Bulnesol

Chemical composition and bioactivities of Magnolia candollii H.Keng essential oil.[Pubmed:36018718]

Z Naturforsch C J Biosci. 2022 Aug 29;77(11-12):519-523.

Several Magnolia species have exhibited potent biological activities such as anti-inflammatory, anti-angiogenesis, anticonvulsant, anti-obesity, and antiviral activities. However, the Magnolia candollii from Malaysia has not been investigated yet. Hence, this study aims to investigate the chemical composition and bioactivities of the essential oil of Magnolia candollii H.Keng from Malaysia. The hydrodistillation process was used to produce the essential oil, and gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) were used to analyse it. In total, 44 chemical components were identified in the bark oil, accounting for 98.4%. The major components of the essential oil were alpha-pinene (29.7%), elemol (10.2%), beta-pinene (8.5%), beta-caryophyllene (7.2%), alpha-terpineol (7.0%), guaiol (5.4%), and Bulnesol (4.9%). Acetylcholinesterase and anti-inflammatory activities were also evaluated using the Ellman method and lipoxygenase enzyme, respectively, in which the essential oil showed moderate inhibitory activity against acetylcholinesterase (I%: 70.2%) and lipoxygenase (I%: 72.5%). Thus, the findings may be helpful for identifying the medicinal and therapeutic uses of the essential oil from the Magnolia genus.

Neuropeltis acuminata (P. Beauv.): Investigation of the Chemical Variability and In Vitro Anti-inflammatory Activity of the Leaf Essential Oil from the Ivorian Species.[Pubmed:35744884]

Molecules. 2022 Jun 10;27(12):3759.

The variability of chemical composition of the leaf essential oil (EO) from Neuropeltis acuminata, a climbing liana growing wild in Ivory Coast, was investigated for the first time. The in vitro anti-inflammatory activity was also evaluated. Thirty oil samples were isolated from leaves collected in three forests of the country and analyzed using a combination of Column Chromatography (CC), Gas Chromatography with Retention Indices (GC(FID)), Gas Chromatography-Mass Spectrometry (GC-MS), and (13)Carbon-Nuclear Magnetic Resonance ((13)C-NMR). Fractionation by CC led to the first-time isolation from natural source of delta-cadinen-11-ol, whose structural elucidation by one dimension (1D) and 2D-NMR spectroscopy is reported here. Finally, 103 constituents accounting for 95.7 to 99.6% of the samples' compositions were identified. As significant variations of the major constituents were observed, the 30 oil compositions were submitted to hierarchical cluster and principal components analyses. Five distinct groups were evidenced: Group I, dominated by (E)-beta-caryophyllene, kessane, and delta-cadinene, while the main constituents of Group II were germacrene B, ledol, alpha-humulene, (E)-gamma-bisabolen-12-ol, and gamma-elemene. Group III exhibited guaiol, germacrene D, atractylone, (E)-gamma-bisabolen-12-ol, delta-cadinene and Bulnesol as main compounds. Group IV was dominated by (E)-nerolidol, guaiol, selina-4(15),7(11)-diene and Bulnesol, whereas (E)-beta-caryophyllene, alpha-humulene and alpha-muurolene were the prevalent compounds of Group V. As the harvest took place in the same dry season in the three forests, the observed chemical variability could be related to harvest sites, which includes climatic and pedologic factors, although genetic factors could not be excluded. The leaf oil sample S24 behaved as a high inhibitor of LipOXygenase (LOX) activity (half maximum Inhibitory Concentration, IC(50): 0.059 +/- 0.001 mg mL(-1)), suggesting an anti-inflammatory potential.

Terpenes and Cannabinoids Yields and Profile from Direct-Seeded and Transplanted CBD-Cannabis sativa.[Pubmed:35436102]

J Agric Food Chem. 2022 Aug 31;70(34):10417-10428.

