Terpenes isolated from Polyalthia simiarum and their cytotoxic activities

Duan, Xing; Guo, Kunyuan; Lv, Dongjin; Mei, Ren‐Qiang; Zhang, Meide

doi:10.1016/j.fitote.2020.104734

Cited by 4 publications

(4 citation statements)

References 14 publications

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“…Scientific reports on leaves, bark, stem bark, root, twigs, and seeds of Polyalthia have revealed dozens of types of alkaloids and terpenes with numerous biological and pharmacological activities with chemopreventive potentials, such as anti-bacterial [18][19][20], anti-fungal [21], anti-viral [22,23], anti-plasmodial [24][25][26], anti-inflammatory [27][28][29], anti-ulcer [30], antitumor [31][32][33], and anti-cancer [34][35][36] effects.…”

Section: Phytochemical Constituents In Species Of Polyalthiamentioning

confidence: 99%

Phytochemicals from Polyalthia Species: Potential and Implication on Anti-Oxidant, Anti-Inflammatory, Anti-Cancer, and Chemoprevention Activities

2021

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Polyalthia belong to the Annonaceae family and are a type of evergreen tree distributed across many tropical and subtropical regions. Polyalthia species have been used long term as indigenous medicine to treat certain diseases, including fever, diabetes, infection, digestive disease, etc. Recent studies have demonstrated that not only crude extracts but also the isolated pure compounds exhibit various pharmacological activities, such as anti-oxidant, anti-microbial, anti-tumor, anti-cancer, etc. It is known that the initiation of cancer usually takes several years and is related to unhealthy lifestyle, as well as dietary and environmental factors, such as stress, toxins and smoking. In fact, natural or synthetic substances have been used as cancer chemoprevention to delay, impede, or even stop cancer growing. This review is an attempt to collect current available phytochemicals from Polyalthia species, which exhibit anti-cancer potentials for chemoprevention purposes, providing directions for further research on the interesting agents and possible clinical applications.

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Section: Phytochemical Constituents In Species Of Polyalthiamentioning

confidence: 99%

Phytochemicals from Polyalthia Species: Potential and Implication on Anti-Oxidant, Anti-Inflammatory, Anti-Cancer, and Chemoprevention Activities

2021

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“…Compound 1 was found to be a mixture of epimers of 16α (S) and 16β (R) forms (1:1) based on the analysis of NMR spectra of the isolated compound 1 and the hexane fraction before purification ( Figure S6 ). The single epimer 16α (S) form of compound 1 was previously isolated from P. longifolia [ 28 ], P. barnesii [ 35 ], and P. simiarum [ 36 ] (the Annonaceae family). A mixture of 16S and 16R epimers (1:1) was also found in P. longifolia [ 24 ] and chemically synthesized [ 30 ].…”

Section: Discussionmentioning

confidence: 99%

Clerodane Diterpenoids from an Edible Plant Justicia insularis: Discovery, Cytotoxicity, and Apoptosis Induction in Human Ovarian Cancer Cells

et al. 2021

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Objectives: The toxicity of chemotherapeutic anticancer drugs is a serious issue in clinics. Drug discovery from edible and medicinal plants represents a promising approach towards finding safer anticancer therapeutics. Justicia insularis T. Anderson (Acanthaceae) is an edible and medicinal plant in Nigeria. This study aims to discover cytotoxic compounds from this rarely explored J. insularis and investigate their underlying mechanism of action. Methods: The cytotoxicity of the plant extract was evaluated in human ovarian cancer cell lines and normal human ovarian surface epithelia (HOE) cells using a sulforhodamine B assay. Bioassay-guided isolation was carried out using column chromatography including HPLC, and the isolated natural products were characterized using GC-MS, LC-HRMS, and 1D/2D NMR techniques. Induction of apoptosis was evaluated using Caspase 3/7, 8, and 9, and Annexin V and PI based flow cytometry assays. SwissADME and SwissTargetPrediction web tools were used to predict the molecular properties and possible protein targets of identified active compounds. Key finding: The two cytotoxic compounds were identified as clerodane diterpenoids: 16(α/β)-hydroxy-cleroda-3,13(14)Z-dien-15,16-olide (1) and 16-oxo-cleroda-3,13(14)E-dien-15-oic acid (2) from the Acanthaceous plant for the first time. Compound 1 was a very abundant compound (0.7% per dry weight of plant material) and was shown to be more potent than compound 2 with IC50 values in the micromolar range against OVCAR-4 and OVCAR-8 cancer cells. Compounds 1 and 2 were less cytotoxic to HOE cell line. Both compounds induced apoptosis by increasing caspase 3/7 activities in a concentration dependent manner. Compound 1 further increased caspase 8 and 9 activities and apoptosis cell populations. Compounds 1 and 2 are both drug like, and compound 1 may target various proteins including a kinase. Conclusions: Clerodane diterpenoids (1 and 2) in J. insularis were identified as cytotoxic to ovarian cancer cells via the induction of apoptosis, providing an abundant and valuable source of hit compounds for the treatment of ovarian cancer.

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“…Adsorption chromatography uses a stationary phase, made up of matrices (resins) that interact with the compounds to be separated, and a mobile phase that drags the compounds through the stationary phase. Column chromatography continues to be one of the main tools for the primary fractionation of extracts to obtain terpenes/terpenoids (Duan et al 2020;Huang et al 2016;Li et al 2017;Xu et al 2019). New highly selective chromatographic resins for terpenoids are currently available, which can be used for column chromatography, preparative plate, and liquid chromatography (Table 3).…”

Section: Adsorption Chromatographymentioning

confidence: 99%

Factors that influence the extraction methods of terpenes from natural sources

González-Hernández,

Valdez-Cruz,

Trujillo-Roldán

2024

Chem. Pap.

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Due to their various applications, terpenes and terpenoids are secondary metabolites of industrial interest. These compounds can be found in a wide variety of organisms from virtually all biological kingdoms. However, it has been identified that various factors in the production process, such as the place and time of harvest, pretreatments, extraction, and purification, generate differences in the profile of terpenes and terpenoids that can be obtained from organisms. The first factor that influences the extraction of compounds is drying since an inappropriate choice of the drying method can lead to the loss of the compounds of interest or the appearance of others that arise due to the decomposition of the original molecules. Similarly, Soxhlet extraction is the most used method in the recovery of terpenoids due to its high extraction efficiency. However, unconventional extraction methods have proven to be effective alternatives for terpenoid recovery, particularly the use of microwave and high-pressure extraction, as well as the use of unconventional solvents, achieving extraction efficiencies equal to or greater than Soxhlet in shorter times. This review will address the differences observed in the extraction of terpenoids and the main factors that cause them, as well as a comparison of the advantages and disadvantages of the various methodologies for drying, extraction, and separation of these compounds.

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Terpenes isolated from Polyalthia simiarum and their cytotoxic activities

Cited by 4 publications

References 14 publications

Phytochemicals from Polyalthia Species: Potential and Implication on Anti-Oxidant, Anti-Inflammatory, Anti-Cancer, and Chemoprevention Activities

Phytochemicals from Polyalthia Species: Potential and Implication on Anti-Oxidant, Anti-Inflammatory, Anti-Cancer, and Chemoprevention Activities

Clerodane Diterpenoids from an Edible Plant Justicia insularis: Discovery, Cytotoxicity, and Apoptosis Induction in Human Ovarian Cancer Cells

Factors that influence the extraction methods of terpenes from natural sources

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