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Terpenes and Terpene Derivatives
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Terpenes and Terpene Derivatives

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (30 October 2020) | Viewed by 61934

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editors

Prof. Dr. Pavel B. Drasar

E-Mail Website
Guest Editor
Department of Chemistry of Natural Compounds, University of Chemistry and Technology, Technicka 5, CZ 166 28 Prague, Czech Republic
Interests: natural product chemistry; synthesis of heterocycles; non-hormonally active steroids; terpenes; supramolecular systems with chiral natural products; fluorescent labelling
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Vladimir A. Khripach

E-Mail Website
Guest Editor
The Institute of Bioorganic Chemistry, The National Academy of Sciences of Belarus, 5/2 Academician V.F.Kuprevich Street, BY-220141 Minsk, Belarus
Interests: steroids; natural product heterocyclic and pesticide chemistry; synthesis, bioactivity, and practical application of natural bioregulators and their analogs in agriculture and medicine
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Terpenes, their derivatives and generally isoprenoids, as natural secondary metabolites, are playing stable and growing roles in human and veterinary medicine, supramolecular chemistry, in food and cosmetic R&D and industry, and in other, increasing numbers of fields. Their importance is based i.a. on the fact that they are mostly bound to renewable sources, which in fact makes them valuable within a circular economy. Terpenes and steroids are also an origin of stereochemistry, regioselectivity, chirality, and many other features and disciplines within science, development, and industry on a scope which is indispensable.

This Special Issue aims to underline current developments in all fields that are connected to terpene research and utilisation and will present a sequel to the successful Special Issue of Molecules "Synthesis, Study and Utilization of Natural Products" to commemorate the heritage of the great terpene scientist, Prof. Kenji Mori, who passed away recently.

Prof. Dr. Pavel B. Drasar
Prof. Dr. Vladimir A. Khripach
Guest Editors

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • terpene chemistry, biochemistry, repurposing, and practical utilization
  • terpene derivatives synthesis
  • isolation and analysis of terpenes
  • terpenes medicinal and cosmetic utilization
  • fluorescent labelling, bio-imaging
  • any topic with terpenes not mentioned above
  • all connected topics

Published Papers (18 papers)

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Editorial

Jump to: Research, Review

3 pages, 183 KiB  
Editorial
Terpene Research Is Providing New Inspiration for Scientists
by Pavel B. Drasar and Vladimir A. Khripach
Molecules 2021, 26(18), 5480; https://doi.org/10.3390/molecules26185480 - 09 Sep 2021
Cited by 1 | Viewed by 1346
Abstract
This current Special Issue of Molecules gathers selected communications on terpenes and terpene derivatives, clearly demonstrating the sustained interest in and importance of natural products in this field; fields connected to secondary metabolites; and renewable resources of plant and animal compounds for medicinal, [...] Read more.
This current Special Issue of Molecules gathers selected communications on terpenes and terpene derivatives, clearly demonstrating the sustained interest in and importance of natural products in this field; fields connected to secondary metabolites; and renewable resources of plant and animal compounds for medicinal, material, supramolecular, and general chemistry research [...] Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)

