Document Type : Original Article

Authors

1 Department of Chemistry, Faculty of Science, Lagos State University, Lagos, Nigeria

2 Foresight Institute of Research and Translation, Nigeria

3 Dipartimento di Farmacia, Università di Pisa, Italy

Abstract

The chemical constituents, anti-inflammatory and anti-nociceptive activities of the leaf essential oil hydrodisitlled from the Gardenia jasminoides J. Ellis (Rubiaceae) were reported. The chemical constituents of the essential were analyzed using gas chromatography-flame ionization detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC/MS). The hot plate and carrageenan-induced models were used to determine the anti-nociceptive and anti-inflammatory activities. The main compounds of the oil were pentadecanal 17 (49.2%), geranial 4 (12.3%), ar-turmerone 14 (8.2%) and 10-epi-γ-eudesmol 10 (6.2%). The essential oil of G. jasminoides at 100 and 400 mg.kg-1 doses significantly (p < 0.001) increased the latency period for the reaction duration in the anti-nociceptive study. The carrageenan-induced edema model reveals the suppression of inflammatory mediators (p < 0.001) within 1st, 2nd and 4th h for 100 mg.kg-1 dose, 1st and 4th h (200 mg.kg-1) and 1st-3rd h (400 mg.kg-1). The results indicate the potential of G. jasminoides essential oil as a source of pain relieving agent.

Graphical Abstract

In vivo anti-inflammatory and anti-nociceptive activities, and chemical constituents of essential oil from the leaf of Gardenia jasminoides J. Ellis (Rubiaceae)

Keywords

In vivo anti-inflammatory and anti-nociceptive activities, and chemical constituents of essential oil from the leaf of Gardenia jasminoides J. Ellis (Rubiaceae)

 

ABSTRACT

 

The chemical constituents, anti-inflammatory and anti-nociceptive activities of the leaf essential oil hydrodisitlled from the Gardenia jasminoides J. Ellis (Rubiaceae) were reported. The chemical constituents of the essential were analyzed using Gas chromatography-flame ionization detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC/MS). The hot plate and carrageenan-induced models were used to determine the anti-nociceptive and anti-inflammatory activities. The main compounds of the oil were pentadecanal 17 (49.2%), geranial 4 (12.3%), ar-turmerone 14 (8.2%) and 10-epi-γ-eudesmol 10 (6.2%). The essential oil of G. jasminoides at 100 and 400 mg/kg doses significantly (p <0.001) increased the latency period for the reaction duration in the anti-nociceptive study. The carrageenan-induced edema model reveals the suppression of inflammatory mediators (p <0.001) within 1st, 2nd and 4th h for 100 mg/kg dose, 1st and 4th h (200 m/kg) and 1st-3rd h (400 mg/kg). The results indicate the potential of G. jasminoides essential oil as a source of pain relieving agent.

KEYWORDS:

Anti-inflammatory activity

Anti-nociceptive activity

Essential oil

Gardenia jasminoides

Terpenes

 

1. Introduction

 

Essential oils have been used for a long time as natural products (Ogunwande et al., 2019a,b). Not only are essential oils effective in the control and management of diseases, but their chemical components are also effective against most ailments and natural disaster (Avoseh et al., 2020a,b). Gardenia jasminoides Ellis, commonly called common gardenia or cape jasmine, is native to southern China and Japan. It belongs to the family Rubiaceae. The plant is an evergreen shrub. The flowers are white and extremely fragrant.

The various extracts of the plant and their chemical compounds have been described with several pharmacological activities. The anti-hypertensive effect (Chen et al., 2017) and the anti-allergic activity (Sung et al., 2014) of G. jasminoides were associated with the active component, geniposide. The compounds, genipin and geniposide, found in G. jasminoides exhibited potent inhibitory effects antifungal actions against Pleurotus ostreatus, Fusarium oxysporum and Corynespora cassiicola (Lelono et al., 2009). The anti-ulcer effects of G. jasminoides were derived from some important components namely genipin gentiobioside and gardenoside isolated from the plant (Chen et al., 2014). A study has demonstrated that geniposide and crocins present in G. jasminoides could be responsible for its anti-inflammatory activity (Hu et al., 2019). Some compounds characterized from G. jasminoides including geniposide, 6α-hydroxygeniposide, ixoroside and shanzhiside exhibited significant immunosuppressive action (Chang et al., 2005). The fruits of G. jasminoides elicited cardiovascular effects (Liu et al., 2013). Other phytochemical compounds isolated and characterized from G. jasminoides includes gardaloside and jasminoside G (Chang et al., 2005), imperatorin, isoimperatorin, crocetin, 5-hydroxy-7,3',4',5'-tetrainethoxyflavone, 2-methyl-3,5-dihydroxychromone, sudan III and crocin-3 (Chen et al., 2007). In addition, gardenoside, 6β-hydroxygeniposide, geniposidic acid, crocin-1, crocin-2, and crocin-4 were also obtained from the plant (Wang et al., 2015). A review of the chemical constituents and biological activities of both the non-volatile extracts of the plant was recently carried out (Phatak, 2017; Xiao et al., 2017).

The volatile constituents of G. jasminoides from various parts of the world have been studied and reported. The studies concentrated mainly on the flowers and fruits samples. The major volatile compound found in essential oils of G. jasminoides consists of diverse chemicals such as terpenes, aliphatic acids, ketones, aldehydes, esters, alcohols, fatty acids and aromatic derivatives. The contents and proportions of these phytochemicals varied from one region to another. The main compounds of the essential oils from different origin and plant parts as seen in the literature are summarized in Table 1. The essential oil of G. jasminoides was reported to have exhibited insecticidal activity towards Bemisia tabaci and Tetranychus urticae adult and nymph (Wagan et al., 2018). The oils also possessed good scavenging activities on 1,1-Diphenyl-2-pic-rylhydrazyl [DPPH] and 2,2’-Azinobis (3-ethyl-benzothiazoline-6-sulfonic acid) (ABTS+) with IC50 of 6.26 and 11.58 μg/mL, respectively (Gan et al., 2013).

Although the chemical composition of essential oils from the fruits and flowers of G. jasminoides, as well as biological activities such as antioxidant and insecticidal were reported, no reports exist on the composition and pain relieving action of the leaf oil. This noteworthy observation prompted our interest in the present research. The aim of this paper was to report the chemical constituents, anti-nociceptive and anti-inflammatory activities of essential oil hydrodisitlled from the leaf of G. jasminoides from Nigeria. This is in continuation of our ongoing research (Ogunwande et al., 2019a,b; Avoseh et al., 2020a,b) aimed at sourcing for biologically active products from essential oils form plants grown in Nigeria.