Following recent legalization, the production of hemp (Cannabis sativa L.) for high-value plant compounds became a major crop in many countries across the world. In this study, we profiled popular plant compounds being extracted for emerging markets, terpenes and cannabinoids, developed in two different planting systems of a single, high-cannabidiol (CBD), low-Delta(9)-tetrahydrocannabinol (Delta(9)-THC), dioecious hemp cultivar 'Culver' in central Oregon, U.S.A. One system is the current conventional system of an open, all-female, clonal transplant (OFCT) production system. This is compared to a dioecious, densely seeded (DDS) production system. Overall, the essential oil (EO, chiefly terpenes) and cannabinoid profiles of plants harvested from the two systems were comparable. In comparison to the DDS plots, the EO obtained from colas of the OFCT plots had higher concentrations of alpha-pinene, myrcene, limonene, beta-bisabolene, gamma-cadinene, caryophyllene oxide, guaiol, 10-epi-gamma-eudesmol, beta-eudesmol, Bulnesol, epi-alpha-bisabolol, alpha-humulene, and CBD, although lower concentrations of 1,8-cineole, (E)-caryophyllene, gamma-elemene, alpha-selinene, selina-4(15),7(11)-diene, selina-3,7(11)-diene, and germacrene B. Of the various plant parts (female leaves and chaff, male flowers) tested in the DDS plots, the highest EO yield was obtained from the chaff. The main EO constituents of female leaves were (E)-caryophyllene (14-21%), caryophyllene oxide (13-16%), alpha-humulene (5-6%), humulene epoxide II (3.5-3.8%), epi-alpha-bisabolol (2.7-5.5%), CBD, and alpha-eudesmol (1.1-2.6%). The principal EO constituents of female chaff from the DDS system were (E)-caryophyllene ( approximately 21%), alpha-humulene (6.6%), beta-selinene (4.5%), alpha-selinene (3.6%), selina-3,7(11)-diene (9.8%), selina-4(15),7(11)-diene (6.3%), caryophyllene oxide (5.2%), and cannabichromene (3.1%). The major EO constituents of the male flowers were CBD (19.3%), caryophyllene oxide (11%), alpha-humulene (4.1%), epi-alpha-bisabolol (3.9%), selina-3,7(11)-diene (3.4%), and beta-selinene (3.4%). Cannabinoids were not detected in the EO distilled for 30 min, but they were present in the EO from 240 min of distillation. The EO content of female leaves and male flowers was relatively low, whereas the EO content of the female chaff from the DDS system was significantly greater. Breaking with conventional knowledge, the EO of male flowers may accumulate up to 19% CBD. Distillation of plants from both production systems converted CBD-A to CBD, CBDV-A to CBDV, CBG-A to CBG, and THC-A to THC as a result of the thermal decarboxylation of acidic cannabinoids but otherwise did not affect the total cannabinoid content. Most of the cannabinoids remained in the distilled biomass after the extraction of terpenes (EO). Therefore, the distilled, terpene-free biomass represents a high-value product that could be further extracted for cannabinoids or used as a component in various products.

Antifungal Sesquiterpenoids from Michelia formosana Leaf Essential Oil against Wood-Rotting Fungi.[Pubmed:35408536]

Molecules. 2022 Mar 25;27(7):2136.

Michelia formosana (Kanehira) Masamune is a broad-leaved species widespread in East Asia; the wood extract and its constituents possess antifungal activity against wood-decay fungi. Antifungal activities of leaf essential oil and its constituents from M. formosana were investigated in the present study. Bioassay-guided isolation was applied to isolate the phytochemicals from leaf essential oil. 1D and 2D NMR, FTIR, and MS spectroscopic analyses were applied to elucidate the chemical structures of isolated compounds. Leaf essential oil displayed antifungal activity against wood decay fungi and was further separated into 11 fractions by column chromatography. Four sesquiterpenoids were isolated and identified from the active fractions of leaf essential oil through bioassay-guided isolation. Among these sesquiterpenoids, guaiol, Bulnesol, and beta-elemol have higher antifungal activity against brown-rot fungus Laetiporus sulphureus and white-rot fungus Lenzites betulina. Leaf essential oil and active compounds showed better antifungal activity against L. sulphureus than against L. betulina. The molecular structure of active sesquiterpenoids all contain the hydroxyisopropyl group. Antifungal sesquiterpenoids from M. formosana leaf essential oil show potential as natural fungicides for decay control of lignocellulosic materials.