Research

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11 pages, 951 KiB  
Article
Approach to Optimization of FRAP Methodology for Studies Based on Selected Monoterpenes
by Karolina A. Wojtunik-Kulesza
Molecules 2020, 25(22), 5267; https://doi.org/10.3390/molecules25225267 - 12 Nov 2020
Cited by 23 | Viewed by 6228
Abstract
Terpenes, wide-spread secondary plant metabolites, constitute important parts of many natural compounds that hold various biological activities, including antioxidant, calming, antiviral, and analgesic activities. Due to their high volatility and low solubility in water, studies of compounds based on terpenes are difficult, and [...] Read more.
Terpenes, wide-spread secondary plant metabolites, constitute important parts of many natural compounds that hold various biological activities, including antioxidant, calming, antiviral, and analgesic activities. Due to their high volatility and low solubility in water, studies of compounds based on terpenes are difficult, and methodologies must be adjusted to their specific characteristics. Considering the significant influence of iron ions on dementia development, the activity of terpenes in reducing Fe3+ represents an important area to be determined. Previously obtained results were unreliable because ferric-reducing antioxidant power (FRAP) methodology was not adjusted regarding studying terpenes. Taking this fact into account, the aim of this study was to optimize the method for monoterpene assessment. The study included three modifications, namely, (1) slightly adjusting the entire FRAP procedure, (2) replacing methanol with other solvents (heptane, butanone, or ethyl acetate), and (3) adding Tween 20. Additionally, a thin layer chromatography (TLC) -FRAP assay was performed. The obtained results revealed significant improvement in the reduction activity of selected terpenes (linalool, α-phellandrene, and α-terpinene) in studies with Tween 20, whereas replacing methanol with other solvents did not show the expected effects. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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16 pages, 3301 KiB  
Article
Uvaol Improves the Functioning of Fibroblasts and Endothelial Cells and Accelerates the Healing of Cutaneous Wounds in Mice
by Julianderson Carmo, Polliane Cavalcante-Araújo, Juliane Silva, Jamylle Ferro, Ana Carolina Correia, Vincent Lagente and Emiliano Barreto
Molecules 2020, 25(21), 4982; https://doi.org/10.3390/molecules25214982 - 28 Oct 2020
Cited by 11 | Viewed by 2562
Abstract
Uvaol is a natural pentacyclic triterpene that is widely found in olives and virgin olive oil, exerting various pharmacological properties. However, information remains limited about how it affects fibroblasts and endothelial cells in events associated with wound healing. Here, we report the effect [...] Read more.
Uvaol is a natural pentacyclic triterpene that is widely found in olives and virgin olive oil, exerting various pharmacological properties. However, information remains limited about how it affects fibroblasts and endothelial cells in events associated with wound healing. Here, we report the effect of uvaol in the in vitro and in vivo healing process. We show the positive effects of uvaol on migration of fibroblasts and endothelial cells in the scratch assay. Protein synthesis of fibronectin and laminin (but not collagen type I) was improved in uvaol-treated fibroblasts. In comparison, tube formation by endothelial cells was enhanced after uvaol treatment. Mechanistically, the effects of uvaol on cell migration involved the PKA and p38-MAPK signaling pathway in endothelial cells but not in fibroblasts. Thus, the uvaol-induced migratory response was dependent on the PKA pathway. Finally, topical treatment with uvaol caused wounds to close faster than in the control treatment using experimental cutaneous wounds model in mice. In conclusion, uvaol positively affects the behavior of fibroblasts and endothelial cells, potentially promoting cutaneous healing. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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Graphical abstract

