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The Azorean Cryptomeria japonica forest operations and wood industry generate considerable foliage biomass residues that are used for local essential oil (EO) production. However, research on seasonal variation of C. japonica EO remains scarce. In this study, the EOs from fresh Azorean C. japonica foliage (Az–CJF) collected in autumn (Aut) and spring (Spr) were obtained via hydrodistillation and investigated for their physical properties, yield, chemical composition, and bioactivities. Both EOs presented a strong odor, a yellowish color, a density around 0.9 g·mL−1, and similar yields (approximately 1% v/w, dry matter). Nevertheless, the GC–MS analyses showed a decrease in monoterpene hydrocarbons (MH) and an increase in oxygenated sesquiterpenes (OS) contents in Spr–EO compared with Aut–EO (16% vs. 35% for MH and 45% vs. 31% for OS, respectively). In addition, the predominant components were kaur-16-ene (23%) for Spr–EO and phyllocladene (19%) for Aut–EO, revealing that both EOs were rich in diterpene hydrocarbons (29% vs. 26%). Concerning its toxicity against brine shrimp, a low mortality (0–38%) was observed at a concentration range of 100–180 μg·mL−1. Regarding the anti-cholinesterase properties, both EOs were inactive against acetylcholinesterase but showed anti-butyrylcholinesterase activity superior to (–)-α-pinene, a major compound of Az–CJF EO (IC50 values: 84, 148, and 648 μg·mL−1 for Spr–EO, Aut–EO, and α-pinene, respectively). Overall, the results indicate the potential benefit of both seasonal EOs in Alzheimer's disease treatment. In conclusion, this study demonstrated that season strongly influences the Az–CJF EO quantitative composition and thus its bioactivity, aiding in the selection of the most high-quality raw materials for use in Azorean C. japonica EO aromatherapy industry. [ABSTRACT FROM AUTHOR] more...

Alzheimer's disease (AD), a multifactorial neurodegenerative disorder characterized by severe cognitive impairment, affects millions of people worldwide. However, AD therapy remains limited and mainly symptomatic-focused, with acetylcholinesterase (AChE) inhibitors being the major available drugs. Thus, AD is considered by the WHO as a disorder of public health priority. Among several strategies that have been identified to combat AD, the use of natural multi-target drug ligands (MTDLs) appears to be a promising approach. In this context, we previously found that the essential oils (EOs), obtained via hydrodistillation, from Azorean Cryptomeria japonica sawdust (CJS) and resin-rich bark (CJRRB) were able to exert antioxidant activity via different mechanisms of action. Therefore, in the present work, these EOs were screened for their (i) in vitro anti-AChE and anti-butyrylcholinesterase (BChE) activities, evaluated by a modified Ellman's assay; (ii) in vitro anti-inflammatory potential, using the albumin denaturation method; and (iii) toxicity against Artemia salina. The CJRRB–EO exhibited both anti-AChE and anti-BChE activities (IC50: 1935 and 600 µg/mL, respectively), whereas the CJS–EO only displayed anti-BChE activity, but it was 3.77-fold higher than that of the CJRRB–EO. Molecular docking suggested that α-pinene and ferruginol compounds contributed to the anti-AChE and anti-BChE activities, respectively. Moreover, the anti-inflammatory activity of the CJS–EO, the CJRRB–EO, and diclofenac was 51%, 70%, and 59% (at a concentration of only 2.21 μg/mL), respectively, with the latter two presenting comparable activity. Concerning the EOs' potential toxicity, the CJRRB–EO exhibited a lower effect than the CJS–EO (LC50: 313 and 73 µg/mL, respectively). Overall, the EOs from C. japonica biomass residues, chiefly the CJRRB–EO, displayed antioxidant, anticholinesterase, and anti-inflammatory activities in a concentration-dependent manner. These properties demonstrate that these residues may be suitable natural MTDLs for AD complementary therapy when administered through aromatherapy, or, alternatively, could serve as low-cost sources of valuable ingredients, such as α-pinene. [ABSTRACT FROM AUTHOR] more...