 

 

Fig. 1. The leaf of G. jasminoides

 

2. Experimental

 

2.1. Collection and authentication of the leaves of G. jasminoides

 

Mature leaves of G. jasminoides (Fig. 1, 156 g) were obtained from plants growing wild at Igando Area, Alimosho Local Government Area (GPS 6o36′38′N 3o17′45′E) of Lagos State (Fig. 2), Nigeria. The leaves were collected on a single day in May 2017. The identification of G. jasminoides was done by Curators at Herbarium, University of Lagos Nigeria. A voucher specimen (LUH 3245) was deposited at the herbarium.

 

2.2. Preparing the samples ready for oil isolation

 

The leaves of G. jasminoides were dried in the Education Trust Fund Laboratory of Chemistry Department Lagos State University at ambient temperature. After drying, G. jasminoides were grinded into coarse powder, using locally made instrument to a total weight of 134.6 g which was used to obtain the essential oil.

 

Fig. 2. The geographical map of the sampling area within Lagos State, Nigeria Source: www.lagosgovt.gov.ng

 

2.3. Hydrodistillation of essential oils

 

The leaves of G. jasminoides were subjected to hydrodistillation using the method described earlier in previous studies (Ogunwande et al., 2019a, b; Avoseh et al., 2020a,b). The coarse sample was introduced into a clean and dry 5 L flask and macerated completely with distilled water. Essential oil was then distilled in Clevenger-type distillation unit maintained at normal pressure at a total time of 3 h. Thereafter essential oil was collected into clean weighed sample bottles, from the tap in the receiver arm of the apparatus and separately refrigerated (4oC) till the moment of analyses as described in our previous studies (Ogunwande et al., 2019a, b; Avoseh et al., 2020a,b). The process of hydrodisitllation was done in triplicate analysis.

 

2.4. Analysis of the oil samples

 

The constituents of the essential oils were analyzed comprehensively by using gas chromatography-flame ionization detector (GC-FID) and gas chromatography-mass spectrometry (GC/MS) techniques.Gas chromatography (GC-FID) analysis was accomplished with a HP-5890 Series II instrument equipped with a HP-Wax and HP-5 capillary columns (both 30 m x 0.25 mm, 0.25 μm film thickness), working with the following temperature program: 60 ºC for 10 min, rising at 5 ºC/min to 220 ºC. The injector and detector temperatures were maintained at 250 ºC; carrier gas nitrogen (2 mL/min); detector dual, FID; split ratio 1:30. The volume injected was 0.5 μL. The relative proportions of the oil constituents were percentages obtained by FID peak area normalization without the use of a response factor.

Gas chromatography-mass spectrometry (GC-EIMS) analysis was performed with a Varian CP-3800 gas-chromatograph equipped with a HP-5 capillary column (30 m x 0.25 mm; film thickness 0.25 μm) and a Varian Saturn 2000 ion trap mass detector. Analytical conditions: injector and transfer line temperature 220 ºC and 240 ºC, respectively; oven temperature programmed from 60 ºC-240 ºC at 3 ºC/min.; carrier gas helium at a flow rate of 1mL/min.; injection volume 0.2 μL (10% n-hexane solution); split ratio 1:30. Mass spectra were recorded at 70 eV. The acquisition mass range was m/z 30-300 at a scan rate of 1 scan/sec.

The identification of the constituents of essential oil from the leaves of leaves of G. jasminoides was based on comparison of their retention times with those of authentic samples, comparing their linear indices relative to a series of n-alkanes (C6-C36). Further identifications were also made possible by the use of a homemade library of mass spectra built up from pure substances and components of known oils (NIST, 2018) and MS literature data as described in our previous reports (Ogunwande et al., 2019a,b; Avoseh et al., 2020a,b). Moreover, the molecular weights of all the identified substances were confirmed by GC-CIMS, using MeOH as CI ionizing gas.

 

2.5. Biological studies

 

2.5.1. Drug and Chemicals

Carrageenan drug of analytical grade was obtained from Sigma-Aldrich Chemical Co. (St Louis, MO, USA). Ibuprofen injection (May and Baker) and Diclofenac Injection (Dizpharm, Nigeria Ltd.) were purchased from Lagos State University Pharmacy.

 

2.5.2. Animals used for the study

 

Wistar rats (150-200 g) of both sexes were accommodated in the Biochemistry Department animal facility of Lagos state University, Ojo-Lagos. The rats were kept in a metal steel cage, where they had unrestricted supply to water and standard pellet food. They were acclimatized for two weeks before commencement of experiment. The rats were assigned at random to a group of 5 consisting of 6 animals per group. To select the doses used in the experiment, rats of similar weight were grouped together to obtained average weight. The weight recorded was similar across the groups of rats. The dose was therefore determined from the weight of rats in the assigned group. The essential oil of G. jasminoides was dissolved in saline vehicle. Doses of 100, 200 and 400 mg/kg were administered to the rat in that order.

All experimental procedures were conducted as approved by the Research Ethical Clearance Committee (RECC) of the University (Approval no: 012/2017/LASU/BCH).

 

2.5.3. Toxicity study on the essential oil of G. jasminoides

 

The leaf essential oil of G. jasminoides was tested for acute toxicity study as described previously. Twenty-five Wistar rats (both sexes, 150- 200 g each) were used for the toxicity study as described in previous studies (Ogunwande et al., 2019a,b; Avoseh et al., 2020a,b). The rats were divided into 5 animals in each group and doses of 500, 1000, 1500 and 2000 mg/kg of the leaf essential oil of G. jasminoides were administered per oral route. One group received normal saline that served as a negative control (Ogunwande et al., 2019a, b; Avoseh et al., 2020b).

 

2.5.4. Evaluation of the anti-inflammatory activity of the essential oil of G. jasminoides

 

The method of Carrageenan-induced paw edema in rats was used. Animals in each groups were induced subcutaneously with 0.1 ml of 1% freshly prepared Carrageenan in the right hind paw treated by oral administration of vehicle (water, 10 mL/kg; control), sodium diclofenac (10 mg/kg; positive control) and G. jasminoides essential oil doses (100, 200 and 400 mg/kg) as described in previous studies (Ogunwande et al., 2019a,b; Avoseh et al., 2020a,b). Paw volume of the injected rats were measured hourly on a plethysmometer (Ugo Basile, Italy mod. 7140) commencing 1 h before (basal values) and up to 4 h following Carrageenan injection. Edema was calculated as the difference (L) between injected and control paw. The area under the curve (AUC) time versus Δ paw volume was calculated for each animal and the edema was expressed as the mean±S.E.M. of AUC (Ferreira et al., 2005).

