Citrusin C

Human Saliva-Mediated Hydrolysis of Eugenyl-beta-D-Glucoside and Fluorescein-di-beta-D-Glucoside in In Vivo and In Vitro Models.[Pubmed:33514072]

Biomolecules. 2021 Jan 27;11(2). pii: biom11020172.

Eugenyl-beta-D-glucopyranoside, also referred to as Citrusin C, is a natural glucoside found among others in cloves, basil and cinnamon plants. Eugenol in a form of free aglycone is used in perfumeries, flavourings, essential oils and in medicinal products. Synthetic Citrusin C was incubated with human saliva in several in vitro models together with substrate-specific enzyme and antibiotics (clindamycin, ciprofloxacin, amoxicillin trihydrate and potassium clavulanate). Citrusin C was detected using liquid chromatography with tandem mass spectrometry (LC-MS/MS). Citrusin C was completely degraded only when incubated with substrate-specific A. niger glucosidase E.C 3.2.1.21 (control sample) and when incubated with human saliva (tested sample). The addition of antibiotics to the above-described experimental setting, stopped Citrusin C degradation, indicating microbiologic origin of hydrolysis observed. Our results demonstrate that Citrusin C is subjected to complete degradation by salivary/oral cavity microorganisms. Extrapolation of our results allows to state that in the human oral cavity, virtually all beta-D-glucosides would follow this type of hydrolysis. Additionally, a new method was developed for an in vivo rapid test of glucosidase activity in the human mouth on the tongue using fluorescein-di-beta-D-glucoside as substrate. The results presented in this study serve as a proof of concept for the hypothesis that microbial hydrolysis path of beta-D-glucosides begins immediately in the human mouth and releases the aglycone directly into the gastrointestinal tract.

Identification of Novel Human Serum Albumin (SA) Inhibitors from Scoparia Dulsis for Urolithiasis.[Pubmed:31393255]

Curr Comput Aided Drug Des. 2020;16(3):308-317.

BACKGROUND: Urolithiasis is the process of forming stones in the kidney, bladder, and/or urinary tract. It has been reported that kidney stones are the third most common disorder among urinary diseases. At present, surgical procedures and Extracorporeal Shock Wave Lithotripsy (ESWL) are commonly employed for the treatment of Urolithiasis. The major drawback of these procedures is the recurrence of stones. METHODS: This study aimed to identify potential natural inhibitors against human Serum Albumin (SA) from the plant Scoparia Dulsis for Urolithiasis. As protein-ligand interactions play a key role in structure- based drug design, this study screened 26 compounds from Scoparia Dulsis and investigated their binding affinity against SA by using molecular docking. The three dimensional (3D) structure of SA was retrieved from Protein Data Bank (PDB) and docked with PubChem structures of 26 compounds using PyRX docking tool through Autodock Vina. Moreover, a 3D similarity search on the PubChem database was performed to find the analogs of best scored compound and docking studies were performed. Drug-likeness studies were made using Swiss ADME and Lipinski's rule of five was performed for the compounds to evaluate their anti-urolithiatic activity. RESULTS: The results showed that Citrusin C (Eugenyl beta-D-glucopyranoside) exhibited best binding energy of -8.1 kcal/mol with SA followed by aphidicolin, apigenin, luteolin and scutellarein. Two compounds (PubChem CID 46186820, PubChem CID 21579141) analogous to Citrusin C were selected based on the lowest binding energy. CONCLUSION: This study, therefore, reveals that these compounds could be promising candidates for further evaluation for Urolithiasis prevention or management.

Phenolic antioxidants from Rosa soulieana flowers.[Pubmed:23805936]

Nat Prod Res. 2013;27(21):2055-8.

Rosa soulieana has been widely used in traditional medicine to treat cardiovascular disorders. In this study, antioxidant activity-guided fractionation and purification of the methanol extract from the flowers of R. soulieana has led to the isolation of nine phenolic antioxidants, which were identified as catechin (1), tiliroside (2), astragalin (3), isoquercitrin (4), nicotiflorin (5), eugenol 4-O-beta-d-(6'-O-galloyl) glucoside (6), michehedyosides D (7), Citrusin C (8) and strictinin (9), respectively. Among them, compounds 5-9 were reported from the genus Rosa for the first time. All the compounds were also assayed by in vitro ABTS [2,2'-azinobis(3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt] radical cation scavenging activity. Among these bioactive isolates (1-9), compounds 1, 6, 7 and 9 exhibited strong scavenging activity in ABTS (SC50 = 10.17, 7.38, 8.60, 4.72 mumol/L, respectively) compared with the positive control l-ascorbic acid (SC50 = 15.97 mumol/L).

