Preliminary prospection of phytotherapic compounds from the essential oils from barks and leaves of Umburana (Commiphora Leptophloeos)

Abstract

The potential of the biome caatinga (exclusive from northeastern Brazil) has been evaluated in recent research for application in the pharmaceutical industry. Among the species of medicinal plants from caatinga, one can highlight the Commiphora leptophloeos (umburana), which has been used as infusions and syrups by the regional population for inflammatory and infectious diseases. Essential oils from umburana leaves and barks were obtained in a Clevenger apparatus and analyzed by gas chromatography/mass spectrometry, and total phenolic and flavonoids were determined by spectrophotometric analysis. It was observed that a large part of the major compounds present in the essential oil is described as having antitumor activity, enabling research in investigational oncology with umburana (C. leptophloeos). In addition, some little explored components have been identified, such as cadinene, alpha-selinene, and elemenone. Despite being easily found in several plants, there are no clinical trials involving their biological activity in a well-defined isolated form, which could make exploring new studies possible. Furthermore, the presence of phenolic compounds and flavonoids allows future studies about the potential antimicrobial and antioxidant activity.

Keywords:
Commiphora leptophloeos; Medicinal plant; Gas chromatography; Essential oil

INTRODUCTION

Plants are used as a therapeutic resource by a large part of the population due to the great variety of chemical substances with antimicrobial, expectorant, antiseptic, anti-inflammatory, and hepatoprotective properties (Dutra et al., 2016). However, popular culture often induces the use of plants without any scientific evidence, in the form of essential oil, extracts, infusions, or patches to treat common infections. Bioprospecting studies involving various aspects of plant biology and phytochemistry are proving the traditional uses of several plants for therapeutic purposes (Trentin et al., 2011; Dutra et al., 2016).

Brazil has one of the greatest biodiversity on the planet with the potential to provide products of natural origin, by the extraction of plants, and their respective active principles, for application in foods and drugs. The biome caatinga (exclusive from northeastern Brazil, with an area of around 735,000 km²) has a great diversity of plants with high biological potential and great interest in the pharmaceutical industry, being a key point for the development of prospecting studies of plants, aiming to use as phytotherapics (Trentin et al., 2011).

Among the species of medicinal plants of the caatinga, Commiphora leptophloeos (Mart.) J.B. Gillett is a resinous angiosperm adapted to semi-arid and desert climates that survive in total sun exposure. It has been used in the form of infusions and syrups, by indigenous populations, for inflammatory and infectious diseases (Pereira et al., 2017; Silva et al., 2017). Some studies have demonstrated its anti-inflammatory and healing potential, as too against gastritis, ulcers, bronchitis, coughs, inflammation of the urinary tract, and anesthetic and cytotoxic activities (Dong et al., 2017).

The literature register that secondary metabolites found in these species and other plants of the same genus are condensed tannins, anthocyanins, flavonoids, saponins, alkaloids, albumins, and sesquiterpenes (Dong et al., 2017; Fang et al., 2018).

Few studies on the detailed chemical composition of its essential oil have been reported. Most of the published studies on the chemical composition (by gas chromatographic analyzes) are related to other similar species such as C. guidottii (Yeo et al., 2016), C. myrrha (Ahamad et al., 2017), and C. mukull (Rhourrhi-Frih et al., 2012).

Because of the above, this work aims to evaluate in more detail the chemical composition of the essential oils of the Umburana bark and leaves and to indicate the potential phytotherapy application.

MATERIAL AND METHODS

Samples and Reagents

Samples of bark and leaves of Commiphora leptophloeos were collected in the “Barra da Onça Settlement” located in the city of Poço Redondo, Sergipe, Northeast Brazil (GPS 9° 48‘ 23“ S 37° 41’ 08W”). The exsiccate of the plant material was deposited in the herbarium of Tiradentes University - Aracaju/SE.

The collection of biological material was according to the SISBio (Biodiversity Authorization and Information System), linked to the Chico Mendes Institute for Biodiversity Conservation (ICMBio), under registry number 62387-5. It was also registered in the National System management of Genetic heritage and Traditional Associated Knowledge (SISGEN) under number AD82169.

The plant materials (barks and leaves) were sanitized with deionized water, dried in an oven at 50 ºC for 48 hours, and ground in a stainless-steel knife mill. A mixture of n-alkanes (C7-C37) (Supelco Park, PA, USA) was used in the gas chromatograph coupled to quadrupole mass spectrometry (GC/qMS) to calculate the retention index. The carrier gas used was Helium (He) with purities higher than 99.999%, obtained from White Martins (Aracaju, SE).

Essential oil extraction

The essential oil of C. leptophloeos was obtained by hydrodistillation in a graduated Clevenger apparatus using a method adapted from Hou et al. (2019). 50 g of plant material (leaves and bark) and 500 mL of distilled water was used for the extraction. The temperature was raised to 100 °C until boiling, then reduced to 75 °C and held for 2 hours. After extraction, the oil was collected and filtered in anhydrous sodium sulfate and stored in a vial protected from light with aluminum foil for further chromatographic analysis.