 

2.5.6. Determination of anti-nociceptive effect of the essential oil

 

The experiment was carried out according to the method described previously (Ogunwande et al., 2019a,b; Avoseh et al., 2020a,b). Twenty-five (25) mature Wistar rats of both sexes were randomly divided into 5 groups of equal rats. The animals were fasted for 12 h with provision of clean water ad libitum. Each rat was placed upon the heated metal plate (Hot plate) maintained at the temperature of about 50-55 ºC within the restraining glass cylinder. Solution of essential oils were administered to the rats as follows: Group 1 rats received 10 mg/kg of saline solution which serve as control experiment while 10 mg/kg of sodium salicylate which serves as standard control was administered to Group 2 rats. Furthermore, rats in Groups 3, 4 and 5 received 100, 200 and 400 mg/kg of G. jasminoides respectively p.o.

Animal response to the heat varies and such changes includes kicking of hind foot and jumping about, licking of foot, raising the foot, holding the foot tightly to its body or shaking of the foot (Ogunwande et al., 2019a,b; Avoseh et al., 2020a,b). The reaction time was recorded 30, 60, 90 and 120 min after the administration of the treatments. The maximum reaction time was fixed at 30 s to prevent any injury to the tissues of the paws. If the reading exceeds 30 s, it would be considered as maximum analgesia.

2.6. Statistical analysis

The data represent the Mean ± S.E.M. of the evaluated parameter and were analyzed for statistical significance by one-way analysis of variance (ANOVA) followed by post-hoc Bonferrotti test for the Carrageenan and the hot plate test using GraphPad Prism (version 7.02, San Diego CA, USA, www.graphPad.com). The minimum levels of significance, p < 0.05, p <0.01 and p <0.001, were considered as the statistically significant difference of the means.

 

3. Results and Discussion

 

3.1. Constituents of leaf essential oil of G. jasminoides

 

Table 2 represent the nature, retention indices on HP-5 column and percent compositions of the oil. The average yield of the essential oil was 0.23% (v/w, ±0.01), calculated on a dry weight basis. A total of 17 compounds representing 97.7% of the oil contents were identified in the colourless essential oil as seen in Table 2. The main classes of compounds found in the essential oil of G. jasminoides were long chain aldehydes (51.4%), oxygenated monoterpenes (21.6%) and oxygenated sesquiterpene (20.7%). The terpene hydrocarbons are less common represented by monoterpene hydrocarbons (0.8%) and sesquiterpene hydrocarbons (0.4%). The compounds occurring in higher amount in the essential oil were pentadecanal 17 (49.2%), geranial 4 (12.3%), ar-turmerone 14 (8.2%) and 10-epi-γ-eudesmol 10 (6.2%).

The observed variation on the amount and the composition of the bioactive substances in the present and previous studies on G. jasminoides are germane due to differences in the plant part being analyzed, and according to other factors such as the extraction methods, the geographic and the growing conditions, the harvest time etc. (Sharifi-Rad et al., 2017). Terpene compounds found in previously investigated samples (Guo et al., 1991; Zhang et al., 1991; Liu et al., 2000; Obuzor and Nwakolo, 2011; Gan et al., 2013) were also the main classes of compounds in the studied oil. However, other classes of compounds such as esters (Hunag et al., 2004; Cai et al., 2008; Tan et al., 2012; Kanlayavattanakul and Lourith, 2015), aromatic derivatives (Tan et al., 2012; Wagan et al., 2018; Shang et al., 2019), aliphatic alcohols and acids (Hattori et al., 1978) that are characteristics of previously analyzed samples were not identified in the present study. The quantity of fatty acids in the present oil samples is noteworthy with respect to previous studies (Bao et al., 2011; Wagan et al., 2018; Shang et al., 2019), although the identities of the various fatty acids differ from one oil sample to another. In addition, pentadecanal, geranial and ar-turmerone, the main compounds of the leaf oil were not reported previously as main constituents of previously analyzed flowers and fruits oil. Moreover, α-farnesene, linalool, trans-β-ocimene and α-terpineol, the main constituents of the flowers oil previously analyzed from Nigeria, were not identified in the leaf oil. This indicates existence of chemical forms in the essential oils of G. jasminoides growing in Nigeria brought about by the different plant parts.

 

3.2. Toxicity effect

 

The acute toxicity of the essential oil which was evaluated at 500, 1000, 1500, and 2000 mg/kg body weight showed no contrary effects on the behavioural responses in the tested rats following 14 days of observation. No mortality, size, or weight change observed. Therefore, the highest dose of 400 mg/kg was adopted to be ministered to rats in this study was considered safe.

 

3.3. Anti-nociceptive activity of G. jasminoides oil

 

Figure 3 below shows the effect of G. jasminoides essential oil on the thermal stimuli of Wistar rats.

The leaf essential oil of G. jasminoideswas tested for its anti-nociceptive activity using the hot plate method. The response of Wistar rats to heat was evaluated accordingly. This assay was used to evaluate the analgesic ability of the studied essential oil. It also depicts the strength of essential oil of G. jasminoides to act as an opioid antagonist. Opioid receptor antagonists block one or more of the opioid receptors in the central or peripheral nervous system. Groups of animals administered with different doses of G. jasminoides essential oil were compared with saline-administered groups (control). It was observed that the higher the maximum pain threshold time, the more the inhibitory capacity of G. jasminoides essential oil. As shown in the figure 3, below, the 100 and 400 mg/kg doses of G. jasminoides significantly (p <0.001) increased the latency period for the reaction duration. Conversely, the 200 mg/kg did not showed any significant inhibition.

 

Fig. 3. Effect of the essential oils of G. jasminoides on hot place-induced anti-nociceptive. Control, standard and G. jasminoides represent 1mL saline solution, 100 mg/kg of aspirin injection and 100, 200 and 400 mg of G. jasminoides leaves essential oil respectively. #p < 0.001, ns= non-significant, p<0.5 statistically compared to the control.

 

3.4. Anti-inflammatory action of the oil

 

The results of the anti-inflammatory study are shown in Figure 4. To evaluate the anti-inflammatory activity of G. jasminoides leaf essential oil, the Carrageenan-induced model was adopted. The carrageenan-induced paw inflammation has been accepted as a useful phlogistic tool for investigating systemic anti-inflammatory agent.

 

Fig. 4. Effect of leaf essential oil of G. jasminoides on Carragenan-induced inflammation. Control, standard and G. jasminoides represent 1mL saline solution, 100 mg/kg of Dichlofenac injection and of 100, 200 and 400 mg/kg of G. jasminoides leaf essential oil respectively. *p < 0.01, #p < 0.001, ns= non-significant statistically compared to control.

