Kingiside

Simultaneous Determination of Thirteen Iridoid Glycosides in Crude and Processed Fructus Corni from Different Areas by UPLC-MS/MS Method.[Pubmed:37873817]

J Chromatogr Sci. 2023 Oct 23:bmad083.

Fructus Corni (F. Corni) is the dried mature pulp of Cornus officinalis Sieb. et Zucc.(Cornaceae), which is rich in iridoids. In this study, a simple, sensitive and rapid UPLC-MS/MS method was developed for the simultaneous determination of 13 iridoid glycosides of F. Corni from different areas. Specifically, we included five new compounds (cornusdiridoid C, cornusdiridoid E, cornusdiridoid F, 3'',5''-dehydroxycornuside and 2'-O-p-coumaroyl-Kingiside) and isomers (2'-O-p-E-coumaroylloganin and 2'-O-p-Z-coumaroylloganin) for the first time in the quality markers of F. Corni. A total of 13 compounds and two pairs of isomers were well isolated and tested within just 14 min. All calibration curves showed good linear regression (r2 >/= 0.99) within the tested concentration ranges. The limit of detection and limit of quantification were in the range of 0.19-1.90 and 0.38-3.76 ng/mL, respectively. The intra-day and inter-day precision were <3.21% and 12.49%, the RSD values of repeatability did not exceed 6.81% and the average recoveries were 90.95-113.59% for the analytes. All iridoid glycosides stabilized within 12 h (RSD < 10.99%). This method has been successfully applied to the quality evaluation of crude and processed F. Corni from different areas. The determination of characteristic iridoid glycosides and isomers will provide a more reliable and comprehensive method for the evaluation of F. Corni.

Seco-iridoid glycosides from the Gentiana olivieri Griseb and their bioactivities.[Pubmed:37657663]

Phytochemistry. 2023 Nov;215:113839.

The ethanol extract of the Gentiana olivieri Griseb plant was subjected to an investigation to ascertain the presence of its iridoid constituents. By means of HPLC and TLC monitoring, a total of thirteen previously unreported seco-iridoid glucosides olivierisecoside A-M, as well as seven known seco-iridoid glycosides and one known iridoid glycoside were isolated. Their structures were elucidated by a comprehensive spectroscopic data analysis and ECD calculations. The absolute configuration of olivierisecoside D was further confirmed through single-crystal X-ray diffraction analysis. All the identified compounds were characterized as aromatic conjugated seco-iridoid glucosides, with olivierisecoside F-I representing a particularly rare subtype known as the morroniside type seco-iridoids. In vitro testing of the isolated compounds revealed their potential anti-inflammatory and hepatoprotective effects. The results showed olivieroside B and 6'-gentisoyl-8-epi-Kingiside have good anti-inflammatory activities in LPS induced RAW264.7 cells. Additionally, olivierisecoside M exhibited some improvements in PA-induced L02 and HepG2 cells damage, known compound loganin showed slight hepatoprotective effect in PA-induced HepG2 cells damage.

Leaf tissue metabolomics fingerprinting of Citronella gongonha Mart. by (1)H HR-MAS NMR.[Pubmed:36271238]

Sci Rep. 2022 Oct 21;12(1):17624.

This research characterizes key metabolites in the leaf from Citronella gongonha Martius (Mart.) Howard (Cardiopteridaceae). All metabolites were assessed in intact leaf tissue by proton ((1)H) high-resolution magic angle spinning (HR-MAS) nuclear magnetic resonance (NMR) spectroscopy integrated with the principal component analysis (PCA) to depict molecular association with the seasonal change. The major 'known unknown' metabolites detected in (1)H HR-MAS NMR were derivatives of flavonoid, polyphenolic and monoterpenoid compounds such as kaempferol-3-O-dihexoside, caffeoyl glucoside (2), 3-O-caffeoylquinic acid (3), 5-O-caffeoylquinic acid (4), Kingiside (5), 8-epi-kingisidic acid (6), (7alpha)-7-O-methylmorroniside (7), (7beta)-7-O-methylmorroniside (8) and alpigenoside (9) together with the universally occurring sucrose (10), alpha-glucoses (11, 12), alanine (13), and fatty (linolenic) acid (14). Several of the major metabolites (1, 2-9) were additionally confirmed by liquid chromatography tandem mass spectrometry (LC-MS/MS). In regard with the PCA results, metabolites 1, 2-9 and 14 were influenced by seasonal variation and/or from further (a) biotic environmental conditions. The findings in this work indicate that C. gongonha Mart. is an effective medicinal plant by preserving particularly compounds 2, 3-9 in abundant amounts. Because of close susceptibility with seasonal shift and ecological trends, further longitudinal studies are needed to realize the physiology and mechanism involved in the production of these and new metabolites in this plant under controlled conditions. Also, future studies are recommended to classify different epimers, especially of the phenolics and monoterpenoids in the given plant.

