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Special Issue "Diterpene and Its Significance in Natural Medicine"

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

Deadline for manuscript submissions: closed (31 December 2016)

Special Issue Editors

Guest Editor
Assoc. Prof. Quan-Bin Han

School of Chinese Medicine, Hong Kong Baptist University, Hong Kong, China
Website | E-Mail
Interests: natural product chemistry; quality analysis of herb medicines and natural polysaccharides
Guest Editor
Prof. Jian-Xin Pu

Kunming Institute of Botany, Chinese Academy of Sciences, China
Website | E-Mail
Interests: natural product chemistry; pharmaceutical chemistry

Special Issue Information

Dear Colleagues,

Diterpenes have been studied for nearly 200 years, since the investigation of resin acid’s chemical structure in 1824. Now, they form one of the largest families of natural molecules. According to the Dictionary of Natural Products 2016 (web version), a total of 18,450 diterpenoids, sharing 126 types of skeletons, have been reported.

Bearing diverse linear and cyclic carbon skeletones, diterpenoids have been demonstrated to have a broad spectrum of bioactivities, such as anti-bacterial, anti-inflammatory, anti-viral, anti-tumor, cytotoxic, insecticidal, and immunomodulating effects. Some of them have been developed as new drugs, e.g., taxol in cancer therapy.

Along with advances in analytical instruments, synthesis methods, and biotransformation studies, more and more new diterpenoids are revealed and attract increasing interest of scientists in multiple disciplines. As Guest Editors, we cordially invite researchers to submit their work relevant to these topics to this Special Issue of Molecules.

Dr. Quan-Bin Han
Dr. Jian-Xin Pu
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

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 monthly 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 1800 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

  • isolation and structure elucidation of diterpenoids
  • pharmacological activity
  • medicinal chemistry
  • biotransformation studies
  • qualitative and quantitative analysis
  • synthesis

Published Papers (9 papers)

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Research

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Open AccessArticle Ent-Abietanoids Isolated from Isodon serra
Molecules 2017, 22(2), 309; doi:10.3390/molecules22020309
Received: 17 January 2016 / Revised: 13 February 2017 / Accepted: 14 February 2017 / Published: 17 February 2017
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Abstract
Four new ent-abietane diterpenoids, along with four known ones were isolated from the aerial parts of Isodon serra, a traditional Chinese folk medicine. The new diterpenoids were named as serrin K (1), xerophilusin XVII (2), and enanderianins
[...] Read more.
Four new ent-abietane diterpenoids, along with four known ones were isolated from the aerial parts of Isodon serra, a traditional Chinese folk medicine. The new diterpenoids were named as serrin K (1), xerophilusin XVII (2), and enanderianins Q and R (3 and 4), while the known ones were identified as rubescansin J (5), (3α,14β)-3,18-[(1-methylethane-1,1-diyl)dioxy]-ent-abieta-7,15(17)-diene-14,16-diol (6), xerophilusin XIV (7), and enanderianin P (8), respectively. Their structures were elucidated by extensive spectroscopic analysis and comparison with the literature. Compound 1 showed remarkable inhibitory activity towards NO production in LPS-stimulated RAW264.7 cells (IC50 = 1.8 μM) and weak cytotoxicity towards five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480). Full article
(This article belongs to the Special Issue Diterpene and Its Significance in Natural Medicine)
Figures