 

In this study, the activities of G. jasminoides were compared to that of the control (saline-treated groups), as shown in Fig. 4 above. Reduction in edema was measured hourly post-administration for four hours. The higher the reduction in edema size the more active the G. jasminoides essential oil. Therefore, in this study, G. jasminoides at a dose of 100 mg/kg significantly reduced the edema at the 1st, 2nd, and 4th hour (p <0.001) but shows no activity at the 3rd h. An increase of dose to 200 mg/kg revealed a non-consistent inhibitory pattern. The essential oil reduced the edema proliferation at the 1st and 4th h (p <0.001), but showed a decline in activity at the 2nd and 3rd h (p <0.01). The absorption and inhibitory capacity of the 400 mg/kg dose proceeds from the 1st to the 3rd h at a very high rate (p <0.001) but declined at the 4th h. The proliferation of inflammation mediators (e.g. histamine, prostaglandins, leukotrienes, oxygen- and nitrogen-derived free radicals, serotonin, and cytokines) triggered by the carrageenan-induced model is a time-dependent activity. These mediators primarily increase clotting and reduce the healing period (Juhn et al., 2008). The model is well-defined for acute inflammation. It is time-dependent, characterized by the biphasic release of mediators. This phlogistic agent evokes biphasic edema, the first phase (1 h) of which is mediated by the release of histamine and serotonin from mast cells and the second phase (2-4 h) of which involves neutrophil infiltration and the release of prostaglandin E2, cytokines (mainly IL-1β) and nitric oxide (Coura et al., 2015) . Our result demonstrated that the tested doses of G. jasminoides essential oil significantly reduced the first phase of inflammation, while the doses inhibited the second phase of the carrageenan-induced edema at different hours.

The anti-inflammatory activity of extracts and compounds of G. jasminoides (Hoo et al., 2006; Hong and Yang, 2013; Xiao et al., 2017) and extracts of some other species in the genus such as Gardenia coronaria (Chowdhury et al., 2014), Gardenia carinata (Appalaraju et al., 2018), Gardenia aqualla (Muhammad et al., 2019) and Gardenia latifolia (Ansari et al., 2020) have been reported. Moreover, the anti-inflammatory, anti-nociceptive and antipyretic activities of essential oils from some other plants such as Alpinia allughas (Kumar et al., 2017), Globba sessiliflora (Kumar et al., 2017), Thuja plicata var. Excelsa, Alstonia boonei, Curcuma longa and Allium sativum (Avoseh et al., 2020a), as well as Mucuna pruriens (Avoseh et al., 2020b) among others have been reported in literature. However, no such information could be seen for essential oils of Gardenia plants. The present results are the first of its kind on the chemical constituents, anti-inflammatory and anti-nociceptive activities of the leaf essential oil of G. jasminoides. The presence of monoterpenes, sesquiterpenoids and other class of compounds could be responsible for the observed anti-inflammatory and anti-nociceptive activities of the essential oil of G. jasminoides as previously reported (Savegnago et al., 2016). Synergistic interaction of the components of the essential oil of G. jasminoides could also be responsible for the observed change. However, the abundant constituents of the essential oil mainly pentadecanal, geranial, ar-trumerone etc were known previously for their pharmacological properties. Geranial exhibit significant anti-inflammatory and analgesic activities, inhibiting expression of the inflammatory mediators such as TNF-α and IL-6 secretion of macrophages, pro-IL-1β, iNOS, COX-2 and NLRP-3, phosphorylation of ERK1/2, JNK1/3, p38 and IκB e.t.c. (Mai et al., 2014; Nishijima et al., 2014; Liao et al., 2016). ar-Turmerone also reduced TNF-α, IL-1β, IL-6, and MCP-1 production in amyloid (Aβ) stimulated microglial cells as well as NF-κB, JNK, and p38 MAPK signaling pathways (Park et al., 2012a, b; Yang et al., 2020). Pentadecanal was thought to be responsible for the antimicrobial and cytotoxicity properties (Essien et al., 2012) of some essential oils. However, it is difficult to explain the possible mechanism of the essential oils based on the present findings; further studies are needed to elucidate the exact mechanism.

 

4. Concluding remarks

 

The chemical composition and biological activity of essential oil from the leaf of G. jasminoides were being reported for the first time. The major compounds identified in the oil were pentadecanal, geranial, ar-turmerone and 10-epi-γ-eudesmol. In addition, the essential oil displayed considerable anti-inflammatory and anti-nociceptive activities. Our findings suggest that the essential oils of G. jasminoides may be useful in the prevention or treatment of inflammatory related diseases.

 

Conflict of interest

 

The authors declare that there is no conflict of interest.

 

Acknowledgments

 

The authors are grateful to Mr. Ibrahim Adedotun, Chemistry Department, LAUTECH, Ogbomoso, for technical assistance.

 

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Helm, S., Trescot, A.M., Colson, J., Sehgal, N., Silverman, S., 2008. Opioid antagonists, partial agonists, and agonists/antagonists: The role of office-based detoxification. Pain Phy. 11(2), 225-235.

Hong, Y., Yang, K., 2013. Anti-inflammatory activities of crocetin derivatives from processed Gardenia jasminoides. Arch. Pharm. Res. 36(12), 933-940.

Hu, Y., Liu, X., Xia, Q., Yin, T., Bai, C., Wang, Z., Du, L., Li, X., Wang, W., Sun, L., Liu, Y., Zhang, H., Demg. L., Chen, Y., 2019. Comparative anti-arthritic investigation of iridoid glycosides and crocetin derivatives from Gardenia jasminoides Ellis in Freund's complete adjuvant-induced arthritis in rats. Phytomed. 53, 223-233.

Huang, Q.Q., Jiang, K.Z., Feng, J.Y., Chen, G.X., 2004. Analysis of volatile constituents of Gardenia flowers by GC/MS. Acta Bot. Yunn. 29(4), 471-474.

Huong, L.T., Huong, T.T., Bich, N.T., Viet, N.T., Giwa-Ajeniya, O.A., Ogunwande, I.A., 2020. Antimicrobial efficacy and chemical constituents of pseudo-stem essential oils from Zingiber castaneum. Trends Phytochem. Res. 4(2), 93-100.

Juhn, S.K., Jung, M.K., Hoffman, M.., Drew, B.R., Preciado, D.A., Sausen, N.J., Jung, T.T.K., Kim, B.Y., Park, S.Y., Lin, J., Ondrey F.G., Mains, R.S., Hunag, T. 2008. The role of inflammatory mediators in the pathogenesis of otitis media and sequelae. Clin. Exp. Otorhinolaryngol. 1(3), 117-118.

Kanlayavattanakul, M., Lourith, N., 2015. Volatile profile and sensory property of Gardenia jasminoides aroma extracts. J. Cosm. Sci. 66(6), 371-377.

