Meroterpenoids: A Comprehensive Update Insight on Structural Diversity and Biology

Meroterpenoids are secondary metabolites formed due to mixed biosynthetic pathways which are produced in part from a terpenoid co-substrate. These mixed biosynthetically hybrid compounds are widely produced by bacteria, algae, plants, and animals. Notably amazing chemical diversity is generated among meroterpenoids via a combination of terpenoid scaffolds with polyketides, alkaloids, phenols, and amino acids. This review deals with the isolation, chemical diversity, and biological effects of 452 new meroterpenoids reported from natural sources from January 2016 to December 2020. Most of the meroterpenoids possess antimicrobial, cytotoxic, antioxidant, anti-inflammatory, antiviral, enzyme inhibitory, and immunosupressive effects.

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Terpenoids from Marine Soft Coral of the Genus Xenia in 1977 to 2019

Molecules ◽

10.3390/molecules25225386 ◽

2020 ◽

Vol 25 (22) ◽

pp. 5386

Author(s):

Shean-Yeaw Ng ◽

Chin-Soon Phan ◽

Takahiro Ishii ◽

Takashi Kamada ◽

Toshiyuki Hamada ◽

...

Keyword(s):

Biological Activity ◽

Secondary Metabolites ◽

South China Sea ◽

South China ◽

Coastal Waters ◽

Soft Coral ◽

Structural Diversity ◽

Chemical Diversity ◽

Comprehensive Overview ◽

Coral Genus

Members of the marine soft coral genus Xenia are rich in a diversity of diterpenes. A total of 199 terpenes consisting of 14 sesquiterpenes, 180 diterpenes, and 5 steroids have been reported to date. Xenicane diterpenes were reported to be the most common chemical skeleton biosynthesized by members of this genus. Most of the literature reported the chemical diversity of Xenia collected from the coral reefs in the South China Sea and the coastal waters of Taiwan. Although there was a brief review on the terpenoids of Xenia in 2015, the present review is a comprehensive overview of the structural diversity of secondary metabolites isolated from soft coral genus Xenia and their potent biological activity as reported between 1977 to 2019.

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Insightful Valorization of the Biological Activities of Pani Heloch Leaves through Experimental and Computer-Aided Mechanisms

Molecules ◽

10.3390/molecules25215153 ◽

2020 ◽

Vol 25 (21) ◽

pp. 5153

Author(s):

Naureen Banu ◽

Najmul Alam ◽

Mohammad Nazmul Islam ◽

Sanjida Islam ◽

Shahenur Alam Sakib ◽

...

Keyword(s):

Secondary Metabolites ◽

Methanol Extract ◽

Biological Activities ◽

Biological Effects ◽

Experimental Models ◽

Clot Lysis ◽

Control Group ◽

Anti Inflammatory

Pani heloch (Antidesma montanum) is traditionally used to treat innumerable diseases and is a source of wild vegetables for the management of different pathological conditions. The present study explored the qualitative phytochemicals; quantitative phenol and flavonoid contents; in vitro antioxidant, anti-inflammatory, and thrombolytic effects; and in vivo antipyretic and analgesic properties of the methanol extract of A. montanum leaves in different experimental models. The extract exhibited secondary metabolites including alkaloids, flavonoids, flavanols, phytosterols, cholesterols, phenols, terpenoids, glycosides, fixed oils, emodines, coumarins, resins, and tannins. Besides, Pani heloch showed strong antioxidant activity (IC50 = 99.00 µg/mL), while a moderate percentage of clot lysis (31.56%) in human blood and significant anti-inflammatory activity (p < 0.001) was achieved with the standard. Moreover, the analgesic and antipyretic properties appeared to trigger a significant response (p < 0.001) relative to in the control group. Besides, an in silico study of carpusin revealed favorable protein-binding affinities. Furthermore, the absorption, distribution, metabolism, excretion, and toxicity analysis and toxicological properties of all isolated compounds adopted Lipinski’s rule of five for drug-like potential and level of toxicity. Our research unveiled that the methanol extract of A. montanum leaves exhibited secondary metabolites that are a good source for managing inflammation, pyrexia, pain, and cellular toxicity. Computational approaches and further studies are required to identify the possible mechanism which responsible for the biological effects.

