New 2‘-Oxygenated Flavonoids from <i>Andrographis affinis</i>

Reddy, Mopur Vijaya Bhaskar; Kishore, Pennaka Hari; Rao, C. Venkata; Gunasekar, Duvvuru; Caux, Cristelle; Bodo, Bernard

doi:10.1021/np020331k

Cited by 39 publications

(8 citation statements)

References 18 publications

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“…Each layer was subjected into purification by a combination of conventional chromatographic techniques to result in four new compounds ( 1 – 4 ). In addition, 37 known compounds were identified to be 2′,6′-dihydroxyacetophenone 2′- O -β- d -glucopyranoside ( 5 ) [17], echioidinin 5- O -β- d -glucopyranoside ( 6 ) [15], echioidinin ( 7 ) [13], pinostrobin ( 8 ) [18], andrographidine C ( 9 ) [19], dihydroechioidinin ( 10 ) [13], tectochrysin 5-glucoside ( 11 ) [20], methyl salicylate glucoside ( 12 ) [21], 7,8-dimethoxy-5-hydroxyflavone ( 13 ) [22], 5,7,8-trimethoxyflavone ( 14 ) [23], skullcapflavone I 2′-methyl ether ( 15 ) [13], acetophenone-2- O -β- d -glucopyranoside ( 16 ) [24], androechin ( 17 ) [14], skullcapflavone I 2′- O -β- d -glucopyranoside ( 18 ) [13], tectochrysin ( 19 ) [25], 5,7,2′-trimethoxyflavone [26], echioidin [13], skullcapflavone I [27], 5,7-dimethoxyflavone [28], negletein 6- O -β- d -glucopyranoside [29], andrographidine E [19], 4-hydroxy-3-methoxy- trans -cinnamic acid methyl ester [30], 4-hydroxybenzaldehyde [31], 4-hydroxy- trans -cinnamic acid methyl ester [32], O -coumaric acid [33], 2,6-dihydroxybenzoic acid [34], 13 2 -hydroxy-(13 2 - R )-phaeophytin [35], ( E )-phytyl-epoxide [36], phytol [37], phytene 1,2-diol [38], (+)-dehydrovomifoliol [39], 3β-hydroxy-5α,6α,-epoxy-7-megastigmen-9-one [40], β-sitosterol [41], β-sitosteryl-3- O -β-glucopyranoside [42], squalene [43], 1 H -indole-3-carbaldehyde [44], and loliolide [45] by comparison of their physical and spectral data with those reported in the literature.…”

Section: Resultsmentioning

confidence: 99%

Chemical Constituents from Andrographis echioides and Their Anti-Inflammatory Activity

Shen

Juang

Kuo

et al. 2012

IJMS

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Phytochemical investigation of the whole plants of Andrographis echioides afforded two new 2′-oxygenated flavonoids (1) and (2), two new phenyl glycosides (3) and (4), along with 37 known structures. The structures of new compounds were elucidated by spectral analysis and chemical transformation studies. Among the isolated compounds, (1–2) and (6–19) were subjected into the examination for their iNOS inhibitory bioactivity. The structure-activity relationships of the flavonoids for their inhibition of NO production were also discussed.

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Section: Resultsmentioning

confidence: 99%

Chemical Constituents from Andrographis echioides and Their Anti-Inflammatory Activity

Shen

Juang

Kuo

et al. 2012

IJMS

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“…One of the most important techniques is the combination of liquid chromatography and mass spectrometry that symbolizes a robust, sensitive, quick, and reproducible analytical method for the identification and characterization of secondary metabolites present in bioactive extracts. Several studies have reported the presence of diverse secondary metabolites from leaves, root, stem, or from whole plants of A. paniculata extracts, such as andrographolide (major compound), neoandrographolide, 14-deoxy-11, 12-didehydroandrographide and isoandrographolide [8,25,26], 14-deoxy-17-hydroxyandrographolide, 12S-hydroxyandrographolide, andrographatoside, 14-deoxy-11, 12-didehydroandrographolide, andrographolide, andrographic acid, 14-deoxyandrographolide, andrographolide derivatives, andrograpanin, bisandrographolide, skullcapflavone I, 5-Hydroxy-7,8,2′,5′-tetra-methoxyflavone 5-O-glucoside, and 7-O-methylwogon [27,28].…”

Section: Discussionmentioning

confidence: 99%

Secondary metabolite profiling and characterization of diterpenes and flavones from the methanolic extract of Andrographis paniculata using HPLC-LC-MS/MS

et al. 2021

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Background Andrographis paniculata is a well-known medicinal plant that contains various classes of bioactive secondary metabolites. It is widely used by the traditional medicinal healers for treatment of malaria and other diseases. There is an urgent need for screening of potent novel compounds from the methanol extract of A. paniculata. Earlier, we obtained appreciable in vitro anti-malarial activity (IC50-10.75 μg/ml) in the same plant. In current study, we developed novel analytical methods for rapid identification and characterization of diterpenes and flavones using chromatographic and spectroscopic techniques and identified major compounds that might possess anti-malarial activities. Results Based on the chromatographic and mass spectrometric features, we have identified a total of 74 compounds (25 compounds from positive ion mode; 49 compounds from negative ion mode). The mass spectrum data predicted andrographolide (15%) presence in the highest amount in both positive and negative ion modes. Based on the percentage purity, Andrographolide and skullcapflavone I was selected as representative class of diterpenes and flavones for fragmentation studies. Conclusions The result led to identification of Neoandrographolide, andrographolactone, 14-dehydroxy-11,12-didehydroandrographolide, skullcapflavone I, and 5-Hydroxy-2′,7,8-tri methoxy flavone from the methanolic extract of A. paniculata that is used in traditional medicine by tribal healers of Amarkantak region for treating malaria. These could be lead compounds for the development of novel anti-malarial drugs.

