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3 March 2023

39 Pages

Chemistry and Bioactivity of Croton Essential Oils: Literature Survey and Croton hirtus from Vietnam

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1
Vietnam National Museum of Nature, Vietnam Academy of Science and Technology (VAST), No. 18 Hoang Quoc Viet Road, Cau Giay District, Hanoi 100803, Vietnam
2
Vietnam Academy of Science and Technology (VAST), Graduate University of Science and Technology, No. 18 Hoang Quoc Viet Road, Cau Giay District, Hanoi 100803, Vietnam
3
Mientrung Institute for Scientific Research, Vietnam National Museum of Nature, Vietnam Academy of Science and Technology (VAST), 321 Huynh Thuc Khang, Hue 530000, Thua Thien Hue, Vietnam
4
Aromatic Plant Research Center, 230 N 1200 E, Suite 100, Lehi, UT 84043, USA
Molecules2023, 28(5), 2361;https://doi.org/10.3390/molecules28052361
This article belongs to the Special Issue Essential Oils: Characterization, Biological Activity and Application
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Abstract

Using essential oils to control vectors, intermediate hosts, and disease-causing microorganisms is a promising approach. The genus Croton in the family Euphorbiaceae is a large genus, with many species containing large amounts of essential oils, however, essential oil studies are limited in terms of the number of Croton species investigated. In this work, the aerial parts of C. hirtus growing wild in Vietnam were collected and analyzed by gas chromatography/mass spectrometry (GC/MS). A total of 141 compounds were identified in C. hirtus essential oil, in which sesquiterpenoids dominated, comprising 95.4%, including the main components β-caryophyllene (32.8%), germacrene D (11.6%), β-elemene (9.1%), α-humulene (8.5%), and caryophyllene oxide (5.0%). The essential oil of C. hirtus showed very strong biological activities against the larvae of four mosquito species with 24 h LC50 values in the range of 15.38–78.27 μg/mL, against Physella acuta adults with a 48 h LC50 value of 10.09 μg/mL, and against ATCC microorganisms with MIC values in the range of 8–16 μg/mL. In order to provide a comparison with previous works, a literature survey on the chemical composition, mosquito larvicidal, molluscicidal, antiparasitic, and antimicrobial activities of essential oils of Croton species was conducted. Seventy-two references (seventy articles and one book) out of a total of two hundred and forty-four references related to the chemical composition and bioactivity of essential oils of Croton species were used for this paper. The essential oils of some Croton species were characterized by their phenylpropanoid compounds. The experimental results of this research and the survey of the literature showed that Croton essential oils have the potential to be used to control mosquito-borne and mollusk-borne diseases, as well as microbial infections. Research on unstudied Croton species is needed to search for species with high essential oil contents and excellent biological activities.