Analysis of chemical components in two tree species of magnoliaceae, Magnolia sumatrana var. glauca (Blume) Figlar & Noot and Magnolia hypolampra (Dandy) Figlar.[Pubmed:34328033]

Nat Prod Res. 2023 Jan;37(2):328-332.

The essential oils from roots, branches, leaves and bark of Magnolia sumatrana var. glauca (Blume) Figlar & Noot and Magnolia hypolampra (Dandy) Figlar were extracted by ultrasonic-assisted extraction and the chemicals were determined by gas chromatography-mass spectroscopy (GC-MS). The major constitutes of M. sumatrana var. glauca were trans-cinnamaldehyde (27.55%), caryophyllene (1.20-10.14%), (+)-Bulnesol (9.70%), alpha-caryophyllene (2.35-6.35%), alpha-eudesmol (1.08-6.17%). M. hypolampra was characterized by the presence of safrole (0.18-35.01%), (+) cycloisosativene (18.70%), oxirane, hexadecyl- (0.72-12.79%), beta-cubebene (1.53-8.90%), (Z)-14-tricosenyl formate (8.65%). This is the first study of the composition of essential oils from the roots, branches and bark of M. sumatrana var. glauca and the roots of M. hypolampra, and some compounds were being described for the first time. Combined with present results and literatures, phytochemicals may be affected by multi-factors such as organs, growing location, and extraction methods, providing more approaches for further exploration of the non-wood resources of forestry species.

Effect of essential oils against acaricide-susceptible and acaricide-resistant Rhipicephalus ticks.[Pubmed:33625626]

Exp Appl Acarol. 2021 Apr;83(4):597-608.

The indiscriminate use of acaricides is a problem worldwide and has increased the selection of acaricide-resistant tick populations. The goal of this study was to evaluate the acaricide effects of two essential oils (from Schinus molle and Bulnesia sarmientoi) using the larval immersion test on three Rhipicephalus tick species. Rhipicephalus evertsi, Rhipicephalus appendiculatus and Rhipicephalus pulchelus ticks collected in Kenya, without history of acaricide exposure, were tested, as well as individuals from two populations of Rhipicephalus microplus (with or without history of acaricide exposure), for comparison. The sample most resistant to the treatments was a population of R. microplus with previous acaricide exposure, whereas the least tolerant sample was a strain of the same species that never had contact with acaricides (Porto Alegre strain). Interestingly, the field tick samples without previous acaricide exposure responded to essential oils with a mortality profile resembling that observed in the acaricide-resistant R. microplus field population, and not the susceptible Porto Alegre strain. The essential oil of B. sarmientoi and its two components tested (guaiol and Bulnesol) caused the highest mortality rates in the tested species and are potential molecules for future studies on control methods against these species.

Functional characterization of a defense-responsive bulnesol/elemol synthase from potato.[Pubmed:32880963]

Physiol Plant. 2021 Jan;171(1):7-21.

