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GC-MS fingerprint of Pogostemon cablin in China

Hu LF, Li SP, Cao H, Liu JJ, Gao JL, Yang FQ, et al.

J Pharm Biomed Anal, 2006 Sep 18;42(2):200-6.
PMID: 16242880

Pogostemon cablin, originating in Malaysia and India, is cultivated in southern China including Guangdong and Hainan Province, which was called GuangHuoXiang to differentiate it from the HuoXiang of the north, the species Agastache rugosa, that it resembles. Essential oil of P. cablin mainly contributes to the pharmacological activities and the therapeutic properties of the essential oils are directly correlated with their qualitative and quantitative composition. For controlling the quality, standard fingerprint of P. cablin collected from different regions was developed by using GC-MS. Nine compounds including beta-patchoulene, caryophyllene, alpha-guaiene, seychellene, beta-guaiene, delta-guaiene, spathulenol, patchouli alcohol and pogostone were identified among 10 main peaks in P. cablin. Hierarchical clustering analysis based on characteristics of 10 investigated peaks in GC profiles showed that 18 samples were divided into three main clusters, patchouliol-type, pogostone-type and an interim-type, which was the one between the two chemotypes. The simulative mean chromatogram for the three types P. cablin was generated using the Computer Aided Similarity Evaluation System. The fingerprint can help to distinguish the substitute or adulterant, and further assess the differences of P. cablin grown in various areas of China.

Matched MeSH terms: Sesquiterpenes/analysis*
Essential oil composition of Alseodaphne perakensis (Gamble) Kosterm from Malaysia

Anuar MZA, Salleh WMNHW, Khamis S, Nafiah MA, Mat Said Z

Nat Prod Res, 2021 Feb;35(3):508-511.
PMID: 31266357 DOI: 10.1080/14786419.2019.1636245

The chemical composition of the essential oil from the leaves of Alseodaphne perakensis (Gamble) Kosterm (Lauraceae) growing in Perak, Malaysia was investigated for the first time. The essential oil was obtained by hydrodistillation and fully characterized by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). A total of 37 components (90.9 ± 2.5%) were successfully identified in the essential oil which were characterized by high proportions of bicyclogermacrene (15.8 ± 0.5%), δ-cadinene (11.7 ± 0.2%), γ-cadinene (6.3 ± 0.4%), and aromadendrene (5.6 ± 0.5%).

Matched MeSH terms: Sesquiterpenes/analysis
Fulltext Comparative Chemical Profiles of the Essential Oils from Different Varieties of Psidium guajava L

Hassan EM, El Gendy AEG, Abd-ElGawad AM, Elshamy AI, Farag MA, Alamery SF, et al.

Molecules, 2020 Dec 29;26(1).
PMID: 33383905 DOI: 10.3390/molecules26010119

Guava (Psidium guajava) leaves are commonly used in the treatment of diseases. They are considered a waste product resulting from guava cultivation. The leaves are very rich in essential oils (EOs) and volatiles. This work represents the detailed comparative chemical profiles of EOs derived from the leaves of six guava varieties cultivated in Egypt, including Red Malaysian (RM), El-Qanater (EQ), White Indian (WI), Early (E), El-Sabahya El-Gedida (ESEG), and Red Indian (RI), cultivated on the same farm in Egypt. The EOs from the leaves of guava varieties were extracted by hydro-distillation and analyzed with GC-MS. The EOs were categorized in a holistic manner using chemometric tools. The hydro-distillation of the samples yielded 0.11-0.48% of the EO (v/w). The GC-MS analysis of the extracted EOs showed the presence of 38 identified compounds from the six varieties. The sesquiterpene compounds were recorded as main compounds of E, EQ, ESEG, RI, and WI varieties, while the RM variety attained the highest content of monoterpenes (56.87%). The sesquiterpenes, β-caryophyllene (11.21-43.20%), and globulol (76.17-26.42%) were detected as the major compounds of all studied guava varieties, while trans-nerolidol (0.53-10.14) was reported as a plentiful compound in all of the varieties except for the RM variety. A high concentration of D-limonene was detected in the EOs of the RM (33.96%), WI (27.04%), and ESEG (9.10%) varieties. These major compounds were consistent with those reported for other genotypes from different countries. Overall, the EOs' composition and the chemometric analysis revealed substantial variations among the studied varieties that might be ascribed to genetic variability, considering the stability of the cultivation and climate conditions. Therefore, this chemical polymorphism of the studied varieties supports that these varieties could be considered as genotypes of P. guajava. It is worth mentioning here that the EOs, derived from leaves considered to be agricultural waste, of the studied varieties showed that they are rich in biologically active compounds, particularly β-caryophyllene, trans-nerolidol, globulol, and D-limonene. These could be considered as added value for pharmacological and industrial applications. Further study is recommended to confirm the chemical variations of the studied varieties at a molecular level, as well as their possible medicinal and industrial uses.

