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Автор: Grafiati

Опубліковано: 2 лютого 2024

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1

Lewinsohn, Efraim, Lothar Britsch, Yehuda Mazur, and Jonathan Gressel. "Flavanone Glycoside Biosynthesis in Citrus." Plant Physiology 91, no. 4 (December 1, 1989): 1323–28. http://dx.doi.org/10.1104/pp.91.4.1323.

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2

Aquino, Rita, M. Letizia Ciavatta, Francesco De Simone, and Cosimo Pizza. "A flavanone glycoside from Hamelia patens." Phytochemistry 29, no. 7 (January 1990): 2359–60. http://dx.doi.org/10.1016/0031-9422(90)83076-d.

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3

Takahashi, Hironobu, Sachiyo Hirata, Hiroyuki Minami, and Yoshiyasu Fukuyama. "Triterpene and flavanone glycoside from Rhododendron simsii." Phytochemistry 56, no. 8 (April 2001): 875–79. http://dx.doi.org/10.1016/s0031-9422(00)00493-3.

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4

Intekhab, Javed, Mohammad Aslam, Vivek Bhadauria, and Preeti Singh. "A new flavanone glycoside from Clausena pentaphylla." Chemistry of Natural Compounds 48, no. 4 (September 2012): 568–69. http://dx.doi.org/10.1007/s10600-012-0312-3.

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5

Chen, R. C., G. B. Sun, J. Wang, H. J. Zhang, and X. B. Sun. "Naringin protects against anoxia/reoxygenation-induced apoptosis in H9c2 cells via the Nrf2 signaling pathway." Food & Function 6, no. 4 (2015): 1331–44. http://dx.doi.org/10.1039/c4fo01164c.

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6

Jangwan, J. S., and R. P. Bahuguna. "Puddumin-B, a New Flavanone Glycoside fromPrunus cerasoides." International Journal of Crude Drug Research 27, no. 4 (January 1989): 223–26. http://dx.doi.org/10.3109/13880208909116906.

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7

Zou, Wei, Yonggang Wang, Haibin Liu, Yulong Luo, Si Chen, and Weiwei Su. "Melitidin: A Flavanone Glycoside from Citrus grandis ‘Tomentosa’." Natural Product Communications 8, no. 4 (April 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800411.

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Анотація:

Citrus grandis ‘Tomentosa’ is a traditional Chinese medicine, used as an antitussive. In this research, melitidin, a flavanone glycoside, was isolated from this species for the first time by using chromatographic methods. The structure was confirmed through comprehensive analyses of its ultraviolet, infrared, 1H and 13C NMR, HMBC and HMQC spectroscopic and high-resolution mass spectrometric data. Meliditin showed a good antitussive effect on cough induced by citric acid in Guinea pig, suggesting that it was a contributor to the antitussive effect of C. grandis ‘Tomentosa’.

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8

Diao, Shengbao, Mei Jin, Chun Shi Jin, Cheng-Xi Wei, Jinfeng Sun, Wei Zhou, and Gao Li. "A new flavanone glycoside isolated from Tournefortia sibirica." Natural Product Research 33, no. 20 (December 22, 2018): 3021–24. http://dx.doi.org/10.1080/14786419.2018.1512995.

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9

Chen, Yu-Jie, Guo-Yong Xie, Guang-Kai Xu, Yi-Qun Dai, Lu Shi, and Min-Jian Qin. "Chemical Constituents of Pyrrosia calvata." Natural Product Communications 10, no. 7 (July 2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000714.

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Анотація:

A novel flavanone glycoside, 3′,5′,5,7-tetrahydroxy-6- C- β-D-glucopyranosyl-flavanone (1), along with 16 known compounds, ( R/ S)-eriodictyol-8- C- β-D-glucopyranoside (2), quercetin-3- O- α-D-rhamnosyl (1′”→3′”)- β-D-glucopyranoside (3), hemipholin (4), 4 β-carboxymethyl-(-)-epicatechin methyl ester (5), kaempferol (6), quercetin (7), mangiferin (8), chlorogenic acid (9), 1,5- O-dicaffeoylquinic acid (10), 3,5- O-dicaffeoylquinic acid (11), 3- O-caffeoylquinic acid methyl ester (12), 1- O-caffeoyl glycoside (13), 4- O- β-D-glucopyranosyl-caffeic acid (14), 3′- O-methyleplcatechin-7- O- β-D-glucopyranoside (15), hop-22(29)-en-30-ol (16) and diploptene (17), were isolated from the whole plant of Pyrrosia calvata (Backer) Ching. Among them, compounds 2, 3, 4, 10, 11, 13 and 14 were isolated from the family Polypodiaceae for the first time, and compound 5 has not been recorded previously from the genus Pyrrosia.

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10

Okwu, D. E., and F. N. I. Morah. "Isolation and Characterization of Flavanone Glycoside 4I,5, 7-Trihydroxy Flavanone Rhamnoglucose from Garcinia kola Seed." Journal of Applied Sciences 7, no. 2 (January 1, 2007): 306–9. http://dx.doi.org/10.3923/jas.2007.306.309.