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“…Pharmacokinetic interaction experiments propose that A. paniculata could cause the inhibition of UDPglucuronosyltransferase in drug metabolism [13]. The flavonoids isolated from the ethyl acetate fraction derived from ethanolic or methanolic extraction were reported to contain 5-hydroxy-7,8dimethoxyflavone, 5-hydroxy-7,8,2',5'-tetramethoxyflavone, 5-hydroxy-7,8,2',3'-tetramethoxyflavone, 5-hydroxy-7,8,2'-trimethoxyflavone, 7-O-methylwogonin, and 2'-methyl ether [14][15][16]. The ethyl acetate fraction of A. paniculata in conjunction with doxorubicin considerably (p<0.05) escalated programed cell death in mice fibrosarcoma cells and diminished vascular endothelial growth factor production (p<0.05) [17].…”

Section: Introductionmentioning

confidence: 99%

“…The primary diterpene of A. paniculata was stated to be rographolide and has been chronicled to constitute 4%, 0.8~1.2%, and 0.5~6% in dried whole plant, stem, and leaf preparations, respectively [18][19][20]. Other prominent labdane diterpenoids were deoxyandrographolide, neoandrographolide, 14-deoxy-11,12-didehydroandrographide, and isoandrographolide [15,17].…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Labdane Diterpenoids From Andrographis Paniculata (BURM.F.) Nees

Tan

Oyong

Shen

et al. 2017

Asian J Pharm Clin Res

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Objective: The primary objective of this study was to probe the cytotoxic capacity of the labdane diterpenoids andrographolide (1), 14-deoxyandrographolide (2), 14-deoxy-12-hydroxyandrographolide (3), and neoandrographolide (4) on mutant and wild-type immortalized cell lines.Methods: Breast adenocarcinoma (MCF-7), colon carcinomas (HCT-116 and HT-29), small cell lung carcinoma (H69PR), human acute monocytic leukemia (THP-1), and wild-type primary normal human dermal fibroblasts - neonatal cells (HDFn) were incubated with 1-4, and the degree of cytotoxicity was analyzed by employing the in vitro PrestoBlue® cell viability assay. Working solutions of 1-4 were prepared in complete cell culture medium to a final non-toxic dimethyl sulfoxide concentration of 0.2%. The plates were incubated at 37°C with 5% CO2 in a 98% humidified incubator throughout the assay. Nonlinear regression and statistical analyses were done to extrapolate the half maximal inhibitory concentration 50% (IC50). One-way ANOVA (p<0.05) and multiple comparison, Tukey’s post hoc test (p<0.05), were used to compare different pairs of data sets. Results were considered statistically significant at p<0.05.Results: The highest cytotoxicity index was exhibited by the H69PR and 1 trials which displayed the lowest IC50 value of 3.66 μg/mL, followed by HT-29 treated with 2, HCT-116 and 1 trials, and H69PR treated with 4 (IC50=3.81, 3.82, and 4.19 μg/mL, respectively). Only 1 and 4 were detrimental toward MCF-7, while 1, 3, and 4 were degenerative against H69PR. Tukey’s post hoc multiple comparison indicated no significant difference in the cytotoxicity of 1-4 on HCT-116 cells which afforded IC50 values ranging from 3.82 to 5.12 μg/mL. Evaluation of the two colon carcinoma cell lines showed that HCT-116 was categorically more susceptible to cellular damage caused by treatments with 1-4 than was HT-29. Cytotoxicity was not detected in THP-1 and HDFn cells (IC50>100 μg/mL).Conclusion: Diterpenoids 1-4 isolated from the dichloromethane extract of the leaves of A. paniculata exhibited different cytotoxic activities against MCF-7, HCT-116, HT-29, and H69PR. All constituents had comparable action on HCT-116 cells but were not found to be cytotoxic to normal HDFn cells and mutant THP-1 cells.

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New 2‘-Oxygenated Flavonoids from Andrographis affinis

Cited by 39 publications

References 18 publications

Chemical Constituents from Andrographis echioides and Their Anti-Inflammatory Activity

Chemical Constituents from Andrographis echioides and Their Anti-Inflammatory Activity

Secondary metabolite profiling and characterization of diterpenes and flavones from the methanolic extract of Andrographis paniculata using HPLC-LC-MS/MS

Cytotoxic Labdane Diterpenoids From Andrographis Paniculata (BURM.F.) Nees

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