1. Introduction

In the family Euphorbiaceae, the genus Croton has the largest number of species with about 13,000 species, which are distributed mainly in tropical and subtropical areas [1]. Secondary metabolites in this genus include terpenoids, alkaloids, phenolic compounds, and phenylpropanoids [2]. The volatile compounds (essential oils) in Croton species are important products with many biological activities such as antioxidant [3,4,5,6,7], antibacterial, antifungal [8,9,10], anti-inflammatory [2,11,12,13], cytotoxic [6,11,14,15,16,17], antitumor [16,17], insecticidal, amebicidal [18], anti-parasitic, anti-ulcerogenic [19,20,21], antinociceptive [22,23], modulation of antibiotic and antifungal activities [24], myorelaxant [25], antispasmodic [26], anxiolytic, [2,27], anthelmintic [28], vasorelaxant [29], and pharmacological effects.
Mosquito-borne diseases are a global health problem, particularly diseases with a high number of annual infections such as human malaria (148–304 million), dengue (67–136 million), yellow fever (84,000–170,000 in Africa), chikungunya (693,000 in the Americas), Zika (500,000 in the Americas), lymphatic filariasis (31.3–46.7 million), Japanese encephalitis (35,000–50,000), and West Nile fever (2588) [30].
Parasitic diseases transmitted by snails are a serious health problem in addition to mosquito-borne diseases. In 2021, 136 million school-aged children and 115.4 million adults in 51 countries required preventive chemotherapy for schistosomiasis, which represents a slight increase over that in 2020 (239.6 million) [31]. It is estimated that the acute and chronic symptoms of this disease result in a loss of 4.5 million disability-adjusted life years (DALY) [32]. Food-borne trematodiases are most prevalent in east Asia and South America and can result in severe liver and lung disease. Estimates from the WHO show that food-borne trematodes are important causes of disability with an estimated annual total of 200,000 illnesses and more than 7000 deaths per year, resulting in more than 2 million disability-adjusted life years globally [33].
Antibiotic-resistant bacteria are the biggest global health threat today, affecting anyone of any age in any country. The overuse of antibiotics in humans and animals is accelerating this process. Antibiotic resistance leads to an increasing number of infections, less effective treatment with traditional antibiotics, longer hospital stays, higher medical costs, and increased mortality [34]. Overuse and frequent repeated use of traditional insecticides have created resistant mosquito populations [35]. Although resistance to schistosomiasis has not been formally reported, it is a persistent and probable concern [36,37,38,39]. Disease control measures based on a small number of traditional medicines are unsustainable and present risks.
Essential oils, characterized by a complex chemical composition of volatile compounds, are emerging as potential candidates for the control of vectors, intermediate hosts, parasites, and bacteria. The synergistic and antagonistic effects of the complex chemical constituents of essential oils determine the expression of the bioactivity of the essential oil. Many authors believe that it is the complex nature of their chemical composition and the interactions between the components that make it difficult for the target organisms to develop resistance to essential oils [32,40,41]. The trend of synergistic combinations of essential oils with antibiotics [42,43] and pesticides [44,45,46,47,48] to reduce drug use, increase control efficiency, and limit resistance may be an effective solution.
The aim of this study was to obtain and characterize the essential oil from Croton hirtus L’Hér from Vietnam and to screen the essential oil for its larvicidal activity against four species of mosquitoes, molluscicidal activity against Physella acuta, and antimicrobial activity against a panel of pathogenic microorganisms. In addition, a literature survey of essential oils from Croton spp. for the potential control of mosquitoes, snails, parasitic species, and microorganisms was carried out.

2. Results and Discussion

2.1. Chemical Composition

The extraction yield of the essential oil was 0.62% (w/w), which was consistent with the range of 0.3–0.6% mentioned in previous reports. Yields of essential oils from Croton spp. species range from 0.02 to 6.41% [49,50].
The chemical composition of C. hirtus was dominated by sesquiterpenoids (95.4%). The main chemical components included β-caryophyllene (32.8%), germacrene D (11.6%), β-elemene (9.1%), α-humulene (8.5%), and caryophyllene oxide (5.0%). The full analytical results are available in the Supplementary Materials, Table S1.
Previous studies have shown that the main chemical composition of this plant’s essential oil varies by season and geographical location. The essential oil samples collected in the study by Simões included spathulenol (26.7%), β-caryophyllene (10.0%), bicyclogermacrene (9.5%), α-cadinol (7.7%), and cubenol (7.0%) [51]. The essential oil samples collected in Teresina showed seasonal variations in the content of major components, namely β-caryophyllene (27.9–37.3%), germacrene D (6.3–33.7%), α-cadinene (7.0–16.1%), δ-cadinene (1.8–13.5%), and α-humulene (3.6–4.6%) [51]. Essential oil samples collected in the Ivory Coast showed main components that included β-caryophyllene (31.75%), germacrene-D (22.57%), and α-humulene (7.42%) [8].
Essential oils from Croton species, in addition to being characterized by monoterpenoids and sesquiterpenoids, are particularly characterized by phenylpropanoids [15,28,52,53,54,55,56]. Essential oils of several species are dominated by a major component such as (E)-anethole [52], linalool [57], guaiol, estragole [54], andmethyl eugenol [55].