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11

Yunlong, Xu, Isao Kubo, and Ma Yunbao. "A cytotoxic flavanone glycoside from Onychium japonicum: Structure of onychin." Phytochemistry 33, no. 2 (May 1993): 510–11. http://dx.doi.org/10.1016/0031-9422(93)85552-3.

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12

Nguyen, Quang An, Hanh Trinh Van-Dufat, Sylvie Michel, François Tillequin, Vincent Dumontet, and Thierry Sévenet. "A New Phenylpropanoid Ester from the Bark of Zanthoxylum scandens (Rutaceae)." Zeitschrift für Naturforschung C 57, no. 11-12 (December 1, 2002): 986–89. http://dx.doi.org/10.1515/znc-2002-11-1205.

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Анотація:

The alkaloids norchelerythrine, magnoflorine and (-)(S)-O-methylbalfourodinium cation were isolated from Zanthoxylum scandens bark collected in Vietnam, together with the flavanone glycoside hesperidin and the phenylpropanoids (E)-O-geranylconiferyl alcohol and (E)-O-geranylconiferyl alcohol (9Z, 12Z)-linoleate. This latter is a novel compound whose structure was elucidated on the basis of its spectral data and confirmed by chemical correlation.

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13

Sreedevi, E., and J. T. Rao. "A new prenylated flavanone glycoside from the seeds of Glircidia maculata." Fitoterapia 71, no. 4 (August 2000): 392–94. http://dx.doi.org/10.1016/s0367-326x(00)00137-4.

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14

Hammami, S., H. Jannet, A. Bergaoui, L. Ciavatta, G. Cimino, and Z. Mighri. "Isolation and Structure Elucidation of a Flavanone, a Flavanone Glycoside and Vomifoliol from Echiochilon Fruticosum Growing in Tunisia." Molecules 9, no. 7 (June 30, 2004): 602–8. http://dx.doi.org/10.3390/90700602.

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15

Ukida, Kouki, Takashi Doi, Sachiko Sugimoto, Katsuyoshi Matsunami, Hideaki Otsuka, and Yoshio Takeda. "Schoepfiajasmins A–H: C-Glycosyl Dihydrochalcones, Dihydrochalcone Glycoside, C-Glucosyl Flavanones, Flavanone Glycoside and Flavone Glycoside from the Branches of Schoepfia jasminodora." Chemical and Pharmaceutical Bulletin 61, no. 11 (2013): 1136–42. http://dx.doi.org/10.1248/cpb.c13-00466.

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16

Bhat, Gulzar A., Fauzia Mir, Abdul S. Shawl, Bashir A. Ganai, Azra N. Kamili, Akbar Masood, and Mudasir A. Tantry. "Crocetenone, a New Rotenoid with an Unusual trans-fused Ring System from Iris crocea." Natural Product Communications 10, no. 3 (March 2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000331.

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Анотація:

Crocetenone, a new rotenoid (1), along with five known compounds apocyanin (2), tectorigenin (3), 5,2′,3′-trihydroxy-7-methoxy flavanone (4), tectoridin (5) and tectoridin glycoside (6), were isolated from the methanolic extract of the root of Iris crocea. The structure of compounds was elucidated on the basis of 1D- and 2D-NMR spectroscopic and MS analysis. Antibacterial and antioxidant activities of compounds 1-6 were evaluated. Crocetenone (1) showed a prominent antibacterial activity.

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17

Ding, Yuanqing, Xing-Cong Li, and Daneel Ferreira. "Theoretical Calculation of Electronic Circular Dichroism of a Hexahydroxydiphenoyl-Containing Flavanone Glycoside⊥." Journal of Natural Products 72, no. 3 (March 27, 2009): 327–35. http://dx.doi.org/10.1021/np800146v.

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18

MIYAKE, Yoshiaki, Kenichiro MINATO, Syuichi FUKUMOTO, Kanefumi YAMAMOTO, Tomoko OYA-ITO, Syunro KAWAKISHI, and Toshihiko OSAWA. "New Potent Antioxidative Hydroxyflavanones Produced withAspergillus saitoifrom Flavanone Glycoside in Citrus Fruit." Bioscience, Biotechnology, and Biochemistry 67, no. 7 (January 2003): 1443–50. http://dx.doi.org/10.1271/bbb.67.1443.

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19

Han, Ah-Reum, Jong-Bin Kim, Jun Lee, Joo-Won Nam, Ik-Soo Lee, Chang-Koo Shim, Kyung-Tae Lee, and Eun-Kyoung Seo. "A New Flavanone Glycoside from the Dried Immature Fruits of Poncirus trifoliata." CHEMICAL & PHARMACEUTICAL BULLETIN 55, no. 8 (2007): 1270–73. http://dx.doi.org/10.1248/cpb.55.1270.

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20

Hegazi, Nesrine M., Hamada H. Saad, Mona M. Marzouk, Mohamed F. Abdel Rahman, Mahitab H. El Bishbishy, Ahmed Zayed, Roland Ulber, and Shahira M. Ezzat. "Molecular Networking Leveraging the Secondary Metabolomes Space of Halophila stipulaceae (Forsk.) Aschers. and Thalassia hemprichii (Ehrenb. ex Solms) Asch. in Tandem with Their Chemosystematics and Antidiabetic Potentials." Marine Drugs 19, no. 5 (May 18, 2021): 279. http://dx.doi.org/10.3390/md19050279.