[Chemical constituents from the tubers of Ipomoea batata].[Pubmed:23236827]

Zhong Yao Cai. 2012 Jun;35(6):913-7.

OBJECTIVE: To investigate the chemical constituents from the tubers of Ipomoea batata. METHODS: The chemical constituents were isolated and purified by solvent extraction together with various chromatographic techniques. The structures were elucidated on the basis of physiochemical property and spectral data. RESULTS: 6 compounds were identified from the CHCl3 extract as Batatinoside I (1), Citrusin C(2), octadecyl caffeate (3), beta-amyrin acetate (4), caffeic acid (5), scopoletin (6). CONCLUSION: Compound 1 is isolated from Ipomoea batata for the first time.

[Studies on chemical constituents from Ipomoea batatas].[Pubmed:19230398]

Zhong Yao Cai. 2008 Oct;31(10):1501-3.

OBJECTIVE: To investigate the chemical constituents of Ipomoea batatas. METHODS: Silica gel column chromatography and Sephadex LH-20 were used to separate and purify the compounds from the EtOAc and n-BuOH soluble fraction of ethanol extracts. The chemical structures were elucidated on the basis of physic-chemical properties and spectral data. RESULTS: Four compounds were isolated and identify as Citrusin C (1), caffeicacid (2), 3,4-di-O-caffeoylquinic acid (3), 1,2,3,4-tetrahydro-beta-carboline-3-carboylic acid (4). CONCLUSION: Compounds 1-4 are isolated for the first time from I. batatas.

Phytochemical constituents of Carpesium macrocephalum F(R). et S(AV).[Pubmed:15554259]

Arch Pharm Res. 2004 Oct;27(10):1029-33.

From the methanol extract of the whole plants of Carpesium macrocephalum F(R). et S(AV)., five sesquiterpene lactones (1: carabron, 2: tomentosin, 3: ivalin, 4: 4H-tomentosin, 5: carabrol) and three terpenoids (6: loliolide, 7: vomifoliol, 8: Citrusin C) were isolated. The structures and stereochemistry of compounds 1-8 were established on the basis of chemical analysis as well as 1D- and 2D-NMR spectroscopy. Among them, compounds 2, 4, and 6-8 were isolated for the first time from Carpesium species.

NMR assignments and single-crystal X-ray diffraction analysis of deoxyloganic acid.[Pubmed:15505818]

Magn Reson Chem. 2005 Jan;43(1):92-6.

7-Deoxyloganic acid (1), Citrusin C (2), 3,4-dihydroxyl benzoic acid (3) and (E)-caffeic acid (4) were isolated from the water-soluble fraction of ethanol extracts of Morina nepalensis var. alba Hand.-Mazz. and their structures were determined on the basis of spectroscopic evidence. The total assignments of 1H and 13C NMR spectra of 1 in solvents CD3OD, D2O and CDCl3 were reported, in addition to the single-crystal X-ray diffraction analysis of its tetraacetate 1a. All compounds were obtained from Morina genus for the first time.

Phytochemical constituents ofCarpesium macrocephalum FR- et SAV.[Pubmed:27518388]

Arch Pharm Res. 2004 Oct;27(10):1029-33.

From the methanol extract of the whole plants ofCarpesium macrocephalum FR. et SAV., five sesquiterpene lactones (1: carabron,2: tomentosin,3: ivalin,4: 4H-tomentosin,5: carabrol) and three terpenoids (6: loliolide,7: vomifoliol,8: Citrusin C) were isolated. The structures and stereochemistry of compounds1-8 were established on the basis of chemical analysis as well as 1D- and 2D-NMR spectroscopy. Among them, compounds2, 4, and6-8 were isolated for the first time fromCarpesium species.