11 pages, 931 KiB  
Article
Lasianosides F–I: A New Iridoid and Three New Bis-Iridoid Glycosides from the Leaves of Lasianthus verticillatus (Lour.) Merr.
by Gadah Abdulaziz Al-Hamoud, Raha Saud Orfali, Yoshio Takeda, Sachiko Sugimoto, Yoshi Yamano, Nawal M. Al Musayeib, Omer Ibrahim Fantoukh, Musarat Amina, Hideaki Otsuka and Katsuyoshi Matsunami
Molecules 2020, 25(12), 2798; https://doi.org/10.3390/molecules25122798 - 17 Jun 2020
Cited by 6 | Viewed by 2460
Abstract
A series of iridoid glycosides were isolated from the leaves of Lasianthus verticillatus (Lour.) Merr., belonging to family Rubiaceae. A new iridoid glycoside, lasianoside F (1), and three new bis-iridoid glycosides, lasianosides G–I (2–4), together with four [...] Read more.
A series of iridoid glycosides were isolated from the leaves of Lasianthus verticillatus (Lour.) Merr., belonging to family Rubiaceae. A new iridoid glycoside, lasianoside F (1), and three new bis-iridoid glycosides, lasianosides G–I (2–4), together with four known compounds (5–8) were isolated. The structures were established by spectroscopic methods, including 1D and 2D NMR experiments (1H, 13C, DEPT, COSY, HSQC, HMBC, and NOESY) in combination with HR-ESI-MS and CD spectra. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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9 pages, 945 KiB  
Article
Atypical Lindenane-Type Sesquiterpenes from Lindera myrrha
by Thuc-Huy Duong, Mehdi A. Beniddir, Nguyen T. Trung, Cam-Tu D. Phan, Van Giau Vo, Van-Kieu Nguyen, Quynh-Loan Le, Hoang-Dung Nguyen and Pierre Le Pogam
Molecules 2020, 25(8), 1830; https://doi.org/10.3390/molecules25081830 - 16 Apr 2020
Cited by 12 | Viewed by 3061
Abstract
Two new lindenane sesquiterpenes were obtained from the roots of Lindera myrrha. These compounds were structurally elucidated by HRMS data, extensive NMR analyses, and comparison between experimental and theoretical 13C-NMR data. Myrrhalindenane A is the first monomeric seco-d lindenane displaying [...] Read more.
Two new lindenane sesquiterpenes were obtained from the roots of Lindera myrrha. These compounds were structurally elucidated by HRMS data, extensive NMR analyses, and comparison between experimental and theoretical 13C-NMR data. Myrrhalindenane A is the first monomeric seco-d lindenane displaying a non-rearranged, cyclohexanic C-ring. Myrrhalindenane B is the second occurrence of an angular lindenane-sesquiterpene related to a C6-C7 lactonization. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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10 pages, 585 KiB  
Article
Antibacterial and Antifungal Sesquiterpenoids from Aerial Parts of Anvillea garcinii
by Shagufta Perveen, Jawaher Alqahtani, Raha Orfali, Hanan Y. Aati, Areej M. Al-Taweel, Taghreed A. Ibrahim, Afsar Khan, Hasan S. Yusufoglu, Maged S. Abdel-Kader and Orazio Taglialatela-Scafati
Molecules 2020, 25(7), 1730; https://doi.org/10.3390/molecules25071730 - 09 Apr 2020
Cited by 13 | Viewed by 2790
Abstract
Two new sesquiterpenoids belonging to the guaiane, 4α,9α,10α-trihydroxyguaia-11(13)en-12,6α-olide (1), and germacrane, 9β-hydroxyparthenolide-9-O-β-D-glucopyranoside (2), classes have been isolated from the leaves of the Saudi medicinal plant Anvillea garcinii along with seven known compounds (3–9). [...] Read more.
Two new sesquiterpenoids belonging to the guaiane, 4α,9α,10α-trihydroxyguaia-11(13)en-12,6α-olide (1), and germacrane, 9β-hydroxyparthenolide-9-O-β-D-glucopyranoside (2), classes have been isolated from the leaves of the Saudi medicinal plant Anvillea garcinii along with seven known compounds (3–9). The structures of the new metabolites were elucidated by spectroscopic analysis, including one-dimensional (1D) and two-dimensional (2D) Nuclear Magnetic Resonance (NMR) and high-resolution electrospray ionization mass spectrometry (HR-ESIMS). The antimicrobial properties of 1–9 were screened against seven different pathogenic microbes, and compounds 1–3 showed a potent antifungal activity. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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12 pages, 1680 KiB  
Article
Phytochemical and Safety Evaluations of Volatile Terpenoids from Zingiber cassumunar Roxb. on Mature Carp Peripheral Blood Mononuclear Cells and Embryonic Zebrafish
by Raktham Mektrirat, Terdsak Yano, Siriporn Okonogi, Wasan Katip and Surachai Pikulkaew
Molecules 2020, 25(3), 613; https://doi.org/10.3390/molecules25030613 - 30 Jan 2020
Cited by 16 | Viewed by 4064
Abstract