Terpene synthases (TPSs) produce a variety of terpenoids that play numerous functional roles in primary and secondary metabolism, as well as in ecological interactions. Here, we report the functional characterization of an inducible potato TPS gene encoding Bulnesol/elemol synthase (StBUS/ELS). The expression of StBUS/ELS in potato leaves was significantly induced in response to both bacterial (Pseudomonas syringae) and fungal (Alternaria solani) infection as well as methyl jasmonate treatment, indicating its role in defense. The leaves exhibited the highest StBUS/ELS expression followed by the stem with least and similar expression in tuber, sprout and root. Recombinant StBUS/ELS catalyzed the formation of different sesquiterpenes by utilizing farnesyl diphosphate as substrate, and the monoterpene geraniol from geranyl diphosphate. Among the sesquiterpenes formed by StBUS/ELS, elemol was the predominant product followed by alpha-bulnesene, Bulnesol and beta-elemene. Further gas chromatography-mass spectrometry (GC-MS) analysis of StBUS/ELS assay products at different injection temperatures revealed elemol and Bulnesol as the major products at 275 and 200/150 degrees C, respectively, without much change in the levels of minor products. This indicated thermal rearrangement of Bulnesol into elemol at higher temperatures. Transient overexpression of StBUS/ELS in potato leaves conferred tolerance against the growth of bacteria P. syringae and Ralstonia solanacearum, and the fungus A. solani. Further, expression analysis of pathogenesis-related (PR) genes in StBUS/ELS overexpressing leaves showed no significant change in comparison to control, indicating a direct involvement of StBUS/ELS enzymatic products against pathogens. Overall, our study suggested that StBUS/ELS is a pathogen-inducible TPS encoding Bulnesol/elemol synthase and could provide a direct role in defense against biotic stress in potato.

Mosquito Larvicidal Activity, Antimicrobial Activity, and Chemical Compositions of Essential Oils from Four Species of Myrtaceae from Central Vietnam.[Pubmed:32331486]

Plants (Basel). 2020 Apr 22;9(4):544.

Mosquitoes are important vectors of several diseases, and control of these insects is imperative for human health. Insecticides have proven useful in controlling mosquito populations, but insecticide resistance and environmental concerns are increasing. Additionally, emerging and re-emerging microbial infections are problematic. Essential oils have been shown to be promising mosquito larvicidal agents as well as antimicrobial agents. In this work, the essential oils from four species of Myrtaceae (Baeckea frutescens, Callistemon citrinus, Melaleuca leucadendra, and Syzygium nervosum) growing wild in central Vietnam have been obtained by hydrodistillation and analyzed by gas chromatographic techniques. The essential oils have been screened for mosquito larvicidal activity against Aedes aegypti, Aedes albopictus, and Culex quinquefasciatus, and for antimicrobial activity against Enterococcus faecalis, Staphylococcus aureus, and Candida albicans. Callistemon citrinus fruit essential oil, rich in alpha-pinene (35.1%), 1,8-cineole (32.4%), limonene (8.2%), and alpha-terpineol (5.8%) showed good larvicidal activity with 24-h LC(50) = 17.3 mug/mL against both Ae. aegypti and Cx. quinquefasciatus, and good antibacterial activity against E. faecalis (minimum inhibitory concentration (MIC) = 16 mug/mL) The 48-h larvicidal activities of M. leucadendra leaf essential oil, rich in alpha-eudesmol (17.6%), guaiol (10.9%), linalool (5.1%), (E)-caryophyllene (7.0%), and Bulnesol (3.6%) were particularly notable, with LC(50) of 1.4 and 1.8 mug/mL on Ae. aegypti and Cx. quinquefasciatus. Similarly, M. leucadendra bark essential oil, with alpha-eudesmol (24.1%) and guaiol (11.3%), showed good antibacterial activity against. E. faecalis. Both B. frutescens and C. citrinus leaf essential oils demonstrated anti-Candida activities with MIC values of 16 mug/mL. The results of this investigation suggest that essential oils derived from the Myrtaceae may serve as "green" alternatives for the control of mosquitoes and/or complementary antimicrobial agents.

A comprehensive review on ethnomedicine, phytochemistry, pharmacology, and toxicity of Tephrosia purpurea (L.) Pers.[Pubmed:32147928]

Phytother Res. 2020 Aug;34(8):1902-1925.

