Chemistry, Antioxidant and Antimicrobial Potentials of White Pepper (Piper nigrum L.) Essential Oil and Oleoresins

A comparison of chemical, antioxidant and antimicrobial studies of cinnamon leaf and bark volatile oils, oleoresins and their constituents

GC and GC‐MS analysis of fruit volatile oil of star anise (Illicium verum Hook) showed the presence of 25 components which account for the 99.9% of the total amount. The major components were trans‐anethole (94.37%), methyl chevicol (1.82%) and cis‐anethole (1.59%). 15 Components were identified from its acetone extract accounting for 80.27% of the total amount. trans‐Anethole (51.81%) was found as a major component along with linoleic acid (11.6%), 1‐(4‐methoxyphenyl)‐prop‐2‐one (6.71%), foeniculin (5.29%) and palmitic acid (1.47%). Using an inverted petriplate method, the volatile oil completely inhibited the growth of Fusarium moniliforme at 6 µl dose. In case of extract, 50% mycelial zone inhibition was obtained for Penicillium citrinum and Penicillium viridicatum. Moreover, using food poison technique, the volatile oil was found to be effective for controlling the growth of F. moniliforme and Aspergillus niger whereas the extract has been found to be highly effective for Aspergillus flavus. In antibacterial investigations, using agar well diffusion method, the extract has shown better activity for Staphylococcus aureus and Bacillus cereus in comparison with volatile oil and commercial bactericide, ie Ampicillin. However, volatile oil has shown better activity for Salmonella aeruginosa and Bacillus subtilis. Moreover, the extract has shown excellent activity for the inhibition of primary and secondary oxidation products in rapeseed oil which were evaluated using peroxide, thiobarbituric acid, p‐anisidine and carbonyl values. The activity of extract was further confirmed using other antioxidant properties such as ferric thiocyanate method in linoleic acid system, reducing power and scavenging effect (%) on 1,1‐diphenyl‐2‐picrylhydrazyl radical (DPPH) radical. Hence, the extract could be considered as natural antioxidant which may be used for chemoprevention of diseases occurring due to oxidative deterioration. Copyright © 2005 Society of Chemical Industry

Essential oil and oleoresins (ethanol, ethyl acetate, and iso-propyl alcohol) of Myristica fragrans were extracted by using Clevenger and Soxhlet apparatus, respectively. Gas chromatography-mass spectrometry analysis of essential oil showed the presence of 38 components representing about 99.6% of the total weight. Sabinene (29.4%) was found to be a major component along with beta pinene (10.6%), alpha pinene (10.1%), terpene-4-ol (9.6%), and several other minor components. The major component of all oleoresins contained elemicin. It has been observed that the essential oil and ethanol oleoresin showed better activity compared to other tested oleoresins and synthetic antioxidants, butylated hydroxyl anisole and butylated hydroxyl toluene. Furthermore, the activity of essential oil and oleoresins was measured for the inhibition of primary and secondary oxidation products in mustard oil by using peroxide, thiobarbituric acid, and p-anisidine values. In addition, these experiments were further supported by other complementary antioxidant assays, such as ferric thiocyanate method in a linoleic acid system, reducing power, chelating effect, and scavenging effects on 1,1′-diphenyl-2-picrylhydrazyl radical. Hence, the essential oil and ethanol oleoresin of M. fragrans could be considered as a natural food preservative.

Microwave treatment on white pepper was conducted to damage cell tissue to facilitate the distillation and increase the yield of essential oils. The research objective was to determine the effect of pepper varieties and microwave treatment on the profiles of volatile compounds and the characteristics of white pepper essential oils. The research was conducted with 50 grams of white pepper placed into a 15 cm diameter petri dish and put in a microwave oven at the power of 600 watts for 90 seconds then white pepper milled by hammer mill. Essential oils were obtained using the water distillation method then were tested for their characteristics and compounds using Gas chromatography-Mass Spectrometry (GC-MS). White pepper was analyzed using the water content, piperine content, and its cell tissue microstructure was analyzed using Scanning Electron Microscope (SEM). The results showed that different pepper as accession produced different profiles of volatile compounds, characteristics, and antioxidant activity (p<0.05). The number of volatile compounds of white pepper essential oils identified by GC-MS was 42, where the largest compound was β-caryophyllene (50.51%). Microwave treatment damaged the cell wall of white pepper, lowered water content (17.43%), increased piperine content (10.57%) and essential oil yield (25%), and changed the profiles of volatile compounds of essential oils of Lampung daun lebar accession. Color became bluer (b*value rises by 201.99%), increased specific gravity (1.27%) and antioxidant activity (7.4%), decreased solubility in 95% ethanol (17.95%) and acid number (20.8%) while the refractive index was not affected by pepper accessions and microwave treatment.