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Анотація:

The Red Sea is one of the most biodiverse aquatic ecosystems. Notably, seagrasses possess a crucial ecological significance. Among them are the two taxa Halophila stipulacea (Forsk.) Aschers., and Thalassia hemprichii (Ehrenb. ex Solms) Asch., which were formally ranked together with the genus Enhalus in three separate families. Nevertheless, they have been recently classified as three subfamilies within Hydrocharitaceae. The interest of this study is to explore their metabolic profiles through ultra-high-performance liquid chromatography-high-resolution mass spectrometry (UPLC-HRMS/MS) analysis in synergism with molecular networking and to assess their chemosystematics relationship. A total of 144 metabolites were annotated, encompassing phenolic acids, flavonoids, terpenoids, and lipids. Furthermore, three new phenolic acids; methoxy benzoic acid-O-sulphate (16), O-caffeoyl-O-hydroxyl dimethoxy benzoyl tartaric acid (26), dimethoxy benzoic acid-O-sulphate (30), a new flavanone glycoside; hexahydroxy-monomethoxy flavanone-O-glucoside (28), and a new steviol glycoside; rebaudioside-O-acetate (96) were tentatively described. Additionally, the evaluation of the antidiabetic potential of both taxa displayed an inherited higher activity of H. stipulaceae in alleviating the oxidative stress and dyslipidemia associated with diabetes. Hence, the current research significantly suggested Halophila, Thalassia, and Enhalus categorization in three different taxonomic ranks based on their intergeneric and interspecific relationship among them and supported the consideration of seagrasses in natural antidiabetic studies.

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21

Ukida, Kouki, Takashi Doi, Sachiko Sugimoto, Katsuyoshi Matsunami, Hideaki Otsuka, and Yoshio Takeda. "ChemInform Abstract: Schoepfiajasmins A-H: C-Glycosyl Dihydrochalcones, Dihydrochalcone Glycoside, C-Glucosyl Flavanones, Flavanone Glycoside and Flavone Glycoside from the Branches of Schoepfia jasminodora." ChemInform 45, no. 19 (April 23, 2014): no. http://dx.doi.org/10.1002/chin.201419218.

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22

Chen, Yingfong, Jian Liu, R. Stephen Davidson, and Oliver W. Howarth. "Isolation and structure of clematine, a new flavanone glycoside from Clematis armandii franch." Tetrahedron 49, no. 23 (June 1993): 5169–76. http://dx.doi.org/10.1016/s0040-4020(01)81881-0.

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23

Chen, Yingfong, Jian Liu, R. Stephen Davidson, and Oliver W. Howarth. "Isolation and structure of clematine, a new flavanone glycoside from Clematis armandii French." Tetrahedron 49, no. 34 (August 1993): 7393. http://dx.doi.org/10.1016/s0040-4020(01)87217-3.

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24

Fazary, Ahmed E., Yi-Hsu Ju, Ayed S. Al-Shihri, Mutasem Z. Bani-Fwaz, Mohammad Y. Alfaifi, Mohammed A. Alshehri, Kamel A. Saleh, Serag Eldin I. Elbehairi, Khaled F. Fawy, and Hisham S. M. Abd-Rabboh. "Platinum and vanadate Bioactive Complexes of Glycoside Naringin and Phenolates." Open Chemistry 15, no. 1 (August 10, 2017): 189–99. http://dx.doi.org/10.1515/chem-2017-0022.

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Анотація:

AbstractPlatinum(II) and vanadium(V) solid binary and ternary complexes involving naringin, a flavanone glycoside in found in grapefruit, and some phenolic acids were synthesized and fully characterized using detailed structural and spectroscopic analysis techniques such as IR, NMR, and SEM techniques. The magnetic susceptibility results as well line drawings of the platinum and vanadium complexes showed four-coordinate square-planar and remarkable low-spin diamagnetic species; which is in agreement with the structures proposed. The cytotoxic activities of the binary and ternary vanadium and platinum metal complexes of phenolic acids and naringin were tested and evaluated against HepG2 (human hepatocellular carcinoma), MCF-7 (human breast adenocarcinoma), and HCT116 (human colorectal carcinoma) tumor cell lines. Also, their antioxidant activities were examined by free radical scavenging assay. The relationship between the chemical structure of the synthesized complexes and their biological influence was studied and evaluated.

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25

Chang, Yung-Lung, Yao-Feng Li, Chung-Hsing Chou, Li-Chun Huang, Yi-Ping Wu, Ying Kao, and Chia-Kuang Tsai. "Diosmin Inhibits Glioblastoma Growth through Inhibition of Autophagic Flux." International Journal of Molecular Sciences 22, no. 19 (September 28, 2021): 10453. http://dx.doi.org/10.3390/ijms221910453.