Matched MeSH terms: Sesquiterpenes/analysis
Assessment of the phytochemical profiles of novel hop (Humulus lupulus L.) cultivars: A potential route to beer crafting

Yan D, Wong YF, Shellie RA, Marriott PJ, Whittock SP, Koutoulis A

Food Chem, 2019 Mar 01;275:15-23.
PMID: 30724181 DOI: 10.1016/j.foodchem.2018.09.082

This study investigated the volatile phytochemical diversity of 30 samples obtained from experimental hybrid and commercial H. lupulus L. plants. Essential oils distilled from these samples were analysed by high resolution gas chromatography coupled with accurate mass time-of-flight mass spectrometry (GC-accTOFMS). A total of 58 secondary metabolites, mainly comprising 18 esters, 6 monoterpene hydrocarbons, 2 oxygenated monoterpenes, 20 sesquiterpene hydrocarbons, 7 oxygenated sesquiterpenes, and 4 ketones, were positively or tentatively identified. A total of 24 metabolites were detected in all samples, but commercial cultivars (selected for brewing performance) had fewer compounds identified compared to experimental genotypes. Chemometrics analyses enabled distinct differentiation of experimental hybrids from commercial cultivars, discussed in terms of the different classes of compounds present in different genotypes. Differences among the mono- and sesquiterpenoids, appear to be related to either: i) the genetic origin of the plants; or ii) the processes of bioaccumulation of the identified secondary metabolites.

Matched MeSH terms: Sesquiterpenes/analysis
The phytochemistry and biological diversity of Ferulago genus (Apiaceae): a systematic review

Salleh WMNHW, Abed SA, Taher M, Kassim H, Tawang A

J Pharm Pharmacol, 2021 Mar 01;73(1):1-21.
PMID: 33791809 DOI: 10.1093/jpp/rgaa034

OBJECTIVES: The genus Ferulago belonging to the family Apiaceae is a flora widely distributed in Central Asia and the Mediterranean and used in folk medicine. It is administered as a sedative, tonic, digestive, aphrodisiac, also as a treatment for intestinal worms and haemorrhoids. Herein, we reported a review on phytochemistry and its biological activities reported from 1990 up to early 2020. All the information and reported studies concerning Ferulago plants were summarized from the library and digital databases (e.g. Scopus, Medline, Scielo, ScienceDirect, SciFinder and Google Scholar).
KEY FINDINGS: The phytochemical investigations of Ferulago species revealed the presence of coumarins as the main bioactive compounds, including daucane derivatives, sesquiterpenes aryl esters, phenol derivatives, flavonoids and essential oils. Moreover, the therapeutic potentials of the pure compounds isolated from the genus Ferulago possess promising properties namely anticholinesterase, antimicrobial, anticoagulant, antileishmanial, antioxidant, antibacterial and antiproliferative.
SUMMARY: Today, significant advances in phytochemical and biological activity studies of different Ferulago species have been revealed. The traditional uses and reported biological results could be correlated via the chemical characterization of these plants. All these data will support the biologists in the elucidation of the biological mechanisms of these plants.