Cryptomeria japonica wood industry generates large amounts of foliage biomass residues. Due to the increasing applications and markets for essential oils (EOs), fresh Azorean C. japonica foliage (Az–CJF) residues are used for local EO production. Hydrodistillation (HD), a common process for obtaining EOs, also provides the possibility to fractionate them. Thus, this study evaluated the in vitro antimicrobial and antioxidant activities of six Az–CJF EO fractions (Frs. 1–6), collected at sequential HD timeframes (HDTs: 0–2, 2–10, 10–30, 30–60, 60–120, and 120–240 min), in comparison to the crude EO, obtained from a non-fractionated HD (0–240 min HDT). Antimicrobial activities were assessed via disc diffusion method against seven bacteria (foodborne and/or human pathogens) and two Penicillium spp. (phytopathogenic fungi), and antioxidant activity was estimated using DPPH and ABTS assays. Concerning the antibacterial activity, all the EO samples were effective only toward Gram-positive bacteria. Fractions 1–3 (<30 min HDT) were the most active, with growth inhibition zones (GIZ) of 7.0–23.3 mm (1.4–2.2 times higher than those of the crude EO), being Bacillus spp. (B. licheniformis and B. subtilis) the most sensitive, followed by Staphylococcus aureus and Micrococcus luteus. Regarding the antifungal activity, Frs. 1–3 also displayed the best activities, but only against P. italicum (GIZ around 9.0 mm), while the crude EO showed no antifungal activity. Overall, the best antimicrobial properties of Frs. 1–3 could be attributed, at least in part, to their highest content in α-pinene and bornyl acetate. On the other hand, Frs. 4–6 (>30 min HDT) exhibited the strongest antioxidant activities (EC50 values: 1.5–2.3 and 1.0–1.7 mg mL−1 for DPPH and ABTS, respectively), being at least 1.3-fold higher than those of the crude EO. The presence of nezukol, elemol, and eudesmol isomers could strongly contribute to the best free radical scavenging properties of Frs. 4–6. In conclusion, HD was found to be an efficient process for obtaining new Az–CJF EO fractions with variable and enhanced bioactivities due to their differential composition, as assessed using GC–MS. Hence, these findings could contribute to increasing the commercial potential of the C. japonica EO industry, namely, the Fr2 and Fr6, which presented the most significant activities and can have potential applications in the food, medical, and agriculture sectors. [ABSTRACT FROM AUTHOR] more...

In the Azores archipelago (Portugal), forest operations and wood industry generate large amounts of Cryptomeria japonica biomass residues (CJBR), which can be used to produce valuable essential oils (EOs). In this study, we evaluated the chemical composition and antioxidant activities of EOs from Azorean C. japonica sawdust (CJS) and resin-rich bark (CJRRB). The CJS and CJRRB EOs, obtained via hydrodistillation, showed different yield values (0.27% vs. 0.80% v/w, dry weight) and also different chemical profiles, as assessed using GC/MS. A total of 64 and 85 components were identified in CJS and CJRRB EOs, representing 95.7% and 96.9% of the total composition, respectively. The major components in CJS EO were oxygenated sesquiterpenes (mainly α+β-eudesmol, 1-epicubenol, and cubebol), while in CJRRB EO, the major components were monoterpene hydrocarbons, including α-pinene, δ-3-carene, and limonene (66.6% vs. 6.4% for oxygenated sesquiterpenes and 0% vs. 64% for monoterpene hydrocarbons, respectively). Antioxidant activity was estimated using (i) two radical-based assays, 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) radical scavenging activity, and (ii) a lipid model assay, β-carotene-linoleic acid bleaching activity (BCBA). Both CJS and CJRRB EOs exhibited concentration-dependent antioxidant activities, and their DPPH, ABTS, and BCBA EC50 values were 1107 vs. 1275 µg/mL, 260 vs. 498 µg/mL, and 1764 vs. 662 µg/mL, respectively. The results indicate that both EOs were able to exert antioxidant activity via different mechanisms of action. Therefore, Azorean CJS and CJRRB may be sustainable sources for antioxidant compounds. This study expands the chemical and biological knowledge of CJBR EOs and, consequently, adds more value to the C. japonica EO industry. [ABSTRACT FROM AUTHOR] more...

