Molecules

2 pages, 161 KB

Open AccessEditorial

Special Issue “Structure–Activity Relationship of Natural Products”

by Jean-Marc Sabatier

Laboratory INSERM UMR 1097, Aix-Marseille University, 163, Parc Scientifique et Technologique de Luminy, Avenue de Luminy, Bâtiment TPR2, Case 939, 13288 Marseille, France

Molecules 2017, 22(5), 697; https://doi.org/10.3390/molecules22050697 - 27 Apr 2017

Viewed by 3981

Abstract

This Special Issue of Molecules deals with the structure–activity relationship of natural compounds which possess some pharmacological/chemical properties of potential interest (from basic research to the clinical applications) in a wide range of areas, such as bacteriology, parasitology, cancerology, inflammation, etc.[...] Full article

(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products)

15 pages, 1386 KB

Open AccessArticle

Structure-Activity and Lipophilicity Relationships of Selected Antibacterial Natural Flavones and Flavanones of Chilean Flora

by Javier Echeverría^*

, Julia Opazo, Leonora Mendoza, Alejandro Urzúa^*

and Marcela Wilkens^*

Facultad de Química y Biología, Universidad de Santiago de Chile, Santiago 9170022, Chile

Molecules 2017, 22(4), 608; https://doi.org/10.3390/molecules22040608 - 10 Apr 2017

Cited by 135 | Viewed by 9684

Abstract

In this study, we tested eight naturally-occurring flavonoids—three flavanones and five flavones—for their possible antibacterial properties against four Gram-positive and four Gram-negative bacteria. Flavonoids are known for their antimicrobial properties, and due their structural diversity; these plant-derived compounds are a good model to [...] Read more.

In this study, we tested eight naturally-occurring flavonoids—three flavanones and five flavones—for their possible antibacterial properties against four Gram-positive and four Gram-negative bacteria. Flavonoids are known for their antimicrobial properties, and due their structural diversity; these plant-derived compounds are a good model to study potential novel antibacterial mechanisms. The lipophilicity and the interaction of antibacterial compounds with the cell membrane define the success or failure to access its target. Therefore, through the determination of partition coefficients in a non-polar/aqueous phase, lipophilicity estimation and the quantification of the antibacterial activity of different flavonoids, flavanones, and flavones, a relationship between these parameters was assessed. Active flavonoids presented diffusion coefficients between 9.4 × 10⁻¹⁰ and 12.3 × 10⁻¹⁰ m²/s and lipophilicity range between 2.0 to 3.3. Active flavonoids against Gram-negative bacteria showed a narrower range of lipophilicity values, compared to active flavonoids against Gram-positive bacteria, which showed a wide range of lipophilicity and cell lysis. Galangin was the most active flavonoid, whose structural features are the presence of two hydroxyl groups located strategically on ring A and the absence of polar groups on ring B. Methylation of one hydroxyl group decreases the activity in 3-O-methylgalangin, and methylation of both hydroxyl groups caused inactivation, as shown for 3,7-O-dimethylgalangin. In conclusion, the amphipathic features of flavonoids play a crucial role in the antibacterial activity. In these compounds, hydrophilic and hydrophobic moieties must be present and could be predicted by lipophilicity analysis. Full article

(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products)

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8 pages, 1222 KB

Open AccessArticle

The Structure–Antioxidant Activity Relationship of Ferulates

by Magdalena Karamać¹

, Lidiya Koleva², Vessela D. Kancheva² and Ryszard Amarowicz^1,*

¹ Department of Chemical and Physical Properties of Food, Institute of Animal Reproduction and Food Research, Polish Academy of Sciences, Tuwima 10, 10-748 Olsztyn, Poland

² Lipid Chemistry Department, Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia 1113, Bulgaria

Molecules 2017, 22(4), 527; https://doi.org/10.3390/molecules22040527 - 25 Mar 2017

Cited by 58 | Viewed by 8916

Abstract

The antioxidant activity of ferulic acid (1), iso-ferulic acid (2), coniferyl aldehyde (3), methyl ferulate (4), and ethyl ferulate (5) were investigated using 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and ferric-reducing antioxidant power (FRAP) assays [...] Read more.