GC/qMS analysis

The chromatographic analysis was performed by GC/qMS (SHIMADZU-GCMS-QP2010-Ultra, Japan), with automatic injector AOC- 20 (SHIMADZU, AOC- 20i, Japan), capillary column SLB-5 (equivalent to 5% phenyl methyl silicone) with 60 m x 0.25 mm x 0.25 μm. Helium (99.999%) was used as carrier gas with a linear velocity of 31 cm s^-1.

Initially, 1 μL of the sample (1.000 mg L^-1 in dichloromethane) was injected in splitless mode. The temperatures of the injector, the interface, and the ion source were 280 ºC, ionization energy by electron impact (70 eV), and spectra scanning in masses in the range of 35 to 450 Daltons. The analysis was performed in the temperature ramp, with the initial temperature of 40 °C for 2 min, heating at 4 °C min^-1 until reaching the temperature of 300 °C, holding for 40 min.

Chromatography data were handled by the GCMS solution software, version 4.3. The identification of the compounds was performed by comparing the fragmentation profile of each compound with those present in the NIST 14 library (National Institute of Standards and Technology). Spectral similarity ≥ 80%, and Linear Temperature Programmed Retention Indices (LPTRI) with a maximum difference of 15 units for columns with similar polarities, were used as criteria for considering the compound tentatively identified. The retention index was automatically calculated by the software of the equipment, using a mixture of linear alkanes from seven to thirty- seven carbon atoms in the chain.

Total phenolic and flavonoids

The spectrophotometric analysis was performed in an equipment Shimadzu (model - 1900 UV-VIS, Japan) measured in triplicate in quartz cuvettes.

The total phenolic compounds of the essential oil were determined using the Folin-Ciocalteau reagent according to the methodology described by Djeridane et al. (2006). Five milligrams of each essential oil were weighed separately and transferred to volumetric flasks of 5 mL and completed their volume with methanol. After, 0.5 mL of this solution were added to test tubes, previously prepared with 2.5 mL of reagent Folin- Ciocalteau, distilled water (1:10) (v/v), and 2 mL of Na₂CO₃ solution 7.5 % (m/v). Subsequently, the test tubes with the samples were kept in a low-light environment and externally protected with aluminum foil for 2 hours. The absorbance was measured at 760 nm.

The flavonoid content was determined using the aluminum nitrate colorimetric method. as(Barbosa et al., 2019).

RESULTS AND DISCUSSION

Gas Chromatographic Analysis

The essential oil yield for the bark was 3.13% ± 0.30, while for the leaves it was 2.05% ± 0.24. These results may be justified by the resinous character of the plant. In addition, the extraction of the essential oil from leaves was more efficient when compared to the extraction performed by Da Silva et al. (2015) (Da Silva et al., 2015), which obtained only 0.08% oil using the same technique, but a higher amount of sample (150 g) and higher extraction time (4 h).

The chromatograms of the essential oils of barks and leaves of C. Leptophloeos can be viewed in Figure 1. It is possible to observe a different profile for each sample. In bark, the essential oil has highlighted the presence of compounds with lower boiling points, compared with the leaves essential oil.

FIGURE 1
Chromatogram analysis of the essential oil from C. leptophloeos barks (black) and leaves (pink) analyzed by GC/ qMS.

The complete identification of compounds can be found in the ^{Supplementary Electronic Material} (Table SI). This Table shows the tentatively identified compounds, retention time, chemical class of compounds, relative area (%), and retention index.

Figure 2 shows the distribution of relative area for each identified chemical class of compounds in both samples, while the main compounds (area % > 3 %) for at least one of the samples are presented in Figure 3.

FIGURE 2
Distribution of relative area for each identified chemical class of compounds.

FIGURE 3
Percentage area of the terpenes identified in the essential oil of barks and leaves from C. leptophloeos.

In the bark essential oil, 127 peaks were found, of which it was possible to identify 94 compounds (84.3%) and 29 remained without identification (15.7%). In the sample, sesquiterpenes present a larger percentage area (79.4%), followed by fatty acids (13.1%), aldehydes (3.1%), and esters (2.2%). Among the major compounds are β-caryophyllene, trans-α-bergamotene, α-selinene, δ-cadinene, β-elemenone, and hexadecenoic acid.

In the essential oil obtained from the leaves, 95 peaks were found, of which 83 compounds (87.3%) were tentatively identified and 12 were not identified (12.7%). In this sample, hydrocarbons correspond to 28.0%, sesquiterpenes 20.8%, and other classes are also present, such as sterols (19.1%), triterpenes (14.2%), fatty acids (6.3%), fatty alcohols (3.1%). Among the major compounds of leaf essential oil are β-elemenone, nonacosane, hentriacontane, γ-sitosterol, tritriacontane, lupeol, hexadecanoic acid, 5α-Stigmasta-7,16-dien-3β-ol.

