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A Themed Issue in Memory of Academician Xing Qiyi (1911–2002)

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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 (30 November 2021) | Viewed by 27825

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Prof. Dr. Minghua Qiu

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State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China
Interests: novel chemical ctructure of natural product and their bioactives; chemical constituents of edible medicinal plant and their biologic functions;effect mechanism of bioactive compounds and development of phytomedicines

Prof. Dr. De-An Guo

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Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, China
Interests: active ingredients of traditionnal chinese medicines; quality standards of traditionnal chinese medicines; biotransformation of natural products
Special Issues, Collections and Topics in MDPI journals

Prof. Dr. Pengfei Tu

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State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, China
Interests: effect ingredients of traditionnal chinese medicines and developments of new drugs; structural modifications and structure–activity relationship of bioactive natural products; quality analysis of traditionnal chinese medicines

Prof. Dr. Wencai Ye

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International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development, Ministry of Education (MOE) of China, School of Pharmacy, Jinan University, Guangzhou, China
Interests: effect ingredients of traditionnal chinese medicines and natural medicines; chemical biology of bioactive natural products; developments of new drugs fromtraditionnal chinese medicines and natural medicines

Special Issue Information

Dear Colleagues,

Academician Xing Qiyi, born on November 24, 1911, in Tianjin, China, was one of the chemist and educators who has made outstanding contributions in the field of organic chemistry, including natural organic chemistry, peptide chemistry protein synthesis and other fields. In 1936, he obtained PhD in Organic Chemistry from the University of Illinois at in the United States (supervised by Professor R. Adams). In the same year, he went to the University of Munich, Germany, for post-doctoral research, and cooperated with the famous organic chemist Professor H. Wieland who was Nobel Prize Winner in Chemistry, carried on bafotoxin research. During the period, the chemical structure and synthesis of gramine were completed, and the indole methylation method developed in it was widely applied in organic synthesis later. In 1952, he became a full professor of organic chemistry at the School of Chemistry and Molecular Engineering of Peking University, and he was elected as an academician of the Chinese Academy of Sciences in 1980. He proposed using nitrobenzoic anhydride to react with amino acids to generate colored amino ketones at the end of the amino acid, which is a good way to identify the carboxyl end of the amino acid. He led and achieved the project of the total synthesis of bovine insulin, which was the first example of successfully artificially synthesized insulin in the world. He is also engaged in the research of peptide synthesis and natural products such as ginseng peptide and aroma components of flowers and fruits, and has conducted various research in basic research fields such as organic reaction mechanism, molecular structure determination methods and stereochemistry. His book Basic Organic Chemistry is the earliest and most systematic Organic Chemistry textbook in China, which is well received by readers and has influenced several generations of students majoring in chemistry and related field. He passed away at Peking University on November 4, 2002.

Academician Xing Qiyi was an important scientific contributor, winning the first prize of the National Natural Science Award of People’s Republic of China in 1982 for the synthetic synthesis of natural active protein bovine insulin for first time. He therefore obtained the QIUSHI Outstanding Achievement Collective Award of QIUSHI Foundation, and the new synthesis method of chloramphenicol won the National Science Conference Award of People’s Republic of CHINA in 1978. He also received some awards from the State Education Commission.

Molecules is pleased to announce a Special Issue honoring Academician Xing Qiyi on the occasion of his 110th birthday for his outstanding achievements in natural organic chemistry, especially protein synthesis . This Special Issue is dedicated to all aspects of Natural Product Chemistry, including chemistry of medicinal plants, animal, insect, marine organisms; chemical biology of natural products; etc.

It is a pleasure to invite you to submit a manuscript to this Special Issue; regular articles, communications, as well as reviews are all welcome.