The antioxidant activity of ferulic acid (1), iso-ferulic acid (2), coniferyl aldehyde (3), methyl ferulate (4), and ethyl ferulate (5) were investigated using 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and ferric-reducing antioxidant power (FRAP) assays and autoxidation of triacylglycerols of commercially available sunflower oil (TGSO). The compounds tested for ability to scavenge ABTS radical cations was in the order of ferulic acid > coniferyl aldehyde ≈ iso-ferulic acid > ethyl ferulate ≈ methyl ferulate. The results of the FRAP assay for ferulic acid, iso-ferulic acid, and coniferyl aldehyde were similar to and higher than those of methyl ferulate and ethyl ferulate. In the lipid system, iso-ferulic acid showed weak antioxidant activity. The other ferulates exhibited much stronger, yet similar, activities. Full article

(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products)

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10 pages, 412 KB

Open AccessArticle

Antiprotozoal Activity of Triazole Derivatives of Dehydroabietic Acid and Oleanolic Acid

by Mariano Walter Pertino^1,*, Celeste Vega², Miriam Rolón², Cathia Coronel², Antonieta Rojas de Arias² and Guillermo Schmeda-Hirschmann¹

¹ Laboratorio de Química de Productos Naturales, Instituto de Química de Recursos Naturales, Universidad de Talca, 3460000 Talca, Chile

² Centro para el Desarrollo de la Investigación Científica (CEDIC), Manduvirá 635 entre 15 de Agosto y O’Leary, Barrio La Encarnación 1255, 2511 Asunción, Paraguay

Molecules 2017, 22(3), 369; https://doi.org/10.3390/molecules22030369 - 28 Feb 2017

Cited by 39 | Viewed by 6854

Abstract

Tropical parasitic diseases such as Chagas disease and leishmaniasis are considered a major public health problem affecting hundreds of millions of people worldwide. As the drugs currently used to treat these diseases have several disadvantages and side effects, there is an urgent need [...] Read more.

Tropical parasitic diseases such as Chagas disease and leishmaniasis are considered a major public health problem affecting hundreds of millions of people worldwide. As the drugs currently used to treat these diseases have several disadvantages and side effects, there is an urgent need for new drugs with better selectivity and less toxicity. Structural modifications of naturally occurring and synthetic compounds using click chemistry have enabled access to derivatives with promising antiparasitic activity. The antiprotozoal activity of the terpenes dehydroabietic acid, dehydroabietinol, oleanolic acid, and 34 synthetic derivatives were evaluated against epimastigote forms of Trypanosoma cruzi and promastigotes of Leishmaniabraziliensis and Leishmania infantum. The cytotoxicity of the compounds was assessed on NCTC-Clone 929 cells. The activity of the compounds was moderate and the antiparasitic effect was associated with the linker length between the diterpene and the triazole in dehydroabietinol derivatives. For the oleanolic acid derivatives, a free carboxylic acid function led to better antiparasitic activity. Full article

(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products)

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14 pages, 8263 KB

Open AccessArticle

An Investigation on the Quantitative Structure-Activity Relationships of the Anti-Inflammatory Activity of Diterpenoid Alkaloids

by Xiao Li¹, Ning Li², Zhenyu Sui¹, Kaishun Bi¹ and Zuojing Li^3,*

¹ School of Pharmacy, Shenyang Pharmaceutical University, Shenyang 110016, China

² School of Chinese Traditional Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China

³ School of Medical Devices, Shenyang Pharmaceutical University, Shenyang 110016, China

Molecules 2017, 22(3), 363; https://doi.org/10.3390/molecules22030363 - 27 Feb 2017

Cited by 16 | Viewed by 6989

Abstract

Diterpenoid alkaloids are extracted from plants. These compounds have broad biological activities, including effects on the cardiovascular system, anti-inflammatory and analgesic actions, and anti-tumor activity. The anti-inflammatory activity was determined by carrageenan-induced rat paw edema and experimental trauma in rats. The number of [...] Read more.