Only one study was found in the literature (Da Silva et al., 2015), approaching the GC-MS analysis of essential oil of the C. leptophloeos leaves. In that work was observed the presence of only 55 compounds, with 46 tentatively identified compounds, being α-phellandrene, trans -caryophyllene, and β-phellandrene, the majors (Da Silva et al., 2015).

The antioxidant activity has been described in the literature for fatty acids (Elagbar et al., 2016) and gamma-sitosterol (Yoshida, Niki, 2003), a triterpene phytosterol present in the essential oil. Phytosterols have a well-known activity, being that one of the main, is the reduction of serum cholesterol and lipid levels (Styrczewska et al., 2015). In addition, triterpenes have been described as compounds that improve the quality of healing by regulating pro-and anti-inflammatory mediators, chemokines, growth factors, inducing granulation formation, re-epithelization, and wound contraction (Kim et al., 2013). Styrczewska et al. (2015) (Styrczewska et al., 2015). demonstrated the synergistic activity of cannabidiol with β-sitosterol inducing anti- inflammatory and collagen production activities, being phytosterol responsible for the matrix remodeling effect.

The essential oil of the leaves also presented lupeol as one of its major compounds, which presents involvement in the healing of cutaneous wounds by stimulating the migration of keratinocytes and increasing the contraction of fibroblasts in a collagen matrix (Beserra et al., 2018). Lupeol is a triterpene widely found in medicinal plants and has a varied pharmacological potency with anti-inflammatory, antioxidant, anti- infectious, antihyperglycemic, antiasthmatic, antiarthritic, cardioprotective, neuroprotective, hepatoprotective, and chemosensitizing effects (Badshah et al., 2016).

Wang et al. (2018) demonstrated the in vitro anti- cancer effect of lupeol by modifying cell viability, induction of apoptosis, migration, cell cycle arrest, and inactivation of Wnt-β-catenin signaling activity in human colorectal cancer cells. Other authors further suggest that this compound may be used in the future as an inhibitor of human osteosarcoma cell metastases (Hsu et al., 2019).

The γ-sitosterol, another phytosterol presented in leaves, has been described by its ability to increase the secretion of insulin in the presence of glucose (Sirikhansaeng et al., 2017) and anti-cancer activities interrupting the cell cycle causing apoptosis of cancer cells, being cytotoxic to cell lines the colon and liver (Endrini et al., 2014). Suttiarporn et al. (2015) also claim that phytosterol concentrations in the blood may increase the proliferation of antileukemic cells and suggest extraction of the compound for addition at higher doses in other foods and dietary supplements.

The identification and isolation of plant-derived antioxidant compounds may be a solution to treat a variety of lesions and diseases caused by oxidative stress, such as depression and hepatotoxicity (Mhalla et al., 2018).

Sesquiterpenes are the chemical class with the highest number of compounds in the essential oils of barks of C. Leptophloeos, being were found 63 sesquiterpenes (Table SI) corresponding to 67% of the total area of the chromatogram (considering the identified and unknown peaks).

As can be seen in Figures 1 and 3 the major compounds in sesquiterpenes were trans-α-bergamotene (10.8%), followed by trans-β-elemenone (5.3%), β-caryophyllene (5.1%) and α-selinene (4.4%). Already in the essential oil of leaves, 42 sesquiterpenes were found (Table SI) corresponding to only 18.5% (Figure 2) of the total area of the chromatogram. Although the essential oil of leaves of C. Leptophloeos presents many peaks of sesquiterpenes, the total percentual area was inferior when compared to the essential oil of the bark. The sesquiterpene that presented the highest relative area (Figure 4) was trans-β- Elemenone (6.3%).

FIGURE 4
Analytical curve for the analysis of phenols and flavonoids. a) Gallic acid with concentrations of 20, 40, 60, 80, 100 and 120 mg GAE g^-1 analyzed at 765 nm, b) Quercitina with concentrations of 20, 40, 60, 80, 100 mg QE g^-1 analyzed at 420 nm.

Govindarajan et al. (2018) identified the trans- β-elemenone compound as a major component in the essential oil of the pitanga leaves (Eugenia uniflora) and demonstrated efficacy against Anopheles subpictus, Aedes albopictus, and Culex tritaeniorhynchus larvae, as well as low toxicity for humans.

Another important compound of the essential oil, β-caryophyllene, is a bicyclic sesquiterpene with a cyclobutene ring also found in several plants, which has biological importance, anticonvulsive, antimalarial, antileishmanial, local anesthetic, spasmolytic and antimicrobial activities have been described (Fidyt et al., 2016). In addition, this compound has potential for the treatment of inflammatory diseases, atherosclerosis, ischemia, and cerebral inflammation (Viveros-Paredes et al., 2017; Hammad et al., 2018), as well as ischemic heart and liver lesions (Hammad et al., 2018).