Isolation of a new natural kingiside aglucone derivative and other anti-inflammatory constituents from Syringa reticulata.[Pubmed:30470127]

Nat Prod Res. 2020 Feb;34(4):518-524.

A new secoiridoid, (1R,5S,8S,9R)-1-methyl-Kingiside aglucone (1), along with nine known compounds (2-10), were isolated from the ethanol extract of the stem bark of Syringa reticulata (Bl.) Hara. The structure of compound 1 was elucidated using HR-ESI-MS, 1D and 2D NMR spectroscopy. Compounds 1-10 were evaluated for their inhibitory activity against NO, TNF-alpha and IL-6 production. Compounds 1, 3, 5 and 7-10 significantly inhibited the levels of NO, TNF-alpha and IL-6 in LPS-induced RAW264.7 cells from concentrations of 3 to 30 muM.

[Studies on chemical constituents of aqueous extract of Lonicera japonica flower buds].[Pubmed:26978994]

Zhongguo Zhong Yao Za Zhi. 2015 Sep;40(17):3496-504.

From an aqueous extract of Lonicera japonica flower buds, sixteen compounds were isolated by a combination of various chromatographic techniques including column chromatography over macroporous resin, MCI gel, silica gel, and sephadex LH-20 and reversed-phase HPLC. Their structures were elucidated by spectroscopic data analysis as 6'-O-acetylvogeloside (1), 6'-O-acetylsecoxyloganin (2), dichlorogelignate (3), guanosinyl-(3' --> 5')-adenosine monophosphate(GpA,4) , 5'-O-methyladenosine (5), 2'-O-methyladenosine (6), adenosine (7), syringin (8), methyl 4-O-beta-D-glucopyranosyl caffeate (9), (-)-dihydrophaseic acid 4'-O-beta-D-glucopyranoside (10), ketologanin (11), 7alpha-morroniside (12), 7beta-morroniside (13), Kingiside (14), cryptochlorogenic acid methyl ester (15), and 6-hydroxymethyl-3-pyridinol (16). All the compounds were obtained from this plant for the first time, compounds 1 and 2 are new compounds, 3 and 5 are new natural products, and 4 is the first example of dinucleoside monophosphate isolated from a plant extract.

The anti-inflammatory secoiridoid glycosides from gentianae scabrae radix: the root and rhizome of Gentiana scabra.[Pubmed:25750086]

J Nat Med. 2015 Jul;69(3):303-12.

Gentianae Scabrae Radix is a well-known traditional medicine that is used for the treatment of hepatitis, cholecystitis and inflammatory diseases. It consists mainly of secoiridoid glycosides, with representatives of gentiopicroside, sweroside and swertiamarin. In the present study, a chemical investigation of the CHCl3 extract of Gentianae Scabrae Radix derived from Gentiana scabra Bunge yielded seven new (1-7) and ten known (8-17) secoiridoid glycosides. Their structures were elucidated by extensive spectroscopic analyses and comparison with literature data. All 17 compounds were evaluated for their inhibitory effects against NO, IL-6 and TNF-alpha productions induced by lipopolysaccharide (LPS) in RAW264 cells. Among them, 8-epi-Kingiside derivatives 1-3; Kingiside derivatives 4, 5 and 10; and a sweroside derivative 6 showed inhibition activity against IL-6 production with IC50 values of 51.70-61.10 muM, whereas sweroside derivatives 12 and 15-17 and a swertiamarin derivative 13 showed inhibition effects on both NO and IL-6 productions with IC50 values of 64.74-94.95 and 48.91-75.45 muM, respectively. All the compounds exhibited weak inhibitory activity (IC50 > 100 muM) in a TNF-alpha bioassay. Finally, a primary structure-activity relationship of these secoiridoid glycosides is discussed.

A novel lactone from Tripterospermum chinense.[Pubmed:23387086]

Yao Xue Xue Bao. 2012 Nov;47(11):1517-20.