Koo, H.J., Lim, K.H., Jung, H.J., Park, E.H., 2006. Anti-inflammatory evaluation of Gardenia extract, geniposide and genipin. J. Ethnopharmacol. 103(3), 496-500.

Kumar, R., Sethi, S., Om, P., Anil, K.P., Mahesh, K., Isidorov, V.A., Szczepaniak, L., 2017. Chemical composition of rhizome oleoresin and anti-inflammatory, antinociceptive and antipyretic activity of oleoresins of Alpinia allughas Roscoe. from Tarai region of Uttarakhand. Ind. J. Pharm. 28(3), 136-146.

Kumar, R., Om, P., Anil, K.P., Mahesh, K., Isidorov, V.A., Szczepaniak, L., 2017. Chemical composition and anti-inflamatory, anti -nociceptive and antipyretic activity of rhizome essential oil of Globba sessiliflora Sims. collected from Garhwal region of Uttarakhand. J. Herb. Drugs. 8(1), 59-59.

Lelono, R.A.A., Tachibana, S., Itoh, K., 2009. Isolation of antifungal compounds from Gardenia jasminoides. Pak. J. Biol. Sci. 12(13), 949-956.

Liao, P.C., Yang, T.S., Chou, J.C., Chen, J., Lee, S.C., Kuo, Y.S., Ho, C.L., Chao, L.K.P., 2015. Anti-inflammatory activity of neral and geranial isolated from fruits of Litsea cubeba Lour. J. Funct. Foods. 19(Part A), 248-258.

Liu, B.Z., Gao, Y., 2000. Analysis of headspace constituents of Gardenia flower by GC/MS with solid-phase microextraction and dynamic headspace sampling. Chin. J. Chromatogr. 18(5), 452-455.

Liu, H., Chen, Y.F., Li, F., Zhang, H.Y., 2013. Fructus gardenia (Gardenia jasminoides J. Ellis) phytochemistry, pharmacology of cardiovascular, and safety with the perspective of new drugs development. J. Asian Nat. Prod. Res. 15(1), 94-110.

Mai, M., Isoko, K., Hiroto, N., Hironari, M., Keiichiro, S., Yuko K., T., Tomoko, J., Kuramochi, K., Yoshida, H., Yoshiyuki, M., 2014. Suppression of allergic and inflammatory responses by essential oils derived from herbal plants and citrus fruits. Int. J. Mol. Med. 33(6), 1643-1651.

Muhammad, B.W., Nadia, Z.S., Fatima, H.E., Doaa, A.G., 2019. Antioxidant, anti-inflammatory, antiproliferative and antimicrobial activities of Combretum glutinosum and Gardenia aqualla extracts in vitro. Free Rad. Antioxid. 29(2), 66-72,

Nishijima, C.M., Ganev, E.G., Mazzardo-Martins, L., Martins, D.F., Rocha, L.R.M., Santos, A.R.S., Kiruma-Lima, C.A., 2014. Citral: A monoterpene with prophylactic and therapeutic anti-nociceptive effects in experimental models of acute and chronic pain.  Eur. J. Pharmacol. 736, 16-25.

Obuzor, G.U., Nwaokolo, M. I., 2011. Essential oil of Nigerian (Niger Delta) grown Gardenia jasminoide flower. Int. Arch. Appl. Sci. Technol. 1(1), 32-36.

Ogunwande, I.A., Avoseh, N.O., Olasunkanmi, K.N., Lawal, O.A., Ascrizzi, R., Guido, F., 2019a. Chemical composition, anti-nociceptive and anti-inflammatory and activities of essential oil of Bougainvillea glabra. J. Ethnopharmacol. 232, 188 -192.

Ogunwande, I.A., Avoseh, N.O., Igile, D.A., Lawal, O.A., Ascrizzi, R., Flamini, G., 2019b. Chemical constituents, anti-nociceptive and anti-inflammatory and activities of essential oil of Phyllathus muellerianus (O. Kuntze) Excell. Nat. Prod. Commun. 14(5), 1-7.

Park, S.Y., Jin, M.L., Kim, Y.H., Kim, Y., Lee, S.J., 2012a. Anti-inflammatory effects of aromatic-turmerone through blocking of NF-kappaB, JNK, and p38 MAPK signaling pathways in amyloid beta-stimulated microglia. Int. Immunopharmacol. 14(1), 13-20.

Park, S.Y., Kim, Y.H., Kim, Y., Lee, S.J., 2012. Aromatic-turmerone’s anti-inflammatory effects in microglial cells are mediated by protein kinase A and heme oxygenase-1 signaling. Neurochem. Int. 61, 767-777.

Phatak, R.S., 2017. Phytochemistry, pharmacological activities and intellectual property landscape of Gardenia jasminoides Ellis: a review. Pharmacog. J. 7(5), 254-265.

Pooja, V.K., Shang, Y.F., Zhang, Y.G., Heng, C., Ma, Y.L., Wei, Z.J., 2019. Comparative study of chemical compositions and antioxidant activities of Zhizi fruit extracts from different regions. Heliyon 5(12), e02853.

Sharifi-Rad, M., Elena, M.V., Bahare, S., Sharifi-Rad, J., Karl, R.M., Seyed, A.A., Farzad, K., Salam, A.I., Dima, M., Zainul, A.Z., Sharifi-Rad, M., Zubaida, Y., Marcello, I., Adriana, B., Daniela, R., 2017. Plants of the genus Zingiber as source of antimicrobial agents: from tradition to pharmacy. Molecules 22(12), 2145-2162.

Sung, Y.Y., Lee, A.Y., Kim, H.K., 2014. The Gardenia jasminoides extract and its constituent, geniposide, elicit anti-allergic effects on atopic dermatitis by inhibiting histamine in vitro and in vivo. J. Ethnopharmacol. 156(), 33-40.

Tan, Y.T., Xue, S., Tang, H.Z., 2012. Analysis of aroma constituents in Gardenia jasminoides at different flowering stages. Food Sci. 33(2), 205-207.

Wagan, T.A., Wanlun, C., Hua, H.X., 2018. Repellency, toxicity, and anti-oviposition of essential oil of Gardenia jasminoides and its four major chemical components against whiteflies and mites. Sci. Rep. 8, 9375.

Wang, Y., Chen, Y., Deng, L., Cai, S., Liu, J., Li, W., Du, L., Cui, G., Xu, X., Lu, T., Chen, P., Zhang, H.,2015. Systematic separation andpurification of iridoid glycosides and crocetin derivatives from Gardenia jasminoides Ellis by high-speed counter-current chromatography. Phytochem. Anal. 26(3), 202-208.

