Advanced Chemophenetic Analysis of Essential Oil from Leaves of Piper gaudichaudianum Kunth (Piperaceae) Using a New Reduction-Oxidation Index to Explore Seasonal and Circadian Rhythms

The aromatic species Piper gaudichaudianum Kunth (Piperaceae) is widely used in Brazil for medicinal and ritualistic applications. In the current study, chemophenetic patterns were realized across season and circadian rhythm based on the chemical profile of essential oils (EOs) from leaves. Hydrodistilled essential oils were analyzed by GC-MS and GC-FID, and a new calculation of metabolite oxidation level, averaged for each individual molecule component of the EO, was used to explore the patterns of metabolism/biosynthesis. This new index used an intermediate calculation, the ‘weighted average redox standard’ (SRO), to enable a value for mixtures of metabolites to be generated, the ‘general mixture redox index’ (GMOR). The indices were subjected to a proof-of-concept approach by making comparison to outcomes from multivariate analyses, i.e., PCA and HCA. Chemical analysis demonstrated that the essential oils were dominated by sesquiterpenes, constructed of 15 classes of compound (C-skeletons), and 4 C-skeletons were recognized in the monoterpene group, giving a total of 19. The variation of chemical profiles was distinct at different phenological stages, but stronger chemical variation was evident between day and night as compared to season. Furthermore, due to comprehensive sampling across different regions, nine chemotypes were recognized, including those previously reported. The SRO and GMRO indices demonstrate that phenological variation of chemistry is mainly an outcome of redox fluctuations in terpene biosynthesis, changing from day to night. These indices also corroborate that chemical diversity is increased with oxidative metabolism. Lastly, the current study demonstrates pronounced phenotypic plasticity in P. gaudichaudianum, which makes it a suitable candidate to help further our understanding of chemophenetics and chemical ecology.

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New Reduction-Oxidation Indices Applied to Mixtures in the Impact on Seasonal and Circadian Rhythm Studies of The Essential Oil From Leaves of Piper Gaudichaudianum Kunth (Piperaceae) – A Folk Medicine and Ritualistic Plant

10.21203/rs.3.rs-730506/v1 ◽

2021 ◽

Author(s):

Ygor Jessé Ramos ◽

Claudete da Costa-Oliveira ◽

Irene Candido-Fonseca ◽

George Azevedo de Queiroz ◽

Elsie Franklin Guimarães ◽

...

Keyword(s):

Circadian Rhythm ◽

Chemical Composition ◽

Folk Medicine ◽

Weighted Average ◽

Redox Balance ◽

Phenological Stages ◽

Composition Variation ◽

Piper Gaudichaudianum ◽

The Impact ◽

First Time

Abstract Piper gaudichaudianum Kunth (Piperaceae) is widely used in Brazil as medicinal and ritualistic. In this study, chemophenetic patterns were evaluated based on leaves’ essential oils (EOs) chemical composition. Several collections were performed to accomplish circadian rhythm and seasonal studies. Besides, a predictive methodology was developed and submitted to Proof of Concept (PoC) to determine the metabolism pattern and evaluate the reduction-oxidation of complex mixtures: Weighted Average Redox Standard (SRO) and General Mixture Redox Index (GMOR). Fresh leaves EOs obtained by hydrodistillation were analyzed by GC-MS and GC-FID. The main identified compounds were sesquiterpenes. Nineteen terpene skeletons were registered. There was chemical composition variation at different phenological stages. EOs varied more between day and night than seasonally. Nine chemotypes are proposed based on our results and those from literature. SRO and GMRO analyzes highlighted a possible redox balance throughout day and night. Compounds per carbon skeleton diversification in EOs are matched by an increase in compounds SRO. We also report for the first time high chemical phenotype plasticity based on EOs analysis and its implications for P. gaudichaudianum chemophenetics, chemosystematics and ecology.

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The Diversity of Volatile Compounds in Australia’s Semi-Desert Genus Eremophila (Scrophulariaceae)

Plants ◽

10.3390/plants10040785 ◽

2021 ◽

Vol 10 (4) ◽

pp. 785

Author(s):

Nicholas J. Sadgrove ◽

Guillermo F. Padilla-González ◽

Alison Green ◽

Moses K. Langat ◽

Eduard Mas-Claret ◽

...