2.2. Larvicidal Activity

The C. hirtus essential oil showed good larvicidal activity against mosquitoes with LC50 values in the range of 15.38–78.27 μg/mL (Table 1). The compounds β-caryophyllene, α-humulene, and caryophyllene oxide were active against the larvae of Aedes albopictus with LC50 values at 24 h of exposure of 56.87, 43.86, and 20.61 μg/mL, respectively [58]. The compounds germacrene D and β-elemene showed very strong toxicity against the larvae of Ae. aegypti, Ae. albopictus, and Cx. quinquefasciatus [59,60,61,62,63,64].
Table 1. Mosquito larvicidal activity of Croton hirtus essential oil (μg/mL).
β-Caryophyllene and its mixtures with caryophyllene oxide and α-humulene (ratio tested relative to the percentage in the essential oil) (Table 2 and Table 3) exhibited distinctly different toxicities against Ae. aegypti and Ae. albopictus. This mixture played a major role in the larvicidal activity against Ae. aegypti, but conversely it did not play a role in the larvicidal activity against Ae. albopictus.
Table 2. Larvicidal activity of major compounds against Aedes aegypti (μg/mL).
Table 3. Larvicidal activity of major compounds against Aedes albopictus (μg/mL).

2.3. Literature Survey

In order to put this current investigation into context, a survey of the literature on Croton essential oils and their biological activities was carried out. A total of two hundred and forty-four references were collected, which included one hundred and seven species of Croton. The distribution of the study samples collected was as follows: Brazil (one hundred and seventy-six), Venezuela (six), South Africa (six), Cuba (five), Colombia (five), Ecuador (five), Madagascar (four), Nigeria (three), Costa Rica (three), Vietnam (two, not included in this study), Kenya (two), India (two), Cameroon (two), Kenya (two), Peru (two), Ethiopia (two), Mexico (two), Korea (one), Laos (one), Central African Republic (one), Gabon (one), Curacao (one), Benin (one), Argentina (one), Ivory Coast (one), Congo-Brazzaville (one), Sudan (one), Guadeloupe (one), China (one), Thailand (one), Island (one) and Malaysia (one). After reviewing the articles based on the set criteria, seventy-one articles and one book satisfied the criteria and were included herein. Most of the studies collected plant material and were conducted in Brazil.
The previously reported larvicidal activities of Croton species against mosquitoes are summarized in Table 4. Most of the essential oils of Croton spp. showed good activity (LC50 < 100 μg/mL). It is worth noting that C. zehntneri essential oil has been characterized by its main component (E)-anethole, which has shown very good larvicidal activity against Ae. aegypti [52,65]. Furthermore, studies have reported that the yield of essential oil from the leaves of this species is greater than 1%, and it is non-toxic to mice (LD50: 3464 mg/kg) [65], so this essential oil may be considered for potential use as a biological pesticide. However, since this essential oil has shown geographical variation in terms of its chemical composition [66], an evaluation of the larvicidal activity of all of its chemotypes has not been performed.
Table 4. Summary of Aedes aegypti larvicidal activity of essential oils of Croton spp.
The main constituents of the essential oils of Croton spp. were evaluated for their larvicidal activity against mosquito species (Table 5). There were differences between different authors when reporting the activities of the compounds β-caryophyllene, α-pinene, β-pinene, α-terpineol, α-humulene, and α-phellandrene. This difference may have been due to the different health or developmental stages of the larvae between the groups. The larvicidal activity of (E)-anethole was weaker than that of C. zehntneri essential oil [52,65], which demonstrated the important role of components in small concentrations, such as anysyl-acetate and dihydroaromadendrene. Bicyclogermacrene did not have synergistic effects with the compounds spathulenol, β-caryophyllene, camphor, or germacrene D in the larvicidal activity of the essential oils of C. argyrophyllus, C. heliotropiifolius, and C. pulegiodorus. This trend was also observed in the larvicidal activity of Eugenia calycina essential oil [76].
Table 5. Summary of mosquito larvicidal activity of main components in Croton spp. essential oils (24 h or 48 h exposure).