Diterpenoid alkaloids are extracted from plants. These compounds have broad biological activities, including effects on the cardiovascular system, anti-inflammatory and analgesic actions, and anti-tumor activity. The anti-inflammatory activity was determined by carrageenan-induced rat paw edema and experimental trauma in rats. The number of studies focused on the determination, quantitation and pharmacological properties of these alkaloids has increased dramatically during the past few years. In this work we built a dataset composed of 15 diterpenoid alkaloid compounds with diverse structures, of which 11 compounds were included in the training set and the remaining compounds were included in the test set. The quantitative chemistry parameters of the 15 diterpenoid alkaloids compound were calculated using the HyperChem software, and the quantitative structure–activity relationship (QSAR) of these diterpenoid alkaloid compounds were assessed in an anti-inflammation model based on half maximal effective concentration (EC₅₀) measurements obtained from rat paw edema data. The QSAR prediction model is as follows:

\log (E C_{50}) = - 0.0260 \times SAA + 0.0086 \times SAG + 0.0011 \times VOL - 0.0641 \times HE - 0.2628 \times LogP - 0.5594 \times REF - 0.2211 \times POL - 0.1964 \times MASS + 0.088 \times BE + 0.1398 \times HF

(R² = 0.981, Q² = 0.92). The validated consensus EC₅₀ for the QSAR model, developed from the rat paw edema anti-inflammation model used in this study, indicate that this model was capable of effective prediction and can be used as a reliable computational predictor of diterpenoid alkaloid activity. Full article

(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products)

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11 pages, 23815 KB

Open AccessArticle

The Structure-Activity Relationship of Pterostilbene Against Candida albicans Biofilms

by Dan-Dan Hu¹, Ri-Li Zhang¹, Yong Zou², Hua Zhong¹, En-Sheng Zhang^3,4, Xiang Luo^2,4, Yan Wang^1,*

and Yuan-Ying Jiang^1,*

¹ New Drug Research and Development Center, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

² School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China

³ School of Chemistry and Chemical Engineering, Yan’an University, Yan’an 716000, China

⁴ ZhongshanWanYuan New Drug R & D Co., Ltd., Zhongshan 528451, China

Molecules 2017, 22(3), 360; https://doi.org/10.3390/molecules22030360 - 27 Feb 2017

Cited by 20 | Viewed by 6367

Abstract

Candida albicans biofilms contribute to invasive infections and dramatic drug resistance, and anti-biofilm agents are urgently needed in the clinic. Pterostilbene (PTE) is a natural plant product with potentials to be developed as an anti-biofilm agent. In this study, we evaluated the structure-activity [...] Read more.

Candida albicans biofilms contribute to invasive infections and dramatic drug resistance, and anti-biofilm agents are urgently needed in the clinic. Pterostilbene (PTE) is a natural plant product with potentials to be developed as an anti-biofilm agent. In this study, we evaluated the structure-activity relationship (SAR) of PTE analogues against C. albicans biofilms. XTT (Sodium 2,3-bis(2-methoxy-4-nitro-5-sulfophenyl)-2H-tetrazolium-5-carboxanilide inner salt) reduction assay was used to evaluate the activity of the analogues against C. albicans biofilms. Knowing that hyphal formation is essential for C. albicans biofilms, anti-hyphal assay was further carried out. By comparing a series of compounds tested in this study, we found that compounds with para-hydroxy (–OH) in partition A exhibited better activity than those with other substituents in the para position, and the double bond in partition B and meta-dimethoxy (–OCH₃) in partition C both contributed to the best activity. Consistent results were obtained by anti-hyphal assay. Collectively, para-hydroxy (–OH), double bond and meta-dimethoxy (–OCH₃) are all needed for the best activity of PTE against C. albicans biofilms. Full article

(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products)

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14 pages, 1307 KB

Open AccessArticle

Structure-Antioxidative and Anti-Inflammatory Activity Relationships of Purpurin and Related Anthraquinones in Chemical and Cell Assays

by Woo Nam¹, Sung Phil Kim^2,3, Seok Hyun Nam^1,* and Mendel Friedman^4,*

¹ Department of Biological Science, Ajou University, Suwon 16499, Korea

² Research Institute of Basic Sciences, Ajou University, Suwon 16499, Korea

³ STR Biotech. Ltd., Chuncheon 24232, Korea

⁴ Western Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, Albany, CA 94710, USA

Molecules 2017, 22(2), 265; https://doi.org/10.3390/molecules22020265 - 10 Feb 2017

Cited by 67 | Viewed by 9212

Abstract

Anthraquinone (9,10-anthraquinone) and several hydroxy derivatives, including purpurin (1,2,4-trihydroxyanthraquinone), anthrarufin (1,5-dihydroxyanthraquinone), and chrysazin (1,8-dihydroxyanthraquinone), were evaluated for antioxidative and anti-inflammatory activities in chemical assays and mammalian cells (murine macrophage RAW 264.7 cells). Several tests were used to assess their activities: 1,1-diphenyl-2-picrylhydrazyl (DPPH) free [...] Read more.