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Validation of a RP-HPLC-DAD Method for Chamomile (Matricaria recutita) Preparations and Assessment of the Marker, Apigenin-7-glucoside, Safety and Anti-Inflammatory Effect

Evidence-based Complementary and Alternative Medicine ◽

10.1155/2015/828437 ◽

2015 ◽

Vol 2015 ◽

pp. 1-9 ◽

Cited By ~ 6

Author(s):

Felipe Galeti Miguel ◽

Amanda Henriques Cavalheiro ◽

Nathália Favaretto Spinola ◽

Diego Luis Ribeiro ◽

Gustavo Rafael Mazzaron Barcelos ◽

...

Keyword(s):

High Performance ◽

Biological Effects ◽

Reversed Phase ◽

Natural Sources ◽

Rp Hplc ◽

Anti Inflammatory ◽

Interday Precision ◽

Lps Treatment ◽

Chamomile Flower ◽

Inflammatory Effect

Chamomile is a medicinal plant, which presents several biological effects, especially the anti-inflammatory effect. One of the compounds related to this effect is apigenin, a flavonoid that is mostly found in its glycosylated form, apigenin-7-glucoside (APG), in natural sources. However, the affectivity and safety of this glycoside have not been well explored for topical application. In this context, the aim of this work was to develop and validate a reversed-phase high-performance liquid chromatography (RP-HPLC-DAD) method to quantify APG in chamomile preparations. Additionally, the safety and the anti-inflammatory potential of this flavonoid were verified. The RP-HPLC-DAD method was developed and validated with linearity at 24.0–36.0 μg/mL range (r=0.9994). Intra- and interday precision (RSD) were 0.27–2.66% and accuracy was 98.27–101.21%. The validated method was applied in the analysis of chamomile flower heads, glycolic extract, and Kamillen cream, supporting the method application in the quality control of chamomile preparations. Furthermore, the APG safety was assessed by MTT cytotoxicity assay and mutagenic protocols and the anti-inflammatory activity was confirmed by a diminished TNF-αproduction showed by mice macrophages treated with APG following LPS treatment.

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Exploring novel secondary metabolites from natural products using pre-processed mass spectral data

Scientific Reports ◽

10.1038/s41598-019-54078-1 ◽

2019 ◽

Vol 9 (1) ◽

Author(s):

Hyun Woo Kim ◽

Seong Yeon Choi ◽

Hyeon Seok Jang ◽

Byeol Ryu ◽

Sang Hyun Sung ◽

...

Keyword(s):

Natural Products ◽

Secondary Metabolites ◽

Natural Product ◽

Spectral Data ◽

Structural Diversity ◽

Natural Material ◽

Natural Sources ◽

Mass Spectral ◽

Aerial Parts ◽

Similar Chemical

AbstractMany natural product chemists are working to identify a wide variety of novel secondary metabolites from natural materials and are eager to avoid repeatedly discovering known compounds. Here, we developed liquid chromatography/mass spectrometry (LC/MS) data-processing protocols for assessing high-throughput spectral data from natural sources and scoring the novelty of unknown metabolites from natural products. This approach automatically produces representative MS spectra (RMSs) corresponding to single secondary metabolites in natural sources. In this study, we used the RMSs of Agrimonia pilosa roots and aerial parts as models to reveal the structural similarities of their secondary metabolites and identify novel compounds, as well as isolation of three types of nine new compounds including three pilosanidin- and four pilosanol-type molecules and two 3-hydroxy-3-methylglutaryl (HMG)-conjugated chromones. Furthermore, we devised a new scoring system, the Fresh Compound Index (FCI), which grades the novelty of single secondary metabolites from a natural material using an in-house database constructed from 466 representative medicinal plants from East Asian countries. We expect that the FCIs of RMSs in a sample will help natural product chemists to discover other compounds of interest with similar chemical scaffolds or novel compounds and will provide insights relevant to the structural diversity and novelty of secondary metabolites in natural products.

