The essential oil (EO) from Mentha longifolia aerial parts showed the presence menthone, eucalyptol (1,8-cineole) and pulegone as the main compounds. Chemical composition of the EOs of many M. longifolia grown around the world showed different chymotypes. Menthone and iso-menthone were found in the range amount of (2.8-15.05%) and (0.96–43.79%), respectively, from the plant grown in Iran-Asia.54 Menthone (10.7%), pulegone (47.15%), and 1,8-cineole (11.54%) from the plant grown in Tunisia,55 while menthol (19.4–32.5%), menthone (20.7–28.8%), 1,8-cineole (5.6–10.8%), terpineol-4 (3.1–4.9%) and pulegone (7.8–17.8%) from the plant grown in Southern Africa.29 In addition, the plant growing in Serbia, menthone (11.2%) and piperitone (8.8%) were identified as main compounds.35 The main compounds from the plant growing in South Africa were menthone, 1,8-cineole, and pulegone.56 Piperitone as the major one (30.77%), followed by eucalyptol (14.85%) and caryophellene (5.58%) were observed in the EO of leaves from Saudi M. longifolia,37 while Desam et al.57 reported that the menthone (39.55%), isopulegone (30.49%), eucalyptol (10.38%), and α-terpineol (3.15%) were major components from the aerial parts that were air-dried under shade with promising antibacterial activity against Staphylococcus aureus, Enterococcus faecalis and Bacillus cereus and antifungal activity against Aspergillus flavus, A. fumigates, Alternaria alternaria, Fusarium oxyporum, and Penicillum spp.
1,8-cineole found in 21.66% in M. longifolia oil, was also reported to be one of the major compound in Mentha species EO, which ranged from 1.6–15.58% from Iran,58–60 Tunisia,55,61 and Italy.62 Pulegone, 1.8-cineole, and L-menthone with percentages of 26.92%, 21.3%, and 10.66%, respectively, were found as main compounds in the EO of the plant grown in the winter season, while the main compounds found in the EO from the plant grown in spring were pulegone, oleic acid and palmitic acid with percentages of 38.2%, 23.79% and 15.26%, respectively.32
Other chymotypes were piperitenone oxide and piperitone oxide in plants growing in the Mediterranean region.27,59,62−64 The plant growing in Iran,65 and Sudan,66 are rich in carvone type, while the EOs from Jordan,64 and Tunisia,61 are rich in pulegone type. Also, plants grown in Iran are contains 1,8-cineole rich-chemotype,58 or rich in carveol.67 M. longifolia EO grown in Croatia showed the presence of piperitenone oxide, β-caryophyllene, carvone, and limonene as main compounds.68 The EO from M. longifolia flowers collected from Zlatar, Belgrade, Serbia, showed the presence of trans and cis-dihydrocarvone, piperitone, 1,8-cineole and neoisodihydrocarveol, as main compounds with 23.64%, 15.68%, 17.33%, 8.18% and 7.87%, respectively.31 Piperitone oxide with high amount and piperitenon oxide were found in M. longifolia EO from Morocco.69 While cis-carveol was the dominant compound in M. longifolia from Iran with percentage ranged from 53 to 78%.70 Piperitone oxide, and piperitenone oxide were found as main compounds from the EO from the plant grown in Turkey.71 From Iran, they were piperitone, limonene and trans-piperitol,72 and from France, were carvone, 1,8-cineole and limonene.73 The EO of M. longifolia growing wild in the Bahcesaray area (Van Province, Turkey) showed the presence of menthone (19.31%), pulegone (12.42%), piperitone (11.05%), dihydrocarvon (8.32%), limonene (6.1%), 3-terpinolenone (5.66%), 1,8-cineole (4.37%), germacrene D (3.38%) and caryopyllene (3.19%) as main components.74
The plant grown in India in different locations showed the presence of piperitenone oxide, cis/trans-piperitone oxide, 1,8-cineole, piperitenone, dl-limonene, piperitone, 4-hydroxy piperitone, β-caryophyllene.58,75−79 EOs with their main compounds (carvone, limonene and 1,6-dihydrocarveol) from plants grown from five regions (Saudi Arabia), showed moderate antifungal activity against A. niger, A. flavus and Fusarium solani.28 At 250 ppm EO of M. longifolia inhibited the growth of F. oxysporum (92%) followed by Sclerotuim rolfsii (70.66%) and Rhizoctonia solani (57.04%).75 The EO from M. longifolia at the 10 µl/ml observed potent fungicidal activity against Aspergillus niger, A. ochraceus, A. flavus, A. versicolor, F. tricinctum, F. sporotrichioides, Penicillium funiculosum and Trichoderma viride.31