Tephrosia purpurea (L.) Pers. is a well-known plant in Ayurveda and named "Sarwa wranvishapaka" for its property to heal wounds. Traditionally, it is practiced for impotency, asthma, dyspepsia, hemorrhoids, syphilis gonorrhea, rheumatism, enlargement of kidney and spleen. It is an important component of herbal preparations like Tephroli and Yakrifti used to cure liver disorders. Various phytocompounds including pongamol, purpurin, purpurenone, tephrosin, Bulnesol, tephrostachin, beta-sitosterol, and so on have been reported. Modern pharmacological studies have shown that the plant have wound healing, antileishmanial, anticarcinogenic, antimicrobial, antioxidant, hepatoprotective, antifertility, antispermatogenic, anti-diarrheal, diuretic, and insecticidal properties. Acetylcholinesterase inhibitory action reported from this plant aids its utilization for the development of drugs for Alzheimer's and dementia neurological disorders. Among the known active compounds of T. purpurea, tephrostachin is responsible for antiplasmodial activity, tephrosin, pongaglabol, and semiglabrin exerts antiulcer activity while quercetin, rutin, beta-sitosterol, and lupeol are mainly responsible for its anti-inflammatory and anti-cancer properties. From different toxicological studies, concentrations up to 2,000 mg/kg were considered safe. The present review comprehensively summarizes the ethnomedicine, phytochemistry, pharmacology, and toxicology of T. purpurea. Further research on elucidation of the structure-function relationship among active compounds, understanding of multi-target network pharmacology and clinical applications will intensify its therapeutic potential.

Chemical composition and biological activity of the essential oil from the root of Jatropha pelargoniifolia Courb. native to Saudi Arabia.[Pubmed:30662311]

Saudi Pharm J. 2019 Jan;27(1):88-95.

The chemical composition of the essential oil from Jatropha pelargoniifolia roots was determined via GC-FID. There were 80 compounds, representing 99.99% of the total oil constituents. Among these, 77.31% were sesquiterpenes, 14.62% were fatty acids, 7.21% were other components (i.e., phenolics, hydrocarbons, etc.), and 0.85% were monoterpenes. The major compounds in the oil were gamma-eudesmol (35.31%), 5-guaien-11-ol (14.43%), epi-cedrol (8.19%), oleic acid (5.23%), Bulnesol (4.45%), alpha-linoleic acid (4.20%), 3,4-dimethoxycinnamic acid (3.83%), palmitic acid (2.69%), isolongifolanone (2.68%), eicosane (1.41%), and cedrol (1.14%). Oxygenated sesquiterpenes were found to represent more than 50% percent of the total oil content. Moreover, the essential oil was evaluated for anti-inflammatory, antioxidant, antipyretic, and antinociceptive activities using in vivo and in vitro models. Additionally, the antioxidant potential of the oil was evaluated using various in vitro antioxidant tests, including DPPH(*), ABTS(*+) and FRAP. At a dose of 240 microl/kg, the oil showed anti-inflammatory (59.12%), antipyretic (37.00 +/- 0.11), and antinociceptive (47.58%) activities and showed significant (p < 0.001) effect as compared to a standard drug (phenylbutazone and indomethacin). These findings demonstrated that the essential oil of Jatropha pelargoniifolia root could be used as a natural source for their anti-inflammatory, antinociceptive, antipyretic, and antioxidant effects.

Biosynthesis of tovarol and other sesquiterpenoids in Thapsia laciniata Rouy.[Pubmed:30412824]

Phytochemistry. 2019 Jan;157:168-174.

The genus Thapsia produces a wide variety of sesquiterpenoids. The Mediterranean plant Thapsia laciniata Rouy is known to have a product profile that differs from several other species in the genus. Thus, the biosynthesis of sesquiterpenoids in Thapsia laciniata Rouy was investigated. Here we describe three terpene synthases, TlTPS820, TlTPS509 and TlTPS18983. TlTPS18983 is a multi-product enzyme with farnesene as the major product, while TlTPS509 produces guaiol and Bulnesol along with other major and several minor unknown products. TlTPS820 is orthologous to TgTPS2 from Thapsia garganica L. and is an epikunzeaol synthase. TgCYP76AE2 from Thapsia garganica performs a triple hydroxylation of epikunzeaol at C-12 to make dihydrocostunolide. It was therefore investigated if the cytochrome P450, TlCYP76AE4 was able to use epikunzeaol as a substrate. It was found that TlCYP76AE4 hydroxylates epikunzeaol at C-8 to yield tovarol instead of dihydrocostunolide.