Yang, S., Liu, J., Jiao, J., Jiao, L., 2020. Ar-Turmerone exerts anti-proliferative and anti-inflammatory activities in HaCaT keratinocytes by inactivating Hedgehog pathway. Inflammat. 43(2), 478-486.

Xiao, W., Li, S., Wang, S., Ho, C.T., 22017. Chemistry and bioactivity of Gardenia jasminoides. J. Food Drug Anal. 25(1), 43-61.

Zhang, Y.H., Xiong, X.F., Xu, Y., 1999. Analysis of Hubei volatile oil of Gardenia flower by GC/MS. J. Wuhan Bot. Res. 17(1), 61-63.

 

 

Plant parts

Origin

Main constituents

References

Fruits

N.k

myristic acid (15.3%)

Bao et al., 2011

Flowers

N.k

linalool, myristic acid, benzyl aceate etc were among the volatiles present above 1%

Buchbauer et al., 1996

Flowers

China

linalool (27.73%), (Z)-3-hexenyl pentenoate (24.38%) and hexyl tiglate (11.42%)

Cai et al., 2008

Flowers

China

linalool (21.09%), camphene (7.25%), α-caryophyllene (6.49%), geraniol (5.72%) and α-farnesene (5.35%).

Gan et al., 2013

Flowers

‘’

methyl benzoate (32.34%), linalool (20.54%), cis-3-hexenyl tiglate (20.30%) and carveol (10.33%)

Guo et al., 1991

Flowers

‘’

jasmin lactone, cis-3-hexenol, esters of cis-3-hexenol, cis-3-hexenoic acid and tiglic acid a

Hattori et al., 1978

Flowers

China

linalool, β-myrcene, methyl benzoate, L-limonene, ocimene, cis-3-hexenyl tiglate and cis-3-hexenylisovalerate a

Hunag et al., 2004

Floral

N.k

farnesene, (Z)-3-hexenyl tiglate, (Z)-3-hexenyl benzoate and indole a

Kanlayavattanakul and Lourith, 2015

Flowers

China

farnesene (64.86%) and cis-ocimene (29.33 %)

Liu et al., 2000

Flowers

Nigeria

α-farnesene (28.41%), linalool (22.05%), trans-β-ocimene (10.59%) and α-terpineol (9.03%).

Obuzor and Nwakolo, 2011

Flowers

China

palmitic acid, linoleic acid, cis-13-octadedienoic acid, octadedienoic acid, squalene, and vitamin E a

Shang et al., 2019

Flowers

China

ocimene, α-farnesene, benzoic acid methyl ester, isopropyl cyclohexane and 3,7-dimethyl 1,6-octadiene-3-alcohol propionate a

Tan et al., 2012

Flowers

China

squalene, ethyl linoleate, n-hexadecanoic acid and 9-12-octadecadienoic a

Wagan et al., 2018

Flowers

China

linalool (17.92%), 7-decen-5-olide (9.11%) and cis-3-hexenyl tiglate (6.54%)

Zhang et al., 1991

Table 1

Chemical constituents of essential oils of Gardenia jasminoidesrepresented in the literature

aQuantitative composition not available; N.k. Not known

 


 

Table 2

Chemical constituents found in Gardenia jasminoidesleaf oil

Sr. No

Constituents a

LRIb

LRIc

Percentd

MI

1

Myrcene

993

992

0.8

RI, MS

2

Neral

1242

1243

4.6

RI, MS

3

Geraniol

1256

1256

3.3

RI, MS

4

Geranial

1271

1270

12.3

RI, MS, Co

5

Daucene

1381

1380e

0.4

RI, MS

6

Geranyl acetate

1383

1386

1.4

RI, MS

7

Neryl acetone

1436

1435

1.0

RI, MS

8

(E)-β-Ionone

1487

1488

0.7

RI, MS

9

Caryophyllene oxide

1582

1581

2.6

RI, MS

10

Humulene epoxide II

1607

1609

0.6

RI, MS, Co

11

Tetradecanal

1614

1613

2.2

RI, MS, Co

12

10-epi-γ-eudesmol

1619

1619

6.2

RI, MS, Co

13

α-Eudesmol

1653

1630

0.7

RI, MS

14

ar-Turmerone

1666

1658

8.1

RI, MS, Co

15

n-Heptadecane

1700

1700e

1.1

RI, MS, Co

16

Curlone

1701

1701

2.5

RI, MS, Co

17

Pentadecanal

1716

1715

49.2

RI, MS, Co

Total

97.7

 

Monoterpene hydrocarbons (Sr. No. 1)

0.8

 

Oxygenated monoterpenes (Sr. No. 2-4, 6)

21.6

 

Sesquiterpene hydrocarbons (Sr. No. 0.4)

0.4

 

Oxygenated sesquiterpenes (Sr. No. 9, 10, 12-14, 16)

20.7

 

Apocarotenes (Sr. No. 7, 8)

1.7

 

Long chain aldehydes (Sr. No. 11, 17)

51.4

 

Alkane (Sr. No. 15)

1.1

 

a Elution order on HP-5 Column; b Linear retention indices on HP-5 column; c Literature retention indices (NIST 2018); d SD Standard deviation were insignificant and excluded from the Table to avoid congestion; e, U.S. National Library of Medicine, PubChem, 2018; Sr. No, Serial number; MI, Mode of identification; RI, Retention indices, MS, Mass spectral, Co, Co-injection with known compounds

 

 

 

Ansari, F., Khare, S., Dubey, B.K., Joshi, A., Jain, A., Dhakad, S., 2019. Phytochemical analysis, antioxidant, antidiabetic and anti-inflammatory activity of bark of Gardenia latifolia. J. Drug Del. Therap. 9(1), 141-45.

Appalaraju, V.V., Ismail, N.E., Adimoolam, S., Xin, Y.T., 2019. Phytochemical screening and evaluation of anti-inflammatory activity of Gardenia carinata leaves. Front. Pharmacol. Conference Abstract: International Conference on Drug Discovery and Translational Medicine 2018 (ICDDTM '18) “Seizing Opportunities and Addressing Challenges of Precision Medicine”. doi: 0.3389/conf.fphar.2018.63.00097.

Avoseh, N.O., Ogunwande, I.A., Ebere, A., Hassan, N.., Dai, D.N., Ascrizzi, R., Flamini, G., 2020a. Pharmacology of Essential Oils: Chemical Constituents, Anti-Inflammatory and Anti-Nociceptive Activities of Essential Oils from Nigerian Plants, in: Kjeldsen, M.M. (Eds.), What to Know About Essential Oils. Nova Science Publisher, New York, pp. 59-102.