As well as other compounds present in essential oil from C. leptophloeos that present anti-cancer activities, studies have already demonstrated that β-caryophyllene has chemo-preventive or antimutagenic properties, besides having an antioxidant role, being able to be desensitized chemo-resistant cancer cells when combined with other drugs (Di Giacomo et al., 2017 and 2018).

The trans-α-bergamotene compound has been identified as an active compound that can attract ectoparasites such as Melittobia digitata (wasps), serving as a trapping strategy, where pests are attracted away from the main crop (Yin, Wong 2019).

Li et al. (2017) found trans-α-bergamotene as one of the main compounds in the distilled fraction of basil oil and associated its presence with the ability of this oil in reducing inflammatory cytokines.

Several studies have identified the compounds α-selinene, cadinene, and elemenone, however, there is a deficiency of clinical trials demonstrating its isolated properties. Cadinene has recently been identified in the study by Zhu et al. (2019) which demonstrated its cytotoxicity and selectivity for the human liver cancer cell line. In general, studies have described such compounds as part of the class of sesquiterpenes with anti-inflammatory, bactericidal, antioxidant, and antitumor activities (Dutra et al., 2016; Fidyt et al., 2016; Viveros-Paredes et al., 2017).

Determination of phenolic and flavonoids compounds

The phenolic compounds have in their structure one or more hydroxyls directly connected to an aromatic ring. Flavonoids, inserted within phenolic compounds, are subdivided into flavonols, flavones, flavanones, anthocyanidins, and isoflavones according to their chemical structure (Singh et al., 2017; Gandhi et al., 2018).

For the analysis of phenolics compounds and flavonoids was constructed analytical curves which can be viewed in Figure 4.

The analytical curve for the quantification of the phenolic compounds showed a coefficient of determination of 0.9954 (Figure 4a), which reflects a high degree of linearity. The obtained polyphenols content, measured in mg GAE g^-ˡ, was 60.02 ± 0.19 for barks and 62.56 ± 0.2 for leaves.

These values were higher than those presented by Pereira et al. (2017) (Pereira et al., 2017), which obtained

20.3 ± 0.78 mg GAE g^-ˡ in its aqueous extract from barks obtained in Catimbau National Park (Pernambuco/ Brazil). Phenolic substances have a higher affinity for polar solvents such as ethyl alcohol (Tiwari et al., 2011), but high concentrations of these compounds were found in essential oil too.

The coefficient of determination obtained from the analytical curve for flavonoids was 0.9972 (Figure 4b). The total flavonoids of samples varied from 64.56 ± 0.2 mg QE g^-ˡ in essential oil from barks, slightly higher than the leaves, 57.18 ± 0.17 mg QE g^-ˡ.

The phenolic compounds tentatively identified by GC/qMS in the leaves correspond to only 2.15% of the area (eugenol, gamma-tocopherol, and α-tocopherol). In the bark sample, no phenolic compounds were identified. About f lavonoids, no component was tentatively identified in the samples by GC/qMS. The difficulty in identifying these classes of molecules is associated with the complexity of the sample since more than 10% of the area in both samples refers to unidentified compounds. For a more complete elucidation of these components, it is necessary to employ a methodology with greater separation power, such as comprehensive two-dimensional gas chromatography.

Phenolic compounds and flavonoids are described in the literature as they have important biological activities such as antioxidant (Rufino et al., 2009), immunomodulating (Talhaoui et al., 2016; Jarger, Parylak, Gage, 2018), anti-inflammatory (Oteiza et al., 2018), gastroprotective (Yousefian et al., 2018) and antimicrobial activity (Santos et al., 2015; Silva et al., 2016). The plant is responsible for the bactericidal activity against gram- positive bacteria E. faecalis, B. subtilis, M. luteus, and S. aureus, according to Pereira et al. (2017) (Pereira et al., 2017). This result may be promising for the evaluation of the bactericidal and bacteriostatic activity of these and other strains using the essential oil of Commiphora leptophloeos collected in the state of Sergipe.

CONCLUSIONS

In this work, several constituents of the essential oil of umburana (Commiphora leptophloeos) were tentatively identified, which present new biotechnological possibilities, indicating the beginning of great research involving plants of the caatinga biome of northeastern Brazil.

It was observed that the major compounds on the essential oil are known by their antitumor activity, creating the possibility of investigations in investigational oncology with the essential oil of umburana. Still, compounds little exploited, like cadinene, alpha-selinene, and elemenone, despite being easily found in several plants, have no clinical trials involving their biological activity in a well-defined isolated form, which could make possible the exploration in new studies.

The presence of phenolic compounds and flavonoids allows the exploration of studies with bactericidal activity investigation with strains of various bacteria, which helps in the possibility of new therapies against microbial resistance.

