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

Deadline for manuscript submissions: closed (31 August 2019) | Viewed by 24674

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Special Issue Editors

Dr. Martin C. Gruhlke

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Guest Editor

Society for Natural Product and Drug Research, 52070 Aachen, Germany
Interests: natural products; active ingredient; molecular biology; biochemistry; apoptosis
Special Issues, Collections and Topics in MDPI journals

Prof. Dr. Alan J. Slusarenko

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Guest Editor

Head of the Plant Physiology Department at RWTH Aachen University, Aachen, Germany
Interests: resistance mechanisms of Arabidopsis to infection; natural products in plant protection
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

When plants are attacked by pathogens or pests, they often actively defend themselves by accumulating antimicrobial secondary metabolites called ‘phytoalexins’. Furthermore, many plants accumulate secondary metabolites as a matter of course during their development, and these preformed substances, or ‘phytoanticipins’, have a defence role which can be antimicrobial or antifeedant. In addition, many organisms produce ‘allelochemicals’, which are physiologically active against other species in their immediate environment and result in the phenomenon of ‘allelopathy’, helping them in the competition for survival.

Natural Products active in plant protection have been tried and tested in the course of evolution and can be very effective. However, their properties are often not suitable for large-scale industrial production, marketing, and agricultural application. Nevertheless, the emerging resistance to many current fungicides and increasing concerns about the environmental impact of synthetic chemicals mean that new effective treatments based on Natural Products as lead compounds are urgently needed.

We would like to encourage the submission of papers reporting on Natural Products in plant protection, either in a natural context (e.g., phytoanticipins or phytoalexins) or reports showing disease-reduction in a given pathosystem in a ‘nature-inspired’ plant protection strategy. Reports of novel antimicrobial, antifeedant, or other potentially protective properties, for named and characterized secondary products, against disease-causing agents and pests are also welcome. However, reports on activities of uncharacterized mixtures from plants or other organisms, without a chemically defined and identified active principle, will be rejected without being sent out for review.

Dr. Martin C. Gruhlke
Prof. Dr. Alan J. Slusarenko
Guest Editors

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Published Papers (5 papers)

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Research

10 pages, 1574 KiB

Open AccessArticle

Structural Elucidation of Three Novel Kaempferol O-tri-Glycosides that Are Involved in the Defense Response of Hybrid Ornithogalum to Pectobacterium carotovorum

by Iris Yedidia, Keren Schultz, Avner Golan, Hugo E. Gottlieb and Zohar Kerem

Molecules 2019, 24(16), 2910; https://doi.org/10.3390/molecules24162910 - 10 Aug 2019

Cited by 6 | Viewed by 3089

Abstract

Ornithogalum is an ornamental flowering species that grows from a bulb and is highly susceptible to soft-rot disease caused by Pectobacterium carotovorum (Pc). Interspecific hybridization between O. thyrsoides and O. dubium yielded hybrids with enhanced resistance to that pathogen. The hybrids displayed distinct phenolic-compound profiles with several peaks that were specifically heightened following Pc infection. Three of these compounds were isolated and identified as novel kaempferol O-tri-glycosides. The structures of these compounds were elucidated using reversed phase high-performance liquid chromatography (RP-LC), RP-LC coupled to high-resolution mass spectrometry (RP-LC-MS), and nuclear magnetic resonance (NMR) (1D ¹H and ¹³C, DEPT, HMQC, HMBC, COSY, and NOE), in order to achieve pure and defined compounds data. The new compounds were finally identified as kaempferol 3-O-[4-O-α-l-(3-O-acetic)-rhamnopyranosyl-6-O-β-d-xylopyranosyl]-β-d-glucopyranoside, kaempferol 3-O-[4-O-α-l-(2-O-acetic)-rhamnopyranosyl-6-O-β-d-xylopyranosyl]-β-d-glucopyranoside and kaempferol 3-O-[4-O-α-l-(2,3-O-diacetic)-rhamnopyranosyl-6-O-β-d-xylopyranosyl]-β-d-glucopyranoside. Full article