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Анотація:

Diosmin, a natural flavone glycoside acquired through dehydrogenation of the analogous flavanone glycoside hesperidin, is plentiful in many citrus fruits. Glioblastoma multiforme (GBM) is the most malignant primary brain tumor; the average survival time of GBM patients is less than 18 months after standard treatment. The present study demonstrated that diosmin, which is able to cross the blood–brain barrier, inhibited GBM cell growth in vitro and in vivo. Diosmin also impeded migration and invasion by GBM8401and LN229 GBM cells by suppressing epithelial-mesenchymal transition, as indicated by increased expression of E-cadherin and decreased expression of Snail and Twist. Diosmin also suppressed autophagic flux, as indicated by increased expression of LC3-II and p62, and induced cell cycle arrest at G1 phase. Importantly, diosmin did not exert serious cytotoxic effects toward control SVG-p12 astrocytes, though it did reduce astrocyte viability at high concentrations. These findings provide potentially helpful support to the development of new therapies for the treatment of GBM.

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26

Yang, Peng-Fei, Ya-Nan Yang, Chun-Yu He, Zhi-Fei Chen, Qi-Shan Yuan, Sheng-Chen Zhao, Yu-Feng Fu, Pei-Cheng Zhang, and Duo-Bin Mao. "New Caffeoylquinic Acid Derivatives and Flavanone Glycoside from the Flowers of Chrysanthemum morifolium and Their Bioactivities." Molecules 24, no. 5 (February 28, 2019): 850. http://dx.doi.org/10.3390/molecules24050850.

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Анотація:

The Chrysanthemum morifolium flower is widely used in China and Japan as a food, beverage, and medicine for many diseases. In our work, two new caffeoylquinic acid derivatives (1, 2), a new flavanone glycoside (3), and six reported flavanones (4–9) were isolated and identified from the flowers of C. morifolium. The chemical structures of all isolates were elucidated by the analysis of comprehensive spectroscopic data as well as by comparison with previously reported data. The isolated constituents 1–8 were evaluated for their neuroprotective activity, and compounds 3 and 4 displayed neuroprotective effects against hydrogen peroxide-induced neurotoxicity in human neuroblastoma SH-SY5Y cells.

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27

Kumar, Neeraj, Bikram Singh, and Vijay K. Kaul. "Flavonoids from Rosa Damascena Mill." Natural Product Communications 1, no. 8 (August 2006): 1934578X0600100. http://dx.doi.org/10.1177/1934578x0600100805.

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Анотація:

A new flavanone glycoside, butin 4′-O-(2″-O-β-D-apiofuranosyl)-β-D-glucopyranoside (1), together with liquiritin (2), liquiritin apioside (3), isoliquiritn apioside (4), davidioside (5), quercetin (6), kaempferol (7), kaempferol 3-O-β-D-glucopyranoside (8) and kaempferol 3-O-α-L-arabinofuranoside (9) were isolated from the marc of Rosa damascena flowers after industrial distillation of essential oil. This is the first report of the occurrence of compounds 2, 3, 4 and 5 in R. damascena. The structures of the isolated constituents were established on the basis of spectroscopic {UV, IR, 1D, 2D NMR (DEPT, HMQC, HMBC and COSY)}, spectrometric (ESI-QTOF-MS), and chemical evidence.

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28

Selvaraj, Palanisamy, and Kodukkur Viswanathan Pugalendi. "Hesperidin, a flavanone glycoside, on lipid peroxidation and antioxidant status in experimental myocardial ischemic rats." Redox Report 15, no. 5 (October 2010): 217–23. http://dx.doi.org/10.1179/135100010x12826446921509.

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29

Mouly, Pierre P., Emile M. Gaydou, Robert Faure, and Jacques M. Estienne. "Blood Orange Juice Authentication Using Cinnamic Acid Derivatives. Variety Differentiations Associated with Flavanone Glycoside Content." Journal of Agricultural and Food Chemistry 45, no. 2 (February 1997): 373–77. http://dx.doi.org/10.1021/jf9605097.

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30

ZHANG, Mi, Rong-Rong WANG, Man CHEN, Han-Qing ZHANG, Shi SUN, and Lu-Yong ZHANG. "A New Flavanone Glycoside with Anti-proliferation Activity from the Root Bark of Morus alba." Chinese Journal of Natural Medicines 7, no. 2 (March 2009): 105–7. http://dx.doi.org/10.1016/s1875-5364(09)60046-7.

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31

de Souza, Priscila, Rita de Cássia Vilhena da Silva, Luisa Nathália Bolda Mariano, Sabrina Lucietti Dick, Giovana Cardozo Ventura, and Valdir Cechinel-Filho. "Diuretic and Natriuretic Effects of Hesperidin, a Flavanone Glycoside, in Female and Male Hypertensive Rats." Plants 12, no. 1 (December 21, 2022): 25. http://dx.doi.org/10.3390/plants12010025.