2.4. Molluscicidal and Antiparasitic Activities

The essential oil of C. hirtus demonstrated molluscicidal activity against adult P. acuta with a 48 h LC50 value of 10.09 μg/mL (Table 6). Based on the classification by the World Health Organization (WHO) [114], this essential oil is considered as an active plant molluscicide (LC50 < 20 μg/mL). Croton rudolphianus essential oil, which is characterized by the main components β-caryophyllene, bicyclogermacrene, δ-cadinene, and germacrene D, was active against Biomphalaria glabrata with a 48 h LC50 of 47.89 μg/mL [115].
Table 6. Molluscicidal activity of Croton hirtus essential oil and its major components against Physella acuta adults (μg/mL).
Although only a few studies have been carried out evaluating the toxicity of Croton essential oils against snails as disease vectors, a number of essential oil components have been evaluated for their molluscicidal activity [32]. β-Caryophyllene exhibited strong toxicity against Bulinus truncatus with an LC50 value of 1.66 μg/mL [116].
In contrast to the molluscicidal activity, the antiparasitic activities of essential oils and single components have been extensively studied and have also been studied at the in-vivo level [117,118] (Table 7 and Table 8). Table 7 and Table 8 show that essential oils with high concentrations of β-caryophyllene and/or caryophyllene oxide showed a trend of stronger activity than other essential oils.
Table 7. Summary of antiparasitic activities of Croton spp. essential oils.
Table 8. Summary of antiparasitic activities of essential oil components.

2.5. Antimicrobial Activity

The essential oil C. hirtus exhibited strong antimicrobial activity with MIC values for E. faecalis of 8.0 and 16.0 μg/mL for S. aureus, B. cereus, E. coli, and S. enterica (Table 9). The compound β-caryophyllene showed strong antimicrobial activity [151], whereas β-elemene in contrast showed weak antimicrobial activity (MIC > 1000 µg/mL) [151]. The essential oils from the leaves and stems of Orthosiphon stamineus, which are characterized by the main components β-caryophyllene (24.0–35.1%), α-humulene (14.2–18.4%), and β-elemene (11.1–8.5%), showed strong antimicrobial activity [152]. Stachys officinalis essential oil, which is characterized by the main components germacrene D (19.9%), β-caryophyllene (14.1%), and α-humulene (7.5%), exhibited very strong antimicrobial activity [153]. The main components showed weaker antimicrobial activity than essential oils themselves, which suggests synergistic effects between them.
Table 9. Antimicrobial activity of Croton hirtus essential oil and major compounds (MIC, IC50, and µg/mL).
The antimicrobial activities of the essential oils of Croton species are summarized in Table 10. It is noteworthy that there are reports on the synergism of essential oils and antibiotics, although essential oils alone or antibiotics alone have shown weakness.
Table 10. Summary of antimicrobial activity of Croton spp. essential oils.

3. Materials and Methods

3.1. Plant Material and Isolation of Essential Oil

The specimens of Croton hirtus L’Hér. were collected at Phong Dien Nature Reserve, Thua Thien Hue Province (16°24′15,84″ N 107°12′00,01″ E, 415 m elevation) in July 2022. The specimen (label: NCXS-H 110) of this species was identified by Van Huong Bui and was deposited in the Vietnam National Museum of Nature (VNMN) herbarium. The fresh aerial parts were chopped and hydrodistilled with a Clevenger apparatus (Witeg Labortechnik, Wertheim, Germany) for 6 h. The EO was dried over anhydrous Na2SO4 and stored at 4 °C until use.

