Iridoid derivatives from Vitex rotundifolia L. f. with their anti-inflammatory activity

Le, Duc Dat; Han, Sanghee; Yu, Jayeon; Ahn, Jeongjun; Kim, Chang‐Kwon; Lee, Mina

doi:10.1016/j.phytochem.2023.113649

Cited by 4 publications

(5 citation statements)

References 32 publications

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“…This observation suggested that the rhamnosidation at C-3 might be favorable to inhibiting IL-1β production. Compounds (20)(21)(22) shared the same luteolin glycosides. However, compounds (21 and 22) have an OCH 3 attached B-ring, showing a strong anti-inflammatory effect.…”

Section: Discussionmentioning

confidence: 90%

“…Therefore, rhamnosidation at C-3 may promote an inhibitory effect against IL-8 production. Compounds (20)(21)(22) shared the same luteolin glycosides. However, compound 22 has 3 -OCH 3 , showing the best anti-inflammatory effect.…”

Section: Discussionmentioning

confidence: 90%

“…As a result, this active fraction was chosen for the isolation and identification of four phenolics, five alkaloids, and 13 flavonoid glycosides from the flowers of V. tenuifolia. Among isolates, vicia D (1) is a new compound, 6-methoxykaempferol 3-O-sophoroside (15) and diosmetin 7-O-(2 -apiosyl)-glucoside (22) were first reported NMR data from this study, and ferulic acid (2), trans-p-coumaroyl-D-glucopyranose (3), cis-p-coumaroyl-D-glucopyranose (4), L-tryptophan (5) and D-tryptophan (6), D-phenylalanine (7), L-phenylalanine (8), adenosine (9), afzelin (10), rhamnocitrin 3-O-glucoside (11), kaempferol 7-O-glucoside (12), kaempferol 3-O-(2 -O-β-D-glucopyranosyl)-α-L-rhamnopyranoside (13) [30], kaempferol 3-O-rutinoside ( 14), quercetin-3-O-rhamnoside (16), rutin (17), rhamnetin 3-O-rutinoside (18), 6 -acetylapiin (19), graveobioside A (20), and diosmetin 7-O-rutinoside (21), were isolated for the first time from this plant. All the isolated compounds exhibited some significant inhibition against inflammatory cytokines and mediators.…”

Section: Discussionmentioning

confidence: 99%

“…Fraction Bu5 was subjected to a prep HPLC using a Triat C 18 column (10 × 250 mm, 5 µm), UV detection at wavelength 265 nm, flow rate 3.0 mL/min, eluting with a gradient solvent system from 0 min (19% B) to 85 min (100% B) to obtain compounds 2 (t R 38 min), 10 (t R 17 min), 15 (t R 27 min), and further purified using the same conditions by exchange the isocratic elution of 17% B for 65 min, compound 13 (t R 49 min) and 20 (t R 52 min). Fraction Bu6 was subjected to a prep HPLC using a Triat C 18 column (10 × 250 mm, 5 µm), UV detection at wavelength 265 nm, flow rate 3.0 mL/min, eluting with a gradient solvent system from 0 min (19% B) to 85 min (100% B) to obtain compounds 5 ( Cell culture and viability were discussed in our previous report [22]. Briefly, human colon epithelial (HT-29) and mouse macrophage (RAW264.7) cells were maintained in Dulbecco's modified Eagle's medium (DMEM), followed by adding 10% FBS, streptomycin sulfate (100 µg/mL), and penicillin (100 IU/mL).…”

Section: Extraction and Separation Of Compounds (1-22)mentioning

confidence: 99%

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Molecular Networking and Bioassay-Guided Preparation and Separation of Active Extract and Constituents from Vicia tenuifolia Roth

Le,

Yu,

Dang

et al. 2023

Antioxidants

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Molecular networking drove the selection of material from V. tenuifolia organs that targeted active flavonoid glycosides. To optimize the extraction process, the flowers of V. tenuifolia were used to produce an anti-inflammatory extract. The effects of variables—organic solvent ratio; extraction time; and temperature—were investigated by the response of anti-inflammatory activity. Bioactivities-guided experiments helped identify fractions with high total phenolic and flavonoid content as well as antioxidant potential. Furthermore, one new compound (1), 19 first isolated together, and two known compounds were obtained and identified from the active fraction of this plant. Among them, compounds (15 and 22) were first reported for nuclear magnetic resonance (NMR) data from this study. All the isolates were evaluated for their anti-inflammatory capacity throughout, modulating nitric oxide (NO), interleukin (IL)-1β, and IL-8 production. Active compounds were further investigated for their regulation and binding affinity to the inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins by Western blot and in silico approaches, respectively. The findings of this study suggested that the developed extract method, active fraction, and pure components should be further investigated as promising candidates for treating inflammation and oxidation.

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Section: Discussionmentioning

confidence: 90%

Section: Discussionmentioning

confidence: 90%

Section: Discussionmentioning

confidence: 99%

Section: Extraction and Separation Of Compounds (1-22)mentioning

confidence: 99%

See 2 more Smart Citations

Molecular Networking and Bioassay-Guided Preparation and Separation of Active Extract and Constituents from Vicia tenuifolia Roth

Le,

Yu,

Dang

et al. 2023

Antioxidants

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“…negundo L. var. cannabifolia, has shown anti-inflammatory properties. , The mechanism of this effect involves regulating the expression of iNOS and COX-2 proteins . Agnuside is also a chemical marker of the Vitex species and is employed to control the quality of this medicinal plant. ,− Thus, agnuside is exclusive to chaste honey from V.…”

Section: Resultsmentioning

confidence: 99%

Exploring the Formation of Chemical Markers in Chaste Honey by Comparative Metabolomics: From Nectar to Mature Honey

Yan,

Mu,

Yuan

et al. 2024

J. Agric. Food Chem.

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Identification of chemical markers is important to ensure the authenticity of monofloral honey; however, the formation of chemical markers in honey has received little attention. Herein, using comparative metabolomics, we first identified chemical markers in chaste honey and then explored their formation and accumulation from nectar to mature honey. We identified agnuside and p-hydroxybenzoic acid glucosides as chemical markers for chaste honey. Besides, we developed an UHPLC−MS/MS method for quantifying these markers and found that their levels varied significantly across sample sources. We compared the presence of these compounds in chaste nectar and mature honey. The outcomes underscore that these characteristic compounds are not simply delivered from nectar to mature honey, and activities of honeybees (collecting and processing) play a pivotal role in their formation and accumulation. These observations shed light on how mature honey can form its unique qualities with a rich assortment of natural bioactive compounds, potentially supporting health benefits.

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Iridoid for drug discovery: Structural modifications and bioactivity studies

Wang,

Zheng,

Yang

et al. 2024

Med Chem Res

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Iridoid derivatives from Vitex rotundifolia L. f. with their anti-inflammatory activity

Cited by 4 publications

References 32 publications

Molecular Networking and Bioassay-Guided Preparation and Separation of Active Extract and Constituents from Vicia tenuifolia Roth

Molecular Networking and Bioassay-Guided Preparation and Separation of Active Extract and Constituents from Vicia tenuifolia Roth

Exploring the Formation of Chemical Markers in Chaste Honey by Comparative Metabolomics: From Nectar to Mature Honey

Iridoid for drug discovery: Structural modifications and bioactivity studies

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