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Анотація:

Hesperidin (HSP) is a major flavanone glycoside in citrus fruits, including sweet oranges and lemons. It demonstrates numerous pharmacological activities, such as antihypertensive effects and cardiac and kidney tissue protection. However, its effect on modulating renal function has yet to be properly explored. Female and male Wistar spontaneously hypertensive rats (SHR) were used to test the effect of HSP on renal function. The rats were divided into different groups, treated orally, and placed in metabolic cages for urine collection for 8 h. HSP, at doses of 0.3–3 mg/kg, led to an increase in urine volume in both female and male SHR. This effect was associated with increased Na+ elimination (3 mg/kg) without causing any change in K+ excretion or pH and conductivity values. When given HSP in combination with hydrochlorothiazide (HCTZ) or amiloride (AMLR), urine volume and Na+ elimination were significantly increased compared to the group that received only HSP. In relation to K+ excretion, the depleting effect of HCTZ and the sparing of AMLR prevailed in both groups. Pre-treatment with a non-selective cholinergic receptor antagonist, atropine, partially prevented HSP-induced diuresis and natriuresis in male SHR, but this effect was not demonstrated with the non-selective inhibitor of the enzyme cyclooxygenase, indomethacin. This study shows the diuretic action of HSP in hypertensive rats, an activity probably associated with the cholinergic pathway. Although various biological actions have already been defined for HSP, this pioneering research reveals its potential as a diuretic medicine.

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32

Wang, Lanxiang, Pui Ying Lam, Andy C. W. Lui, Fu-Yuan Zhu, Mo-Xian Chen, Hongjia Liu, Jianhua Zhang, and Clive Lo. "Flavonoids are indispensable for complete male fertility in rice." Journal of Experimental Botany 71, no. 16 (May 9, 2020): 4715–28. http://dx.doi.org/10.1093/jxb/eraa204.

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Анотація:

Abstract Flavonoids are essential for male fertility in some but not all plant species. In rice (Oryza sativa), the chalcone synthase mutant oschs1 produces flavonoid-depleted pollen and is male sterile. The mutant pollen grains are viable with normal structure, but they display reduced germination rate and pollen-tube length. Analysis of oschs1/+ heterozygous lines shows that pollen flavonoid deposition is a paternal effect and fertility is independent of the haploid genotypes (OsCHS1 or oschs1). To understand which classes of flavonoids are involved in male fertility, we conducted detailed analysis of rice mutants for branch-point enzymes of the downstream flavonoid pathways, including flavanone 3-hydroxylase (OsF3H; flavonol pathway entry enzyme), flavone synthase II (CYP93G1; flavone pathway entry enzyme), and flavanone 2-hydroxylase (CYP93G2; flavone C-glycoside pathway entry enzyme). Rice osf3h and cyp93g1 cyp93g2 CRISPR/Cas9 mutants, and cyp93g1 and cyp93g2 T-DNA insertion mutants showed altered flavonoid profiles in anthers, but only the osf3h and cyp93g1 cyp93g2 mutants displayed reduction in seed yield. Our findings indicate that flavonoids are essential for complete male fertility in rice and a combination of different classes (flavanones, flavonols, flavones, and flavone C-glycosides) appears to be important, as opposed to the essential role played primarily by flavonols that has been previously reported in several plant species.

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33

Nouga, Achille B., Jean C. Ndom, Emmanuel M. Mpondo, Judith Caroline Ngo Nyobe, Alain Njoya, Luc M. Meva'a, Phillipa B. Cranwell, James A. S. Howell, Laurence M. Harwood, and Jean Duplex Wansi. "New furoquinoline alkaloid and flavanone glycoside derivatives from the leaves ofOricia suaveolens and Oricia renieri(Rutaceae)." Natural Product Research 30, no. 3 (July 29, 2015): 305–10. http://dx.doi.org/10.1080/14786419.2015.1057727.

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34

Shaiq Ali, Muhammad, Muhammad Saleem, Waqar Ahmad, Masood Parvez та Raghav Yamdagni. "A chlorinated monoterpene ketone, acylated β-sitosterol glycosides and a flavanone glycoside from Mentha longifolia (Lamiaceae)". Phytochemistry 59, № 8 (квітень 2002): 889–95. http://dx.doi.org/10.1016/s0031-9422(01)00490-3.

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35

Morita, Tokio, Takeshi Akiyoshi, Ryo Sato, Yoshinori Uekusa, Kazuhiro Katayama, Kodai Yajima, Ayuko Imaoka, Yoshikazu Sugimoto, Fumiyuki Kiuchi, and Hisakazu Ohtani. "Citrus Fruit-Derived Flavanone Glycoside Narirutin is a Novel Potent Inhibitor of Organic Anion-Transporting Polypeptides." Journal of Agricultural and Food Chemistry 68, no. 48 (November 19, 2020): 14182–91. http://dx.doi.org/10.1021/acs.jafc.0c06132.

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36

Konishi, Tenji, Kiyonori Yamazoe, Masahiro Kanzato, Takao Konoshima, and Yasuhiro Fujiwara. "Three Diterpenoids (Excoecarins V1—V3) and a Flavanone Glycoside from the Fresh Stem of Excoecaria agallocha." CHEMICAL & PHARMACEUTICAL BULLETIN 51, no. 10 (2003): 1142–46. http://dx.doi.org/10.1248/cpb.51.1142.