3.2. Gas Chromatographic Analysis

Gas chromatography–mass spectral analyses (GC–MS) of C. hirtus essential oil were carried out using previously published instrumentation and protocols [58,114]. A Shimadzu GCMS-QP2010 Ultra (Shimadzu Scientific Instruments, Columbia, MD, USA) with a ZB-5 ms fused silica capillary column (60 m length, 0.25 mm diameter, and 0.25 μm film thickness) (Phenomenex, Torrance, CA, USA), He carrier gas, 2.0 mL/min flow rate, injection and ion source temperatures of 260 °C, and a GC oven program of 50 to 260 °C at 2.0 °C/min was used. A 0.1 μL amount of a 5% (w/v) sample of essential oil in CH2Cl2 was injected in split mode with a 24.5:1 split ratio. Identification of the essential oil components was carried out with a comparison of MS fragmentation and retention indices (RI) with those available in the databases [189,190,191,192]. Quantification was performed using external standards of representative compounds from each compound class.

3.3. Screening for Larvicidal Activity

Two species of Aedes mosquitoes were maintained continuously at Duy Tan University [193]. Egg rafts of Cx. fuscocephala were collected from rice fields in Hoa Vang district, Da Nang (GPS: 16°00′49″ N, 108°06′12″ E). Egg rafts of Cx. quinquefasciatus were collected from car tires containing decomposing organic matter in Da Nang City. Each Culex egg raft was hatched separately in plastic trays with tap water overnight to facilitate the precise examination of the species. The larvae were fed a mixture of dog food and yeast (ratio 3:1, w/w).
Essential oil and purified compounds were dissolved with ethanol (Sigma–Aldrich, Ho Chi Minh, Vietnam) to obtain a 1% stock solution. Twenty-five larvae of each mosquito species were transferred into 250 mL beakers containing 150 mL of distilled water. Different volumes of each the stock solution were transferred into the beakers containing larvae to obtain exposure concentrations of 100, 75, 50, 25, 12.5, and 6.25 μg/mL. Each concentration was cloned 4 times, and permethrin (Sigma–Aldrich) was used as a positive control. After 24 h and 48 h of exposure, the larvae were determined for mortality.

3.4. Screening for Molluscicidal Activity

Adult snails about 1.0 cm in size were collected in the wild (GPS: 16°01′08″ N, 108°07′44″ E), and they were acclimated to laboratory conditions 24 h prior to testing. The five snail adults were transferred into 200 mL plastic beakers, which were then filled with 195 mL of distilled water. The adults were exposed to concentrations of 50, 25, 12.5, 6.25, and 3.125 μg/mL. After 24 h of exposure, the snails were recovered by transferring them to plastic beakers containing only distilled water. After 24 h of recovery, the number of dead snails at the exposure concentrations was recorded. Copper sulfate (Xilong Chemicals, Shantou, China) was used as a positive control.

3.5. Screening for Antimicrobial Activity

The ATCC international standard for control of microorganisms include three Gram-negative bacteria strains (E. coli ATCC25922, P. aeruginosa ATCC27853, and S. enterica ATCC13076), three Gram-positive strains (E. faecalis ATCC299212, S. aureus ATCC25923, and B. cereus ATCC 14579), and a strain of C. albicans ATCC10231, which were provided by the National Institute for Food Control, Vietnam.
The antimicrobial activity was analyzed based on the multi-concentration dilution method. Samples of essential oils or pure compounds were diluted in DMSO at a decreasing concentration range of 256, 128, 64, 32, 16, 4, and 2 µg/mL, with three replicates for each concentration. Microbial solutions were prepared at a concentration of 2 × 105 CFU/mL, and antimicrobial assays were carried out in 96-well microtiter plates. A 5.12 μL sample solution with a 10 mg/ml concentration was aspirated into the first row containing 100 μL of LB medium and then diluted successively by concentration into rows containing 50 μL until reaching a concentration of 2 μg/mL. Then, 50 μL of microbial solution was added at a concentration of 2 × 105 CFU/ml and incubated at 37 °C. After incubation for 24 hours at 37 °C, the absorbance at 650 nm was measured using a microplate reader (Epoch, BioTek Instruments Inc., Winooski, VT, USA) [194]. Streptomycin, kanamycin, tetracycline, nystatin, and cycloheximide (all compounds were purchased from Sigma–Aldrich) were used as positive controls.