Prof. Dr. Minghua Qiu
Prof. Dr. De-An Guo
Prof. Dr. Pengfei Tu
Prof. Dr. Wencai Ye
Guest Editors

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Keywords

isolation and identification of natural products
bioactive molecules
peptide chemistry
effect ingredients
structural modifications
structure-activity relationship
effect mechanism of bioactive natural products
chemical biology of bioactive natural products
synthesis of natural products
synthesis of protein
biotransformation and biosynthesis of natural products

Published Papers (11 papers)

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Research

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12 pages, 2207 KiB

Open AccessArticle

Molecular Cloning and Identification of NADPH Cytochrome P450 Reductase from Panax ginseng

by Xian Zou, Yue Zhang, Xu Zeng, Tuo Liu, Gui Li, Yuxin Dai, Yuanzhu Xie and Zhiyong Luo

Molecules 2021, 26(21), 6654; https://doi.org/10.3390/molecules26216654 - 3 Nov 2021

Cited by 3 | Viewed by 2074

Abstract

Ginseng (Panax ginseng C.A. Mey.) is a precious Chinese traditional medicine, for which ginsenosides are the most important medicinal ingredients. Cytochrome P450 enzymes (CYP450) and their primary redox molecular companion NADPH cytochrome P450 reductase (CPR) play a key role in ginsenoside biosynthesis pathway. However, systematic studies of CPR genes in ginseng have not been reported. Numerous studies on ginsenoside synthesis biology still use Arabidopsis CPR (AtCPR1) as a reductase. In this study, we isolated two CPR genes (PgCPR1, PgCPR2) from ginseng adventitious roots. Phylogenetic tree analysis showed that both PgCPR1 and PgCPR2 are grouped in classⅡ of dicotyledonous CPR. Enzyme experiments showed that recombinant proteins PgCPR1, PgCPR2 and AtCPR1 can reduce cytochrome c and ferricyanide with NADPH as the electron donor, and PgCPR1 had the highest enzymatic activities. Quantitative real-time PCR analysis showed that PgCPR1 and PgCPR2 transcripts were detected in all examined tissues of Panax ginseng and both showed higher expression in stem and main root. Expression levels of the PgCPR1 and PgCPR2s were both induced after a methyl jasmonate (MeJA) treatment and its pattern matched with ginsenoside accumulation. The present investigation suggested PgCPR1 and PgCPR2 are associated with the biosynthesis of ginsenoside. This report will assist in future CPR family studies and ultimately improving ginsenoside production through transgenic engineering and synthetic biology. Full article

(This article belongs to the Special Issue A Themed Issue in Memory of Academician Xing Qiyi (1911–2002))

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11 pages, 2354 KiB

Open AccessArticle

Monoterpene Indole Alkaloids with Ca_v3.1 T-Type Calcium Channel Inhibitory Activity from Catharanthus roseus

by Zhen-Tao Deng, Wen-Yan Li, Lei Wang, Zhi-Ping Zhou, Xing-De Wu, Zhong-Tao Ding and Qin-Shi Zhao

Molecules 2021, 26(21), 6516; https://doi.org/10.3390/molecules26216516 - 28 Oct 2021

Cited by 4 | Viewed by 1752

Abstract

Catharanthus roseus is a well-known traditional herbal medicine for the treatment of cancer, hypertension, scald, and sore in China. Phytochemical investigation on the twigs and leaves of this species led to the isolation of two new monoterpene indole alkaloids, catharanosines A (1) and B (2), and six known analogues (3–8). Structures of 1 and 2 were established by ¹H-, ¹³C- and 2D-NMR, and HREIMS data. The absolute configuration of 1 was confirmed by single-crystal X-ray diffraction analysis. Compound 2 represented an unprecedented aspidosperma-type alkaloid with a 2-piperidinyl moiety at C-10. Compounds 6–8 exhibited remarkable Ca_v3.1 low voltage-gated calcium channel (LVGCC) inhibitory activity with IC₅₀ values of 11.83 ± 1.02, 14.3 ± 1.20, and 14.54 ± 0.99 μM, respectively. Full article

(This article belongs to the Special Issue A Themed Issue in Memory of Academician Xing Qiyi (1911–2002))

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18 pages, 6209 KiB

Open AccessArticle

Integrated Network Pharmacology Analysis and In Vitro Validation Revealed the Potential Active Components and Underlying Mechanistic Pathways of Herba Patriniae in Colorectal Cancer

by Huihai Yang, Man-Kit Cheung, Grace Gar-Lee Yue, Ping-Chung Leung, Chun-Kwok Wong and Clara Bik-San Lau

Molecules 2021, 26(19), 6032; https://doi.org/10.3390/molecules26196032 - 5 Oct 2021