ACKNOWLEDGMENT

The author thanks CAPES and CNPq for the financial support.

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SUPPLEMENTARY ELECTRONIC MATERIAL

TABLE SI
Tentatively identified compounds in Essential Oils from barks and leaves of Commiphora Leptophloeos by GC/qMS

Compound name	Chemical Classes	R.T.	Area %		LTPRI			Reference (NIST WEB BOOK)
			Barks	Leaves	Exp	Lit.	Diff
1-Hexanol, 3,5,5-trimethyl	Alcohol	20.57	0.04	0.00	1039	1049	-10	Begnaud, Pérès, et al., 2003
Geraniol (2,6-Octadien-1-ol, 3,7-dimethyl)	Alcohol	28.85	0.07	0.00	1252	1260	-8	Cao, Li, et al., 2011
Isophytol	Alcohol	49.53	0.00	0.07	1947	1947	0	Todua, 2011
Phytol	Alcohol	53.47	0.00	1.84	2114	2114	0	Skaltsa, Mavrommati, et al., 2001
alcohols			0.11	1.91
Benzoic acid, octyl ester	Esters	44.54	0.13	0.00	1754	1757	-3	Korhonen, 1986,
abd-7,13(E)-dien-15-yl acetate	Esters	59.32	1.16	0.00	2387	2393	-6	Anastasaki, Demetzos, et al., 1999
Kolavenol acetate	Esters	59.88	0.72	0.00	2415	2412	3	Andriamaharavo, 2014
Octacosyl acetate	Esters	76.09	0.00	1.08	3215	3215	0	Zheng and White, 2008
esteres			2.02	1.08
Octanoic acid	Fatty acid	25.87	0.81	0.00	1172	1170	2	Andriamaharavo, 2014
Geranic acid	Fatty acid	32.27	0.02	0.30	1350	1355	-5	Andriamaharavo, 2014
Decanoic acid	Fatty acid	32.72	0.36	0.00	1363	1373	-10	Engel and Ratel, 2007
Tetradecanoic acid	Fatty acid	44.69	1.24	0.19	1760	1759	1	Lalel, Singh, et al., 2003
Pentadecanoic acid	Fatty acid	47.28	0.50	0.00	1858	1867	-9	Tret'yakov, 2008
9-Hexadecenoic acid	Fatty acid	49.35	0.25	0.00	1949	1957	-8	Tret'yakov, 2007
Hexadecanoic acid	Fatty acid	49.97	8.54	4.46	1966	1963	3	Yu, Liao, et al., 2007
Linolenic acid, methyl ester	Fatty acid	53.35	0.06	0.00	2109	2108	1	Rout, Rao, et al., 2007
9,12-Octadecadienoic acid	Fatty acid	53.92	1.27	0.00	2134	2133	1	Radulovic, Dordevic, et al., 2010
Linoleic acid	Fatty acid	54.17	0.00	0.72	2145	2144	1	Saroglou, Dorizas, et al., 2006
Octadecanoic acid	Fatty acid	54.62	0.00	0.59	2165	2166	-1	bin Jantan, Yalvema, et al., 2005
Palmitic acid β-monoglyceride	Fatty acid	61.93	0.00	0.54	2520	2519	1	Andriamaharavo, 2014
fatty acids			13.05	6.80
1-Hexacosanol	Fatty Alcohol	68.97	0.00	0.26	2907	2906	1	Andriamaharavo, 2014
Octacosanol	Fatty Alcohol	73.38	0.00	2.80	3113	3110	3	Andriamaharavo, 2014
fatty alcohols			0.00	3.05
Pentadecanal	Fatty Aldehyde	43.49	0.80	0.00	1715	1717	-2	Flamini, Tebano, et al., 2006
Heptadecanal	Fatty Aldehyde	48.92	0.00	0.18	1922	1922	0	Tkachev, Dobrotvorsky, et al., 2000
Tetradec-(7Z)-enal	Fatty Aldehyde	54.05	2.27	0.00	2140	2141	-1	Radulovic, Blagojevic, et al., 2009
fatty aldehydes			3.07	0.18
Hexadecanoic acid, methyl ester	Fatty Esters	49.14	0.19	0.00	1931	1926	5	Quijano, Salamanca, et al., 2007
Hexadecanoic acid, ethyl ester	Fatty Esters	50.63	0.00	0.06	1992	1992	0	Rout, Rao, et al., 2007
fatty esters			0.19	0.06
Decane, 4- methyl-	branched-alkane	21.17	0.05	0.00	1052	1054	-2	Oruna-Concha, Ames, et al., 2002
Decane, 5- methyl-	branched-alkane	21.27	0.15	0.00	1054	1057	-3	Rembold, Wallner, et al., 1989