(This article belongs to the Special Issue Natural Products in Plant Protection)

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18 pages, 2136 KiB

Open AccessArticle

Cordycepin Isolated from Cordyceps militaris: Its Newly Discovered Herbicidal Property and Potential Plant-Based Novel Alternative to Glyphosate

by Tran Ngoc Quy, Tran Dang Xuan, Yusuf Andriana, Hoang-Dung Tran, Tran Dang Khanh and Rolf Teschke

Molecules 2019, 24(16), 2901; https://doi.org/10.3390/molecules24162901 - 9 Aug 2019

Cited by 29 | Viewed by 8363

Abstract

There is currently much interest in finding new phytochemicals among plants and fungi as nature-based alternatives to replace problematic herbicides such as glyphosate, which are preferentially used in agricultural production. We discovered striking herbicidal potency in Cordyceps militaris (L.) and identified cordycepin as its principal plant growth inhibitor. Cordycepin obtained as an ethyl acetate extract was subjected to column chromatography and evaluated for its bioassay-guided phytotoxic capacity against Raphanus sativus (radish), showing a maximum inhibition on germination and growth of radish (IC₅₀ = 0.052–0.078 mg/mL). Gas chromatography-mass spectrometry (GC-MS) (m/z: 251.2) and liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) ([M + Na]⁺ m/z: 274.1; [M + H]⁺ m/z: 252.1) analyses confirmed cordycepin as the major component of the tested column fraction (55.38%). At 0.04 mg/mL, cordycepin showed 3.8–5.9- and 3.3–3.7-fold greater inhibition of the germination and growth of radish than benzoic acid (BA) and glyphosate, respectively. Compared with BA, isolated cordycepin reduced plant chlorophyll and carotenoid contents (2.0–9.5 -fold), while proline, total phenolic and total flavonoid contents were increased 1.2–1.8-fold. Finally, cordycepin promoted electrolyte leakage and malondialdehyde accumulation in radish aerial parts. Thus, cordycepin successfully isolated from Cordyceps militaris is a highly potent plant growth inhibitor with pending worldwide patent and may become a potential plant-based novel alternative to the disputed glyphosate. Full article

(This article belongs to the Special Issue Natural Products in Plant Protection)

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10 pages, 599 KiB

Open AccessArticle

Facile and Efficient Syntheses of (11Z,13Z)-Hexadecadienal and Its Derivatives: Key Sex Pheromone and Attractant Components of Notodontidae

by Fu Liu, Xiangbo Kong, Sufang Zhang and Zhen Zhang

Molecules 2019, 24(9), 1781; https://doi.org/10.3390/molecules24091781 - 8 May 2019

Cited by 4 | Viewed by 3632

Abstract

Syntheses of (11Z,13Z)-hexadecadienal (1), (11Z,13Z)-hexadecadienol (2), (11Z,13Z)-hexadecadien-1-yl acetate (3), and (Z)-13-hexadecen-11-ynal (4) from commercially available starting material 10-bromo-1-decanol are reported. These (Z,Z)-dienes and conjugated en-yne moieties are common in sex pheromone and attractant components for many Notodontide insect pests. The synthetic scheme, using the C10 + C3 + C3 strategy, was mainly based on three key steps: alkylation of lithium alkyne under a low temperature, cis-Wittig olefination of the aldehyde with propylidentriphenylphosphorane, and hydroboration-protonolysis of alkyne. This synthetic route provided (11Z,13Z)-hexadecadienal (1) in a 23.0% total yield via an eight-step sequence, alcohol (2) in a 21.9% total yield, acetate (3) in a 21.4% total yield, and (Z)-13-hexadecen-11-ynal (4) in a 34.7% total yield. This simple strategy provides a new way to achieve syntheses of the key sex pheromones of Notodontide insect pests. Full article

(This article belongs to the Special Issue Natural Products in Plant Protection)

