Anti-melanoma cancer activity and chemical profile of the essential oil of Seseli yunnanense Franch

Lili Chen; Xiaoling Ju; Xuemei Wu; Zongbao Zuo

doi:10.1515/chem-2024-0080

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Anti-melanoma cancer activity and chemical profile of the essential oil of Seseli yunnanense Franch

Lili Chen , Xiaoling Ju , Xuemei Wu and Zongbao Zuo

Published/Copyright: September 30, 2024

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From the journal Open Chemistry Volume 22 Issue 1

Abstract

Seseli yunnanense appertains to the Apiaceae family. S. yunnanense is known as an herbal remedy to treat several illnesses in Chinese traditional medicine. In this research, the essential oil (EO) of the aerial part of S. yunnanense (SYEO) was isolated by hydro-distillation apparatus. The chemical composition of the volatile oil was recognized using Gas chromatography (GC)/flame ionization detector and GC-Mass spectrometry methods. 1,1-Diphenyl-2-picrylhydrazyl and MTT assays were carried out to investigate the antioxidant and anti-melanoma cancer activity of the oil. The chromatography results showed SYEO was dominated by sesquiterpenes of α-bisabolol 40.19%, β-eudesmol 13.12%, and the phenolic compound eugenol 12.06%. SYEO scavenged the free radical of DPPH by IC₅₀ of 454.66 ± 7.25 μg/mL. In the MTT assay, SYEO showed a dose depending on the viability of the melanoma cell lines of HMV-II, SK-ML-2, G-361, and HT144. The highest activity was obtained against the HMV-II cell line with IC₅₀ of 116.82 ± 2.34 μg/mL. The cytotoxicity of SYEO was examined against HUVEC cell lines. The results exhibited the safety of EO for the human normal cells. The results showed the EO of S. yunnanense is a potent agent for treating melanoma cancer.

Keywords: Seseli yunnanense ; α-bisabolol; β-eudesmol; eugenol; melanoma cancer

1 Introduction

Skin color is determined by pigments like melanin in the epidermis, serving a crucial role in shielding the skin against UV rays and external aggressors. Nevertheless, excessive production and accumulation of melanin on the skin may lead to skin-related issues [1,2]. Melanocytes, originating from the neural crest, predominantly reside in the basal layer of the epidermis in human skin, although they can also be found in areas such as the hair follicle, uvea, mucosal epithelia, and meninges. These cells generate two types of melanin pigment, eumelanin (black/brown) and pheomelanin (red/blond), both derived from the precursor tyrosine [3]. Melanoma, a prevalent form of cancer affecting melanocytes in skin tissue, has been on the rise globally over the past decades [3,4]. It is a malignancy of melanocytes, the pigment-producing cells located in the basal layer of the epidermis, originating from the neural crest and exhibiting the expression of various signaling molecules and factors that facilitate migration and metastasis post-malignant transformation [3]. Despite the advancements in understanding the molecular, pathological, and biological aspects of melanoma, the disease continues to present significant challenges, particularly in advanced stages due to drug resistance. This underscores the critical need for the identification of innovative and efficacious treatments [5].

In recent years, plant-derived compounds have demonstrated their efficacy in treating various diseases, including melanoma [6]. Essential oils (EOs) extracted from plants are known for their diverse functional properties, such as potent antibacterial effects, anti-aging properties, and skin regeneration effects [1,7]. These EOs are considered safe for pharmaceutical use and could serve as a natural source of anticancer agents, warranting further research to understand their mechanisms of action and validate their potential clinical applications as alternative or complementary antitumor agents [6]. EOs, as herbal remedies, have a rich history of use in traditional medicine. Numerous in vitro and in vivo studies have investigated the antibacterial, antifungal, anti-inflammatory, and anticancer properties of EOs, highlighting their therapeutic potential in the treatment of various conditions, including cancer [8].