Decane, 3- methyl-	branched-alkane	21.64	0.19	0.00	1068	1069	-1	Zaikin and Borisov, 2002
Decane, 2- methyl-	branched-alkane	22.13	0.13	0.00	1075	1076	-1	Saroglou, Marin, et al., 2007
Undecane, 5- methyl-	branched-alkane	25.46	0.08	0.00	1161	1159	2	Kallio, Jussila, et al., 2006
Undecane, 2- methyl-	branched-alkane	25.65	0.08	0.00	1166	1164	2	Kallio, Jussila, et al., 2006
branched alkanes			0.69	0.00
Undecane	n-alkane	23.06	0.11	0.00	1099	1100	-1	Standard
Dodecane	n-alkane	26.89	0.04	0.00	1200	1200	0	Standard
Tetracosane	n-alkane	59.58	0.00	0.10	2400	2400	0	Standard
Heptacosane	n-alkane	65.29	0.00	2.71	2700	2700	0	Standard
Octacosane	n-alkane	67.02	0.00	0.25	2799	2800	-1	Standard
Nonacosane	n-alkane	68.85	0.00	4.93	2901	2900	1	Standard
Triacontane	n-alkane	70.80	0.00	0.91	2999	3000	-1	Standard
Hentriacontane	n-alkane	73.14	0.00	10.55	3104	3100	4	Standard
Dotriacontane	n-alkane	75.69	0.00	1.31	3202	3200	2	Standard
Tritriacontane	n-alkane	78.85	0.00	6.38	3304	3300	4	Standard
Hexatriacontane	n-alkane	92.67	0.00	0.91	3607	3600	7	Standard
n-alkanes			0.14	28.04
6-Methyl-2-heptene-5-one	Ketone	18.47	0.06	0.00	985	982	3	Bastos, Ishimoto, et al., 2006
5,9-Undecadien-2-one, 6,10-dimethyl-, (Z)-	Ketone	35.55	0.05	0.00	1449	1456	-7	Xian Q., Chen H., et al., 2006
Phytone	Ketone	46.90	0.10	0.11	1843	1842	1	Bendiabdellah, El Amine Dib, et al., 2012
Farnesyl acetone	Ketone	48.72	0.10	0.75	1915	1913	2	Mondello, 2012
ketones			0.30	0.86
Hinokinin	Lignan	73.63	0.00	1.28	3103	3096	7	Andriamaharavo, 2014
Loliolide	ketone	45.57	0.00	0.22	1792	1784	8	Andriamaharavo, 2014
Eugenol	Phenols	32.66	0.00	0.03	1361	1365	-4	Mondello, Sciarrone, et al., 2007
others			0.00	1.54
Myrcene	Monoterpene	18.65	0.05	0.00	989	989	0	Dharmawan, Kasapis, et al., 2007
Ocimene (1,3,6-Octatriene, 3,7-dimethyl)	Monoterpene	20.98	0.05	0.00	1047	1048	-1	Dob, Dahmane, et al., 2006,
Linalool	Monoterpene	23.13	0.29	0.00	1100	1100	0	Cho, Namgung, et al., 2008
Linalool oxide <trans->	Monoterpene	26.21	0.00	0.03	1180	1176	4	Adams, 2017
Terpineol, cis-ß-	Monoterpene	27.03	0.11	0.00	1202	1207	-5	Cho, Namgung, et al., 2008
Myrtenyl acetate	Monoterpene	31.45	0.11	0.00	1326	1326	0	Houël., 2015
8-Hydroxylinalool	Monoterpene	32.84	0.00	0.04	1367	1367	0	Andriamaharavo, 2014
Isogermacrene D	Monoterpene	35.11	0.00	0.09	1435	1439	-4	Radulovic, Lazarevic, et al., 2007
monoterpenes			0.59	0.17
4,8,12,16-Tetramethylheptadecan-4-olide	Diterpenes	58.75	0.00	0.13	2359	2364	-5	Andriamaharavo, 2014
Methyl kolavenate	Diterpenes	59.16	0.50	0.00	2379	2372	7	Andriamaharavo, 2014
diterpenes			0.50	0.13
Supraene	Triterpene	67.40	0.00	0.80	2820	2822	-2	Steiner, Steidle, et al., 2005
Lup-20(29)-en-3-one	Triterpene	82.01	0.00	0.36	3390	3384	6	Andriamaharavo, 2014
Cycloartenol	Triterpene	84.59	0.00	2.32	3454	3466	-12	Andriamaharavo, 2014
Lupeol	Triterpene	85.04	0.00	9.24	3459	3450	9	Leite, 2018
Friedelan-3-one	Triterpene	87.36	0.00	1.47	3510	3511	-1	Andriamaharavo, 2014
triterpenes			0.00	14.19
Bicycloelemene	Sesquiterpene	32.06	0.23	0.00	1344	1338	6	Houël., 2015