Open AccessArticle Penduliflaworosin, a Diterpenoid from Croton crassifolius, Exerts Anti-Angiogenic Effect via VEGF Receptor-2 Signaling Pathway
Molecules 2017, 22(1), 126; doi:10.3390/molecules22010126
Received: 20 October 2016 / Revised: 4 January 2017 / Accepted: 4 January 2017 / Published: 13 January 2017
Cited by 1 | PDF Full-text (10384 KB) | HTML Full-text | XML Full-text
Abstract
Anti-angiogenesis targeting vascular endothelial growth factor receptor-2 (VEGFR-2) has been considered as an important strategy for cancer therapy. Penduliflaworosin is a diterpenoid isolated from the plant Croton crassifolius. Our previous study showed that this diterpenoid possesses strong anti-angiogenic activity by inhibiting vessel
[...] Read more.
Anti-angiogenesis targeting vascular endothelial growth factor receptor-2 (VEGFR-2) has been considered as an important strategy for cancer therapy. Penduliflaworosin is a diterpenoid isolated from the plant Croton crassifolius. Our previous study showed that this diterpenoid possesses strong anti-angiogenic activity by inhibiting vessel formation in zebrafish. This study was conducted to further investigate the anti-angiogenic activity and mechanism of penduliflaworosin. Results revealed that penduliflaworosin significantly inhibited VEGF-induced angiogenesis processes including proliferation, invasion, migration, and tube formation of human umbilical vein endothelial cells (HUVECs). Moreover, it notably inhibited VEGF-induced sprout formation of aortic rings and blocked VEGF-induced vessel formation in mice. Western blotting studies showed that penduliflaworosin inhibited phosphorylation of the VEGF receptor-2 and its downstream signaling mediators in HUVECs, suggesting that the anti-angiogenic activity was due to an interference with the VEGF/VEGF receptor-2 pathway. In addition, molecular docking simulation indicated that penduliflaworosin could form hydrogen bonds within the ATP-binding region of the VEGF receptor-2 kinase unit. Finally, cytotoxicity assay showed that penduliflaworosin possessed little toxicity toward both cancer and normal cells. Taken together, our findings demonstrate that penduliflaworosin exerts its anti-angiogenic effect via the VEGF receptor-2 signaling pathway. The anti-angiogenic property and low cytotoxicity of penduliflaworosin suggest that it may be useful in cancer treatments. Full article
(This article belongs to the Special Issue Diterpene and Its Significance in Natural Medicine)
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Open AccessArticle Anti-Neuroinflammatory ent-Kaurane Diterpenoids from Pteris multifida Roots
Molecules 2017, 22(1), 27; doi:10.3390/molecules22010027
Received: 29 November 2016 / Revised: 21 December 2016 / Accepted: 22 December 2016 / Published: 26 December 2016
Cited by 2 | PDF Full-text (1496 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Activated microglia are known to be a major source of cellular neuroinflammation which causes various neurodegenerative diseases, including Alzheimer’s disease. In our continuing efforts to search for new bioactive phytochemicals against neuroinflammatory diseases, the 80% methanolic extract of Pteris multifida (Pteridaceae) roots was
[...] Read more.
Activated microglia are known to be a major source of cellular neuroinflammation which causes various neurodegenerative diseases, including Alzheimer’s disease. In our continuing efforts to search for new bioactive phytochemicals against neuroinflammatory diseases, the 80% methanolic extract of Pteris multifida (Pteridaceae) roots was found to exhibit significant NO inhibitory activity in lipopolysaccharide (LPS)-activated BV-2 microglia cells. Three new ent-kaurane diterpenoids, pterokaurane M1 2-O-β-d-glucopyranoside (4), 2β,16α-dihydroxy-ent-kaurane 2,16-di-O-β-d-glucopyranoside (10), and 2β,16α,17-trihydroxy-ent-kaurane 2-O-β-d-glucopyranoside (12), were isolated along with nine other known compounds from P. multifida roots. The chemical structures of the new compounds were determined by 1D- and 2D-NMR, HR-ESI-MS, and CD spectroscopic data analysis. Among the isolates, compounds 1 and 7 significantly inhibited NO production in LPS-stimulated BV-2 cells reducing the expression of the cyclooxygenase-2 (COX-2) protein and the level of pro-inflammatory mediators such as prostaglandin E2 (PGE2), tumor necrosis factor (TNF)-α, interleukin (IL)-1β, and IL-6. These results suggest that ent-kaurane diterpenes from P. multifida could be potential lead compounds that act as anti-neuroinflammatory agents. Full article
(This article belongs to the Special Issue Diterpene and Its Significance in Natural Medicine)
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Open AccessArticle An Ingenol Derived from Euphorbia kansui Induces Hepatocyte Cytotoxicity by Triggering G0/G1 Cell Cycle Arrest and Regulating the Mitochondrial Apoptosis Pathway in Vitro
Molecules 2016, 21(6), 813; doi:10.3390/molecules21060813
Received: 5 May 2016 / Revised: 16 June 2016 / Accepted: 17 June 2016 / Published: 22 June 2016
Cited by 1 | PDF Full-text (8974 KB) | HTML Full-text | XML Full-text
Abstract
Natural product lingenol, a purified diterpenoid compound derived from the root of Euphorbia kansui, exerts serious hepatotoxicity; however, the molecular mechanisms remain to be defined. In the present study, cell counting Kit-8 (CCK-8), inverted phase contrast microscope and flow cytometry were used
[...] Read more.
Natural product lingenol, a purified diterpenoid compound derived from the root of Euphorbia kansui, exerts serious hepatotoxicity; however, the molecular mechanisms remain to be defined. In the present study, cell counting Kit-8 (CCK-8), inverted phase contrast microscope and flow cytometry were used to demonstrate that lingenol significantly inhibited L-O2 cells proliferation, and induced cell cycle arrest and apoptosis. Moreover, the results investigated that lingenol markedly disrupted mitochondrial functions by high content screening (HCS). In addition, the up-regulation of cytochrome c, AIF and Apaf-1 and activation of caspases were found in L-O2 cells detected by Western blotting and ELISA assay, which was required for lingenol activation of cytochrome c-mediated caspase cascades and AIF-mediated DNA damage. Mechanistic investigations revealed that lingenol significantly down-regulated the Bcl-2/Bax ratio and enhanced the reactive oxygen species (ROS) in L-O2 cells. These data collectively indicated that lingenol modulation of ROS and Bcl-2/Bax ratio led to cell cycle arrest and mitochondrial-mediated apoptosis in L-O2 cells in vitro. All of these results will be helpful to reveal the hepatotoxicity mechanism of Euphorbia kansui and to effectively guide safer and better clinical application of this herb. Full article