Avoseh, N.O., Ogunwande, I.A., Ojenike, G.O., Mtunzi, F.M., 2020b. Volatile composition, toxicity, analgesic and anti-inflammatoryactivities of Mucuna pruriens. Nat. Prod. Commun. 15(7), 1-9.

Bao, Y., Dong, J., Yuan. F., 2011. Effect of supercritical carbon dioxide extraction conditions on fatty acid composition and antioxidant activity of Gardenia fruit oil. Food Sci. 32(10), 12-17.

Buchbauer, G., Jirovetz, L., Alexej, N., Vijay, K.K., Norbert, W., 1996. Volatiles of the absolute of Gardenia jasminoides Ellis (Rubiaceae). J. Essent. Oil Res. 8(3), 241-245.

Cai, J., Zhao, C., Cheng, L., Zhang, Q.J., 2008. Study on the chemical components in flower essential oil of Gardenia jasminoides from Guizhou by SPME-GC-MS. Guizhou Sci. 15(3), 122-125.

Chang, W.L., Wang, H.Y., Shi, L.S., Lai, J.H., Lin, H.C., 2005. Immunosuppressive iridoids from the fruits of Gardenia jasminoides. J. Nat. Prod. 68(11), 1683-1685.

Chen, H., Xiao, Y.Q., Li, L., Zhang, C., 2007. Studies on chemical constituents in fruit of Gardenia jasminoides. Zhong Yao Za Zhi. 32(11), 1041-1043.

Chen, S., Zhao, X., Sun, P., Qian, J., Shi, Y., Wang, R., 2017. Preventive effect of Gardenia jasminoides on HCl/ethanol induced gastric injury in mice. J. Pharmacol. Sci. 133(1), 1-8.

Chen, S., Sun, P., Zhao, X., Yi, R., Qian, J., Shi, Y., Wang, R., 2017. Gardenia jasminoides has therapeutic effects on L‑NNA‑induced hypertension in vivo. Mol. Med. Rep. 15(6), 4360-4373.

Chowdhury, A., Shofiul, A., Mohammed, A.J., Kazi, O.F., Atiqul, I., 2014. Antibacterial activities and in vitro anti-inflammatory (membrane stability) properties of methanolic extracts of Gardenia coronaria leaves. Int. J. Microbiol. 2014: 410935.

Coura, C.O., Souza, R.B., Rodrigues, J.A.G., de Souza Oliveira, E.V., de Araujo, I.W.F., Ribeiro, N.A., Forta, A.F., Ribeiro, K.A., Chaves, H.V., pereira, K.M.A., da Cunha, R.M.S., Bezerra, M.M., Benevides, N.M.B., 2015. Mechanisms involved in the anti inflammatory action of a polysulfated fraction from Gracilaria cornea in rats. PLoS ONE. 10(3), 1-18.

Essien, E.E., Ogunwande, I.A., Setzer, W.N., Ekundayo, O. 2012. Chemical composition, antimicrobial and cytotoxicity studies on Solanum erianthum and Solanm macranthum essential oil. Pharm. Biol. 50(4), 474-480.

Ferreira, A.A., Amaral, F.A., Duarte, D.G., Oliveira, P.M., Alves, R.B., Silveira, D., Azevedo, A.O., Raslan, D.S., Castro, M.S.A., 2005. Antinociceptive effect from Ipomoea cairica extract. J. Ethnopharmacol. 105(1-2), 148-153.

Gan, X.H., Zhao, C., Zhao, Y., Zhou, X., 2013. Study on chemical constituents and antioxidant activity of essential oil from flowers of Gardenia jasminoides. Sci. Technol. Food Ind. 35(1), 77-79.

Guo, Z., Liu, L., Jin, B., Zhang, J.C., 1991. A study on chemical constituents of headspace volatiles which was extracted by supercritical carbon dioxide from fresh flowers of Gardenia jasminoides Ellis. Nat. Prod. Res. Dev. 3(3), 74-78.

Hattori, R., Shigeru, M., Toshio, Y., 1978. Chemical Composition of the absolute from Gardenia flower. Agric. Biol. Chem. 42(7), 1351-1356.

Helm, S., Trescot, A.M., Colson, J., Sehgal, N., Silverman, S., 2008. Opioid antagonists, partial agonists, and agonists/antagonists: The role of office-based detoxification. Pain Phy. 11(2), 225-235.

Hong, Y., Yang, K., 2013. Anti-inflammatory activities of crocetin derivatives from processed Gardenia jasminoides. Arch. Pharm. Res. 36(12), 933-940.

Hu, Y., Liu, X., Xia, Q., Yin, T., Bai, C., Wang, Z., Du, L., Li, X., Wang, W., Sun, L., Liu, Y., Zhang, H., Demg. L., Chen, Y., 2019. Comparative anti-arthritic investigation of iridoid glycosides and crocetin derivatives from Gardenia jasminoides Ellis in Freund's complete adjuvant-induced arthritis in rats. Phytomed. 53, 223-233.

Huang, Q.Q., Jiang, K.Z., Feng, J.Y., Chen, G.X., 2004. Analysis of volatile constituents of Gardenia flowers by GC/MS. Acta Bot. Yunn. 29(4), 471-474.

Huong, L.T., Huong, T.T., Bich, N.T., Viet, N.T., Giwa-Ajeniya, O.A., Ogunwande, I.A., 2020. Antimicrobial efficacy and chemical constituents of pseudo-stem essential oils from Zingiber castaneum. Trends Phytochem. Res. 4(2), 93-100.

Juhn, S.K., Jung, M.K., Hoffman, M.., Drew, B.R., Preciado, D.A., Sausen, N.J., Jung, T.T.K., Kim, B.Y., Park, S.Y., Lin, J., Ondrey F.G., Mains, R.S., Hunag, T. 2008. The role of inflammatory mediators in the pathogenesis of otitis media and sequelae. Clin. Exp. Otorhinolaryngol. 1(3), 117-118.

Kanlayavattanakul, M., Lourith, N., 2015. Volatile profile and sensory property of Gardenia jasminoides aroma extracts. J. Cosm. Sci. 66(6), 371-377.

Koo, H.J., Lim, K.H., Jung, H.J., Park, E.H., 2006. Anti-inflammatory evaluation of Gardenia extract, geniposide and genipin. J. Ethnopharmacol. 103(3), 496-500.

Kumar, R., Sethi, S., Om, P., Anil, K.P., Mahesh, K., Isidorov, V.A., Szczepaniak, L., 2017. Chemical composition of rhizome oleoresin and anti-inflammatory, antinociceptive and antipyretic activity of oleoresins of Alpinia allughas Roscoe. from Tarai region of Uttarakhand. Ind. J. Pharm. 28(3), 136-146.