3.6. Data Analysis

Mortality data were analyzed by log-probit analysis [195] to acquire LC50 and LC90 values as well as 95% confidence limits using Minitab® version 19.2020.1 (Minitab, LLC, State College, PA, USA).

3.7. Literature Survey

The materials used in this literature survey were searched on the databases https://scholar.google.com, https://pubmed.ncbi.nlm.nih.gov, and https://www.researchgate.net (accessed on 1 January 2023) with a keyword structure including “essential oil” and Croton; bioactive keywords that were searched for included antimicrobial, antifungal, antibacterial, antiparasitic, and “mosquito larvicidal”. There were no language restrictions for the selection of articles. The following criteria were included when considering articles:
(1)
The articles fully reported the chemical composition and mosquito larvicidal activity of the essential oils.
(2)
The articles fully reported the chemical composition and the molluscicidal and antiparasitic activities of the essential oils.
(3)
The articles fully reported the chemical composition and antibacterial activity of the essential oils.
(4)
Articles that reported unreliable GC/MS analysis results, such as chemical compositions that did not match the elution order, retention time, and retention index, were not considered.

4. Conclusions

This work presented a literature survey of the volatile phytochemistry and biological activities of Croton species and illustrated the potential utility of these essential oils. Furthermore, the essential oil composition, mosquito larvicidal, molluscicidal, and antimicrobial activities of Croton hirtus from Vietnam was included, which adds to our knowledge of the genus Croton. β-Caryophyllene occurred abundantly in the essential oils [196], and it was present in most of the essential oils of the Croton species. Mixtures of β-caryophyllene, α-humulene, and caryophyllene oxide showed synergistic or antagonistic effects against various organisms. Investigations into the bioactivity of combinations of β-caryophyllene with other major compounds in their respective percentages in the essential oils will help in the development of β-caryophyllene-based products. Based on the results of the antiparasitic activity of β-caryophyllene, caryophyllene oxide, and the Croton essential oils containing these two compounds, we suggest that an investigation into the antiparasitic activity of C. hirtus essential oil may provide interesting results.

Supplementary Materials

The following supporting information can be downloaded at: https://www.mdpi.com/article/10.3390/molecules28052361/s1. Table S1: Chemical composition of Croton hirtus essential oil.

Author Contributions

Conceptualization, N.A.L.-d. and W.N.S.; methodology, N.A.L.-d., C.V.C.L., V.H.B. and P.S.; software, P.S.; validation, W.N.S. and N.A.L.-d.; formal analysis, W.N.S., H.H.N., and N.A.L.-d.; investigation, N.A.L.-d., V.H.B., P.S., T.M.H.L., G.H.N., V.H.V., T.C.B. and H.H.N.; resources, V.H.B. and P.S.; data curation, V.H.B., H.H.N., P.S. and W.N.S.; writing—original draft preparation, N.A.L.-d., H.H.N. and W.N.S.; writing—review and editing, W.N.S.; visualization, V.H.B.; supervision, N.A.L.-d.; project administration, N.A.L.-d.; funding acquisition, N.A.L.-d., C.V.C.L. and V.H.B. All authors have read and agreed to the published version of the manuscript.

Funding

This research was funded by the Vietnam Academy of Science and Technology (VAST), grant number NCXS02.04/22-23.

Institutional Review Board Statement

Not applicable.

Data Availability Statement

All data are available upon reasonable request from the corresponding authors (N.H.H. and W.N.S.).

Acknowledgments

P.S. and W.N.S. participated in this work as part of the activities of the Aromatic Plant Research Center (APRC, https://aromaticplant.org/, accessed on 1 March 2023).

Conflicts of Interest

The authors declare no conflict of interest.

Sample Availability

Samples of C. hirtus essential oil are available from the corresponding author H.H.N.

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