Essential oil composition and antibacterial activity of Lindera nacusua (D. Don) Merr.[Pubmed:30919694]

Nat Prod Res. 2016 Dec;30(23):2704-2706.

This study represents the first report on the chemical composition and biological activity of the essential oils from the leaves of Lindera nacusua (D. Don) Merr. Twenty-two compounds were identified and quantified, and the major components of the oil were Caryophyllene oxide (8.79%), Hexahydrofarnesyl acetone (6.83%), beta-Selinene (5.02%), Neophytadiene (4.53%), Palmitic acid (4.42%), Phytol (4.36%), alpha-Copaene (3.89%), 4a,5,8,8a-beta-Tetrahydro-2,4,5-trimethyl-1,4-naphthalindione (3.83%), alpha-Cadinol (3.17%), Bulnesol (2.65%) and 1,4-Dimethyl-7-(1-methylethyl) azulene (2.38%). The in vitro antibacterial activities of the essential oils were evaluated by the disc diffusion method. The inhibition zones against Staphylococcus aureus and Candida albicans were 23.7 and 23 mm. So the essential oil of L. nacusua showed potent antibacterial activity and potential high selectivity against S. aureus and C. albicans.

Comparison of the formation of peppery and woody sesquiterpenes derived from alpha-guaiene and alpha-bulnesene under aerial oxidative conditions.[Pubmed:25626924]

J Agric Food Chem. 2015 Feb 25;63(7):1932-8.

Deuterium-labeled guaiane derivatives and their precursors, namely, d5-2R-rotundol (11a), d5-2S-rotundol (11b), d5-bulnesone (14), d5-2R-Bulnesol (16), d7-alpha-guaiene (10), and d7-alpha-bulnesene (15), were synthesized in good yields as GC-MS internal standards for comparing the behavior of alpha-guaiene (1) and alpha-bulnesene (5) under autoxidative conditions. It was found that approximately 99% of alpha-guaiene coated onto filter paper and exposed to air at ambient temperature was autoxidized after 48 h and up to 7% of rotundone (3) and 0.6% of rotundols (2a/b) were formed during this period. Autoxidation of alpha-bulnesene (5) was considerably slower, with approximately 80% remaining after 2 days and yielding less than 1.5% of alpha-bulnesone (7) and 0.3% and 0.9% of Bulnesols 6a and 6b, respectively, after 5 days. The results indicate the feasibility of rapid changes of aroma profiles of herbs and other plant materials over time when exposed to air.

Constituents of essential oils from the leaves, stem barks and resins of Canarium parvum Leen., and Canarium tramdenanum Dai et Yakovl. (Burseracea) grown in Vietnam.[Pubmed:24443833]

Nat Prod Res. 2014;28(7):461-6.

The chemical constituents of essential oils from the leaf, stem bark and resins of Canarium parvum Leen., and Canarium tramdenanum Dai et Yakovl. (Burseracea) grown in Vietnam are being reported. The hydrodistilled oils were analysed for their chemical constituents by means of gas chromatography-flame ionisation detector and gas chromatography coupled with mass spectrometry. The main compounds of C. parvum were beta-caryophyllene (18.7%), (E)-beta-ocimene (12.9%), (Z)-beta-ocimene (11.9%), germacrene D (8.8%) and alpha-humulene (8.4%) in the leaf; beta-caryophyllene (30.4%), alpha-copaene (20.5%) and (E)-beta-ocimene (7.7%) in the stem. However, germacrene D (23.2%), alpha-amorphene (14.9%), alpha-copaene (9.8%) and beta-elemene (8.6%) were present in the resin. The leaf of C. tramdenanum comprises beta-caryophyllene (16.8%), alpha-phellandrene (15.9%), gamma-elemene (13.1%) and limonene (11.8%), while limonene (25.7%), alpha-phellandrene (21.7%), alpha-pinene (12.3%) and beta-caryophyllene (10.9%) were present in the stem. However, delta-elemene (14.6%) and Bulnesol (16.0%) are the main constituents in the resin.