The Apiaceae family of flowering plants is well-known for its distinctive inflorescences and fruits, as well as the diverse chemistry that gives rise to the characteristic odor, flavor, and sometimes toxicity of many of its members. This family comprises approximately 300 genera and 2,500–3,000 species found worldwide [9]. Within the Apiaceae family, the genus Seseli stands out with 100–120 species distributed from Europe to East Asia [9,10]. Seseli consists of aromatic herbs and economically significant species that have been utilized in folk medicine since ancient times. These herbs have been traditionally incorporated into daily nutrition for health maintenance and medicinal purposes, with their use often based on ethnopharmacological studies [11]. Species of the genus Seseli demonstrate a range of beneficial properties, including antimicrobial and insect repellent activities, emmenagogue and anti-flatulence effects, anti-inflammatory and antinociceptive properties, anti-tumor and antirheumatic characteristics, as well as a protective effect on DNA from human lymphocytes. Additionally, the EOs derived from Seseli species exhibit antimicrobial and antifungal activities, further highlighting the therapeutic potential of these plants [12,13,14,15,16]. Seseli yunnanense Franch is one of the Seseli plants distributed in different regions [17]. The plant is used to cure several diseases in traditional Chinese medicine [18]. It is a remedy to treat cold, flu, joint pain, and rheumatism. The plant is also used for skin problems and digestive tract [19,20,21]. So far, there is no report on the chemical profile of Seseli yunnanense essential oil (SYEO) and no study on its anti-cancer activity against melanoma cell lines. In this research, we focused on the isolation of the EO of the plant and the recognition of the phytochemical constituents as well as study the anticancer activity of SYEO against melanoma cancer cell lines, namely, HMV-II, SK-ML-2, G-361, and HT144. Furthermore, the cytotoxicity of SYEO was measured against the normal cell line of HUVEC. The DPPH assay was run to study the antioxidant activity of SYEO.

2 Experimental methods

2.1 Materials

1,1-Diphenyl-2-picrylhydrazyl (DPPH), butylhydroxytoluene (BHT), and Na₂SO₄ were purchased from Merck. Dabrafenib (Dab) was purchased from Zhengzhou Alfa. C8–C20 and C21–C40) were from Fluka. The carcinoma cell lines of HMV-II, SK-ML-2, G-361, and HT144, and normal cells line (HUVEC) were purchased from the Beijing Bestopbio Technology Co., Ltd, China.

2.2 Plant material

The aerial parts of S. yunnanense were collected from its natural habitat near Liuyan in the west of Nanchang, China. The plant parts were washed with tap water and kept in a cold place (4°C) before the extraction of the EO.

2.3 Isolation of SYEO

Hydrodistillation of plant sample weighing 100 g was performed in a Clevenger apparatus for 4 h. This distillation process was iterated five times to extract the EO. The resulting oil was dehydrated using Na₂SO₄ at room temperature and then preserved in a sealed vial, stored at −20°C in a dark environment, in preparation for subsequent biological and analytical examinations.

2.4 Gas chromatography analysis

2.4.1 GC/FID analysis

The ES extracted was analyzed using GC with FID on a Hewlett-Packard 5890 GC system. The analysis utilized a DB-5 capillary column (30 m × 0.25 mm i.d.; film thickness 0.1 mm; J.W. Scientific, USA). Helium gas served as the carrier gas at the rate of 1.0 mL/min. The injector and detector were maintained at a temperature of 250°C. The temperature program involved an initial holding at 40°C for 2 min, followed by a ramping rate of 3°C/min until reaching 240°C, where it was held for 10 min. The split ratio was set at 1:20, and hydrogen was utilized as the fuel in the detector. To quantify the components present, an external standard method was employed. Calibration curves were constructed by running GC analyses of a Homologous series of saturated hydrocarbons (C8–C20 and C21–C40) using the same column and conditions to measure retention indices.