In the Azores Archipelago, Cryptomeria japonica is, currently, the most cultivated forestry tree for timber production, landscaping, and gardening, generating large amounts of foliage waste that is used for local essential oils (EOs) production. However, the existing literature on the biological potential of EOs from different C. japonica foliage parts, such as female cones (FC), remains limited. Thus, in the present study, EOs extracted by hydrodistillation from Azorean C. japonica immature and mature FC (IFC and MFC), as well as some major EO components, were screened for their: (i) antioxidant capacity, evaluated by DPPH free-radical-scavenging activity (FRSA) and β-carotene-linoleic acid bleaching activity (BCBA), (ii) antimicrobial activities, assessed by the disc diffusion method against eight bacteria and one fungus, and (iii) toxicity against Artemia salina. Among both FC EO samples, the IFC EO exhibited the best DPPH–FRSA, BCBA, and growth inhibitory activity against Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis, and Penicillium italicum, as well as a slightly increased toxic potential, due to their differential compositions, as assessed by GC–MS analysis. Thus, the FC's maturation process decreased their EOs' bioactivities. In conclusion, this finding could help in determining the optimal developmental stage for enhancing the antioxidant and antimicrobial compounds content in FC EOs. In turn, this contributes to increasing the commercial potential of C. japonica's EO industry. [ABSTRACT FROM AUTHOR] more...

Cryptomeria japonica (Thunb. ex L.f.) D. Don (Cupressaceae) is widely cultivated in the Azores archipelago (Portugal) for landscaping and timber production, generating a huge amount of biomass residues. Among these, female cones (FC) emerge as a source of particularly valuable essential oils (EOs), namely, as promising broad-spectrum antimicrobial agents. However, phytochemical research on C. japonica FC EOs remains scarce. This study evaluated the EO yields and chemical compositions of immature and mature FC (IFC and MFC) from the same batch of Azorean C. japonica. IFC and MFC EOs, obtained via hydrodistillation, presented different yields (0.72% vs. 1.12% w/w, dry weight), and their composition, determined via gas chromatography/mass spectroscopy, revealed that the monoterpenes class was dominant (51.84% vs. 69.13%), followed by the sesquiterpenes (36.44% vs. 26.28%) and diterpenes (10.96% vs. 3.03%) classes. However, the correspondent oxygen-containing terpenes classes were 1.5–2.0 times higher in IFC. Thus, the maturation process revealed an increase in EO yield and α-pinene content (19.5% vs. 41.3%) but a decrease in other important bioactive terpenes/terpenoids (terpinen-4-ol, bornyl acetate, elemol, γ-eudesmol, phyllocladene, and nezukol) content. In conclusion, IFC and MFC EOs, due to their unique composition, may have differential commercial applications and, consequently, contribute to increasing the commercial potential of C. japonica's EO industry. [ABSTRACT FROM AUTHOR] more...

