New Cucurbitacin Glycosides from<i>Picrorhiza kurrooa</i>

Stuppner, Hermann; Wagner, Hildebert

doi:10.1055/s-2006-962095

Cited by 72 publications

(33 citation statements)

References 5 publications

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“…3), indicated that these four CO groups belonged to the isochebulic or chebulic acid moiety. Other correlations were observed between the CO signals at d C 167.5 and 165. and 165.5 ppm, respectively, and indicated that the HHBP moiety was connected to C(4) and C (6). Similarly, the galloyl residue at C(1) and the isochebulic or chebulic acid moiety at C(2) and C(4) were evident from HMBC correlations (Fig.…”

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confidence: 81%

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Novel Lipid‐Peroxidation‐ and Cyclooxygenase‐Inhibitory Tannins from Picrorhiza kurroa Seeds

Zhang

DeWitt

Murugesan

et al. 2004

Chemistry & Biodiversity

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From the AcOEt extract of the seeds of Picrorhiza kurroa were isolated picrorhiza acid (1), picrorhizoside A (2), picrorhizoside B (3), picrorhizoside C (4), (-)-shikimic acid (5), gallic acid (6), ellagic acid (7), isocorilagin (8), 1-O-galloyl-beta-D-glucose (9), 1-O,3-O,6-O-trigalloyl-beta-D-glucose (10), and 1-O,2-O,3-O,4-O,6-O-pentagalloyl-beta-D-glucose (11), and their structures were established by extensive NMR and chemical studies. Constituents 1-4 are novel compounds, and the known compounds 5-11 have been isolated for the first time from the seeds of P. kurroa. Compounds 2 and 3 were hydrolyzed and yielded 12, isochebulic acid. Compounds 1-12 showed 89.6, 77.3, 56.1, 50.5, 11.0, 86.4, 50.5, 29.2, 70.9, 50.5, 56.5, and 86.1% inhibition of lipid peroxidation at 5 microg/ml, respectively. The commercial antioxidants BHA (1.8 microg/ml), BHT (2.2 microg/ml), and TBHQ (1.66 microg/ml) inhibited lipid peroxidation at 85.6, 87.1, and 81.1%, respectively. The inhibition of cyclooxygenase-1 (COX-1) by 2-5, 7, 8, and 10-12 at 100 microg/ml was 41.9, 28.4, 32.9, 9.3, 70.7, 34.7, 16.0, 89.6, and 53.4%, respectively. Similarly, compounds 1-8 and 11 and 12, at 100 microg/ml, inhibited COX-2 by 12.6, 15.3, 25.1, 5.3, 13.2, 21.7, 2.0, 42.4, 43.4, and 36.9%, respectively.

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confidence: 81%

“…7.04 ppm was assigned to HÀC (6). The signals at d H 2.87 and 2.36 were correlated to the signal at d C 35.2.…”

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confidence: 93%

Novel Lipid‐Peroxidation‐ and Cyclooxygenase‐Inhibitory Tannins from Picrorhiza kurroa Seeds

Zhang

DeWitt

Murugesan

et al. 2004

Chemistry & Biodiversity

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“…Other constituents are obtained from the dried root and rhizome. [67] The medicinal importance of PK is due to its pharmacological properties such as hepatoprotective,[8] antioxidant (particularly in liver),[9] antiallergic and antiasthmatic,[10] anticancer activity particularly in liver,[11] and immunomodulatory. [12] A hepatoprotective drug formulation, picroliv, has been prepared from the extracts of PK.…”

Section: Introductionmentioning

confidence: 99%

Picroside I and picroside II from tissue cultures of Picrorhiza kurroa

2017

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Background:Picrorhiza kurroa (PK) belongs to Scrophulariaceae family and is a representative endemic, medicinal herb, widely distributed throughout the higher altitudes of alpine Himalayas from west to east, between 3000 and 4500 m above mean sea level.Objective:The objective of the present study is to assess the production of picroside I and picroside II from tissue cultures of PK.Materials and Methods:Auxiliary shoot tips of PK were incubated in Murashige and Skoog medium supplemented with indole-3-butyric acid and kinetin phytohormones. The callus produced was collected at different time intervals and was processed for extraction of picroside I and picroside II followed by thin layer chromatography and high-performance liquid chromatography HPLC analysis.Results:The maximum growth index was found to be 5.109 ± 0.159 at 16-week-old callus culture. The estimation of picroside-I and picroside-II was carried out by (HPLC) analysis; quantity of secondary metabolite found to be 16.37 ± 0.0007 mg/g for PK-I and 6.34 ± 0.0012 mg/g for PK-II.Conclusion:This is the first attempt to produce the Picroside-I and II in large amount by the tissue culture technique. It can be observed that the method of callus culture can be used in production of secondary metabolites Picroside-I and II from PKSUMMARYPicrorhiza kurroa is a high value medicinal herb due to rich source of hepatoprotective metabolites, Picroside-I and Picroside-II. The medicinal importance of P. kurroa is due to its pharmacological properties like hepatoprotective, antioxidant (particularly in liver), antiallergic and antiasthamatic, anticancer activity particularly in liver and immunomodulatory. Shoot apices which were produced a good response was inoculated on selected medium i.e., on MS medium containing 2, 4 D (mg/l) + KN (1mg/l) for induction of callus. The initiation of callus was observed after 4weeks and it was light green and fragile Maximum growth was observed with 3% w/v of sucrose supplement. The callus culture was maintained and growth index was recorded after every subculture. The growth index was calculated from the obtained final dried weight divided by initial weight.Abbreviations Used: PK-Picrorhizakurroa, IBA-Indole-3-butyricacid, KN-Kinetin, 2,4D-2,4Dichlorophenoxy acetic acid.

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“…During our systematic chemical investigation, two new iridoid glucosides, piscrosides A (1) and B (2), were isolated from the stems of P. scrophulariiflora, together with nine known iridoid glucosides, picroside I (3), picroside II (4), picroside III (5), picroside IV (6), 6-O-trans-feruloylcatalpol (7), minecoside (8), verminoside (9), catalposide (10), and aucubin (11) [11,12] ( figure 1). Additionally, the stems of the plant afforded only three cucurbitacin glucosides, 2b-glucopyranosyloxy-3,16,20,22-tetrahydroxy-9-methyl-19-norlanosta-5,24-diene (12) [13], 2b-glucopyranosyloxy-3,16,20,22-tetrahydroxy-19-norlanosta-5,23-diene-22-ol (13) [14], and 25-aceloxy-2b-glucopyranosyloxy-3,16,20-trihydroxy-19-norlanosta-5,23-diene-22-ol (14) [14]. The known compounds were identified by comparisons of spectroscopic data with those of reported ones.…”

Section: Introductionmentioning

confidence: 99%