A novel lactone, tripterospermumcins E (1), along with four known compounds, sweroside (2), loganic acid (3), 8-epi-Kingiside (4) and bergenin (5), were isolated from the aerial parts of Tripterospermum chinense. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, and chemical methods. Compound 1 is rare beta-lactone with a glucoside.

Two novel secoiridoid glucosides from Tripterospermum chinense.[Pubmed:23088535]

J Asian Nat Prod Res. 2012;14(12):1097-102.

Two novel secoiridoid glucosides, tripterospermumcins C (1) and D (2), were isolated from the aerial parts of Tripterospermum chinense, along with four known compounds, tripterospermumcin B (3), sweroside (4), loganic acid (5), and 8-epi-Kingiside (6). Their structures were determined by analysis of 1D and 2D NMR data, as well as by comparison with model compounds. Compound 1 was a rare iridoid tetramer with four glucosides.

[A new secoiridoid from the flowers of Jasminum officinale L. var. grandiflorum].[Pubmed:18717340]

Yao Xue Xue Bao. 2008 May;43(5):513-7.

To study the chemical constituents of the flowers of Jasminum officinale L. var. grandiflorum, the compounds were isolated and purified by HPLC, recrystallization and chromatography on silica gel and Sephadex LH-20 column. Their structures were elucidated on the basis of physicochemical properties and spectral analysis. Six secoiridoids were identified as jasgranoside (I), jaspolyoside (II), 8-epi-Kingiside (III), 10-hydroxy-oleuropein (IV), 10-hydroxy-ligstroside (V), oleoside-7, 11-dimethyl ester (VI). Compound I is a new compound. Compounds II, III, IV, V and VI were isolated from Jasminum officinale L. var. grandiflorum for the first time.

Iridoidal glucosides from Gentiana rhodantha.[Pubmed:18470799]

J Asian Nat Prod Res. 2008 May-Jun;10(5-6):491-8.

Six new iridoidal glucosides, 2'-O-(3''-hydroxybenzoyl)-8-epiKingiside (1), 2'-O-(3''-hydroxybenzoyl)-Kingiside (2), 6'-O-p-coumaroyl-8-epiKingiside (3), loganic acid 11-O-beta-glucopyranosyl ester (4), 6'-O-beta-glucopyranosyl secologanoside (5), and 6'-O-beta-glucopyranosyl secologanol (6), together with seven known iridoidal glucosides, loganic acid (7), 6'-O-beta-d-glucopyranosyl loganic acid (8), 8-epiKingiside (9), Kingiside (10), secologanoside (11), secoxyloganin (12), and alpigenoside (13), were isolated from the whole plant of Gentiana rhodantha (Gentianaceae). Their structures were elucidated by detailed spectroscopic analysis and chemical methods.

seco-iridoids from Calycophyllum spruceanum (Rubiaceae).[Pubmed:12943773]

Phytochemistry. 2003 Sep;64(2):549-53.

Three seco-iridoids 7-methoxydiderroside, 6'-O-acetyldiderroside and 8-O-tigloyldiderroside, were isolated from the wood bark of Calycophyllum spruceanum together with the known iridoids loganetin, loganin and the seco-iridoids secoxyloganin, Kingiside and diderroside. Their structures were elucidated by means of NMR and MS spectral data analysis. Using NOE correlations and coupling constants, the relative stereochemistry of the new derivatives was established. 7-Methoxydiderroside, 6'-O-acetyldiderroside and the known secoxyloganin and diderroside showed in vitro activity against trypomastigote forms of Trypanosoma cruzi, with IC(50) values of 59.0, 90.2, 74,2 and 84.9 microg/mL, respectively and were compared to the standard gentian violet (IC(50) 7.5 microg/ml).

[Studies on the constituents of Ligustrum species. XIX. Structures of iridoid glucosides from the leaves of Ligustrum lucidum AIT].[Pubmed:10376004]

Yakugaku Zasshi. 1999 Jun;119(6):444-50.

Two new iridoid glucosides, named iso-8-epiKingiside and 8-demethyl-7-ketologanin, were isolated together with 8-epiKingiside, Kingiside, ligustroside, 10-hydroxyligustroside, ligustaloside A and ligustaloside B from the leaves of Ligustrum lucidum AIT. (Oleaceae). The stereochemical structures of these new compounds were elucidated on the basis of spectroscopic evidence.