Keyword(s):

Essential Oils ◽

Volatile Compounds ◽

2D Nmr ◽

Chemical Diversity ◽

Desert Shrubs ◽

Multiple Sampling ◽

Australian Continent ◽

Chemical Profiles ◽

Chemical Studies ◽

New Metabolites

Australia’s endemic desert shrubs are commonly aromatic, with chemically diverse terpenes and phenylpropanoids in their headspace profiles. Species from the genus Eremophila (Scrophulariaceae ex. Myoporaceae) are the most common, with 215 recognised taxa and many more that have not yet been described, widely spread across the arid parts of the Australian continent. Over the years, our research team has collected multiple specimens as part of a survey to investigate the chemical diversity of the genus and create leads for further scientific enquiry. In the current study, the diversity of volatile compounds is studied using hydrodistilled essential oils and leaf solvent extracts from 30 taxa. Several rare terpenes and iridoids were detected in chemical profiles widely across the genus, and three previously undescribed sesquiterpenes were isolated and are assigned by 2D NMR—E-11(12)-dehydroisodendrolasin, Z-11-hydroxyisodendrolasin and 10-hydroxydihydro-α-humulene acetate. Multiple sampling from Eremophila longifolia, Eremophila arbuscular, Eremophila latrobei, Eremophila deserti, Eremophila sturtii, Eremophila oppositifolia and Eremophila alternifolia coneys that species in Eremophila are highly chemovariable. However, taxa are generally grouped according to the expression of (1) furanosesquiterpenes, (2) iridoids or oxides, (3) mixtures of 1 and 2, (4) phenylpropanoids, (5) non-furanoid terpenes, (6) mixtures of 4 and 5, and less commonly (7) mixtures of 1 and 5. Furthermore, GC–MS analysis of solvent-extracted leaves taken from cultivated specimens conveys that many heavier ‘volatiles’ with lower vapour pressure are not detected in hydrodistilled essential oils and have therefore been neglected in past chemical studies. Hence, our data reiterate that chemical studies of the genus Eremophila will continue to describe new metabolites and that taxon determination has limited predictive value for the chemical composition.

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Seasonal variation of the essential oil from two Brazilian native Aldama La Llave (Asteraceae) species

Anais da Academia Brasileira de Ciências ◽

10.1590/0001-376520162015-0732 ◽

2016 ◽

Vol 88 (3 suppl) ◽

pp. 1899-1907 ◽

Cited By ~ 1

Author(s):

TUANE S. DE OLIVEIRA ◽

ALINE B. BOMBO ◽

ADRIANA S.S. DE OLIVEIRA ◽

VERA L. GARCIA ◽

BEATRIZ APPEZZATO-DA-GLÓRIA

Keyword(s):

Essential Oil ◽

Essential Oils ◽

Essential Oil Composition ◽

Seasonal Development ◽

Correct Identification ◽

Oil Composition ◽

Phenological Stages ◽

Aromatic Species ◽

Phases Of Development ◽

First Time

ABSTRACT Aldama arenaria and A. robusta are morphologically similar aromatic species that have seasonal development. The yield and chemical composition of essential oils from aerial and underground vegetative organs of these species were compared to verify the production of volatile metabolites in flowering and dormant phases of development and to identify if there are unique compounds for either species. The major compound in the essential oils from A. arenaria leaves was palustrol (16.22%) and for aerial stems was limonene (15.3%), whereas limonene (11.16%) and α-pinene (19.64%) were the major compounds for leaves and aerial stems from A. robusta, respectively. The major compound for the underground organs was α-pinene, in both species and phenological stages. High amounts of diterpenes were found especially for A. arenaria essential oils. Each analyzed species presented unique compounds, which can provide a characteristic chemical profile for both species helping to solve their taxonomic problems. This study characterized for the first time the yield and essential oil composition of A. arenaria and A. robusta, which have medicinal potential, and some of the compounds in their essential oils are unique to each one and may be useful in helping the correct identification of them.

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Chemical Diversity and Therapeutic Effects of Essential Oils of Aniba Species from the Amazon: A Review

Plants ◽

10.3390/plants10091854 ◽

2021 ◽

Vol 10 (9) ◽

pp. 1854

Author(s):

Rafaela C. S. da Trindade ◽

Júlia Karla A. M. Xavier ◽

William N. Setzer ◽

José Guilherme S. Maia ◽

Joyce Kelly R. da Silva

Keyword(s):