2.4.2 GC/mass spectrometry (MS) analysis

For the GC-MS analysis of SYEO, an Agilent GC/MS system was utilized, comprising a 7,890A GC system coupled with an Agilent 5975C mass detector. The analysis was performed with the sample injected into an HP-5 capillary column (30 m × 0.32 mm i.d.; 0.25 mm film thickness from J.W. Scientific). The analytical parameters matched the GC/FID conditions, maintaining consistency in the analysis protocol. 70 eV ionization voltage was applied, and the mass detector scanned a mass range of 50–600 atomic mass units (amu) to capture a comprehensive spectrum of compounds present in the EO sample.

2.4.3 Component identification

To identify the chemical constituents present in the volatile oil, a combination of methods was employed: GC retention indices and retention time: Kovats indices and retention times were utilized to compare with literature data [22] and NIST standard database information [23] to help identify known compounds based on their elution order and retention times. Mass spectral fragmentation patterns: Mass spectral fragmentation patterns were used to compare with known compounds from literature data and the NIST database. This aids in confirming the presence of specific compounds by matching their mass spectra. Furthermore, structural assignment confirmation was achieved by co-injecting the EO with authentic pure samples of known compounds. This method helps in verifying the identity of specific components in the volatile oil. The quantification of compounds present in the EO was carried out using an external standard method. Calibration curves generated from running GC analyses of representative compounds facilitated accurate quantification of individual components within the sample.

2.4.4 Antioxidant activity assay

In the experiment conducted, a 0.5 mL portion of SYEO solution in acetone (at various concentrations) was mixed with 1 mL of DPPH (0.001 M) and then agitated. After a 2 h incubation period, the optical density was measured at 517 nm [24]. The Radical scavenging activity percentage (RSA%) was calculated using the following formula:

RSA % = ( A c − A s ) A c × 100 ,

where A _c represents the control absorbance (DPPH solution), and A_s signifies the sample absorbance.

2.5 MTT assay

In this research study, HMV-II, SK-MEL-2, G-361, and HT144 were utilized to investigate anti-human melanoma cancer. The HUVEC cell lines were selected to evaluate the cytotoxic effects of SYEO. The experimental procedure was conducted based on previous studies with some adjustments [25,26]. The cell lines were cultured at a density of 1 × 10⁴ cells/well in a microplate and then kept in an incubator at 37°C with 5% CO₂ for 24 h. Subsequently, varying concentrations of SYEO were added to the wells and further incubated for 24 h. After the respective incubation periods, 20 µL of MTT solution (5 mg/mL in PBS) was introduced and left to incubate at 37°C for 4 h. The absorbance of the resulting formazan crystals dissolved in DMSO was measured using a plate reader (Thermo Lab systems, Franklin, MA USA). The IC₅₀ value, representing the concentration of SYEO required for a 50% mortality rate, was determined utilizing Prism software. Each treatment was repeated three times for robustness and accuracy. Dab (0.3 μM) was used as the positive control.

3 Results and discussion

3.1 Chemical composition of SYEO

The Seseli yunnanense volatile oil was collected in a light-yellow color with 0.22 ± 0.04% (W/W) for yield percentage. The density of the EO was calculated for 0.92 ± 0.02 g/mL. Overall, 19 compounds were diagnosed for 91.35% of the EO composition. The compounds were classified into six groups (Table 1). SYEO was dominated by oxygenated sesquiterpenes (57.08%) followed by phenolic compounds (12.06%) and hydrocarbon compounds (10.99%). The results showed the oxygenated sesquiterpenes of α-bisabolol 40.19%, β-eudesmol 13.12%, germacrene B 4.54%, and phenolic compound of eugenol 12.06% as the major compounds of SYEO. The obtained chromatogram of SYEO is presented in Figure 1.