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Vitex trifolia: AN ETHNOBOTANICAL AND PHARMACOLOGICAL REVIEW

Asian Journal of Pharmaceutical and Clinical Research ◽

10.22159/ajpcr.2018.v11s4.31689 ◽

2018 ◽

Vol 11 ◽

Author(s):

Suchitra M,

Keyword(s):

Amino Acids ◽

Secondary Metabolites ◽

Plant Species ◽

Plant Extracts ◽

Clinical Studies ◽

Clinical Relevance ◽

Polyphenolic Compounds ◽

Rich Source ◽

Medicinal Uses ◽

Anti Inflammatory

Objective: The perspective of this review is the list of activities carried out or studied along with description, habitat macro-microscopy, phytoconstituents, medicinal uses, clinical studies, and toxicology on the plant Vitex trifolia. Methods: A large number of the species of the Genus Vitex are widely employed in Indian traditional systems of medicine. A total of 270 plant species of genus Vitex have been identified worldwide. V. trifolia is used in Ayurveda and Unani. These species are rich source of secondary metabolites such as polyphenolic compounds, terpenoids, phytosterols, protein and amino acids, tannins, and saponins.Results: The results of various studies V. trifolia possess larvicidal, analgesic, anti-inflammatory, antimicrobial, antioxidant, hepatoprotective, antihistaminic, and antiasthmatic properties.Conclusion: The review on V. trifolia explains that there is a need for detailed study on its clinical relevance and safety of plant extracts.

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Piper Species: A Comprehensive Review on Their Phytochemistry, Biological Activities and Applications

Molecules ◽

10.3390/molecules24071364 ◽

2019 ◽

Vol 24 (7) ◽

pp. 1364 ◽

Cited By ~ 40

Author(s):

Bahare Salehi ◽

Zainul Amiruddin Zakaria ◽

Rabin Gyawali ◽

Salam A. Ibrahim ◽

Jovana Rajkovic ◽

...

Keyword(s):

Secondary Metabolites ◽

Essential Oils ◽

Traditional Medicine ◽

Biological Activities ◽

Biological Effects ◽

Chemical Constituents ◽

Food Preservation ◽

Piper Nigrum ◽

Piper Betle ◽

Anti Inflammatory

Piper species are aromatic plants used as spices in the kitchen, but their secondary metabolites have also shown biological effects on human health. These plants are rich in essential oils, which can be found in their fruits, seeds, leaves, branches, roots and stems. Some Piper species have simple chemical profiles, while others, such as Piper nigrum, Piper betle, and Piper auritum, contain very diverse suites of secondary metabolites. In traditional medicine, Piper species have been used worldwide to treat several diseases such as urological problems, skin, liver and stomach ailments, for wound healing, and as antipyretic and anti-inflammatory agents. In addition, Piper species could be used as natural antioxidants and antimicrobial agents in food preservation. The phytochemicals and essential oils of Piper species have shown strong antioxidant activity, in comparison with synthetic antioxidants, and demonstrated antibacterial and antifungal activities against human pathogens. Moreover, Piper species possess therapeutic and preventive potential against several chronic disorders. Among the functional properties of Piper plants/extracts/active components the antiproliferative, anti-inflammatory, and neuropharmacological activities of the extracts and extract-derived bioactive constituents are thought to be key effects for the protection against chronic conditions, based on preclinical in vitro and in vivo studies, besides clinical studies. Habitats and cultivation of Piper species are also covered in this review. In this current work, available literature of chemical constituents of the essential oils Piper plants, their use in traditional medicine, their applications as a food preservative, their antiparasitic activities and other important biological activities are reviewed.

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Exploring Chemical Diversity of Phorbas Sponges as a Source of Novel Lead Compounds in Drug Discovery

10.20944/preprints202110.0354.v1 ◽

2021 ◽

Author(s):

Alessia Caso ◽

Fernanda Barbosa da Silva ◽

Germana Esposito ◽

Roberta Teta ◽

Gerardo Della Sala ◽

...

Keyword(s):

Natural Products ◽

Drug Discovery ◽

Secondary Metabolites ◽

Marine Natural Products ◽

Biological Activities ◽

Great Majority ◽

Marine Sponges ◽

Chemical Diversity ◽

Lead Compounds ◽

Anti Inflammatory

Porifera, commonly referred to as marine sponges, have stood out as major producers of marine natural products (MNPs). Sponges of the genus Phorbas have attracted much attention along years. They are widespread in all continents, and several structurally unique compounds have been identified from species of this genus. Terpenes, mainly sesterterpenoids, represent the great majority of secondary metabolites isolated from Phorbas species, even though several alkaloids and steroids have also been reported. Many of these compounds have shown a variety of biological activities. Particularly, Phorbas sponges have been demonstrated to be a source of cytotoxic metabolites. In addition, MNPs exhibiting cytostatic, antimicrobial and anti-inflammatory activities, have been isolated and structurally characterized. This work brings an overview of Phorbas secondary metabolites reported since the first study published in 1993 until 2020, and their biological activities.