α -Cubebene	Sesquiterpene	32.49	0.18	0.00	1357	1356	1	Cardeal, da Silva, et al., 2006
α -Copaene	Sesquiterpene	33.61	2.02	0.06	1389	1393	-4	Carasek and Pawliszyn, 2006
β -Elemene	Sesquiterpene	33.97	2.60	0.34	1400	1396	4	Gauvin-Bialecki and Marodon, 2009
β - Caryophyllene	Sesquiterpene	34.74	5.10	0.58	1424	1423	1	Houël., 2015
γ-Elemene	Sesquiterpene	34.97	0.53	0.00	1431	1432	-1	Houël., 2015
β -Ylangene	Sesquiterpene	35.03	0.21	0.04	1433	1431	2	Mosayebi, Amin, et al., 2008
Caryophyllene	Sesquiterpene	35.18	0.83	0.62	1438	1440	-3	Cardeal, da Silva, et al., 2006
trans- α -Bergamotene	Sesquiterpene	35.31	10.77	1.18	1442	1441	1	Benkaci-Ali, Baaliouamer, et al., 2007
β -Copaene	Sesquiterpene	35.46	0.34	0.11	1447	1437	10	Andriamaharavo, 2014
α -Guaiene	Sesquiterpene	35.50	0.04	0.00	1448	1446	2	Cardeal, da Silva, et al., 2006
β -Farmesene	Sesquiterpene	35.70	0.34	0.00	1454	1459	-5	Flamini, Cioni, et al., 2007
Aromandendrene	Sesquiterpene	35.77	1.50	0.00	1456	1447	9	Elias, Simoneit, et al., 1997
epi-β-Caryophylleno	Sesquiterpene	35.83	0.00	0.03	1458	1463	-5	Yu, Liao, et al., 2007
Valerena-4,7(11)-diene	Sesquiterpene	35.97	0.40	0.04	1462	1465	-3	Andriamaharavo, 2014
Cadina-3,5-diene	Sesquiterpene	36.05	0.06	0.00	1465	1457	8	Dickschat, Martens, et al., 2005
Alloaromadendrene	Sesquiterpene	36.22	0.37	0.00	1470	1464	6	Houël., 2015
Humulene < α ->	Sesquiterpene	36.34	0.48	0.25	1474	1467	7	Dharmawan, Kasapis, et al., 2007
Selina-4,11-diene	Sesquiterpene	36.51	3.11	0.45	1479	1476	3	Houël., 2015
ε-Cadinene -	Sesquiterpene	36.60	0.27	0.00	1482	1482	0	Houël., 2015
Germacrene D	Sesquiterpene	36.70	0.32	0.00	1485	1484	1	Houël., 2015
δ-Selinene -	Sesquiterpene	36.82	2.86	0.12	1489	1489	0	Houël., 2015
β-Selinene	Sesquiterpene	36.93	0.32	0.00	1492	1493	-1	Houël., 2015
Curzerene	Sesquiterpene	37.14	0.56	0.17	1499	1497	2	Houël., 2015
α-Selinene	Sesquiterpene	37.43	4.36	1.91	1508	1499	9	Houël., 2015
α -Muurolene	Sesquiterpene	37.54	1.19	0.11	1512	1517	-5	Jalali-Heravi, Zekavat, et al., 2006
Germacrene A -	Sesquiterpene	37.59	0.45	0.00	1513	1510	3	Houël., 2015
β -Bisabolene	Sesquiterpene	37.64	2.06	0.79	1515	1514	1	Andriamaharavo, 2014
γ-Cadinene	Sesquiterpene	37.78	0.32	0.03	1520	1515	5	Houël., 2015
δ-Cadinene	Sesquiterpene	38.06	0.67	0.09	1529	1519	10	Houël., 2015
Cadinene <delta->	Sesquiterpene	38.15	3.62	0.19	1532	1534	-2	Houël., 2015
Calamenene <trans->	Sesquiterpene	38.27	1.19	0.00	1536	1524	12	Houël., 2015
ο-Cadinene -	Sesquiterpene	38.38	1.06	0.30	1540	1538	2	Houël., 2015
Elemol	Sesquiterpene	38.73	0.62	0.27	1551	1549	2	Houël., 2015
Germacrene B	Sesquiterpene	38.86	2.60	0.00	1555	1557	-2	Oliveira, Leitao, et al., 2006
α -Calacorene	Sesquiterpene	38.91	0.26	0.00	1557	1547	10	Andriamaharavo, 2014
Selina-3,7(11)-diene	Sesquiterpene	39.02	2.39	0.00	1561	1562	-1	Facey, Porter, et al., 2005
Palustrol	Sesquiterpene	39.94	0.81	0.00	1591	1581	10	Courtois, Paine, et al., 2009
Spathulenol	Sesquiterpene	40.06	3.27	0.12	1595	1594	1	Sabulal, Dan, et al., 2007
Ledol (Globulol)	Sesquiterpene	40.19	0.17	2.12	1600	1608	-9	Shivashankar, Roy, et al., 2012
