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Camellia Japonica Leaf and Probable Biosynthesis Pathways of the Metabolome Soumya Majumder, Arindam Ghosh and Malay Bhattacharya*

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Camellia Japonica Leaf and Probable Biosynthesis Pathways of the Metabolome Soumya Majumder, Arindam Ghosh and Malay Bhattacharya* Majumder et al. Bulletin of the National Research Centre (2020) 44:141 Bulletin of the National https://doi.org/10.1186/s42269-020-00397-7 Research Centre RESEARCH Open Access Natural anti-inflammatory terpenoids in Camellia japonica leaf and probable biosynthesis pathways of the metabolome Soumya Majumder, Arindam Ghosh and Malay Bhattacharya* Abstract Background: Metabolomics of Camellia japonica leaf has been studied to identify the terpenoids present in it and their interrelations regarding biosynthesis as most of their pathways are closely situated. Camellia japonica is famous for its anti-inflammatory activity in the field of medicines and ethno-botany. In this research, we intended to study the metabolomics of Camellia japonica leaf by using gas chromatography-mass spectroscopy technique. Results: A total of twenty-nine anti-inflammatory compounds, occupying 83.96% of total area, came out in the result. Most of the metabolites are terpenoids leading with triterpenoids like squalene, lupeol, and vitamin E. In this study, the candidate molecules responsible for anti-inflammatory activity were spotted out in the leaf extract and biosynthetic relation or interactions between those components were also established. Conclusion: Finding novel anticancer and anti-inflammatory medicinal compounds like lupeol in a large amount in Camellia japonica leaf is the most remarkable outcome of this gas chromatography-mass spectroscopy analysis. Developing probable pathway for biosynthesis of methyl commate B is also noteworthy. Keywords: Camellia japonica, Metabolomics, GC-MS, Anti-inflammatory compounds, Lupeol Background genus Camellia originated in China (Shandong, east Inflammation in the body is a result of a natural response Zhejiang), Taiwan, southern Korea, and southern Japan to injury which induces pain, fever, and swelling. Both cor- (Konemann 2004). Camellia japonica is reported as a ticosteroids and non-steroidal anti-inflammatory drugs are bioactive plant in folk medicine of South Korea, Japan, used to reduce this pain by acting on the anti-inflammatory and China. Antioxidant and anti-inflammatory activities pathways.Butthesedrugshaveundesirablesideeffectsas of Camellia japonica leaves are already reported and this gastric ulceration, infrequently myocardial infarction, and plant is proved to be a source of triterpenes, flavonoids, stroke (Maroon et al. 2010). For centuries, many plant and tannin, and fatty acids having antiviral, antioxidant, and animal-derived natural compounds have been used to treat anti-inflammatory activities (Lee et al. 2017). Seed from inflammation. Those compoundsasdietarysupplements this plant is used as a traditional medicine and in folk and herbal remedies are becoming increasingly popular remedies for the treatment of bleeding and inflamma- because of their relatively few side effects unlike steroidal tion. Compounds from seed oil and stem bark extract of and nonsteroidal anti-inflammatory drugs. Camellia japonica are known to have anti-inflammatory Camellia japonica is an ornamental flowering plant activities (Lim 2014). Leaf extract of Camellia japonica belongs to the family Theaceae. The wild plants of the is reported to have a high concentration of vitamin E (25.35%), n-eicosane (10.2%) with other six active compo- * Correspondence: [email protected] nents (neophytadiene; all trans-squalene; n-octacosane; 6,9- Molecular Biology and Tissue Culture Laboratory, Department of Tea Science, pentadecadien-1-ol, α-linolenic acid, and n-hexadecanoic University of North Bengal, Rajarammohanpur, Siliguri, Darjeeling 734013, acid) related to hyperuricemia (Yoon et al. 2017). However, India © The Author(s). 