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Exploring Chemical Diversity of Phorbas Sponges as a Source of Novel Lead Compounds in Drug Discovery

Marine Drugs ◽

10.3390/md19120667 ◽

2021 ◽

Vol 19 (12) ◽

pp. 667

Author(s):

Alessia Caso ◽

Fernanda Barbosa da Silva ◽

Germana Esposito ◽

Roberta Teta ◽

Gerardo Della Sala ◽

...

Keyword(s):

Natural Products ◽

Drug Discovery ◽

Secondary Metabolites ◽

Marine Natural Products ◽

Biological Activities ◽

Marine Sponges ◽

Chemical Diversity ◽

Lead Compounds ◽

Synthetic Routes ◽

Anti Inflammatory

Porifera, commonly referred to as marine sponges, are acknowledged as major producers of marine natural products (MNPs). Sponges of the genus Phorbas have attracted much attention over the years. They are widespread in all continents, and several structurally unique compounds have been identified from this species. Terpenes, mainly sesterterpenoids, are the major secondary metabolites isolated from Phorbas species, even though several alkaloids and steroids have also been reported. Many of these compounds have presented interesting biological activities. Particularly, Phorbas sponges have been demonstrated to be a source of cytotoxic metabolites. In addition, MNPs exhibiting cytostatic, antimicrobial, and anti-inflammatory activities have been isolated and structurally characterized. This review provides an overview of almost 130 secondary metabolites from Phorbas sponges and their biological activities, and it covers the literature since the first study published in 1993 until November 2021, including approximately 60 records. The synthetic routes to the most interesting compounds are briefly outlined.

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Naturally Occurring Chromone Glycosides: Sources, Bioactivities, and Spectroscopic Features

Molecules ◽

10.3390/molecules26247646 ◽

2021 ◽

Vol 26 (24) ◽

pp. 7646

Author(s):

Yhiya Amen ◽

Marwa Elsbaey ◽

Ahmed Othman ◽

Mahmoud Sallam ◽

Kuniyoshi Shimizu

Keyword(s):

Secondary Metabolites ◽

13C Nmr ◽

Biological Activities ◽

Biosynthetic Pathways ◽

Important Group ◽

Naturally Occurring ◽

Nmr Data ◽

Anti Inflammatory ◽

Drug Leads

Chromone glycosides comprise an important group of secondary metabolites. They are widely distributed in plants and, to a lesser extent, in fungi and bacteria. Significant biological activities, including antiviral, anti-inflammatory, antitumor, antimicrobial, etc., have been discovered for chromone glycosides, suggesting their potential as drug leads. This review compiles 192 naturally occurring chromone glycosides along with their sources, classification, biological activities, and spectroscopic features. Detailed biosynthetic pathways and chemotaxonomic studies are also described. Extensive spectroscopic features for this class of compounds have been thoroughly discussed, and detailed 13C-NMR data of compounds 1–192, have been added, except for those that have no reported 13C-NMR data.

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Natural Products from Endophytic Fungi Associated with Rubiaceae Species

Journal of Fungi ◽

10.3390/jof6030128 ◽

2020 ◽

Vol 6 (3) ◽

pp. 128

Author(s):

Jacqueline Santos Cruz ◽

Carla Amaral da Silva ◽

Lidilhone Hamerski

Keyword(s):

Antioxidant Activity ◽

Natural Products ◽

Secondary Metabolites ◽

Neurodegenerative Diseases ◽

Cytotoxic Activity ◽

Endophytic Fungi ◽

Chemical Diversity ◽

Pharmacological Properties ◽

Anti Inflammatory

This review presents the chemical diversity and pharmacological properties of secondary metabolites produced by endophytic fungi associated with various genera of Rubiaceae. Several classes of natural products are described for these endophytes, although, this study highlights the importance of some metabolites, which are involved in antifungal, antibacterial, anti-protozoal activities; neurodegenerative diseases; cytotoxic activity; anti-inflammatory and antioxidant activity; and hyperglycemic control.

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