(This article belongs to the Special Issue Diterpene and Its Significance in Natural Medicine)
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Open AccessArticle Uprolides N, O and P from the Panamanian Octocoral Eunicea succinea
Molecules 2016, 21(6), 819; doi:10.3390/molecules21060819
Received: 11 May 2016 / Revised: 17 June 2016 / Accepted: 18 June 2016 / Published: 22 June 2016
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Abstract
Three new diterpenes, uprolide N (1), uprolide O (2), uprolide P (3) and a known one, dolabellane (4), were isolated from the CH2Cl2-MeOH extract of the gorgonian octocoral Eunicea succinea,
[...] Read more.
Three new diterpenes, uprolide N (1), uprolide O (2), uprolide P (3) and a known one, dolabellane (4), were isolated from the CH2Cl2-MeOH extract of the gorgonian octocoral Eunicea succinea, collected from Bocas del Toro, on the Caribbean coast of Panama. Their structures were determined using spectroscopic analyses, including 1D and 2D NMR and high-resolution mass spectrometry (HRMS) together with molecular modeling studies. Compounds 13 displayed anti-inflammatory properties by inhibiting production of Tumor Necrosis Factor (TNF) and Interleukin (IL)-6 induced by lipopolysaccharide (LPS) in murine macrophages. Full article
(This article belongs to the Special Issue Diterpene and Its Significance in Natural Medicine)
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Open AccessCommunication Cytotoxic Labdane Diterpenes from Hedychium ellipticum Buch.-Ham. ex Sm.
Molecules 2016, 21(6), 749; doi:10.3390/molecules21060749
Received: 11 May 2016 / Revised: 27 May 2016 / Accepted: 3 June 2016 / Published: 9 June 2016
Cited by 4 | PDF Full-text (363 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
In order to reveal the constituents and their biological activities, we carried out a phytochemical study on Hedychium ellipticum Buch.-Ham. ex Sm. (Zingiberaceae). Ten labdane diterpenoids (110) were isolated from the rhizomes of H. ellipticum for the first time.
[...] Read more.
In order to reveal the constituents and their biological activities, we carried out a phytochemical study on Hedychium ellipticum Buch.-Ham. ex Sm. (Zingiberaceae). Ten labdane diterpenoids (110) were isolated from the rhizomes of H. ellipticum for the first time. Their structures were identified on the basis of spectroscopic analyses including two-dimensional NMR and comparison with literature data. All of these compounds were evaluated for their antimycobacterial activity against Mycobacterium tuberculosis and cytotoxicity against KB, MCF7, NCI-H187 and Vero cells. The result showed that compounds 1 and 7 exhibited moderate activity against Mycobacterium tuberculosis and compounds 4, 6 and 7 displayed remarkable cytotoxic activity. This is the first report on the presence of all compounds in H. ellipticum and the first time that their structure activity relationship has been discussed. Full article
(This article belongs to the Special Issue Diterpene and Its Significance in Natural Medicine)
Open AccessArticle Antimicrobial Diterpenoids of Wedelia trilobata (L.) Hitchc
Molecules 2016, 21(4), 457; doi:10.3390/molecules21040457
Received: 11 March 2016 / Revised: 28 March 2016 / Accepted: 30 March 2016 / Published: 7 April 2016
Cited by 1 | PDF Full-text (1240 KB) | HTML Full-text | XML Full-text
Abstract
Continued interest in the metabolites of Wedelia trilobata (L.) Hitchc, a notoriously invasive weed in South China, led to the isolation of twenty-six ent-kaurane diterpenoids, including seven new ones 1–7. Their structures and relative configuration were elucidated on the basis of extensive
[...] Read more.
Continued interest in the metabolites of Wedelia trilobata (L.) Hitchc, a notoriously invasive weed in South China, led to the isolation of twenty-six ent-kaurane diterpenoids, including seven new ones 1–7. Their structures and relative configuration were elucidated on the basis of extensive spectroscopic analysis, including 1D- and 2D-NMR experiments. The antimicrobial activities of all isolated diterpenoids were evaluated against a panel of bacteria and fungi. Full article
(This article belongs to the Special Issue Diterpene and Its Significance in Natural Medicine)
Open AccessArticle Labdane Diterpenes from the Fruits of Sinopodophyllum emodi
Molecules 2016, 21(4), 434; doi:10.3390/molecules21040434
Received: 3 March 2016 / Revised: 21 March 2016 / Accepted: 24 March 2016 / Published: 31 March 2016
PDF Full-text (929 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Two new labdane diterpenes, sinoditerpene A (1) and B (2), were isolated from the fruits of Sinopodophyllum emodi, along with two known analogues 3 and 4. Their structures were established on the basis of extensive spectroscopic analysis. The isolation of compounds 1–4
[...] Read more.
Two new labdane diterpenes, sinoditerpene A (1) and B (2), were isolated from the fruits of Sinopodophyllum emodi, along with two known analogues 3 and 4. Their structures were established on the basis of extensive spectroscopic analysis. The isolation of compounds 1–4 represents the first report of diterpenes from the genus Sinopodophyllum. The cytotoxic activities of all isolated compounds were evaluated in comparison with 5-fluorouracil against the MCF-7 and HepG2 cell lines, towards which 3 showed more potent cytotoxicity. Full article
(This article belongs to the Special Issue Diterpene and Its Significance in Natural Medicine)