Anthraquinone (9,10-anthraquinone) and several hydroxy derivatives, including purpurin (1,2,4-trihydroxyanthraquinone), anthrarufin (1,5-dihydroxyanthraquinone), and chrysazin (1,8-dihydroxyanthraquinone), were evaluated for antioxidative and anti-inflammatory activities in chemical assays and mammalian cells (murine macrophage RAW 264.7 cells). Several tests were used to assess their activities: 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical; ABTS radical cation; hydrogen peroxide scavenging; reduction of potassium ferricyanide; chelation of ferrous ions; inhibition of lipid peroxidation; inhibition of nitric oxide generation; scavenging of the intracellular hydroxyl radical; expression of NLRP3 polypeptide for inflammasome assembly; and quantitation of proinflammatory cytokine interleukin 1β (IL-1β) for inflammasome activation. The results show that purpurin, from the root of the madder plant (Rubia tinctorum L.), exhibited the highest antioxidative activity in both chemical and cultured cell antioxidant assays. The antioxidative activities of the other three anthraquinones were lower than that of purpurin. In addition, purpurin could down-regulate NLRP3 inflammasome assembly and activation, suggesting that it might protect foods against oxidative damage and prevent in vivo oxidative stress and inflammation. Structure-activity relationships and the significance of the results for food quality and human health are discussed. Full article

(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products)

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15 pages, 3585 KB

Open AccessArticle

Phloretin Exerts Anti-Tuberculosis Activity and Suppresses Lung Inflammation

by Dasom Jeon¹, Min-Cheol Jeong¹, Hum Nath Jnawali¹, Chulhee Kwak¹, Sungwon Ryoo²

, In Duk Jung³ and Yangmee Kim^1,*

¹ Department of Bioscience and Biotechnology, Konkuk University, Seoul 05029, Korea

² Korean National Tuberculosis Association, Seoul 06763, Korea

³ Department of Immunology, School of Medicine, Konkuk University, Seoul 05029, Korea

Molecules 2017, 22(1), 183; https://doi.org/10.3390/molecules22010183 - 22 Jan 2017

Cited by 40 | Viewed by 8668

Abstract

An increase in the prevalence of the drug-resistant Mycobacteria tuberculosis necessitates developing new types of anti-tuberculosis drugs. Here, we found that phloretin, a naturally-occurring flavonoid, has anti-mycobacterial effects on H37Rv, multi-drug-, and extensively drug-resistant clinical isolates, with minimum inhibitory concentrations of 182 and [...] Read more.

An increase in the prevalence of the drug-resistant Mycobacteria tuberculosis necessitates developing new types of anti-tuberculosis drugs. Here, we found that phloretin, a naturally-occurring flavonoid, has anti-mycobacterial effects on H37Rv, multi-drug-, and extensively drug-resistant clinical isolates, with minimum inhibitory concentrations of 182 and 364 μM, respectively. Since Mycobacteria cause lung inflammation that contributes to tuberculosis pathogenesis, anti-inflammatory effects of phloretin in interferon-γ-stimulated MRC-5 human lung fibroblasts and lipopolysaccharide (LPS)-stimulated dendritic cells were investigated. The release of interleukin (IL)-1β, IL-12, and tumor necrosis factor (TNF)-α was inhibited by phloretin. The mRNA levels of IL-1β, IL-6, IL-12, TNF-α, and matrix metalloproteinase-1, as well as p38 mitogen-activated protein kinase and extracellular signal-regulated kinase phosphorylation, were suppressed. A mouse in vivo study of LPS-stimulated lung inflammation showed that phloretin effectively suppressed the levels of TNF-α, IL-1β, and IL-6 in lung tissue with low cytotoxicity. Phloretin was found to bind M. tuberculosis β-ketoacyl acyl carrier protein synthase III (mtKASIII) with high affinity (7.221 × 10⁷ M⁻¹); a binding model showed hydrogen bonding of A-ring 2′-hydroxy and B-ring 4-hydroxy groups of phloretin with Asn261 and Cys122 of mtKASIII, implying that mtKASIII can be a potential target protein. Therefore, phloretin can be a useful dietary natural product with anti-tuberculosis benefits. Full article

(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products)