Essential Oils ◽

Biological Activities ◽

Hierarchical Cluster ◽

Geographic Area ◽

Chemical Diversity ◽

Therapeutic Effects ◽

Tropical Regions ◽

Main Compound ◽

Chemical Profiles ◽

Amazonas State

Lauraceae families have great diversity in the world’s tropical regions and are represented mainly by aromatic shrubs and trees with significant production of essential oils (EOs). This work presents a review of the EO chemical profiles from specimens of Aniba, including their seasonal variations, geographical distributions, and biological activities in the Amazon biome. Based on the survey, 15 species were reviewed, representing 167 oil samples extracted from leaves, twig barks, and woods. Brazilian Amazon was the most representative geographic area in the number of specimens, highlighting the locations Belém, (Pará state, PA) (3 spp., 37 samples), Santarém (PA) (3 spp., 10 samples), Carajás (PA) (3 spp., 7 samples), and Manaus (Amazonas state, AM) (3 spp., 16 samples). The main compound classes identified in oils were benzenoids and phenylpropanoids, represented by 1-nitro-2-phenylethane, benzyl salicylate, benzyl benzoate and methyleugenol, along with terpenoids, especially monoterpenes and sesquiterpenes, such as linalool, α-phellandrene, β-phellandrene, β-selinene, and spathulenol. The EOs from Aniba showed considerable variation in the chemical profiles according to season and collection site. The hierarchical cluster analysis classified the samples into two main groups according to chemical composition. This review highlights its comprehensive and up-to-date information on history, conservation, traditional uses, chemosystematics, pharmacological potential of Aniba species.

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Chemical Variability of Peel and Leaf Essential Oils in the Citrus Subgenus Papeda (Swingle) and Few Relatives

Plants ◽

10.3390/plants10061117 ◽

2021 ◽

Vol 10 (6) ◽

pp. 1117

Author(s):

Clémentine Baccati ◽

Marc Gibernau ◽

Mathieu Paoli ◽

Patrick Ollitrault ◽

Félix Tomi ◽

...

Keyword(s):

Essential Oils ◽

13C Nmr ◽

Chemical Diversity ◽

Field Crop ◽

High Chemical ◽

Crop Species ◽

Nmr Spectrometry ◽

Chemical Variability ◽

Almost All ◽

Experimental Crosses

The Papeda Citrus subgenus includes several species belonging to two genetically distinct groups, containing mostly little-exploited wild forms of citrus. However, little is known about the potentially large and novel aromatic diversity contained in these wild citruses. In this study, we characterized and compared the essential oils obtained from peels and leaves from representatives of both Papeda groups, and three related hybrids. Using a combination of GC, GC-MS, and 13C-NMR spectrometry, we identified a total of 60 compounds in peel oils (PO), and 76 compounds in leaf oils (LO). Limonene was the major component in almost all citrus PO, except for C. micrantha and C. hystrix, where β-pinene dominated (around 35%). LO composition was more variable, with different major compounds among almost all samples, except for two citrus pairs: C. micrantha/C. hystrix and two accessions of C. ichangensis. In hybrid relatives, the profiles were largely consistent with their Citrus/Papeda parental lineage. This high chemical diversity, not only among the sections of the subgenus Papeda, but also between species and even at the intraspecific level, suggests that Papeda may be an important source of aroma diversity for future experimental crosses with field crop species.

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Variation in the Chemical Composition of Five Varieties of Curcuma longa Rhizome Essential Oils Cultivated in North Alabama

Foods ◽

10.3390/foods10020212 ◽

2021 ◽

Vol 10 (2) ◽

pp. 212

Author(s):

William N. Setzer ◽

Lam Duong ◽

Ambika Poudel ◽

Srinivasa Rao Mentreddy

Keyword(s):

United States ◽

Essential Oils ◽

Curcuma Longa ◽

Southeastern United States ◽

Traditional Herbal Medicine ◽

Humid Climate ◽

Tropical Regions ◽

Chromatographic Techniques ◽

Chemical Profiles ◽

Bioactive Agents

Turmeric (Curcuma longa L.) is an important spice, particularly is Asian cuisine, and is also used in traditional herbal medicine. Curcuminoids are the main bioactive agents in turmeric, but turmeric essential oils also contain health benefits. Turmeric is a tropical crop and is cultivated in warm humid environments worldwide. The southeastern United States also possesses a warm humid climate with a growing demand for locally sourced herbs and spices. In this study, five different varieties of C. longa were cultivated in north Alabama, the rhizome essential oils obtained by hydrodistillation, and the essential oils were analyzed by gas chromatographic techniques. The major components in the essential oils were α-phellandrene (3.7–11.8%), 1,8-cineole (2.6–11.7%), α-zingiberene (0.8–12.5%), β-sesquiphellandrene (0.7–8.0%), ar-turmerone (6.8–32.5%), α-turmerone (13.6–31.5%), and β-turmerone (4.8–18.4%). The essential oil yields and chemical profiles of several of the varieties are comparable with those from tropical regions, suggesting that these should be considered for cultivation and commercialization in the southeastern United States.

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The Genus Haplophyllum Juss.: Phytochemistry and Bioactivities—A Review

Molecules ◽

10.3390/molecules26154664 ◽

2021 ◽

Vol 26 (15) ◽

pp. 4664

Author(s):

Majid Mohammadhosseini ◽

Alessandro Venditti ◽

Claudio Frezza ◽

Mauro Serafini ◽

Armandodoriano Bianco ◽

...