Matched MeSH terms: Sesquiterpenes/analysis
Bioassay-guided isolation of a sesquiterpene lactone of deoxyelephantopin from Elephantopus scaber Linn. active on Trypanosome brucei rhodesience

Zahari Z, Jani NA, Amanah A, Latif MN, Majid MI, Adenan MI

Phytomedicine, 2014 Feb 15;21(3):282-5.
PMID: 24269185 DOI: 10.1016/j.phymed.2013.09.011

Methanolic extracts of 70 Malaysia plants were screened for their in vitro antitrypanosomal activity using Trypanosome brucei rhodesience, strain STIB 900 and mouse skeletal cell (L-6) in cytotoxicity activity assay. Results indicated that methanol extract from Elephantopus scaber Linn. (E. scaber) possessed the highest value of antitrypanosomal activity with good selectivity index (antitrypanosomal IC50 of 0.22±0.02 μg/ml, SI value of 204.55). Based on these results, E. scaber was chosen for further study by applying bioassay guided fractionation to isolate its antiprotozoal principle. The antiprotozoal principle was isolated from the ethyl acetate partition through solvent fractionation and crystallization process. The isolated active compound 1 was identified as deoxyelephantopin on the basis of its spectral analysis (FTIR, MS, 1D and 2D NMR).

Matched MeSH terms: Sesquiterpenes/analysis
Fulltext Chemical compositions, antioxidant and antimicrobial activities of essential oils of Piper caninum Blume

Salleh WM, Ahmad F, Yen KH, Sirat HM

Int J Mol Sci, 2011;12(11):7720-31.
PMID: 22174627 DOI: 10.3390/ijms12117720

Chemical composition, antioxidant and antimicrobial activities of the fresh leaves and stems oils of Piper caninum were investigated. A total of forty eight constituents were identified in the leaves (77.9%) and stems (87.0%) oil which were characterized by high proportions of phenylpropanoid, safrole with 17.1% for leaves and 25.5% for stems oil. Antioxidant activities were evaluated by using β-carotene/linoleic acid bleaching, DPPH radical scavenging and total phenolic content. Stems oil showed the highest inhibitory activity towards lipid peroxidation (114.9 ± 0.9%), compared to BHT (95.5 ± 0.5%), while leaves oil showed significant total phenolic content (27.4 ± 0.5 mg GA/g) equivalent to gallic acid. However, the essential oils showed weak activity towards DPPH free-radical scavenging. Evaluation of antimicrobial activity revealed that both oils exhibited strong activity against all bacteria strains with MIC values in the range 62.5 to 250 μg/mL, but weak activity against fungal strains. These findings suggest that the essential oils can be used as antioxidant and antimicrobial agents for therapeutic, nutraceutical industries and food manufactures.

Matched MeSH terms: Sesquiterpenes/analysis
Sesquiterpenes rich essential oil from Garcinia celebica L. and its cytotoxic and antimicrobial activities

Tan WN, Tan ZH, Zulkifli NI, Nik Mohamed Kamal NNS, Rozman NAS, Tong WY, et al.

Nat Prod Res, 2020 Dec;34(23):3404-3408.
PMID: 30773054 DOI: 10.1080/14786419.2019.1569012

Garcinia celebica L., locally known as "manggis hutan" in Malaysia is widely used in folkloric medicine to treat various diseases. The present study was aimed to examine the chemical composition of the essential oil from the leaves of G. celebica L. (EO-GC) and its cytotoxic and antimicrobial potential. EO-GC obtained by hydrodistillation was analysed using capillary GC and GC-MS. Twenty-two compounds were identified, dominated by α-copaene (61.25%), germacrene D (6.72%) and β-caryophyllene (5.85%). In the in vitro MTT assay, EO-GC exhibited significant anti-proliferative effects towards MCF-7 human breast cancer cells with IC50 value of 45.2 μg/mL. Regarding the antimicrobial activity, it showed better inhibitory effects on Gram-positive bacteria than Gram-negative bacteria and none on the fungi and yeasts tested.