Green and solvent-free simultaneous ultrasonic-microwave assisted extraction of essential oil from white and black peppers

White and black peppers were subjected to conventional roasting as well as microwave heating in order to study the effects of such techniques on the volatile constituents of each spice oil and its antioxidative activity. Hydrodistillation oil of each spice was analyzed using Gas Chromatography (GC) and Gas chromatography-Mass spectrometry (GC-MS). Twenty six compounds were identified in essential oil of white pepper, whereas, twenty compounds were detected in black pepper essential oil. ô-Carene, limonene, (X - and ß-pinene and ß-caryophyllene were the major components in both. Due to heating treatments, increase in sesquiterpenes and drastic increase in oxygenated terpenes were observed in comparison to the raw samples. Such changes affected the antioxidant activity of the treated samples using 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging as well as ß-carotene bleaching test against tert-Butylhydroquinone (TBHQ). The strongest effect for reduction of DPPH radical was by white pepper microwave heated sample which exhibit 78.2 % ± 2.1), followed by conventionally roasted black pepper sample, (75.2 % ± 1.9) compared to TBHQ (98.8 % ± 2.1) at the same concentration 400 µg/ml. However, conventionally roasted black pepper recorded the highest inhibiting effect for the oxidation of linoleic acid and the subsequent bleaching of ß-carotene (78.2 % ± 2.3), followed by white pepper microwave heated sample (76.2 % ± 1.9) in comparison to TBHQ (98.8 % ± 2.1).

The present study describes the chemical analysis of the essential oil and oleoresins from caraway, which have been studied by using GC-MS. The paper also explains the importance of the extracted oil and oleoresins in the antioxidant activities of target plant species. GC-MS analysis of caraway essential oil showed 51 compounds representing about 96.6% of the total weight. The major components were dillapiole (44.6%), germacrene-beta (14.1%), nothoapiole (8.3%), and beta-selinene (6.8%), along with many other components in minor amounts. Major components in ethyl acetate and iso-octane oleoresins are dillapiole, nothoapiole and germacrene-beta, whereas in ethanol oleoresin contains dillapiole (25%), sitosterol (21.3%) stigmasterol (9.5%) and nothoapiole (8.1%). The antioxidant activity was evaluated by various antioxidant assays such as peroxide, thiobarbituric acid and p-anisidine values. These experiments were further supported by other complementary antioxidant assays such as ferric thiocyanate method in linoleic acid system, reducing power, and scavenging effects on 1,1'-diphenyl-2-picrylhydrazyl (DPPH). Both the caraway volatile oil and its oleoresins showed strong antioxidant activity in comparison with butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT). This study provides additional information about the chemistry and antioxidant activity of caraway. Hence, caraway may be used as natural food preservatives.

The antiradical properties of essential oils and extracts from coriander seeds Coriandrum sativum L., cardamom fruits Elettaria cardamomum L., fruits of white and black pepper Piper nigrum L., and pods of red cayenne and green chili pepper Capsicum frutescens L. were studied in model reactions with the stable free 2,2-diphenyl-1-picrylhydrazyl radical. The essential oils consisted of monoand sesquiterpene hydrocarbons, alcohols, oxides and esters as the main components. Spice extracts contained flavonoids, diand triterpenoids, phenolic acids, alkaloids and carotenoids. The values of antiradical efficiency were low and decreased in the following order: black pepper extract > cayenne pepper extract > cardamom essential oil > chili pepper extract > cardamom extract > white pepper extract > coriander extract > black pepper essential oil > white pepper essential oil > coriander essential oil.

White pepper (Piper nigrum L.) is one of the most popular flavourings targeted for adulteration, i.e., cassava, resulting in quality loss and infringement on consumer rights and interests. Because it is easy and quick cleanup, minimal sample preparation, and excellent performance with strongly or thickly absorbed samples, the Attenuated Total Reflection-Fourier Transform Infrared Spectroscopy (ATR-FTIR) spectrum signal is widely used to measure commercial herbal products. Manipulation of the spectrum signal can be used to quantify a sample as well as reduce its dimensionality. As a result, there is a lot of interest in developing methods for detecting cassava in commercial white pepper (Piper nigrum L.). The aim of the research was to get an ATR-FTIR spectroscopic technique combined with chemometrics to detect cassava as an adulterant in commercial white pepper (Piper nigrum L.). The chemical profiles of white pepper (Piper nigrum L.) and cassava were compared using principal component analysis (PCA). Bangka, Sudu, and Pontianak were used to collect white pepper (Piper nigrum L.) and cassava. White pepper (Piper nigrum L.) and cassava were macerated in 96 percent ethanol for 3×24 hours before being concentrated with a rotary evaporator until thick. Each extract's IR spectral was measured using ATR-FTIR spectroscopy in the 4000-650 cm-1range. In addition, the IR spectral was clustered using PCA in the R program. To obtain the appropriate PCA model, we applied two IR spectral manipulation procedures (normal and derivative IR spectra) of the pure material. The PCA chosen was of the normal IR spectral type, with PC1 and PC2 values of 82.3 percent and 7.5 percent, respectively.. The projection of three commercial samples from the markets revealed that samples A and B were negative for cassava adulterant, while Sample C was suspected to be positive. Finally, the ATR-FTIR spectroscopic method tandem PCA was successful in clustering the presence or absence of cassava content in the commercial of Indonesian White Pepper