Table 1

Chemical constituents of the aerial parts SYEO

No.	Compounds name	RI*	RI**	Area (%)	Class
1	Decane	1,000	1,004	2.66	HC
2	Limonene	1,024	1,026	0.55	MH
3	4-Terpinenol	1,174	1,176	0.74	OM
4	Crypton	1,183	1,180	0.74	OH
5	Dodecane	1,200	1,198	2.73	HC
6	trans-Carveol	1,215	1,213	0.67	OM
7	Carvone	1,239	1,240	0.51	OM
8	Tridecane	1,300	1,302	0.55	HC
9	Eugenol	1,356	1,352	12.06	PH
10	Tetradecane	1,400	1,401	2.44	HC
11	γ-Elemene	1,434	1,430	1.11	SH
12	α-Curcumene	1,479	1,481	0.97	SH
13	α-Amorphene	1,483	1,482	0.42	SH
14	β-Bisabolene	1,505	1,508	0.97	SH
15	Elemol	1,548	1,552	1.04	OS
16	Germacrene B	1,559	1,563	4.54	SH
17	Hexadecane	1,600	1,605	2.61	HC
18	β-Eudesmol	1,649	1,652	13.12	OS
19	α-Bisabolol oxide B	1,656	1,661	2.73	OS
20	α-Bisabolol	1,685	1,690	40.19	OS

Class of compounds
Monoterpene hydrocarbons (MH)	0.55
Oxygenated hydrocarbons (OH)	0.74
Oxygenated monoterpenes (OM)	1.92
Sesquiterpene hydrocarbons (SH)	8.01
Hydrocarbon compounds (HC)	10.99
Phenolic compounds (Ph)	12.06
Oxygenated sesquiterpenes (OS)	57.08
Total	91.35

RI*: Retention indices from literature (Adams 2007); RI**: Retention indices on DB-5.

Figure 1

The chromatogram of SYEO.

Many research groups around the world have reported the chemical compositions of the EOs of the other species of Seseli. The results of some reports are summarized here: α-pinene, Limonene, camphene for S. rigidum [11,27,28]; β-pinene, germacrene D, sabinene for S. montanum [29]; sabinene, α-pinene, β-phellandrene for S. globiferum [30]; β-pinene, α-pinene, cis-β-ocimene for S. tortuosum [31]; terpinolene, γ-terpinene, p-cymene for S. gracile [32]; α-pinene, caryophyllene oxide, germacrene D for S. pallasii [33]; α-Selinene, germacrene D, caryophyllene oxide for S. annuum [10]; sabinene, α-pinene, α-phellandrene for S. rhodopeum [34]; α-pinene, β-pinene, (E)-sesquilavandulol for S. campestre [35] were reported as the main constituent for the mentioned plants. (E)-p-ocimene, myrcene, and (Z)-p-ocimene were recognized as the major constituents of the EO of Lomatopodium staurophyllum synonym of S. staurophyllum by Sefidkon et al. [36]. On the other hand, germacrene B, isospathulenol, and germacrene D were identified as the major components of Libanotis transcaucasica synonym of S. transcaucasica [37]. A comparison of the obtained results of the present study with the reported major compounds of the other Seseli genus reveals a difference between the major components of SYEO and those of the other species; however, germacrene B was reported as one of the major compounds of S. transcaucasica. A summary of the class of compounds of various Seseli species is tabulated in Table 2. The EOs of most species are dominated by monoterpene hydrocarbons, sesquiterpene hydrocarbons, and oxygenated sesquiterpenes. Different factors such as geography, climate, age, and genetics could be responsible for the observed variation in the main constituents and the classes of compounds for various Seseli species [25,38,39].