Matched MeSH terms: Sesquiterpenes/analysis
Chemical profiling and biological properties of Neolitsea kedahense Gamble essential oils

Jani NA, Sirat HM, Ahmad F, Mohamad Ali NA, Jamil M

Nat Prod Res, 2017 Dec;31(23):2793-2796.
PMID: 28278643 DOI: 10.1080/14786419.2017.1294172

Hydrodistillation of the fresh stem and leaf of Neolitsea kedahense Gamble, collected from Gunung Jerai, Malaysia followed by the GC-FID and GC-MS analysis revealed the detection of a total of 47 constituents of which 28 (86.4%) from the stem and 31 (96.4%) constituents from the leaf. δ-Cadinene (17.4%), 1-epi-cubenol (11.8%), cyperotundone (9.0%), cis-cadin-4-en-7-ol (7.7%), τ-cadinol (7.1%) and α-cadinol (7.1%) were the principle constituents in the stem oil, whereas β-caryophyllene (18.9%), bicyclogermacrene (18.6%) and trans-muurola-4(14),5-diene (9.8%) were the major constituents in the leaf oil. Among the identified constituents, three constituents namely 7-epi-α-selinene, junenol and cis-cadin-4-en-7-ol have not been found previously from Neolitsea oils. The stem and leaf oils were screened for their α-glucosidase inhibitory and antibacterial activities. Both oils displayed potential α-glucosidase inhibitory activity, while the stem oil possessed weak antibacterial activity against Bacillus subtilis.

Matched MeSH terms: Sesquiterpenes/analysis
Standardized extract of Zingiber zerumbet suppresses LPS-induced pro-inflammatory responses through NF-κB, MAPK and PI3K-Akt signaling pathways in U937 macrophages

Haque MA, Jantan I, Harikrishnan H, Ghazalee S

Phytomedicine, 2019 Feb 15;54:195-205.
PMID: 30668369 DOI: 10.1016/j.phymed.2018.09.183

BACKGROUND: Zingiber zerumbet rhizome has been used as spices and in traditional medicine to heal various immune-inflammatory related ailments. Although the plant was reported to have potent anti-inflammatory and immunosuppressive properties by several studies, the molecular mechanisms underlying the effects have not been well justified.
PURPOSE: The study was carried out to investigate the molecular mechanisms underlying the anti-inflammatory properties of the standardized 80% ethanol extract of Z. zerumbet through its effect on mitogen-activated protein kinase (MyD88)-dependent nuclear factor-kappa B (NF-кB), mitogen activated protein kinase (MAPK) and phosphatidylinositol 3-kinase/Akt (PI3K-Akt) signaling pathways in lipopolysaccharide (LPS)-induced U937 human macrophages.
METHODS: Standardization of the 80% ethanol extract of Z. zerumbet was performed by using a validated reversed-phase HPLC method, while LC-MS/MS was used to profile the secondary metabolites. The release of pro-inflammatory markers, tumor necrosis factor (TNF)-α, interleukin (IL)-1β and prostaglandin E2 (PGE2) was evaluated by enzyme-linked immunosorbent assay (ELISA), while the Western blot technique was executed to elucidate the expression of mediators linked to MyD88-dependent respective signaling pathways. Real-time quantitative reverse transcription polymerase chain reaction (qRT-PCR) assay was carried out to quantify the relative gene expression of cyclooxygenase (COX)-2 and pro-inflammatory mediators at the transcriptional level.
RESULTS: The quantitative and qualitative analyses of Z. zerumbet extract showed the presence of several compounds including the major chemical marker zerumbone. Z. zerumbet extract suppressed the release of pro-inflammatory mediators, COX-2 protein expression and downregulated the mRNA expression of pro-inflammatory markers. Z. zerumbet-treatment also blocked NF-κB activation by preventing the phosphorylation of IKKα/β and NF-κB (p65) as well as the phosphorylation and degradation of IκBα. Z. zerumbet extract concentration-dependently inhibited the phosphorylation of respective MAPKs (JNK, ERK, and p38) as well as Akt. Correspondingly, Z. zerumbet extract suppressed the upstream signaling adaptor molecules, TLR4 and MyD88 prerequisite for the NF-κB, MAPKs, and PI3K-Akt activation.
CONCLUSION: The findings suggest that Z. zerumbet has impressive role in suppressing inflammation and related immune disorders by inhibition of various pro-inflammatory markers through the imperative MyD88-dependent NF-κB, MAPKs, and PI3K-Akt activation.

Matched MeSH terms: Sesquiterpenes/analysis