Kumar, R., Om, P., Anil, K.P., Mahesh, K., Isidorov, V.A., Szczepaniak, L., 2017. Chemical composition and anti-inflamatory, anti -nociceptive and antipyretic activity of rhizome essential oil of Globba sessiliflora Sims. collected from Garhwal region of Uttarakhand. J. Herb. Drugs. 8(1), 59-59.

Lelono, R.A.A., Tachibana, S., Itoh, K., 2009. Isolation of antifungal compounds from Gardenia jasminoides. Pak. J. Biol. Sci. 12(13), 949-956.

Liao, P.C., Yang, T.S., Chou, J.C., Chen, J., Lee, S.C., Kuo, Y.S., Ho, C.L., Chao, L.K.P., 2015. Anti-inflammatory activity of neral and geranial isolated from fruits of Litsea cubeba Lour. J. Funct. Foods. 19(Part A), 248-258.

Liu, B.Z., Gao, Y., 2000. Analysis of headspace constituents of Gardenia flower by GC/MS with solid-phase microextraction and dynamic headspace sampling. Chin. J. Chromatogr. 18(5), 452-455.

Liu, H., Chen, Y.F., Li, F., Zhang, H.Y., 2013. Fructus gardenia (Gardenia jasminoides J. Ellis) phytochemistry, pharmacology of cardiovascular, and safety with the perspective of new drugs development. J. Asian Nat. Prod. Res. 15(1), 94-110.

Mai, M., Isoko, K., Hiroto, N., Hironari, M., Keiichiro, S., Yuko K., T., Tomoko, J., Kuramochi, K., Yoshida, H., Yoshiyuki, M., 2014. Suppression of allergic and inflammatory responses by essential oils derived from herbal plants and citrus fruits. Int. J. Mol. Med. 33(6), 1643-1651.

Muhammad, B.W., Nadia, Z.S., Fatima, H.E., Doaa, A.G., 2019. Antioxidant, anti-inflammatory, antiproliferative and antimicrobial activities of Combretum glutinosum and Gardenia aqualla extracts in vitro. Free Rad. Antioxid. 29(2), 66-72,

Nishijima, C.M., Ganev, E.G., Mazzardo-Martins, L., Martins, D.F., Rocha, L.R.M., Santos, A.R.S., Kiruma-Lima, C.A., 2014. Citral: A monoterpene with prophylactic and therapeutic anti-nociceptive effects in experimental models of acute and chronic pain.  Eur. J. Pharmacol. 736, 16-25.

Obuzor, G.U., Nwaokolo, M. I., 2011. Essential oil of Nigerian (Niger Delta) grown Gardenia jasminoide flower. Int. Arch. Appl. Sci. Technol. 1(1), 32-36.

Ogunwande, I.A., Avoseh, N.O., Olasunkanmi, K.N., Lawal, O.A., Ascrizzi, R., Guido, F., 2019a. Chemical composition, anti-nociceptive and anti-inflammatory and activities of essential oil of Bougainvillea glabra. J. Ethnopharmacol. 232, 188 -192.

Ogunwande, I.A., Avoseh, N.O., Igile, D.A., Lawal, O.A., Ascrizzi, R., Flamini, G., 2019b. Chemical constituents, anti-nociceptive and anti-inflammatory and activities of essential oil of Phyllathus muellerianus (O. Kuntze) Excell. Nat. Prod. Commun. 14(5), 1-7.

Park, S.Y., Jin, M.L., Kim, Y.H., Kim, Y., Lee, S.J., 2012a. Anti-inflammatory effects of aromatic-turmerone through blocking of NF-kappaB, JNK, and p38 MAPK signaling pathways in amyloid beta-stimulated microglia. Int. Immunopharmacol. 14(1), 13-20.

Park, S.Y., Kim, Y.H., Kim, Y., Lee, S.J., 2012. Aromatic-turmerone’s anti-inflammatory effects in microglial cells are mediated by protein kinase A and heme oxygenase-1 signaling. Neurochem. Int. 61, 767-777.

Phatak, R.S., 2017. Phytochemistry, pharmacological activities and intellectual property landscape of Gardenia jasminoides Ellis: a review. Pharmacog. J. 7(5), 254-265.

Pooja, V.K., Shang, Y.F., Zhang, Y.G., Heng, C., Ma, Y.L., Wei, Z.J., 2019. Comparative study of chemical compositions and antioxidant activities of Zhizi fruit extracts from different regions. Heliyon 5(12), e02853.

Sharifi-Rad, M., Elena, M.V., Bahare, S., Sharifi-Rad, J., Karl, R.M., Seyed, A.A., Farzad, K., Salam, A.I., Dima, M., Zainul, A.Z., Sharifi-Rad, M., Zubaida, Y., Marcello, I., Adriana, B., Daniela, R., 2017. Plants of the genus Zingiber as source of antimicrobial agents: from tradition to pharmacy. Molecules 22(12), 2145-2162.

Sung, Y.Y., Lee, A.Y., Kim, H.K., 2014. The Gardenia jasminoides extract and its constituent, geniposide, elicit anti-allergic effects on atopic dermatitis by inhibiting histamine in vitro and in vivo. J. Ethnopharmacol. 156(), 33-40.

Tan, Y.T., Xue, S., Tang, H.Z., 2012. Analysis of aroma constituents in Gardenia jasminoides at different flowering stages. Food Sci. 33(2), 205-207.

Wagan, T.A., Wanlun, C., Hua, H.X., 2018. Repellency, toxicity, and anti-oviposition of essential oil of Gardenia jasminoides and its four major chemical components against whiteflies and mites. Sci. Rep. 8, 9375.

Wang, Y., Chen, Y., Deng, L., Cai, S., Liu, J., Li, W., Du, L., Cui, G., Xu, X., Lu, T., Chen, P., Zhang, H.,2015. Systematic separation andpurification of iridoid glycosides and crocetin derivatives from Gardenia jasminoides Ellis by high-speed counter-current chromatography. Phytochem. Anal. 26(3), 202-208.

Yang, S., Liu, J., Jiao, J., Jiao, L., 2020. Ar-Turmerone exerts anti-proliferative and anti-inflammatory activities in HaCaT keratinocytes by inactivating Hedgehog pathway. Inflammat. 43(2), 478-486.

Xiao, W., Li, S., Wang, S., Ho, C.T., 22017. Chemistry and bioactivity of Gardenia jasminoides. J. Food Drug Anal. 25(1), 43-61.

Zhang, Y.H., Xiong, X.F., Xu, Y., 1999. Analysis of Hubei volatile oil of Gardenia flower by GC/MS. J. Wuhan Bot. Res. 17(1), 61-63.