The chemical composition, antioxidant and antimicrobial potentials of essential oils and oleoresins obtained from dill (Anethum graveolens L.) seeds and leaves have been studied. The isolated essential oils and oleoresins were analyzed by gas chromatography coupled with mass spectrometry. The antioxidant activity of essential oils and oleoresins in comparison with synthetic antioxidants were evaluated using different antioxidant assays namely peroxide, thiobarbituric acid values. The antioxidant potentials were further confirmed using other methods such as ferric thiocyanate method in linoleic acid system, scavenging effect (%) on DPPH radical and metal chelating activity. Total phenolic content was also calculated using Folin-Ciocalteau method. Their antimicrobial activity was investigated using various methods on an array of microorganisms. Carvone (47.2%) was the major component in seed essential oil whereas dillapiole (90.2%) was the main component of leave essential oil. The oleoresins were mainly having a major fraction of carvone, dillapiole and oleic acid. Both essential oils have shown excellent antioxidant activity. The seed essential oil showed excellent antimicrobial activity against Aspergillus flavus and Fusarium graminearum in food poisoned method. Significant antibacterial activity was recorded for essential oils against Staphylococcus aureus and Bacillus subtilis while nominal inhibitory effects were observed against Escherichia coli and Pseudomonas aeruginosa.

White pepper is one of the staple spices of East Kalimantan. In order to boost the competitiveness of white pepper commodities, it is necessary to raise the added value of the commodity by transforming it into high-value goods, such as white pepper oil. This research intends to evaluate the production of local (LPL) white pepper oil (MLP) with commercial white pepper oil (LPK) using different extraction techniques (microwave-assisted hydro distillation, MAHD; and ultrasonic following hydro distillation, US-HD). This experiment also evaluated the effect of extraction factors on oil yield, including microwave power on MAHD, ultrasonic wave power on US-HD, sonication duration on US-HD, and solvent volume. A comparison of the energy usage of both approaches was also conducted in order to identify the most effective approach. The MAHD and US-HD techniques were used to extract 80 grams of dry white pepper powder mixed with aquadest for 90 and 180 minutes, respectively. Specifically for US-HD, the combination of raw materials was sonicated for 3-5 minutes prior to extraction utilizing the HD method. In both MAHD and US-HD, LPK includes more MLP than LPL, according to experimental findings. MLP yield may be increased by the addition of solvent, wave power (micro and ultrasonic), and sonication time. Based on its efficiency and energy consumption, the US-HD approach is superior to the MAHD.

Spices are considered as a valuable food material owing not only to their special aroma, but also a myriad of nutritional and health benefits. Black pepper (Piper nigrum L.; Piperaceae) is known as the “king of spices”, being commonly used worldwide in its two forms: black and processed white pepper. The main goal of this study was to perform multi-targeted comparative metabolite profiling and fingerprinting approaches targeting primary and secondary metabolites using gas chromatography mass-spectrometry (GC-MS) post-silylation and ultra-performance liquid chromatography (UPLC-MS/MS) coupled to multivariate analyses and molecular networking. A total of 51 metabolites were annotated using GC-MS belonging to fatty acids/esters (9), alkaloids/nitrogenous (6), sugars (3), sugar alcohols (5), organic acids (15), alcohols (4), and aliphatic hydrocarbons (6) in addition to phenols (3). Fatty acids/esters were enriched in black and white pepper at ca. 23.4 mg g−1. Moreover, piperine was detected at higher levels in white pepper at 5.9 mg g−1 compared to 3.4 mg g−1 in black pepper. A total of 71 metabolites were annotated using UPLC-MS/MS, with piperamides as the most abundant class, of which 6 are first time to be detected in P. nigrum fruit “types A, E and O”. In addition, 7 fatty acids were recoded along 4 flavonoids exhibiting novel glycosidic linkage of kaempferol and apigenin. Furthermore, 5 hydroxycinnamic acids have been detected; some were identified for the first time from P. nigrum fruit. Clusters of fatty acids, flavonoids and phenylamides were detected by negative mode GNPS molecular networking, whereas clusters representing the majority of alkaloids were detected in positive mode. Assay of total phenolics and flavonoids revealed higher levels in black compared to white pepper, with values of 45.6 and 37.5 mg GAE per g for total phenolics and 9.4 & 8.5 mg RE per g for flavonoids, respectively. Assessment of antioxidant capacity using DPPH, ABTS scavenging assays, and FRAP assay revealed moderate effects at 49.79, 20.6, and 104.6 (black pepper), 29.0, 11.5, and 77.5 mg TE per g (white pepper), respectively. Moreover, black and white pepper extracts inhibited α-glucosidase enzyme with an IC50 of 0.77 and 0.62 mg mL−1, compared with acarbose.