Pharmaceutical products of essential oil from Zingiber cassumunar Roxb. are extensively being developed, while the research on their safety is seldom documented. The aim of the present study was to evaluate the phytochemical profile and the effect of cassumunar ginger oil on cell-based [...] Read more.
Pharmaceutical products of essential oil from Zingiber cassumunar Roxb. are extensively being developed, while the research on their safety is seldom documented. The aim of the present study was to evaluate the phytochemical profile and the effect of cassumunar ginger oil on cell-based assay and the zebrafish model. The essential oil was isolated from fresh rhizomes of Z. cassumunar using simultaneous steam-distillation. Chemical composition was analyzed using gas chromatograph coupled to a mass spectrometer (GC-MS). Effect of cassumunar ginger oil on adult carp fish peripheral blood mononuclear cells (PBMCs) was investigated using MTT assay. The embryotoxic and teratogenic effects of cassumunar ginger oil were studied in zebrafish embryos. GC-MS results showed that the essential oil was composed of sabinene (43.54%) and terpinen-4-ol (29.52%) as the major phytoconstituents. No fish PBMC cytotoxic effect was observed with the concentration less than 50 µg/mL of cassumunar ginger oil. Our results showed for the first time the embryotoxic and teratogenic effects of cassumunar ginger oil in zebrafish embryos. The result indicated that the cassumunar ginger oil induced zebrafish embryotoxicity in a concentration-dependent manner. At 500 µg/mL of cassumunar ginger oil demonstrated significantly moderated embryotoxicity within 24 h (p < 0.05). The survival rate of 100 µg/mL of cassumunar ginger group was markedly declined to zero at 96-h post-fertilization (log-rank test, p = 0.001). However, survival rates of zebrafish embryo in the 1 and 10 µg/mL cassumunar ginger groups were more than 90% throughout the trial period. Moreover, very low teratogenicity to the zebrafish embryo was also observed in 1 and 10 µg/mL of cassumunar ginger groups. Our findings suggest that there is hardly any cytotoxicity, embryotoxicity and teratogenicity at concentrations less than 10 µg/mL of cassumunar ginger oil. However, the toxicity assessment of its pharmaceutical product should prove for further consumer protection. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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10 pages, 646 KiB  
Article
Cytotoxic and Anti-Inflammatory Effects of Ent-Kaurane Derivatives Isolated from the Alpine Plant Sideritis hyssopifolia
by Axelle Aimond, Kevin Calabro, Coralie Audoin, Elodie Olivier, Mélody Dutot, Pauline Buron, Patrice Rat, Olivier Laprévote, Soizic Prado, Emmanuel Roulland, Olivier P. Thomas and Grégory Genta-Jouve
Molecules 2020, 25(3), 589; https://doi.org/10.3390/molecules25030589 - 29 Jan 2020
Cited by 5 | Viewed by 2915
Abstract
This paper reports the isolation and structural characterization of four new ent-kaurane derivatives from the Lamiaceae plant Sideritis hyssopifolia. Planar structures and relative configurations were determined using both mass spectrometry and nuclear magnetic resonance (1D and 2D). Absolute configurations were determined [...] Read more.
This paper reports the isolation and structural characterization of four new ent-kaurane derivatives from the Lamiaceae plant Sideritis hyssopifolia. Planar structures and relative configurations were determined using both mass spectrometry and nuclear magnetic resonance (1D and 2D). Absolute configurations were determined by comparing experimental and theoretical electronic circular dichroism spectra. The cytotoxic and microbial activities of all new compounds were tested. Compounds that were non-cytotoxic were further evaluated for anti-inflammatory activity. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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9 pages, 1185 KiB  
Article
Prenyleudesmanes and A Hexanorlanostane from the Roots of Lonicera macranthoides
by Hui Lyu, Wenjuan Liu, Bai Bai, Yu Shan, Christian Paetz, Xu Feng and Yu Chen
Molecules 2019, 24(23), 4276; https://doi.org/10.3390/molecules24234276 - 23 Nov 2019
Cited by 4 | Viewed by 2820
Abstract
Three previously undescribed compounds, two prenyleudesmanes (1 and 2), and one hexanorlanostane (3), were isolated from the roots of Lonicera macranthoides. Their structures were established based on 1D and 2D nuclear magnetic resonance (NMR) spectra and high-resolution electrospray [...] Read more.