Caryophyllene oxide	Sesquiterpene	40.36	0.24	0.31	1605	1612	-7	Eyres, Marriott, et al., 2007
Epiglobulol	Sesquiterpene	40.44	1.37	0.88	1608	1608	0	Skaltsa, Mavrommati, et al., 2001
Elemenone<trans-beta->	Sesquiterpene	40.64	5.22	6.28	1615	1607	8	Andriamaharavo, 2014
Viridiflorol	Sesquiterpene	40.71	1.62	0.09	1618	1609	9	Andriamaharavo, 2014
Isospathulenol	Sesquiterpene	41.03	1.88	0.26	1612	1608	4	Dehghan, Solaimanian, et al., 2007
Humulene epoxide II	Sesquiterpene	41.18	0.31	0.12	1634	1635	-1	Cardeal, da Silva, et al., 2006
Germacrone	Sesquiterpene	41.38	0.15	0.00	1649	1658	-9	Marongiu, Piras, et al., 2005
Di-epi-1,10-cubenol	Sesquiterpene	41.54	1.16	0.46	1647	1640	7	Bertoli, Lepnardi, et al., 2011
β -Acorenol	Sesquiterpene	41.74	0.11	0.00	1643	1639	6	Rout, Naik, et al., 2006
Pogostol	Sesquiterpene	41.77	0.32	0.00	1654	1651	3	Adams, 2017
Bulnesol	Sesquiterpene	41.96	0.04	0.00	1661	1670	-9	Adams, 2017
tau-Muurolol	Sesquiterpene	41.99	2.31	0.08	1652	1641	11	Radulovic, Blagojevic, et al., 2010
α -Muurolol	Sesquiterpene	42.01	0.24	0.00	1663	1654	9	Radulovic, Blagojevic, et al., 2010
Intermedeol	Sesquiterpene	42.08	0.00	0.10	1665	1667	-2	Andriamaharavo, 2014
Aristol-1(10)-en-9-ol	Sesquiterpene	42.29	0.24	0.00	1672	1680	-8	Andriamaharavo, 2014
α -Cadinol	Sesquiterpene	42.34	1.15	0.17	1674	1668	6	Kim, Lee, et al., 2003
7-epi-α-Eudesmol	Sesquiterpene	42.43	0.45	0.36	1668	1659	9	Simoniatto, Bonani, et al., 2007
tau-Cadinol	Sesquiterpene	42.53	0.26	0.27	1681	1679	2	Phutdhawong, Kawaree, et al., 2007
Bisabolol <alpha->	Sesquiterpene	42.60	0.40	0.00	1683	1682	1	Benkaci-Ali, Baaliouamer, et al., 2007
α -Bisabolol	Sesquiterpene	42.89	1.12	0.15	1694	1697	-4	Sabulal, Dan, et al., 2007
Longifolol	Sesquiterpene	43.28	0.00	0.20	1707	1713	-6	Adams, 2017
(1R,7S)-Germacra-4(15),5,10(14)-trien-1β-ol	Sesquiterpene	43.36	0.00	0.09	1701	1695	6	Andriamaharavo, 2014
Nootkatol	Sesquiterpene	43.52	0.17	0.00	1717	1715	2	Adams, Habte, et al., 2004
Germacrone	Sesquiterpene	43.62	0.00	0.20	1716	1708	8	Andriamaharavo, 2014
Juniper camphor	Sesquiterpene	43.65	1.35	0.00	1719	1709	10	Andriamaharavo, 2014
Bisabolone	Sesquiterpene	44.58	0.33	0.00	1755	1755	0	Tuberoso, Kowalczyk, et al., 2005
Isovalencenol	Sesquiterpene	45.43	0.40	0.13	1787	1793	-6	Adams, 2017
Neophytadiene	Sesquiterpene	46.71	0.05	0.55	1836	1841	-6	Andriamaharavo, 2014
Curcumenone	Sesquiterpene	47.11	0.00	0.17	1851	1844	7	Andriamaharavo, 2014
sesquiterpenes			79.35	20.80
Ergost-5-en-3-ol, (3β.)-	Sterols	77.93	0.00	1.19	3275	-		n.i.
gamma-Sitosterol	Sterols	81.04	0.00	7.25	3359	3351	8	Andriamaharavo, 2014
5α-Stigmasta-7,16-dien-3β-ol	Sterols	82.94	0.00	10.62	3412	3401	11	Radulovic and Dordevic, 2011
sterols			0.00	19.06
gamma-Tocopherol	Tocopherols	72.42	0.00	0.89	3072	3074	-2	Andriamaharavo, 2014
DL - α -Tocopherol	Tocopherols	74.40	0.00	1.23	3152	3150	3	Andriamaharavo, 2014
tocopherols			0.00	2.12

Publication Dates

• Publication in this collection
  16 Jan 2023
• Date of issue
  2022

History

• Received
  23 July 2021
• Accepted
  18 Dec 2021