The hydrodistillation (HD) process is used to obtain and fractionate essential oils (EOs). In this study, we aimed to evaluate, for the first time, the effects of six different HD timeframes (HDTs: 0–2, 2–10, 10–30, 30–60, 60–120, and 120–240 min) on the yield, physical properties, and chemical profile of Azorean Cryptomeria japonica foliage (Az–CJF) EO. An Az–CJF EO obtained by a typical HD over 4 h was used as a control sample, yielding 0.82%, w/fresh weight (f.w.), and containing eighty-nine components, as determined by GC–MS. The EO fraction yield revealed a narrow range (0.06–0.18%, w/f.w.), with ca. 50% obtained within the first hour. Monoterpene hydrocarbons dominated in Fr1 and Fr2 (92 and 45%, respectively, mainly α-pinene) while oxygen-containing sesquiterpenes prevailed in Frs. 3–6 (42–62%, mainly elemol and eudesmol isomers). Furthermore, Fr2 and Fr3 were the richest in oxygen-containing monoterpenes (9 and 7%, respectively, mainly bornyl acetate) and in sesquiterpene hydrocarbons (6 and 5%, respectively, mainly δ-cadinene), while Fr4 and Fr5 had higher amounts of diterpene hydrocarbons (ca. 22% both, mainly phyllocladene) and Fr6 exhibited the highest oxygen-containing diterpenes content (4%, mainly nezukol). In addition, regression models were established to predict EO yield, HD rate, and composition (major components) for a given HDT. As a result of this study, specific EO fractions can now be targeted in Az–CJF EO by adjusting the HDT. Hence, these findings can help reduce distillation time and, thus, operating costs associated with the HD process. It can also meet specific market demands due to the differential composition of the obtained EO fractions. In turn, this contributes to increasing the commercial potential of C. japonica EO. [ABSTRACT FROM AUTHOR] more...

Azorean Cryptomeria japonica is widely used for local wood production, generating large amounts of aerial-part biomass residues that can be a sustainable source of value-added bioproducts. This comparative study aimed (i) to determine the yield and chemical profile of the essential oils (EOs) extracted by hydrodistillation from Azorean C. japonica foliage, leaves, male cones (MCs), and female cones (FCs), and (ii) to investigate the antimicrobial and brine shrimp lethality (BSL) effects of the obtained EOs and some major components. The EOs yield revealed a wide range (ca. 1–3%, w/d.w.) and their chemical composition, analysed by GC–MS and GC–FID, showed the presence of seventy-one components. Monoterpene hydrocarbons (38–71%) dominated in all the studied EOs, mainly α-pinene (17–45% of total EOs), decreasing as follows: cone EOs > leaf EOs > foliage EOs. Oxygen-containing monoterpenes (mainly terpinen-4-ol) also dominated in cone EOs. Contrariwise, oxygen-containing sesquiterpenes (mainly elemol) and diterpene hydrocarbons (mainly phyllocladene) dominated in foliage/leaf EOs. The studied EOs exhibited activity against Gram-positive bacteria but no activity against Gram-negative bacteria. A similar trend was displayed by α-pinene. Only the cone EOs showed antifungal activity against Penicillium chrysogenum, but this was significantly lower than those of α-pinene and terpinen-4-ol. Moreover, FC EO should also be considered for further investigation due to its high toxicity on BSL bioassay. In conclusion, this study demonstrated the variability of yield, chemical profile, and bioactivities in the EOs from different parts of the Azorean C. japonica, expanding the knowledge of the potentialities of C. japonica aerial-part EOs, particularly the ones from the cone samples. [ABSTRACT FROM AUTHOR] more...

This study reports on the in vivo molluscicidal activity and Artemia salina lethality of Azorean Cryptomeria japonica leaf (CJL) essential oils (EOs) obtained by hydrodistillation (HD) and water-steam distillation (WSD) techniques, especially in light of the recent focus on the use of forestry and wood industry residues in a sustainable world economy. Molluscicidal activity was performed during several life stages of Radix peregra by the immersion method, under laboratory conditions. A first screening through a single-dose bioassay revealed that both EOs were highly active towards eggs, juveniles and adult snails (ca. 100% mortality). Concentration- and time-toxicity assays were carried out only on adult snails to determine the lethal parameters (LC50;90 and LT50;90). The LC50 values were 33 and 62 µg/mL for EO–WSD and EO–HD, respectively, after 48 h. The LT50 of EO–WSD required only 21 h for both 16 h and continous exposure periods, while that of EO–HD was slighty superior (21.8–25.6 h). Although not significant, EO–WSD was also slightly more toxic against A. salina than EO–HD (LC50 = 98 and 115 µg/mL after 24 h, respectively). In conclusion, Azorean CJL EOs, which are rich in α-pinene (mostly EO–WSD), have huge potential to be used as safe raw materials for the development of natural molluscicide products to control snails responsible for transmitting fascioliasis. [ABSTRACT FROM AUTHOR] more...