Capsicum annuum (red sweet and hot cayenne) and Piper nigrum (black and white) pepper powders were evaluated for inhibition of oxidative reactions and extension of the shelf life of fresh pork sausages packaged in a modified atmosphere. Sausages containing either red sweet pepper or cayenne pepper (0.1%, 0.5%, or 2%) or black or white pepper (0.1%, 0.5%, or 1%) were packaged in a modified atmosphere of 80% O2+ 20% CO2, stored for 16 d in the dark at 2 °C, and analyzed each 4 d for pH, CIE L*, a*, and b*, 2‐thiobarbituric acid‐reactive substances (TBARS), psychrotrophic aerobes, sensory discoloration, and off‐odor. Results demonstrated that Capsicum peppers (sweet red and hot cayenne) enhanced red color but failed to prevent discoloration, whereas they were very effective in inhibiting lipid oxidation, chiefly at the highest concentration used (2%), which resulted in a delay of off‐odor formation. Piper peppers (black and white) significantly delayed discoloration with small modification of sausage color; furthermore, they also inhibited lipid oxidation, which led to a delay of off‐odor formation, particularly in the form of black pepper. Besides this, all those spices inhibited microbial growth when added at the highest concentration (1%Piper and 2%Capsicum).

The antimicrobial and antioxidant potentials of hydrodistilled essential oil and oleoresin (obtained using acetone as a solvent) of tailed pepper were carried out by different techniques. The results obtained from antioxidant activity measurements of essential oil and oleoresin against mustard oil were measured for duration of 28 days in terms of peroxide, thiobarbituric acid, total carbonyl and p-anisidine values. The results obtained from butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) was similar to both the oleoresin and essential oil. In addition, the inhibitory action in linoleic acid system was studied by monitoring accumulation of peroxide concentration. The radical scavenging capacity of both essential oil and oleoresin on 2, 2'-diphenyl-1-picrylhydrazyl (DPPH) radical were (71.2%) and (69.77%) respectively at 25 µL/mL. It was relatively lower in comparison with synthetic antioxidants (BHA-96.41%; BHT- 95.91%). The results obtained from reducing power, chelating effect and hydroxyl radical scavenging effect was also supported the antioxidant of essential oil and oleoresin. The tailed pepper essential oil and oleoresin showed 100% mycelial zone inhibition against Penicillium viridicatum at 3000 and 2000 ppm respectively in the poison food method. It is interesting to note that the essential oil revealed 100% clear zone inhibition against Aspergillus flavus at all tested concentrations. The chemical characterization of tailed pepper essential oil by GC and GC-MS resulted in the identification of 44 components accounting for 97.8% of the oil.

Background: Essential oils represent a major classof natural products which are known for their antimicrobial activity.This study aimed to determine the composition of four Piper essential oils by gas chromatography mass spectrometry,attenuated total reflection infrared, and chemometric analysis. Results: Monoterpene was the most predominant class in Piper nigrum and white pepper (87.6 and 80%, respectively)with the dominance of α-pinene, β-pinene, 3-carene, limonene,and β-caryophyllene. Sesquiterpenes represented 50, 19.6, and12.3% of the essential oils of Piper longum, white pepper, and P. nigrum, respectively.Unlike other species, Piper cubeba oilwas found to be rich in aromatics (59%), with eugenol (10.7%) andmethyl eugenol (47.4%) representing the major components along withβ-myrcene (21.2%) and 1,8-cineole (6.4%). Only P. longum essential oil comprised about 18.2% ofalkanes and 13.6% of alkenes. Application of chemometric analysisutilizing GC/MS and ATR-IR data displayed the same segregation patternwhere both principal component analysis and hierarchal cluster analysisrevealed that white pepper was most closely related to P. nigrum while being completely discriminated fromother Piper species. The Piper oils showed promising inhibitory effects on Helicobacter pylori. P. longum oil recorded the most efficient anti-Helicobacter activity [minimum inhibitory concentration (MIC) value of 1.95 μg/ml,which is the same as the MIC of clarithromycin], followed by the oilof white pepper (MIC = 3.90 μg/ml), while P.cubeba and P. nigrum produced the lowest activity (MIC value of 7.81 μg/ml). Conclusion:Piper essentialoils can be used as nutritional supplements or therapeutic drugs toprotect against H. pylori infection.