Table 2

Main class of compounds for various Seseli species EO

Plant name	Class of the major compounds	Ref.
S. yunnanense	Oxygenated sesquiterpenes phenolic compounds hydrocarbon compounds	Present study
S. rigidum	Monoterpene hydrocarbons	[11,27,28]
S. montanum	Monoterpene hydrocarbons	[29]
S. montanum	Sesquiterpene hydrocarbons	[29]
S. globiferum	Monoterpene hydrocarbons	[30]
S. tortuosum	Monoterpene hydrocarbons	[32]
S. gracile	Monoterpene hydrocarbons	[32]
S. pallasii	Monoterpene hydrocarbons	[33]
	Oxygenated sesquiterpenes
	Sesquiterpene hydrocarbons
S. annuum	Sesquiterpene hydrocarbons	[10]
S. annuum	Oxygenated sesquiterpenes	[10]
S. rhodopeum	Monoterpene hydrocarbons	[34]
S. rhodopeum	Sesquiterpene hydrocarbons	[34]
S. campestre	Monoterpene hydrocarbons	[35]
S. campestre	Oxygenated sesquiterpenes	[35]
S. staumpbyllum	Monoterpene hydrocarbons	[36]
Seseli transcaucasica	Sesquiterpene hydrocarbons	[37]

4 Antioxidant activity of SYEO

From ancient times, people have relied on medicinal plants to enhance their health and address various illnesses. In modern times, the prevalence of oxidative stress and free radical-induced cell damage is on the rise, playing a crucial role in the development of many chronic conditions, such as cardiovascular diseases, inflammatory disorders, diabetes, and cancer [40,41]. Natural antioxidants derived from both secondary and primary metabolites found in aromatic and medicinal plants have emerged as potent agents in combating oxidative stress and protecting cells from free radical damage. These plant-derived compounds exhibit strong antioxidant properties, offering potential protective effects against the development and progression of various ailments associated with oxidative stress, emphasizing their importance in contemporary healthcare and disease prevention strategies [40,41,42]. In the present study, the DPPH assay was conducted to evaluate the antioxidant activity of SYEO. The antioxidant activity of SYEO is shown in Figure 2. The oil scavenged the DPPH radical with IC₅₀ of 454.66 ± 7.25 μg/mL. The antioxidant activity of the plant’s EOs depends on the chemical composition of the oil. SYEO is dominated by oxygenated sesquiterpenes and phenolic compounds. So far, the antioxidant activity of this class of compounds has been reported by many research groups [41,42,43]. The results showed less antioxidant activity of SYEO in comparison to the synthetic antioxidant of BHT as the selected positive control (IC₅₀ = 171.60 ± 1.79) μg/mL

Figure 2

The antioxidant activity of SYEO and BHT using DPPH assay.

4.1 Anti-melanoma cancer activity of SYEO

Cancer has been a major contributor to high illness rates among humans in recent decades. Extensive cancer research has shown that the emergence of aggressive, metastatic tumors stems from a complicated interaction of factors, such as the rapid growth and dissemination of abnormal cells [44]. Various triggers such as radiation, chemical substances, viruses, genetic abnormalities, mutations, defective genes, and disrupted cellular processes contribute to carcinogenesis. While numerous cancer therapy options exist, some may fall short due to adverse side effects or increased resistance to conventional anticancer drugs. Conventional treatments also impact healthy cells, posing additional risks. Natural compounds with demonstrated in vitro anticancer activity offer a promising alternative for researchers, influencing a broad spectrum of cellular functions including growth, differentiation, metastasis, apoptosis, and DNA repair. These compounds are valued for their lower toxicity and higher tolerability at increased doses compared to traditional chemotherapy drugs [45,46,47]. EOs, extracted from fragrant plants, have been extensively used in traditional medicine. They have been thoroughly studied in vitro and in vivo to investigate their antibacterial, antifungal, anti-inflammatory, and anticancer properties. Cancer and complementary medicine researchers are primarily focused on boosting the biological effects of plant components such as EOs [5,8].