In the present study, some bioactive compounds were found in the EO from C. reticulata such as β-caryophyllene, β-caryophyllene oxide, β-elemene, γ-elemene, β-bisabolene, spathulenol, α-caryophyllene, longifolene, γ-gurjunene, geranyl acetate, α-bergamotene, linalyl acetate, germacrene D, nerol, D-limonene, and geraniol. Among some citrus EO (Citrus lemon, C. reticulata, C. paradisi and C. sinensis), the EO from C. reticulata showed the lowest activity against Lactobacillus curvatus, L. sakei, Staphylococcus carnosus, S. xylosus, Enterobacter gergoviae and E. amnigenus.22 Hydrocarbons and linalool were mostly found in leaf EO from mandarin (C. reticulata), while thymol and/or terpinen-4-ol, were found leaf EO of some varieties.80,81 In 41 mandarin cultivars, γ-terpinene, sabinene, linalool, limonene, p-cymene, (E)-β-ocimene, β-pinene and terpinen-4-ol were found in the range of (0.2–61.3%), (0.2–59.4%), (0.2–54.3%), (1.5–44.3%), (tr-20.4%), (0.6–13.7%), (0.1–10.7%) and (0.1–10.6%), respectively, in the EO from leaves.40
The EO from peel of fully matured ripen fruits of C. reticulata Blanco with its main compounds of limonene, geranial, neral, geranyl acetate, geraniol, β-caryophyllene, nerol, and neryl acetate showed good activity against some pathogenic fungi Alternaria alternata, Rhizoctonia solani, Curvularia lunata, Fusarium oxysporum and Helminthosporium oryzae.41 Mature fruits EO of C. reticulata showed the presence of citronellol, octanal, decanal, nonanal, β-pinene, limonene, citral, γ-terpinene, linalool, and α-terpineol with high antifungal activity against the growth of Penicillium italicum and P. digitatum.82 Leaves EO from six cultivars of C. reticulata Blanco from Nigeria showed the presence of sabinene, γ-terpinene, p-cymene, δ-3-carene and (E)-β-ocimene, while other constituents include linalool, myrcene, terpinen-4-ol and cis-sabinenehydrate. In addition, limonene, terpinolene, β-pinene, α-pinene, β-sinensal and α-sinensal were detected and isolated.38 Geranial, neryl acetate, geranyl acetate, β-pinene, myrcene, neral, and β-caryophyllene have been identified in the leaf oil of C. limon.83
The applied EOs from M. longifolia and C. reticulata to Pinus halepensis wood showed good activity against the growth of A. flavus, A. niger, A. terreus, and F. culmorum. Previously, EOs and extracts have been used as wood-biofungicides and showed some potential antifungal activity, i.e., treated Acacia saligna wood with Maclura pomifera bark methanol against Alternaria tenuissima,2 A. saligna wood treated with of Cupressus sempervirens methanolic extract against Trichoderma harzianum infestation,3 treated wood samples from Pinus sylvestris, P. rigida and Fagus sylvatica with two EOs of P. rigida (wood) or Eucalyptus camaldulensis (leaves) showed promising antifungal activity against five molds (A. alternata, F. subglutinans, C. globosum, A. niger, and T. viride),50 treated wood samples from A. saligna, F. sylvatica, Juglans nigra and P. rigida the oil from Origanum showed good antifungal activity against T. harzianum and A. niger without changing the wood structures,84 Leucaena leucocephala wood treated with Acer saccharum var. saccharum extract from inner or outer bark extract in combination with citric acid showed bioactivity against the growth of T. viride, F. subglutinans, and A. niger,6 Melia azedarach wood treated with E. camaldulensis or V. agenus-castus n-hexane oily extracts showed potential antifungal against F. culmorum, Rhizoctonia solani and Penicillium chrysogenum,7 M. azedarach wood samples treated with A. saligna flowers extract showed promising antifungal activity against P. chrysogenum,4 M. azedarach wood treated with Musa paradisiaca extract showed good bioactivity against F. culmorum and R. solani,5 treated-chinaberry wood blocks with E. camaldulensis bark extract shpwed potential antifungal activity against F. culmorum and Botrytis cinerea,85 and M. azedarach wood treated with whole plant extract Haplophyllum tuberculatum observed good antifungal activity against F. culmorum and R. solani.86 Corymbia citriodora EOs from leaves (the main compounds were citronellal, citronellol and isopulegol) and fruits (α-pinene, eudesmol, limonene, γ-terpinene as main compounds) applied to wood samples at the amounts of 100, 50 and 25 µL showed of 100% inhibition against Fusarium culmorum.18 Recovered oil dissolved in n-hexane solvent as partitioned from the distillate residue of hydro distillation of fresh flowers from Matricaria chamomilla showed have potent bioactivity activity against A. niger and A. terreus.43
The EOs altered the hyphal morphology by causing loss of cytoplasm, the release of cell constituents, and the total lipid content of molds. In addition, the EOs could generate the cytotoxicity in fungi by disrupting the integrity of cell membrane and causing the leakage of cell components.82,87