Cited by 9 | Viewed by 2926

Abstract

Herba Patriniae (HP) are medicinal plants commonly used in colorectal cancer (CRC) patients. In this study, network pharmacology was used to predict the active components and key signaling pathways of HP in CRC. Patrinia heterophylla, one type of HP, was chosen for validation of the network pharmacology analysis. The phytochemical profile of Patrinia heterophylla water extract (PHW) was determined by UHPLC-MS. MTT, RT-PCR, and Western blot assays were performed to evaluate the bioactivities of PHW in colon cancer cells. Results showed that 15 potentially active components of HP interacted with 28 putative targets of CRC in the compound–target network, of which asperglaucide had the highest degree. Furthermore, the ErbB signaling pathway was identified as the pathway mediated by HP with the most potential against CRC. Both RT-PCR and Western blot results showed that PHW significantly downregulated the mRNA and protein levels of EGFR, PI3K, and AKT in HCT116 cells. Asperglaucide, present in PHW, exhibited an anti-migratory effect in HCT116 cells, suggesting that it could be an active component of PHW in CRC treatment. In conclusion, this study has provided the first scientific evidence to support the use of PHW in CRC and paved the way for further research into the underlying mechanisms of PHW against CRC. Full article

(This article belongs to the Special Issue A Themed Issue in Memory of Academician Xing Qiyi (1911–2002))

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11 pages, 4073 KiB

Open AccessArticle

Quassinoids from the Roots of Eurycoma longifolia and Their Anti-Proliferation Activities

by Wei-Qun Yang, Wei Tang, Xiao-Jun Huang, Jian-Guo Song, Yue-Yue Li, Yu Xiong, Chun-Lin Fan, Zhen-Long Wu, Ying Wang and Wen-Cai Ye

Molecules 2021, 26(19), 5939; https://doi.org/10.3390/molecules26195939 - 30 Sep 2021

Cited by 6 | Viewed by 2085

Abstract

A phytochemical investigation on the roots of medicinal plant Eurycoma longifolia resulted in the isolation of 10 new highly oxygenated C₂₀ quassinoids longifolactones G‒P (1–10), along with four known ones (11–14). Their chemical structures and absolute configurations were unambiguously elucidated on the basis of comprehensive spectroscopic analysis and X-ray crystallographic data. Notably, compound 1 is a rare pentacyclic C₂₀ quassinoid featuring a densely functionalized 2,5-dioxatricyclo[5.2.2.0^4,8]undecane core. Compound 4 represents the first example of quassinoids containing a 14,15-epoxy functionality, and 7 features an unusual α-oriented hydroxyl group at C-14. All isolated compounds were evaluated for their anti-proliferation activities on human leukemia cells. Among the isolates, compounds 5, 12, 13, and 14 potently inhibited the in vitro proliferation of K562 and HL-60 cells with IC₅₀ values ranging from 2.90 to 8.20 μM. Full article

(This article belongs to the Special Issue A Themed Issue in Memory of Academician Xing Qiyi (1911–2002))

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10 pages, 2330 KiB

Open AccessArticle

Fishing of α-Glucosidase’s Ligands from Aloe vera by α-Glucosidase Functionalized Magnetic Nanoparticles

by Hao Yuan, Hong Wan, Yi-Kao Hu, Emmanuel Ayodeji Ayeni, Qiang Chang, Chao Ma and Xun Liao

Molecules 2021, 26(19), 5840; https://doi.org/10.3390/molecules26195840 - 26 Sep 2021

Cited by 4 | Viewed by 2457

Abstract

α-Glucosidase was immobilized on magnetic nanoparticles (MNPs) for selective solid-phase extraction of the enzyme’s ligands present in Aloe vera, which is a medicinal plant used for the treatment of various diseases and possesses anti-diabetic activity. One new compound, aloeacone (2), together with two known compounds, aloenin aglycone (1) and aloin A (3), were fished out as the enzyme’s ligands. The structure of 2 was determined by HR-MS and comprehensive NMR techniques. Compound 3 exhibited a weak inhibitory effect on α-glucosidase, while compounds 1 and 2 were found to possess activation effects on the enzyme for the first time. It is interesting that both an inhibitor and agonists of α-glucosidase were fished out in one experiment. Full article

(This article belongs to the Special Issue A Themed Issue in Memory of Academician Xing Qiyi (1911–2002))