Three previously undescribed compounds, two prenyleudesmanes (1 and 2), and one hexanorlanostane (3), were isolated from the roots of Lonicera macranthoides. Their structures were established based on 1D and 2D nuclear magnetic resonance (NMR) spectra and high-resolution electrospray ionization mass spectral (HR-ESI-MS) data. The absolute configurations of 1 and 3 were determined by X-ray diffraction. To the best of our knowledge, this is the first time that the absolute configuration of a prenyleudesmane with a trans-decalin system and a hexanorlanostane have been unambiguously confirmed by single-crystal X-ray diffraction with Cu Kα radiation. Thecompounds were tested for their antiproliferative activity on the cancer cell lines (HepG2 and HeLa). The compounds 1–3 exhibited moderate inhibitory effects against two human cancer cell lines. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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12 pages, 1335 KiB  
Article
Quantitative Analysis of Terpenic Compounds in Microsamples of Resins by Capillary Liquid Chromatography
by H. D. Ponce-Rodríguez, R. Herráez-Hernández, J. Verdú-Andrés and P. Campíns-Falcó
Molecules 2019, 24(22), 4068; https://doi.org/10.3390/molecules24224068 - 10 Nov 2019
Cited by 6 | Viewed by 2438
Abstract
A method has been developed for the separation and quantification of terpenic compounds typically used as markers in the chemical characterization of resins based on capillary liquid chromatography coupled to UV detection. The sample treatment, separation and detection conditions have been optimized in [...] Read more.
A method has been developed for the separation and quantification of terpenic compounds typically used as markers in the chemical characterization of resins based on capillary liquid chromatography coupled to UV detection. The sample treatment, separation and detection conditions have been optimized in order to analyze compounds of different polarities and volatilities in a single chromatographic run. The monoterpene limonene and the triterpenes lupeol, lupenone, β-amyrin, and α-amyrin have been selected as model compounds. The proposed method provides linear responses and precision (expressed as relative standard deviations) of 0.6% to 17%, within the 0.5–10.0 µg mL−1 concentration interval; the limits of detection (LODs) and quantification (LOQs) were 0.1–0.25 µg mL−1 and 0.4–0.8 µg mL−1, respectively. The method has been applied to the quantification of the target compounds in microsamples. The reliability of the proposed conditions has been tested by analyzing three resins, white copal, copal in tears, and ocote tree resin. Percentages of the triterpenes in the range 0.010% to 0.16% were measured using sample amounts of 10–15 mg, whereas the most abundant compound limonene (≥0.93%) could be determined using 1 mg portions of the resins. The proposed method can be considered complementary to existing protocols aimed at establishing the chemical fingerprint of these kinds of samples. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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14 pages, 1805 KiB  
Article
High-Throughput 1H-Nuclear Magnetic Resonance-Based Screening for the Identification and Quantification of Heartwood Diterpenic Acids in Four Black Pine (Pinus nigra Arn.) Marginal Provenances in Greece
by Kostas Ioannidis, Eleni Melliou and Prokopios Magiatis
Molecules 2019, 24(19), 3603; https://doi.org/10.3390/molecules24193603 - 07 Oct 2019
Cited by 13 | Viewed by 3470
Abstract
A high-throughput quantitative Nuclear Magnetic Resonance 1H-NMR method was developed and applied to screen the quantity of the diterpenic resin acids in the heartwood of black pine, due to the renewed scientific interest in their medicinal properties and use in various diseases [...] Read more.
A high-throughput quantitative Nuclear Magnetic Resonance 1H-NMR method was developed and applied to screen the quantity of the diterpenic resin acids in the heartwood of black pine, due to the renewed scientific interest in their medicinal properties and use in various diseases treatment. The 260 samples were taken from Pinus nigra clones, selected from four provenances of the Peloponnese (Greece), participating in a 35-year-old clonal seed orchard. Total resin acids per dry heartwood weight (dhw) varied greatly, ranging from 30.05 to 424.70 mg/gdhw (average 219.98 mg/gdhw). Abietic was the predominant acid (76.77 mg/gdhw), followed by palustric acid (47.94 mg/gdhw), neoabietic acid (39.34 mg/gdhw), and pimaric acid (22.54 mg/gdhw). Dehydroabietic acid was at moderate levels (11.69 