Keyword(s):

Organic Acids ◽

Essential Oils ◽

Web Of Science ◽

Biological Activities ◽

Scientific Information ◽

Comprehensive Review ◽

Scientific Databases ◽

Organic Extracts ◽

Chemical Profiles ◽

Therapeutic Properties

Herein, a comprehensive review is given focusing on the chemical profiles of the essential oils (EOs), non-volatile compounds, ethnobotany, and biological activities of different Haplophyllum (Rutaceae family) species. To gather the relevant data, all the scientific databases, including Scopus, ISI-WOS (Institute of Scientific Information-Web of Science), and PubMed and highly esteemed publishers such as Elsevier, Springer, Taylor and Francis, etc., were systematically retrieved and reviewed. A wide array of valuable groups of natural compounds, e.g., terpenoids, coumarins, alkaloids, lignans, flavonoids, and organic acids have been isolated and subsequently characterized in different organic extracts of a number of Haplophyllum species. In addition, some remarkable antimicrobial, antifungal, anti-inflammatory, anticancer, cytotoxic, antileishmanial, and antialgal effects as well as promising remedial therapeutic properties have been well-documented for some species of the genus Haplophyllum.

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A Review on Cistus sp.: Phytochemical and Antimicrobial Activities

Plants ◽

10.3390/plants10061214 ◽

2021 ◽

Vol 10 (6) ◽

pp. 1214

Author(s):

Imane Zalegh ◽

Mohamed Akssira ◽

Mohammed Bourhia ◽

Fouad Mellouki ◽

Naima Rhallabi ◽

...

Keyword(s):

Infectious Diseases ◽

Essential Oils ◽

Mediterranean Sea ◽

Scientific Literature ◽

Antimicrobial Activities ◽

Mechanisms Of Action ◽

Pharmacological Activities ◽

Global View ◽

Chemical Profiles ◽

Phytochemical Profiles

Resistance to drugs is reaching alarming levels and is placing human health at risk. With the lack of new antimicrobials drugs, infectious diseases are becoming harder to treat. Hence, there is an increasing awareness of active phytochemicals with therapeutic functions. The tremendous research interest on the Cistus L. genus includes numerous plants used in traditional medicine by people living around the Mediterranean Sea, also resulted in some interesting discoveries and written literature. This review aimed at gathering scientific literature about Cistus species, describing phytochemical profiles and the various pharmacological activities. We also extensively reviewed the antimicrobial activities, including antiviral, antiparasitic, antifungal, and antibacterial potentials of Essential Oils (EO), raw extracts as well as isolated compounds. Mechanisms of action along with methods used are also investigated in this review. Considering the findings of the Cistus species extracts, this genus offers an adequate reserve of active phytochemicals since many have been used to create drugs. Therefore, this review work can serve society by providing a global view on Cistus L. sp. regarding pharmacological potentials and their chemical profiles.

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CHEMICAL DIVERSITY OF ESSENTIAL OILS OF 15 PIPER SPECIES FROM GUATEMALA

Acta Horticulturae ◽

10.17660/actahortic.2012.964.4 ◽

2012 ◽

pp. 39-46 ◽

Cited By ~ 4

Author(s):

S.M. Cruz ◽

A. Cáceres ◽

L.E. Álvarez ◽

M.A. Apel ◽

A.T. Henriques

Keyword(s):

Essential Oils ◽

Chemical Diversity

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Monoterpenes and Sesquiterpenes of Essential Oils from Psidium Species and Their Biological Properties

Molecules ◽

10.3390/molecules26040965 ◽

2021 ◽

Vol 26 (4) ◽

pp. 965

Author(s):

Renan Campos e Silva ◽

Jamile S. da Costa ◽

Raphael O. de Figueiredo ◽

William N. Setzer ◽

Joyce Kelly R. da Silva ◽

...

Keyword(s):

Essential Oils ◽

Biological Activities ◽

Biological Properties ◽

Chemical Diversity ◽

New Drugs ◽

Natural Sources ◽

Biological Potential ◽

The World ◽

Review Reports ◽

Collection Sites

Psidium (Myrtaceae) comprises approximately 266 species, distributed in tropical and subtropical regions of the world. Psidium taxa have great ecological, economic, and medicinal relevance due to their essential oils’ chemical diversity and biological potential. This review reports 18 Psidium species growing around the world and the chemical and biological properties of their essential oils. Chemically, 110 oil records are reported with significant variability of volatile constituents, according to their seasonality and collection sites. Monoterpenes and sesquiterpenes with acyclic (C10 and C15), p-menthane, pinane, bisabolane, germacrane, caryophyllane, cadinane, and aromadendrane skeleton-types, were the primary constituents. The essential oils showed various biological activities, including antioxidant, antifungal, antibacterial, phytotoxic, larvicidal, anti-inflammatory, and cytotoxic properties. This review contributes to the Psidium species rational and economic exploration as natural sources to produce new drugs.

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