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22 pages, 1768 KiB

Open AccessArticle

Trimeric and Dimeric Carbazole Alkaloids from Murraya microphylla

by Xiaoli Ma, Hongwei Chen, Sisi Zhu, Pengfei Tu and Yong Jiang

Molecules 2021, 26(18), 5689; https://doi.org/10.3390/molecules26185689 - 20 Sep 2021

Cited by 6 | Viewed by 2458

Abstract

Seventeen new carbazole alkaloid derivatives, including a trimeric carbazole racemate, (±)-microphyltrine A (1), 15 dimeric carbazole racemates, (±)-microphyldines A–O (2–16), and a C-6–C-3″-methyl-linked dimeric carbazole, microphyldine P (17), were isolated from the leaves and stems of Murraya microphylla (Merr. et Chun) Swingle. The structures of the new compounds were elucidated on the basis of HRESIMS and NMR data analysis. The optically pure isomers of these isolated carbazole alkaloids were obtained by chiral HPLC separation and their absolute configurations were determined by electronic circular dichroism (ECD) data analysis. Full article

(This article belongs to the Special Issue A Themed Issue in Memory of Academician Xing Qiyi (1911–2002))

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8 pages, 744 KiB

Open AccessArticle

Zopfiellasins A–D, Two Pairs of Epimeric Cytochalasins from Kiwi-Associated Fungus Zopfiella sp. and Their Antibacterial Assessment

by Jie-Yu Zhang, Juan He, Zheng-Hui Li, Tao Feng and Ji-Kai Liu

Molecules 2021, 26(18), 5611; https://doi.org/10.3390/molecules26185611 - 16 Sep 2021

Cited by 10 | Viewed by 2098

Abstract

In our continuous search for antibacterial agents against Pseudomonas syringae pv. actinidiae (Psa) from kiwi-associated fungi, two pairs of epimeric cytochalasins, zopfiellasins A–D (1–4), were characterized from the fungus Zopfiella sp. The structures were established on the basis of spectroscopic data analysis, while the absolute configurations were determined by single-crystal X-ray diffraction. Compounds 1 and 3 exhibited antibacterial activity against Psa with MIC values of 25 and 50 μg/mL, respectively. This is the first report of anti-Psa activity of cytochalasin derivatives. Full article

(This article belongs to the Special Issue A Themed Issue in Memory of Academician Xing Qiyi (1911–2002))

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10 pages, 1249 KiB

Open AccessArticle

Macathiohydantoin L, a Novel Thiohydantoin Bearing a Thioxohexahydroimidazo [1,5-a] Pyridine Moiety from Maca (Lepidium meyenii Walp.)

by Ranran Zhang, Junhong Liu, Hui Yan, Xingrong Peng, Ling Zhang and Minghua Qiu

Molecules 2021, 26(16), 4934; https://doi.org/10.3390/molecules26164934 - 14 Aug 2021

Cited by 6 | Viewed by 1802

Abstract

Five new thiohydantoin derivatives (1–5) were isolated from the rhizomes of Lepidium meyenii Walp. NMR (¹H and ¹³C NMR, ¹H−¹H COSY, HSQC, and HMBC), HRESIMS, and ECD were employed for the structure elucidation of new compounds. Significantly, the structure of compound 1 was the first example of thiohydantoins with thioxohexahydroimidazo [1,5-a] pyridine moiety. Additionally, compounds 2 and 3 possess rare disulfide bonds. Except for compound 4, all isolates were assessed for neuroprotective activities in corticosterone (CORT)-stimulated PC12 cell damage. Among them, compound (−)-3 exhibited moderate neuroprotective activity (cell viability: 68.63%, 20 μM) compared to the positive control desipramine (DIM) (cell viability: 88.49%, 10 μM). Full article

(This article belongs to the Special Issue A Themed Issue in Memory of Academician Xing Qiyi (1911–2002))

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12 pages, 1647 KiB

Open AccessArticle

Morphological Changes and Component Characterization of Coffee Silverskin

by Xia Wang, De-Fu Hong, Gui-Lin Hu, Zhong-Rong Li, Xing-Rong Peng, Qiang-Qiang Shi and Ming-Hua Qiu

Molecules 2021, 26(16), 4914; https://doi.org/10.3390/molecules26164914 - 13 Aug 2021