mg/gdhw), while levopimaric, isopimaric, and sandaracopimaric acids were in lower concentrations. The resin acid fraction accounted for 72.33% of the total acetone extractives. Stilbenes were presented in significant quantities (19.70%). The resin acid content was composed mainly of the abietane type resin acids (83.56%). Peloponnesian Pinus nigra heartwood was found to be the richest source of resin acids identified to date and is considered the best natural source for the production of such bioactive extracts. The results indicate a high potential for effective selection and advanced breeding of pharmaceutical and high economic value bioactive substances from Pinus nigra clones. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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16 pages, 2257 KiB  
Article
Betulin Promotes Differentiation of Human Osteoblasts In Vitro and Exerts an Osteoinductive Effect on the hFOB 1.19 Cell Line Through Activation of JNK, ERK1/2, and mTOR Kinases
by Magdalena Mizerska-Kowalska, Adrianna Sławińska-Brych, Katarzyna Kaławaj, Aleksandra Żurek, Beata Pawińska, Wojciech Rzeski and Barbara Zdzisińska
Molecules 2019, 24(14), 2637; https://doi.org/10.3390/molecules24142637 - 19 Jul 2019
Cited by 22 | Viewed by 4833
Abstract
Although betulin (BET), a naturally occurring pentacyclic triterpene, has a variety of biological activities, its osteogenic potential has not been investigated so far. The aim of this study was to assess the effect of BET on differentiation of human osteoblasts (hFOB 1.19 and [...] Read more.
Although betulin (BET), a naturally occurring pentacyclic triterpene, has a variety of biological activities, its osteogenic potential has not been investigated so far. The aim of this study was to assess the effect of BET on differentiation of human osteoblasts (hFOB 1.19 and Saos-2 cells) in vitro in osteogenic (with ascorbic acid as an osteogenic supplement) and osteoinductive (without an additional osteogenic supplement) conditions. Osteoblast differentiation was evaluated based on the mRNA expression (RT-qPCR) of Runt-related transcription factor 2 (RUNX2), alkaline phosphatase (ALP), type I collagen-α1 (COL1A1), and osteopontin (OPN). Additionally, ALP activity and production of COL1A1 (western blot analysis) and OPN (ELISA) were evaluated. The level of mineralization (calcium accumulation) was determined with Alizarin red S staining. BET upregulated the mRNA level of RUNX2 and the expression of other osteoblast differentiation markers in both cell lines (except the influence of BET on ALP expression/activity in the Saos-2 cells). Moreover, it increased mineralization in both cell lines in the osteogenic conditions. BET also increased the mRNA level of osteoblast differentiation markers in both cell lines (except for ALP in the Saos-2 cells) in the osteoinductive conditions, which was accompanied with increased matrix mineralization. The osteoinductive activity of BET in the hFOB 1.19 cells was probably mediated via activation of MAPKs (JNK and ERK1/2) and mTOR, as the specific inhibitors of these kinases abolished the BET-induced osteoblast differentiation. Our results suggest that BET has the potential to enhance osteogenesis. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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8 pages, 2287 KiB  
Communication
New 11,20-Epoxybriaranes from the Gorgonian Coral Junceella fragilis (Ellisellidae)
by Chia-Cheng Lin, Jui-Hsin Su, Wu-Fu Chen, Zhi-Hong Wen, Bo-Rong Peng, Lin-Cyuan Huang, Tsong-Long Hwang and Ping-Jyun Sung
Molecules 2019, 24(13), 2487; https://doi.org/10.3390/molecules24132487 - 07 Jul 2019
Cited by 8 | Viewed by 2210
Abstract
Two new 11,20-epoxybriaranes, fragilides P (1) and Q (2), as well as two known analogues, robustolide F (3) and juncin Z (4), were obtained from the gorgonian coral Junceella fragilis. The structures, including the [...] Read more.
Two new 11,20-epoxybriaranes, fragilides P (1) and Q (2), as well as two known analogues, robustolide F (3) and juncin Z (4), were obtained from the gorgonian coral Junceella fragilis. The structures, including the absolute configurations of briaranes 1 and 2, were elucidated by using spectroscopic methods and comparing the spectroscopic and rotation data with those of known related analogues. Briarane 4 decreased the generation of superoxide anions by human neutrophils. The propionate group in 1 is rarely found. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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Review