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14 pages, 4424 KiB

Open AccessArticle

Spermidine Enhances Heat Tolerance of Rice Seeds by Modulating Endogenous Starch and Polyamine Metabolism

by Yuying Fu, Qingqing Gu, Qian Dong, Zhihao Zhang, Cheng Lin, Weimin Hu, Ronghui Pan, Yajing Guan and Jin Hu

Molecules 2019, 24(7), 1395; https://doi.org/10.3390/molecules24071395 - 9 Apr 2019

Cited by 53 | Viewed by 4660

Abstract

Polyamines have been reported to be involved in grain filling and they might contribute to the construction of heat resistance of some cereals. In this study, the hybrid rice ‘YLY 689’ was used to explore the possible effects of exogenous spermidine (Spd) on seed quality under high temperature during the filling stage. Rice spikes were treated with Spd or its synthesis inhibitor cyclohexylamine (CHA) after pollination, and then the rice plants were transferred to 40 °C for 5-day heat treatment. The results showed that, compared with the control under high temperature, Spd pretreatment significantly improved the germination percentage, germination index, vigor index, seedling shoot height, and dry weight of seeds harvested at 35 days after pollination, while the CHA significantly decreased the seed germination and seedling growth. Meanwhile, Spd significantly increased the peroxidase (POD) activity and decreased the malondialdehyde (MDA) content in seeds. In addition, after spraying with Spd, the endogenous content of spermidine and spermine and the expression of their synthetic genes, spermidine synthase (SPDSYN) and spermine synthase (SPMS1 and SPMS2), significantly increased, whereas the accumulation of amylose and total starch and the expression of their related synthase genes, soluble starch synthase II-3 (SS II-3) and granules bound starch synthase I (GBSSI), also increased to some extent. The data suggests that exogenous Spd pretreatment could alleviate the negative impacts of high temperature stress on rice seed grain filling and improve the rice seed quality to some extent, which might be partly caused by up-regulating endogenous polyamines and starch metabolism. Full article

(This article belongs to the Special Issue Natural Products in Plant Protection)

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11 pages, 2027 KiB

Open AccessArticle

Purification and Structural Analysis of the Effective Anti-TMV Compound ε-Poly-l-lysine Produced by Streptomyces ahygroscopicus

by Jianguang Chen, He Liu, Zihao Xia, Xiuxiang Zhao, Yuanhua Wu and Mengnan An

Molecules 2019, 24(6), 1156; https://doi.org/10.3390/molecules24061156 - 23 Mar 2019

Cited by 32 | Viewed by 4425

Abstract

Microbial secondary metabolites produced by actinomycetes are important natural products widely applied to control plant diseases. A variety of actinomycetes were isolated from soil samples collected from Tianzhu Mountain in Shenyang, China. A Streptomyces strain Shenyang Tianzhu (STZ) exhibits effective antiviral activity against Tobacco mosaic virus (TMV). The isolate was identified as Streptomyces ahygroscopicus based on its cultural, morphological, physiological, biochemical characteristics as well as the phylogenetic analysis using 16S rRNA sequences. To obtain the pure anti-TMV compound from Streptomyces STZ, the culture broth was subjected to Amberlite IRC-50 ion-exchange resin, SX-8 macroporous adsorption resin and Sephadex G-25 gel column chromatography. The purified active compound was confirmed to be ε-poly-l-lysine (ε-PL), with molecular mass in the range of 3454–4352 Da by structural analysis with infrared (IR), matrix-assisted laser desorption ionization-time-of-flight MS (MALDI-TOF), thin-layer chromatography (TLC) and high-resolution magic angle spinning nuclear magnetic resonance (HR-MAS NMR). The protective and curative effects of the purified compound ε-PL were tested and the results showed that the compound exhibited significant protective and curative activity against TMV. The potential application of ε-PL as an efficient anti-plant virus agent was expected. Full article

(This article belongs to the Special Issue Natural Products in Plant Protection)

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