Cited by 6 | Viewed by 2139

Abstract

Nuclear magnetic resonance (NMR) spectroscopy was used for the qualitative and quantitative analysis of aqueous extracts of unroasted and roasted coffee silverskin (CS). Twenty compounds were identified from 1D and 2D NMR spectra, including caffeine, chlorogenic acid (CGA), trigonelline, fructose, glucose, sucrose, etc. For the first time, the presence of trigonelline was detected in CS. Results of the quantitative analysis showed that the total amount of the main components after roasting was reduced by 45.6% compared with values before roasting. Sugars in the water extracts were the main components in CS, and fructose was the most abundant sugar, its relative content accounting for 38.7% and 38.4% in unroasted and roasted CS, respectively. Moreover, 1D NMR combined with 2D NMR technology shows application prospects in the rapid, non-destructive detection of CS. In addition, it was observed by optical microscopy and scanning electron microscopy (SEM) that the morphology of CS changed obviously before and after roasting. Full article

(This article belongs to the Special Issue A Themed Issue in Memory of Academician Xing Qiyi (1911–2002))

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19 pages, 5737 KiB

Open AccessArticle

Structural Insights into the Interactions of Digoxin and Na⁺/K⁺-ATPase and Other Targets for the Inhibition of Cancer Cell Proliferation

by Yulin Ren, Sijin Wu, Joanna E. Burdette, Xiaolin Cheng and A. Douglas Kinghorn

Molecules 2021, 26(12), 3672; https://doi.org/10.3390/molecules26123672 - 16 Jun 2021

Cited by 9 | Viewed by 2460

Abstract

Digoxin is a cardiac glycoside long used to treat congestive heart failure and found recently to show antitumor potential. The hydroxy groups connected at the C-12, C-14, and C-3′a positions; the C-17 unsaturated lactone unit; the conformation of the steroid core; and the C-3 saccharide moiety have been demonstrated as being important for digoxin’s cytotoxicity and interactions with Na⁺/K⁺-ATPase. The docking profiles for digoxin and several derivatives and Na⁺/K⁺-ATPase were investigated; an additional small Asn130 side pocket was revealed, which could be useful in the design of novel digoxin-like antitumor agents. In addition, the docking scores for digoxin and its derivatives were found to correlate with their cytotoxicity, indicating a potential use of these values in the prediction of the cancer cell cytotoxicity of other cardiac glycosides. Moreover, in these docking studies, digoxin was found to bind to FIH-1 and NF-κB but not HDAC, IAP, and PI3K, suggesting that this cardiac glycoside directly targets FIH-1, Na⁺/K⁺-ATPase, and NF-κB to mediate its antitumor potential. Differentially, digoxigenin, the aglycon of digoxin, binds to HDAC and PI3K, but not FIH-1, IAP, Na⁺/K⁺-ATPase, and NF-κB, indicating that this compound may target tumor autophagy and metabolism to mediate its antitumor propensity. Full article

(This article belongs to the Special Issue A Themed Issue in Memory of Academician Xing Qiyi (1911–2002))

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Review

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32 pages, 17182 KiB

Open AccessReview

Xanthone Glucosides: Isolation, Bioactivity and Synthesis

by Qing Huang, Youyi Wang, Huaimo Wu, Man Yuan, Changwu Zheng and Hongxi Xu

Molecules 2021, 26(18), 5575; https://doi.org/10.3390/molecules26185575 - 14 Sep 2021

Cited by 22 | Viewed by 3879

Abstract

Xanthones are secondary metabolites found in plants, fungi, lichens, and bacteria from a variety of families and genera, with the majority found in the Gentianaceae, Polygalaceae, and Clusiaceae. They have a diverse range of bioactivities, including anti-oxidant, anti-bacterial, anti-malarial, anti-tuberculosis, and cytotoxic properties. Xanthone glucosides are a significant branch of xanthones. After glycosylation, xanthones may have improved characteristics (such as solubility and pharmacological activity). Currently, no critical review of xanthone glucosides has been published. A literature survey including reports of naturally occurring xanthone glucosides is included in this review. The isolation, structure, bioactivity, and synthesis of these compounds were all explored in depth. Full article

(This article belongs to the Special Issue A Themed Issue in Memory of Academician Xing Qiyi (1911–2002))

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