Review

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Open AccessReview Anticancer Activities of C18-, C19-, C20-, and Bis-Diterpenoid Alkaloids Derived from Genus Aconitum
Molecules 2017, 22(2), 267; doi:10.3390/molecules22020267
Received: 27 December 2016 / Revised: 5 February 2017 / Accepted: 6 February 2017 / Published: 13 February 2017
PDF Full-text (923 KB) | HTML Full-text | XML Full-text
Abstract
Cancer is one of the most common lethal diseases, and natural products have been extensively studied as anticancer agents considering their availability, low toxicity, and economic affordability. Plants belonging to the genus Aconitum have been widely used medically in many Asian countries since
[...] Read more.
Cancer is one of the most common lethal diseases, and natural products have been extensively studied as anticancer agents considering their availability, low toxicity, and economic affordability. Plants belonging to the genus Aconitum have been widely used medically in many Asian countries since ancient times. These plants have been proven effective for treating several types of cancer, such as lung, stomach, and liver cancers. The main effective components of Aconitum plants are diterpenoid alkaloids—which are divided into C18-, C19-, C20-, and bis-diterpenoid alkaloids—are reportedly some of the most promising, naturally abundant compounds for treating cancer. This review focuses on the progress of diterpenoid alkaloids with different structures derived from Aconitum plants and some of their derivatives with potential anticancer activities. We hope that this work can serve as a reference for further developing Aconitum diterpenoid alkaloids as anticancer agents. Full article
(This article belongs to the Special Issue Diterpene and Its Significance in Natural Medicine)
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