In a particular study, the anticancer potential of a specific EO, referred to as SYEO, was evaluated on various melanoma cell lines. The results indicated a dose-dependent decrease in cell viability upon treatment with SYEO, with significant anticancer activity observed against the tested melanoma cell lines. The concentration of SYEO required to induce cell death in 50% of malignant cells was determined as the IC₅₀. The results are presented in Figure 3. Remarkably, SYEO exhibited high anticancer efficacy against the HMV-II cell line with IC₅₀ of 116.82 ± 2.34 μg/mL followed by SK-ML-2 (IC₅₀ = 201.98 ± 3.29 μg/mL), G-361 (IC₅₀ = 216.28 ± 7.15 μg/mL), and HT144 (IC₅₀ = 252.41 ± 7.45 μg/mL). The obtained results of the anti-melanoma cancer activity of SYEO showed that the EO of Seseli yunnanense has higher activity compared to the positive control of Dab; however, 0.3 μM was the examined concentration for Dab. Importantly, low cytotoxicity was observed against HUVEC cell lines, as normal human cell lines, even at higher concentrations used in comparison to melanoma cell lines (Figure 4).

Figure 3

The effect of different concentrations of SYEO on the viability of HT-144, HMV-II, SK-EML-2, and G-361 as the selected melanoma cell lines using MTT assay.

Figure 4

The effect of different concentrations of SYEO on the viability of normal cell line of HUVEC using MTT assay.

EOs, deeply rooted in traditional medicine as herbal solutions, have undergone extensive in vitro and in vivo studies to uncover their antibacterial, antifungal, anti-inflammatory, and anticancer properties [8,48]. Understanding the biological effects of phyto-components like EOs and enhancing their efficacy are key objectives pursued by researchers in cancer and complementary medicine fields. For instance, the anti-cancer prowess of β-eudesmol against a breast cancer cell line has been demonstrated through the induction of cell ferroptosis [49]. Additionally, the sesquiterpene α-bisabolol has exhibited anticancer potential against various cell lines, including those of lung, liver, and pancreatic cancers [50]. Furthermore, the synergy effect of the components may be considered as the main factor for the responsibility of an EO in bioactivity assays such as antioxidant, antimicrobial, and anticancer activity.

5 Conclusion

Melanoma is a well-recognized form of skin cancer that unfortunately results in numerous fatalities globally. UV light is the major factor in inducing melanoma cancer. Since herbal remedies can be considered potent agents to treat cancers, in the present research, the EO of a medicinal plant, namely, Seseli yunnanense was chosen to investigate for anticancer activity against melanoma cell lines. The chemical constituent of the volatile oil was recognized by chromatography techniques. α-bisabolol, β-eudesmol, and eugenol were determined as the major component. SYEO scavenged the DPPH free radical with less IC₅₀ compared to BHT as the selected positive control. The oil has prevented the growth of the melanoma cell lines of HMV-II, SK-ML-2, G-361, and HT144. The best results were recorded against HMV-II. Besides, the safety of the EO was discerned against human normal cell lines of HUVEC. The results of this study revealed that SYEO can be introduced as an agent to cure melanoma; however, more investigations such as in vivo study are needed for this purpose.

# Lili Chen and Xiaoling Ju contributed equally to this work.

Acknowledgements

The Authors wish to thank the Science and Technology project of Jiangxi Provincial Administration of Traditional Chinese Medicine, Grant No. SZYYB20224592.

Funding information: This research was financially supported by the Science and Technology project of Jiangxi Provincial Administration of Traditional Chinese Medicine (Grant number SZYYB20224592).
Author contributions: Methodology and writing – original manuscript: L.C., X.J., X.W., and Z.Z.; project validation and formal analysis: L.C. and X.J.; investigation: X.W., and Z.Z.; reviewing: X.W., and Z.Z. All the authors agreed on the final version of the manuscript.
Conflict of interest: The authors declare no conflict of interest.
Ethical approval: The conducted research is not related to either human or animal use.
Data availability statement: The data used to support the findings of this study are available from the corresponding author upon request.

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Received: 2024-06-11

Revised: 2024-07-23

Accepted: 2024-08-04

Published Online: 2024-09-30

This work is licensed under the Creative Commons Attribution 4.0 International License.

Articles in the same Issue

https://doi.org/10.1515/chem-2024-0080

Keywords for this article

Seseli yunnanense; α-bisabolol; β-eudesmol; eugenol; melanoma cancer

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