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12 pages, 1224 KiB  
Review
Topical Administration of Terpenes Encapsulated in Nanostructured Lipid-Based Systems
by Elwira Lasoń
Molecules 2020, 25(23), 5758; https://doi.org/10.3390/molecules25235758 - 07 Dec 2020
Cited by 10 | Viewed by 2857
Abstract
Terpenes are a group of phytocompounds that have been used in medicine for decades owing to their significant role in human health. So far, they have been examined for therapeutic purposes as antibacterial, anti-inflammatory, antitumoral agents, and the clinical potential of this class [...] Read more.
Terpenes are a group of phytocompounds that have been used in medicine for decades owing to their significant role in human health. So far, they have been examined for therapeutic purposes as antibacterial, anti-inflammatory, antitumoral agents, and the clinical potential of this class of compounds has been increasing continuously as a source of pharmacologically interesting agents also in relation to topical administration. Major difficulties in achieving sustained delivery of terpenes to the skin are connected with their low solubility and stability, as well as poor cell penetration. In order to overcome these disadvantages, new delivery technologies based on nanostructures are proposed to improve bioavailability and allow controlled release. This review highlights the potential properties of terpenes loaded in several types of lipid-based nanocarriers (liposomes, solid lipid nanoparticles, and nanostructured lipid carriers) used to overcome free terpenes’ form limitations and potentiate their therapeutic properties for topical administration. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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25 pages, 2902 KiB  
Review
Synthesis, Modification and Biological Activity of Diosgenyl β-d-Glycosaminosides: An Overview
by Daria Grzywacz, Beata Liberek and Henryk Myszka
Molecules 2020, 25(22), 5433; https://doi.org/10.3390/molecules25225433 - 20 Nov 2020
Cited by 14 | Viewed by 2620
Abstract
Saponins are a structurally diverse class of natural glycosides that possess a broad spectrum of biological activities. They are composed of hydrophilic carbohydrate moiety and hydrophobic triterpenoid or steroid aglycon. Naturally occurring diosgenyl glycosides are the most abundant steroid saponins, and many of [...] Read more.
Saponins are a structurally diverse class of natural glycosides that possess a broad spectrum of biological activities. They are composed of hydrophilic carbohydrate moiety and hydrophobic triterpenoid or steroid aglycon. Naturally occurring diosgenyl glycosides are the most abundant steroid saponins, and many of them exhibit various pharmacological properties. Herein, we present an overview of semisynthetic saponins syntheses–diosgenyl β-d-glycosaminosides (d-gluco and d-galacto). These glycosides possess a 2-amino group, which creates great possibilities for further modifications. A wide group of glycosyl donors, different N-protecting groups and various reaction conditions used for their synthesis are presented. In addition, this paper demonstrates the possibilities of chemical modifications of diosgenyl β-d-glycosaminosides, associated with functionalisation of the amino group. These provide N-acyl, N-alkyl, N,N-dialkyl, N-cinnamoyl, 2-ureido and 2-thiosemicarbazonyl derivatives of diosgenyl β-d-glycosaminosides, for which the results of biological activity tests (antifungal, antibacterial, anti-cancer and hemolytic) are presented. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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14 pages, 1966 KiB  
Review
Metabolic Engineering Escherichia coli for the Production of Lycopene
by Zhaobao Wang, JingXin Sun, Qun Yang and Jianming Yang
Molecules 2020, 25(14), 3136; https://doi.org/10.3390/molecules25143136 - 09 Jul 2020
Cited by 26 | Viewed by 6934
Abstract
Lycopene, a potent antioxidant, has been widely used in the fields of pharmaceuticals, nutraceuticals, and cosmetics. However, the production of lycopene extracted from natural sources is far from meeting the demand. Consequently, synthetic biology and metabolic engineering have been employed to develop microbial [...] Read more.
