma cell line (HepG2), neuroblastoma cell line (IMR- 32), lung cancer cell line (NCI-H23), gastric cancer cell line (SNU-1), colon adenocarcinoma cell line (LS-174T), erythroleukemia cell line (K-562), human cervical cancer cell line (HeLa), and Burkitt’s lymphoma cell line (Raji) [3]. On the other hand, the leaf extracted with ethanol and ethyl acetate has also been reported to exhibit strong cytotoxic effects against Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland. the estrogen-dependent human breast cancer cell line, MCF-7 [4]. Meanwhile, Fong and This article is an open access article colleagues have collected C. nutans leaves from different countries, such as Malaysia, distributed under the terms and Thailand and Vietnam. They extracted the collected leaves with methanol and found conditions of the Creative Commons that the leaf extracts possess cytotoxicity and apoptotic activities against the human skin Attribution (CC BY) license (https:// cancer cell line, D24 melanoma cells [5]. In addition to the anti-proliferative effects on creativecommons.org/licenses/by/ various cancer cell lines, the aerial parts of the plant have also been reported to exhibit 4.0/). significant antitumor and apoptotic activities on the in vivo mice cancer model [6]. While Processes 2021, 9, 1383. https://doi.org/10.3390/pr9081383 https://www.mdpi.com/journal/processes Processes 2021, 9, 1383 2 of 14 most of the anticancer studies on this plant are focused on the aerial part, our group have conducted an anti-proliferative study on the underground part, i.e., the root (Figure1)[ 7]. The crude methanolic and ethyl acetate extracts of C. nutans roots were found to exhibit Processes 2021, 9, x FOR PEER REVIEW 3 of 14 anti-proliferative and apoptotic effects on breast cancer (MCF-7) and cervical cancer (HeLa) cell lines [Teoh]. Figure 1. A Clinacanthus nutans plant. The arrows show the leaf, stem and root parts of the plant used forFigure extraction 1. A andClinacanthus volatile profiling nutans plant. in this The study. arrows The showroots were the leaf, further stem used and for root the parts isolation of the plant and characterizationused for extraction of lupeol. and volatile profiling in this study. The roots were further used for the isolation and characterization of lupeol. 2. Materials and Methods Owing to its promising anti-proliferative activities, several attempts have been con- 2.1. Solvents,ducted Chemicals to isolate and the Cell anti-proliferative Lines compounds and/or active fractions from the C. nu- Alltans theleaf. solvents Huang used and in colleagues this study [6 were] have of extracted analytical the and/or aerial high parts performance of C. nutans withliquid ethanol, chromatographyfollowed by (HPLC) further grade, fractionation and purchased on a Diaion from HP-20 Fisher macroporous Scientific (Pittsburgh, adsorption PA, resin to USA). produceThe solvents a 30% used ethanol were fraction methanol, (CN30) ethyl and acetate other fractions.and dimethylsulfoxide The CN30 fraction (DMSO). was found The authenticto be able reference to induce standard, inhibition lupeol in tumor(L5632-25 size mg, and ≥ weight94% purity) of the for HepA characterization xenograft model purposesmouse was (hepatomaobtained from cell-injected Sigma-Aldrich mice). (St. The Louis, active MO, components USA). Roswell in CN30Park Memorial were therefore Institutefurther (RPMI) fractionated 1640, Phosphate-Buffered and purified. High-performance Saline (PBS), 2.5 liquid g/L tr chromatographyypsin-1mmol/L EDTA, (HPLC) and and 0.5%mass trypan spectrometry blue stain (LC/MS/MS)solution were analysespurchased revealed from Nacalai that there Tesque were (Kyoto, seven Japan), active com- whereaspounds the Fetal present Bovine in CN30. Serum The (FBS) seven was identified purchased active from components JR Scientific were (Woodland, shaftoside, CA, apigenin USA). 6,8-C-The cellα-L-pyranarabinoside, proliferation kit was orientin, purchased isoorientin, from Roche vitexin, Diagnostics isovitexin, (Mannheim, and gallic Ger- acid. After many).that, the same research group conducted another study to isolate a novel polysaccharide– peptide complex, which they named CNP-1-2, by a series of complex purification methods 2.2. Plantfrom MaterialsC. nutans leaves [8]. This CNP-1-2 complex was found to show the strongest growth Clinacanthusinhibition effect nutans on (Burm. the human f.) Lindau gastric plants cancer were cell line purchased (SGC-7901) from and herbal was ablesuppliers to stimulate at a localthe market activation in Kota of macrophages. Kinabalu, Sabah, On the Mala otherysia. hand, The plants another were research verified group by a led botanist by Mutazah from theand Faculty colleagues of Science [9] has and managed Natural to fractionateResources, twoAssoc. active Prof. fractions Dr. Berhaman from the Ahmad, bark powder and a voucherof C. nutans specimen. These (ACCN two fractions, 001/2013) which was they deposited named in A12 the and herbarium A17, were of foundUniversiti to contain Malaysia Sabah. The plants were first cleaned thoroughly with tap water to remove the dirt, followed by rinsing several times with distilled water and dried with a paper towel. The leaves, stems and roots were excised from the plants, freeze-dried for five days and ground into powder using a heavy-duty blender. The plant samples in powder form were stored at −80 °C until further analysis. Some of the stems of the purchased plants were re- grown in soil for a duration of 6 months for photo shooting purposes. Processes 2021, 9, 1383 3 of 14 sulfur-containing compounds, including entadamide C and clinamide D, that possessed strong cytotoxic activities against MDA-MB-231 and MCF-7 breast cancer cell lines. From the studies above, it can be postulated that the isolation of anti-proliferative compounds from C. nutans is not easy. This may be due to the complexities of the plant’s nature, and also various fractionation/chromatographic steps which need to be optimized. Our study therefore aimed to pre-screen (profile) the volatile compounds present in every part of the plants first, followed by the selection and
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