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37

CHEN, Y., J. LIU, R. S. DAVIDSON, and O. W. HOWARTH. "ChemInform Abstract: Isolation and Structure of Clematine (I), a New Flavanone Glycoside from Clematis armandii Franch." ChemInform 24, no. 41 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199341262.

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38

Ali, Md Yousof, Susoma Jannat, Hyun-Ah Jung, and Jae-Sue Choi. "Structural Bases for Hesperetin Derivatives: Inhibition of Protein Tyrosine Phosphatase 1B, Kinetics Mechanism and Molecular Docking Study." Molecules 26, no. 24 (December 8, 2021): 7433. http://dx.doi.org/10.3390/molecules26247433.

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Анотація:

In the present study, we investigated the structure-activity relationship of naturally occurring hesperetin derivatives, as well as the effects of their glycosylation on the inhibition of diabetes-related enzyme systems, protein tyrosine phosphatase 1B (PTP1B) and α-glycosidase. Among the tested hesperetin derivatives, hesperetin 5-O-glucoside, a single-glucose-containing flavanone glycoside, significantly inhibited PTP1B with an IC50 value of 37.14 ± 0.07 µM. Hesperetin, which lacks a sugar molecule, was the weakest inhibitor compared to the reference compound, ursolic acid (IC50 = 9.65 ± 0.01 µM). The most active flavanone hesperetin 5-O-glucoside suggested that the position of a sugar moiety at the C-5-position influences the PTP1B inhibition. It was observed that the ability to inhibit PTP1B is dependent on the nature, position, and number of sugar moieties in the flavonoid structure, as well as conjugation. In the kinetic study of PTP1B enzyme inhibition, hesperetin 5-O-glucoside led to mixed-type inhibition. Molecular docking studies revealed that hesperetin 5-O-glucoside had a higher binding affinity with key amino residues, suggesting that this molecule best fits the PTP1B allosteric site cavity. The data reported here support hesperetin 5-O-glucoside as a hit for the design of more potent and selective inhibitors against PTP1B in the search for a new anti-diabetic treatment.

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Shilpa, VS, Rafeeya Shams, Kshirod Kumar Dash, Vinay Kumar Pandey, Aamir Hussain Dar, Shaikh Ayaz Mukarram, Endre Harsányi, and Béla Kovács. "Phytochemical Properties, Extraction, and Pharmacological Benefits of Naringin: A Review." Molecules 28, no. 15 (July 25, 2023): 5623. http://dx.doi.org/10.3390/molecules28155623.

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This review describes the various innovative approaches implemented for naringin extraction as well as the recent developments in the field. Naringin was assessed in terms of its structure, chemical composition, and potential food sources. How naringin works pharmacologically was discussed, including its potential as an anti-diabetic, anti-inflammatory, and hepatoprotective substance. Citrus flavonoids are crucial herbal additives that have a huge spectrum of organic activities. Naringin is a nutritional flavanone glycoside that has been shown to be effective in the treatment of a few chronic disorders associated with ageing. Citrus fruits contain a common flavone glycoside that has specific pharmacological and biological properties. Naringin, a flavone glycoside with a range of intriguing characteristics, is abundant in citrus fruits. Naringin has been shown to have a variety of biological, medicinal, and pharmacological effects. Naringin is hydrolyzed into rhamnose and prunin by the naringinase, which also possesses l-rhamnosidase activity. D-glucosidase subsequently catalyzes the hydrolysis of prunin into glucose and naringenin. Naringin is known for having anti-inflammatory, antioxidant, and tumor-fighting effects. Numerous test animals and cell lines have been used to correlate naringin exposure to asthma, hyperlipidemia, diabetes, cancer, hyperthyroidism, and osteoporosis. This study focused on the many documented actions of naringin in in-vitro and in-vivo experimental and preclinical investigations, as well as its prospective therapeutic advantages, utilizing the information that is presently accessible in the literature. In addition to its pharmacokinetic characteristics, naringin’s structure, distribution, different extraction methods, and potential use in the cosmetic, food, pharmaceutical, and animal feed sectors were discussed.

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40

ZHANG, Mi, Rong-Rong WANG, Man CHEN, Han-Qing ZHANG, Shi SUN, and Lu-Yong ZHANG. "A New Flavanone Glycoside with Anti-proliferation Activity from the Root Bark of Morus alba." Chinese Journal of Natural Medicines 7, no. 2 (June 22, 2009): 105–7. http://dx.doi.org/10.3724/sp.j.1009.2009.00105.

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41

da Silva, Luísa Mota, Bruno César Pezzini, Lincon Bordignon Somensi, Luísa Nathália Bolda Mariano, Mariha Mariott, Thaise Boeing, Ana Carolina dos Santos, et al. "Hesperidin, a citrus flavanone glycoside, accelerates the gastric healing process of acetic acid-induced ulcer in rats." Chemico-Biological Interactions 308 (August 2019): 45–50. http://dx.doi.org/10.1016/j.cbi.2019.05.011.