2020 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/. Majumder et al. Bulletin of the National Research Centre (2020) 44:141 Page 2 of 14 the seed oil of this plant is already established as a medi- molecules detected in the extract were squalene cinal ingredient in the pharmaceutical and food industry (27.25%), lupeol (17.26%), diethyl phthalate (5.11%), (Akihisa et al. 1997). Camellianoside is a quercetin O- vitamin E (5.01%), and patchouli alcohol (3.49%) along glucoside isolated from the leaves of Camellia japonica and with other twenty-four anti-inflammatory compounds exhibits antioxidant activity. It has a role as a metabolite contributing a total share over eighty-three percentage and a radical scavenger (Onodera et al. 2006). Our present of peak area (shown in Table 2;Fig.2)wheresomeof investigation aimed to make a GC-MS analysis of Camellia them are reported as pain relievers and as anti-arthritic. japonica leaf extract to find out the compounds involved in Compounds are arranged on the bases of their chem- exhibiting anti-inflammatory activity and study the path- ical groups regarding their biosynthesis pathways, which ways involved in their synthesis. The application of pathway are mainly sesquiterpenes, triterpenes, diterpene, mono- study in this phytochemical analysis is an innovative strat- terpenes, tocopherols, phthalate esters, cannabinoid, and egy for targeting active compounds from this plant extract. others (Table 2; Fig. 3). Interestingly, more than seventy- four percentage of the extract belongs to terpenoids and Methods their derivatives. Total of twenty compounds (patchou- Sample collection and preparation lol, alpha-, and gamma-patchoulene, alpha-gurjunene, Healthy leaves were collected from an organically culti- caryophyllene, isoledene, etc.) with 19.58% percentage of vated Camellia japonica plant, which was collected from total peak area belong to the class sesquiterpene while Darjeeling Himalaya. Leaves of Camellia japonica were triterpenoids like squalene, oxidosqualene, methyl com- crushed in liquid nitrogen and mixed in methanol mate B, and lupeol have occupied 50.02% of peak area (widely used solvent for extraction) to make Camellia (shown in Fig. 3). Furthermore, five compounds are japonica leaf extract (CJLE). The extract was left over- present from the group monoterpenes (including their night on a shaker at 25 °C. The extract was centrifuged derivatives as linalyl acetate) while sclareol (diterpene), and the supernatant was collected for GC-MS analysis. CB-86 (cannabinoid), and vitamin E (tocopherol) are lone representatives of their chemical groups having rich Gas chromatography-mass spectrometry analysis bioactivities. A total of 7.52% area belongs to phthalate Methanolic extract (CJLE) with a concentration of 25 esters where two of them are reported bioactive but mg/ml was used for GC-MS. This method was adopted their biosynthesis or biodegradation pathway in this par- from Das et al. (2014) and Labar et al. (2019) with a ticular plant is not clear due to absence of previous re- slight modification. One microliter of CJLE was injected ports and precursors or intermediates in our result. in split mode in the instrument (GCMS-QP2010 Plus). Injection temperature was 260 °C and the interface Studies on biosynthesis pathways of different terpenoids temperature was set to 270 °C. Ion source temperature found in CJLE was adjusted to 230 °C. Helium was used as carrier gas. Triterpenes, sesquiterpenes, monoterpenes, and tocoph- − Total flow rate was 16.3 ml min 1 and the column flow erol are major groups of bioactive components found in − rate was 1.21 ml min 1. Mass spectra were recorded at 5 plant bodies where their pathways are closely related − scan s 1 with a scanning range of 40-650 m/z. Quantifi- with each other as isopentyl diphosphate (IPP) and cation of compounds was done on the bases of their dimethylallyl diphosphate (DMAPP) play the role of pre- peak areas. The data obtained from GCMS analysis were cursors in their biosynthesis (Fig. 4). The biosynthesis further analyzed from available literature. pathway of terpenoids in plants involves and regulates a number of pathways, where bioactive compounds like Studies on biosynthesis pathways of different terpenoids squalene, lupeol, vitamin E, patchouli alcohol, eucalyptol, found in CJLE and linalyl acetate are synthesized which have been Studies on biosynthesis pathways of different compounds found in CJLE. detected in GC-MS were done by reviewing several litera- tures and databases (The Kyoto Encyclopedia of Genes Triterpenoids and Genomes database 2020 and The PubChem 2020). Triterpenoid (50.02%) is the major group of compounds reported in this GC-MS analysis of CJLE. Squalene, one Results of the triterpenes found in CJLE, is involved as a com- Gas chromatography-mass spectrometry analysis mon precursor for synthesis of various hormones in ani- Total of fifty peaks were found in the chromatogram mals and sterols in plants. Moreover, squalene, itself is a (Table 1; Fig. 1) showing forty-seven different compounds major
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