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9 pages, 1665 KB

Open AccessArticle

Improving Free Radical Scavenging Activity of Soy Isoflavone Glycosides Daidzin and Genistin by 3′-Hydroxylation Using Recombinant Escherichia coli

by Chien-Min Chiang^1,*, Dong-Sheng Wang² and Te-Sheng Chang²

¹ Department of Biotechnology, Chia Nan University of Pharmacy and Science, No. 60, Sec. 1, Erh-Jen Rd., Jen-Te District, Tainan 71710, Taiwan

² Department of Biological Sciences and Technology, National University of Tainan, Tainan 70005, Taiwan

Molecules 2016, 21(12), 1723; https://doi.org/10.3390/molecules21121723 - 15 Dec 2016

Cited by 34 | Viewed by 6665

Abstract

The present study describes the biotransformation of a commercially available crude extract of soy isoflavones, which contained significant amounts of the soy isoflavone glycosides daidzin and genistin, by recombinant Escherichia coli expressing tyrosinase from Bacillus megaterium. Two major products were isolated from [...] Read more.

The present study describes the biotransformation of a commercially available crude extract of soy isoflavones, which contained significant amounts of the soy isoflavone glycosides daidzin and genistin, by recombinant Escherichia coli expressing tyrosinase from Bacillus megaterium. Two major products were isolated from the biotransformation and identified as 3′-hydroxydaidzin and 3′-hydroxygenistin, respectively, based on their mass and nuclear magnetic resonance spectral data. The two 3′-hydroxyisoflavone glycosides showed potent 2,2-diphenyl-1-picrylhydrazyl free radical scavenging activity with IC₅₀ values of 7.4 and 9.8 μM for 3′-hydroxydaidzin and 3′-hydroxygenistin, respectively. The free radical scavenging activities of the two 3′-hydroxyisoflavone glycosides were, respectively, 120 and 72 times higher than the activity of their precursors, daidzin and genistin, and were also stronger than the activity of ascorbic acid, which showed an IC₅₀ value of 15.1 μM. This is the first report of the bio-production and potential antioxidant applications of both 3′-hydroxydaidzin and 3′-hydroxygenistin. Full article

(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products)

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14 pages, 1355 KB

Open AccessArticle

Polyphenols Isolated from Xanthoceras sorbifolia Husks and Their Anti-Tumor and Radical-Scavenging Activities

by Chun-Yan Yang^1,2, Wei Ha¹, Yong Lin³, Kan Jiang¹, Jun-Li Yang^1,* and Yan-Ping Shi^1,*

¹ CAS Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China

² School of Pharmacy, Institute of Materia Medica, North Sichuan Medical College, Nanchong 637007, China

³ Department of Preventive Medicine, North Sichuan Medical College, Nanchong 637007, China

Molecules 2016, 21(12), 1694; https://doi.org/10.3390/molecules21121694 - 9 Dec 2016

Cited by 39 | Viewed by 6637

Abstract

Xanthoceras sorbifolia Bunge. is used in traditional medicine in North China. To evaluate the anti-tumor and radical-scavenging activities of X. sorbifolia husks polyphenols and determine their structure-activity relationships, 37 polyphenols 1–37 were obtained by bioassay-guided fractionation. Two new compounds 1– [...] Read more.

Xanthoceras sorbifolia Bunge. is used in traditional medicine in North China. To evaluate the anti-tumor and radical-scavenging activities of X. sorbifolia husks polyphenols and determine their structure-activity relationships, 37 polyphenols 1–37 were obtained by bioassay-guided fractionation. Two new compounds 1–2, and compounds 5, 6, 8, 9, 11, 14–17, 21–25, 27–29, 31, 33, 34, 36, and 37 were isolated from the genus Xanthoceras for the first time. Compounds 1–37 did not show strong cytotoxicity against the four tested tumor cell lines (A549, HepG2, MGC-803, and MFC) compared to paclitaxel and under the conditions tested in the anti-tumor assay, but compounds 3, 4, 7, 8, 10, 18–20, 25, 26, 29, 30, 32, and 35 exhibited stronger radical-scavenging activity than ascorbic acid in a 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt assay. This was the first report on the anti-tumor and radical-scavenging activities of the polyphenols isolated from X. sorbifolia husks. Overall, the present study contributed valuable information concerning X. sorbifolia husks use in medicine and pharmacology. Full article