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42

Cheng, Fang-Ju, Thanh-Kieu Huynh, Chia-Shin Yang, Dai-Wei Hu, Yi-Cheng Shen, Chih-Yen Tu, Yang-Chang Wu, et al. "Hesperidin Is a Potential Inhibitor against SARS-CoV-2 Infection." Nutrients 13, no. 8 (August 16, 2021): 2800. http://dx.doi.org/10.3390/nu13082800.

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Анотація:

Hesperidin (HD) is a common flavanone glycoside isolated from citrus fruits and possesses great potential for cardiovascular protection. Hesperetin (HT) is an aglycone metabolite of HD with high bioavailability. Through the docking simulation, HD and HT have shown their potential to bind to two cellular proteins: transmembrane serine protease 2 (TMPRSS2) and angiotensin-converting enzyme 2 (ACE2), which are required for the cellular entry of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). Our results further found that HT and HD suppressed the infection of VeroE6 cells using lentiviral-based pseudo-particles with wild types and variants of SARS-CoV-2 with spike (S) proteins, by blocking the interaction between the S protein and cellular receptor ACE2 and reducing ACE2 and TMPRSS2 expression. In summary, hesperidin is a potential TMPRSS2 inhibitor for the reduction of the SARS-CoV-2 infection.

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43

Zeng, Xuan, Weiwei Su, Buming Liu, Ling Chai, Rui Shi, and Hongliang Yao. "A Review on the Pharmacokinetic Properties of Naringin and Its Therapeutic Efficacies in Respiratory Diseases." Mini-Reviews in Medicinal Chemistry 20, no. 4 (April 10, 2020): 286–93. http://dx.doi.org/10.2174/1389557519666191009162641.

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Flavonoids are an important class of phytopharmaceuticals in plants. Naringin (naringenin- 7-O-rhamnoglucoside) is a flavanone glycoside isolated from folk herbal medicine Exocarpium Citri grandis (called Huajuhong in Chinese). Massive experimental works have been performed on naringin describing its phytochemical, pharmacokinetic, and bioactive properties. Naringin was found to possess multiple pharmacological activities in relieving inflammation, diabetes, neurodegeneration, cardiovascular disorders, and metabolic syndrome. Recently, it has been approved as a potential antitussive and expectorant for clinical trials. However, the pharmacokinetic aspects of naringin and its therapeutic potentials in respiratory diseases have not been comprehensively reviewed. The present review provides highlights of naringin with respect to its absorption, distribution, metabolism, excretion and its therapeutic effects on cough, phlegm, and pulmonary inflammation. This review would be helpful for the interpretation of pharmacokinetics and pharmacodynamics of naringin in clinical trials.

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44

Ağçam, Erdal, and Asiye Akyıldız. "A Study on the Quality Criteria of Some Mandarin Varieties and Their Suitability for Juice Processing." Journal of Food Processing 2014 (August 26, 2014): 1–8. http://dx.doi.org/10.1155/2014/982721.

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In this study, some composition properties of juices of different mandarin varieties (Robinson (R), Fremont (F), and Satsuma (S)) were determined before and after pasteurisation. L*, a*, b*, and C* values of all varieties were increased after the pasteurisation process. Degradation of ascorbic acid was calculated as 2.20, 16.86, and 24.31% for R, F, and S samples, respectively, after pasteurisation. The highest total carotenoid and phenolic contents were determined in S samples. In general, after the pasteurisation treatment, the total carotenoid content of juices was increased slightly, but total phenolic contents were dramatically decreased. The antioxidant activity of pasteurised samples was increased by approximately 6%. The most abundant carotenoid and flavanone glycoside compound was shown to be β-cryptoxanthin and hesperidin, respectively, in all samples. The most popular fresh and pasteurised juice samples were made from the Robinson variety of mandarin with regard to taste, smell, and general impression.

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45

Ravetti, Soledad, Ariel G. Garro, Agustina Gaitán, Mariano Murature, Mariela Galiano, Sofía G. Brignone, and Santiago D. Palma. "Naringin: Nanotechnological Strategies for Potential Pharmaceutical Applications." Pharmaceutics 15, no. 3 (March 7, 2023): 863. http://dx.doi.org/10.3390/pharmaceutics15030863.

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Анотація:

Polyphenols comprise a number of natural substances, such as flavonoids, that show interesting biological effects. Among these substances is naringin, a naturally occurring flavanone glycoside found in citrus fruits and Chinese medicinal herbs. Several studies have shown that naringin has numerous biological properties, including cardioprotective, cholesterol-lowering, anti-Alzheimer’s, nephroprotective, antiageing, antihyperglycemic, antiosteoporotic and gastroprotective, anti-inflammatory, antioxidant, antiapoptotic, anticancer and antiulcer effects. Despite its multiple benefits, the clinical application of naringin is severely restricted due to its susceptibility to oxidation, poor water solubility, and dissolution rate. In addition, naringin shows instability at acidic pH, is enzymatically metabolized by β-glycosidase in the stomach and is degraded in the bloodstream when administered intravenously. These limitations, however, have been overcome thanks to the development of naringin nanoformulations. This review summarizes recent research carried out on strategies designed to improve naringin’s bioactivity for potential therapeutic applications.