This study mainly deals with the effect of hydrodistillation (HD) and water-steam distillation (WSD) methods on the color, yield, and chemical profile of the essential oil (EO) from Cryptomeria japonica fresh leaves from São Miguel Island (Azores Archipelago, Portugal). The yields of EO–HD (pale-yellowish) and EO–WSD (colorless) samples were 1.21% and 0.45% (v/w), respectively. The GC–FID, GC–MS, and 13C-NMR analyses of EO–HD vs. EO–WSD revealed (i) a high-content of monoterpenes (72.8% vs. 86.7%), mainly α-pinene (34.5% vs. 46.4%) and sabinene (20.2% vs. 11.6%), and oxygenated mono- and sesquiterpenes (20.2% vs. 9.6%); (ii) similar sesquiterpene (1.6% vs. 1.6%), β-myrcene (5.9% vs. 5.8%), and camphene (3.5% vs. 3.8%) contents; and (iii) significant differences in other classes/components: EO–HD is richer in oxygenated sesquiterpenes (17.1%, mainly elemol (10.4%) and α-eudesmol (3.4%)) and diterpenes (3%; mostly phyllocladene), while EO–WSD is richer in oxygenated monoterpenes (7.2%, mainly terpinen-4-ol (5.4%)), p-cymene (4.4%), and limonene (3.2%). Overall, the color, yield, and quantitative composition of the EO samples studied are strongly influenced by the distillation method. Nonetheless, this C. japonica leaf EO displayed a consistent α-pinene- and sabinene-rich composition. The same chemotype was found in a commercial Azorean C. japonica leaf EO sample, obtained by industrial steam distillation (SD), as well as in Corsica C. japonica leaf EO–HD. Furthermore, the bioactive composition of our EO samples revealed the potential to be used in green plant protection and in the medical, food, cosmetic, and household industries. [ABSTRACT FROM AUTHOR] more...

Forest operations and wood industry generate large amounts of residues that are discarded in the field and cause environmental pollution. However, these biomass residues are still raw materials to obtain value-added products, such as essential oils, organic/aqueous extracts and resins that are among the great natural sources of bioactive metabolites. Thus, in recent years, the scientific community is giving special attention to their valorization. To date, different uses of biomass residues have been proposed, such as a source of renewable energy, fertilizers, animal feed and bioactive molecules. In this context, Cryptomeria japonica biomass residues (e.g., bark and its exudate, heartwood, sapwood, leaves, cones and roots) represent a source of diverse specialized metabolites (e.g., sesqui-, di-, tri- and sesquarterpenes, flavonoids, lignans and norlignans) with potential application in different fields, particularly in the agrochemical, food, cosmeceutical, pharmaceutical, phytomedicine and esthetic, due to their valuable multi-bioactivities determined over the last decades. Thus, this review provides an overview of the reported biological activities of organic extracts/fractions and their specialized metabolites obtained from different parts of C. japonica , in order to encourage the alternative uses of C. japonica wastes/byproducts, and implement a sustainable and circular bioeconomy. [Display omitted] • Cryptomeria japonica has been investigated for long time owing to its industrial importance. • C. japonica residues (e.g., bark) are an inexpensive source of natural bioactive compounds. • Terpenes and norlignans from C. japonica have therapeutic/pest-control properties. • Ferruginol, sandaracopimarinol, cryptotrione and sequirin C are relevant C. japonica compounds. • Green extraction techniques for obtaining C. japonica bioactive compounds should be exploited. [ABSTRACT FROM AUTHOR] more...