(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products)

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12 pages, 1929 KB

Open AccessArticle

Glycyrrhizic Acid Reduces Heart Rate and Blood Pressure by a Dual Mechanism

by Kailash Singh¹, Aung Moe Zaw¹, Revathi Sekar¹, Ahuja Palak¹, Ahmed A. Allam^2,3, Jamaan Ajarem² and Billy K. C. Chow^1,*

¹ School of Biological Sciences, The University of Hong Kong, Pokfulam Road, Hong Kong SAR, China

² Department of Zoology, College of Science, King Saud University, Riyadh 11451, Saudi Arabia

³ Department of Zoology, Faculty of Science, Beni-Suef University, Beni-Suef 62511, Egypt

Molecules 2016, 21(10), 1291; https://doi.org/10.3390/molecules21101291 - 27 Sep 2016

Cited by 15 | Viewed by 8133

Abstract

Beta adrenergic receptors are crucial for their role in rhythmic contraction of heart along with their role in the pathological conditions such as tachycardia and high risk of heart failure. Studies report that the levels of beta-1 adrenergic receptor tend to decrease by [...] Read more.

Beta adrenergic receptors are crucial for their role in rhythmic contraction of heart along with their role in the pathological conditions such as tachycardia and high risk of heart failure. Studies report that the levels of beta-1 adrenergic receptor tend to decrease by 50%, whereas, the levels of beta-2 adrenergic receptor remains constant during the risk of heart failure. Beta blockers—the antagonistic molecules for beta-adrenergic receptors, function by slowing the heart rate, which thereby allows the left ventricle to fill completely during tachycardia incidents and hence helps in blood pumping capacity of heart and reducing the risk of heart failure. In the present study, we investigate the potential of glycyrrhizic acid (GA) as a possible principal drug molecule for cardiac arrhythmias owing to its ability to induce reduction in the heart rate and blood pressure. We use in vitro and in silico approach to study GA′s effect on beta adrenergic receptor along with an in vivo study to examine its effect on heart rate and blood pressure. Additionally, we explore GA′s proficiency in eliciting an increase in the plasma levels of vasoactive intestinal peptide, which by dilating the blood vessel consequently, can be a crucial aid during the occurrence of a potential heart attack. Therefore, we propose GA as a potential principal drug molecule via its potential in modulating heart rate and blood pressure. Full article

(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products)

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13 pages, 1400 KB

Open AccessArticle

The Changes in Color, Soluble Sugars, Organic Acids, Anthocyanins and Aroma Components in “Starkrimson” during the Ripening Period in China

by Yulian Liu^1,2, Nianlai Chen², Zonghuan Ma¹, Fei Che³, Juan Mao¹ and Baihong Chen^1,*

¹ College of Horticulture, Gansu Agricultural University, Lanzhou 730070, China

² College of Resources and Environmental Sciences, Gansu Agricultural University, Lanzhou 730070, China

³ Sichuan Kaijiang Middle School, Dazhou 626350, China

Molecules 2016, 21(6), 812; https://doi.org/10.3390/molecules21060812 - 22 Jun 2016

Cited by 27 | Viewed by 7142

Abstract

“Starkrimson” is a traditional apple cultivar that was developed a long time ago and was widely cultivated in the arid region of the northern Wei River of China. However, little information regarding the quality characteristics of “Starkrimson” fruit has been reported in this [...] Read more.

“Starkrimson” is a traditional apple cultivar that was developed a long time ago and was widely cultivated in the arid region of the northern Wei River of China. However, little information regarding the quality characteristics of “Starkrimson” fruit has been reported in this area. To elucidate these characteristics, the color, soluble sugars, organic acids, anthocyanins and aroma components were measured during the ripening period through the use of high performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS). The results indicated that the changes in anthocyanin contents took place later than the changes in the Commission International Eclairage (CIE) parameters. Meanwhile, cyanidin 3-galactoside (cy3-gal), fructose, sucrose, glucose and malic acid were the primary organic compounds, and 1-butanol-2-methyl-acetate, 2-hexenal and 1-hexanol were the most abundant aroma components in the skin. Furthermore, rapidly changing soluble sugars and organic acid synchronization took place in the early ripening period, while rapidly changing aroma components occurred later, on the basis of fresh weight. This result suggested that the production of aroma components might be a useful index of apple maturity. Full article

(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products)

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