Lycopene, a potent antioxidant, has been widely used in the fields of pharmaceuticals, nutraceuticals, and cosmetics. However, the production of lycopene extracted from natural sources is far from meeting the demand. Consequently, synthetic biology and metabolic engineering have been employed to develop microbial cell factories for lycopene production. Due to the advantages of rapid growth, complete genetic background, and a reliable genetic operation technique, Escherichia coli has become the preferred host cell for microbial biochemicals production. In this review, the recent advances in biological lycopene production using engineered E. coli strains are summarized: First, modification of the endogenous MEP pathway and introduction of the heterogeneous MVA pathway for lycopene production are outlined. Second, the common challenges and strategies for lycopene biosynthesis are also presented, such as the optimization of other metabolic pathways, modulation of regulatory networks, and optimization of auxiliary carbon sources and the fermentation process. Finally, the future prospects for the improvement of lycopene biosynthesis are also discussed. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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10 pages, 445 KiB  
Review
Traps and Pitfalls—Unspecific Reactions in Metabolic Engineering of Sesquiterpenoid Pathways
by Maximilian Frey
Molecules 2020, 25(8), 1935; https://doi.org/10.3390/molecules25081935 - 22 Apr 2020
Cited by 4 | Viewed by 2562
Abstract
The characterization of plant enzymes by expression in prokaryotic and eukaryotic (yeast and plants) heterologous hosts has widely been used in recent decades to elucidate metabolic pathways in plant secondary metabolism. Yeast and plant systems provide the cellular environment of a eukaryotic cell [...] Read more.
The characterization of plant enzymes by expression in prokaryotic and eukaryotic (yeast and plants) heterologous hosts has widely been used in recent decades to elucidate metabolic pathways in plant secondary metabolism. Yeast and plant systems provide the cellular environment of a eukaryotic cell and the subcellular compartmentalization necessary to facilitate enzyme function. The expression of candidate genes in these cell systems and the identification of the resulting products guide the way for the identification of enzymes with new functions. However, in many cases, the detected compounds are not the direct enzyme products but are caused by unspecific subsequent reactions. Even if the mechanisms for these unspecific reactions are in many cases widely reported, there is a lack of overview of potential reactions that may occur to provide a guideline for researchers working on the characterization of new enzymes. Here, an across-the-board summary of rearrangement reactions of sesquiterpenes in metabolic pathway engineering is presented. The different kinds of unspecific reactions as well as their chemical and cellular background are explained and strategies how to spot and how to avoid these unspecific reactions are given. Also, a systematic approach of classification of unspecific reactions is introduced. It is hoped that this mini-review will stimulate a discussion on how to systematically classify unspecific reactions in metabolic engineering and to expand this approach to other classes of plant secondary metabolites. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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20 pages, 3269 KiB  
Review
Recent Achievements in Medicinal and Supramolecular Chemistry of Betulinic Acid and Its Derivatives ‡
by Uladzimir Bildziukevich, Zülal Özdemir and Zdeněk Wimmer
Molecules 2019, 24(19), 3546; https://doi.org/10.3390/molecules24193546 - 30 Sep 2019
Cited by 42 | Viewed by 4530
Abstract
The subject of this review article refers to the recent achievements in the investigation of pharmacological activity and supramolecular characteristics of betulinic acid and its diverse derivatives, with special focus on their cytotoxic effect, antitumor activity, and antiviral effect, and mostly covers a [...] Read more.
The subject of this review article refers to the recent achievements in the investigation of pharmacological activity and supramolecular characteristics of betulinic acid and its diverse derivatives, with special focus on their cytotoxic effect, antitumor activity, and antiviral effect, and mostly covers a period 2015–2018. Literature sources published earlier are referred to in required coherences or from historical points of view. Relationships between pharmacological activity and supramolecular characteristics are included if such investigation has been done in the original literature sources. A wide practical applicability of betulinic acid and its derivatives demonstrated in the literature sources is also included in this review article. Several literature sources also focused on in silico calculation of physicochemical and ADME parameters of the developed compounds, and on a comparison between the experimental and calculated data. Full article
(This article belongs to the Special Issue Terpenes and Terpene Derivatives)
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