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46

Nadar, Jegan Sakthivel, Pravin Popatrao Kale, Pramod Kerunath Kadu, Kedar Prabhavalkar, and Ruchita Dhangar. "Potentiation of Antidepressant Effects of Agomelatine and Bupropion by Hesperidin in Mice." Neurology Research International 2018 (October 28, 2018): 1–7. http://dx.doi.org/10.1155/2018/9828639.

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Анотація:

Hesperidin, a well-known flavanone glycoside mostly found in citrus fruits, showed neuroprotective and antidepressant activity. Agomelatine, a melatonergic MT1/MT2 agonist and 5-HT2C receptor antagonist, exhibits good antidepressant efficacy. Bupropion has been widely used for the treatment of depression because of its dopamine and norepinephrine reuptake inhibition. The objective of present study was to assess the antidepressant effects of hesperidin combination with agomelatine or bupropion. Male Swiss Albino mice received treatment of saline, vehicle, ‘hesperidin alone’, ‘agomelatine alone’, hesperidin+agomelatine, ‘bupropion alone’, hesperidin+bupropion, and agomelatine+bupropion for 14 days. The immobility period was analysed 30 min after the treatment in forced swim and tail suspension tests. Dopamine and serotonin levels were analysed in hippocampus, cerebral cortex, and whole brain using HPLC with fluorescence detector. Hesperidin plus agomelatine treated group was better in terms of decrease in immobility period and increase in dopamine and serotonin levels when compared to their respective monotherapy treated groups.

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47

Kim, Bo-Ram, Ah-Reum Han, and Ik-Soo Lee. "Microbial Transformation of Flavonoids in Cultures of Mucor hiemalis." Natural Product Communications 15, no. 12 (December 2020): 1934578X2097774. http://dx.doi.org/10.1177/1934578x20977743.

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Анотація:

Flavonoids are plant secondary metabolites that are well known for their health-promoting properties as nutraceuticals in diets. Bioavailability and biological activities of flavonoids vary among the individual subclasses with different patterns of substitution, inclusive of glycosylation, to their basic structures. Many flavonoids exist as glycosides in plants. This study investigated the possibility of glycosylation of flavonoids through biotransformation using filamentous fungi as whole-cell biocatalysts. Microbial transformations of ten flavonoids (four flavones, four flavonols, a flavanone, and an aurone) were performed in cultures of Mucor hiemalis KCTC 26779. As a result, a flavonoid glycoside was obtained which has not been described previously. The chemical structure of this product was elucidated as 6,2′-dimethoxyflavonol-3- O-β-d-glucopyranoside by analyzing 1-dimensional and 2-dimensional-nuclear magnetic resonance spectral and high-resolution electrospray ionization mass spectral data. This compound could be useful for further biological and bioavailability studies, as well as expanding the library of flavonoid derivatives.

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48

Jiang, Hao, Mutang Zhang, Xiaoling Lin, Xiaoqing Zheng, Heming Qi, Junping Chen, Xiaofang Zeng, Weidong Bai, and Gengsheng Xiao. "Biological Activities and Solubilization Methodologies of Naringin." Foods 12, no. 12 (June 9, 2023): 2327. http://dx.doi.org/10.3390/foods12122327.

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Анотація:

Naringin (NG), a natural flavanone glycoside, possesses a multitude of pharmacological properties, encompassing anti-inflammatory, sedative, antioxidant, anticancer, anti-osteoporosis, and lipid-lowering functions, and serves as a facilitator for the absorption of other drugs. Despite these powerful qualities, NG’s limited solubility and bioavailability primarily undermine its therapeutic potential. Consequently, innovative solubilization methodologies have received considerable attention, propelling a surge of scholarly investigation in this arena. Among the most promising solutions is the enhancement of NG’s solubility and physiological activity without compromising its inherent active structure, therefore enabling the formulation of non-toxic and benign human body preparations. This article delivers a comprehensive overview of NG and its physiological activities, particularly emphasizing the impacts of structural modification, solid dispersions (SDs), inclusion compound, polymeric micelle, liposomes, and nanoparticles on NG solubilization. By synthesizing current research, this research elucidates the bioavailability of NG, broadens its clinical applicability, and paves the way for further exploration and expansion of its application spectrum.

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Nascimento, Adriana C., Ligia M. M. Valente, Mário Gomes, Rodolfo S. Barboza, Thiago Wolff, Rômulo L. S. Neris, Camila M. Figueiredo, and Iranaia Assunção-Miranda. "Antiviral activity of Faramea bahiensis leaves on dengue virus type-2 and characterization of a new antiviral flavanone glycoside." Phytochemistry Letters 19 (March 2017): 220–25. http://dx.doi.org/10.1016/j.phytol.2017.01.013.

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50

Barboza, RS, LMM Valente, T. Wolff, IA Miranda, RSL Neris, and M. Gomes. "An anti-DENV-2 flavanone glycoside isolation from Faramea hyacinthina (Rubiaceae) by a simple and low-cost SPE method." Planta Medica 81, S 01 (December 14, 2016): S1—S381. http://dx.doi.org/10.1055/s-0036-1596465.

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