Naturstoffe aus Arzneipflanzen, XXV Isolierung und Strukturaufklärung neuer Inhaltsstoffe aus dem sodaalkalischen Extrakt von <i>Picrorhiza kurrooa</i>

Weinges, Klaus; Schick, Hartmut; Neuberger, Karl; Ziegler, H. J.; Lichtenthäler, Jochen; Irngartinger, Hermann

doi:10.1002/jlac.198919890278

Cited by 13 publications

(8 citation statements)

References 18 publications

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“…The large coupling between H-6 and H-7 (7.3 Hz) corresponded to a dihedral angle of approximately 160°, which was in excellent agreement with molecular models. Similar iridoids with a rigid three-ring skeleton have been isolated from Catalpa bignonioides , the Chinese herb, Rehmannia glutinosa and also obtained through bromination and dehydration of the catalposide extracted from the roots of P. kurroa …”

Section: Resultsmentioning

confidence: 69%

Pikuroside: A Novel Iridoid from Picrorhiza kurroa

1999

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A new iridoid, pikuroside (1), was isolated from the roots of Picrorhiza kurroa, together with three known iridoids, picroside I (2), picroside II (3), and 6-feruloyl catalpol (4). The structure of 1 was established by interpretation and full assignments of NMR spectral data. Pikuroside (1) had no antiinflammatory activity, although the crude extract and picroside II (3) demonstrated moderate activity.

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Section: Resultsmentioning

confidence: 69%

Pikuroside: A Novel Iridoid from Picrorhiza kurroa

1999

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“…38 The conguration of the H-3 proton was determined to be b on the basis of the formation of the intramolecular acetal of C-3 with the C-10 OH. 44 Compound 3 is a derivative of glutinoside, which was isolated previously from the dried root of Rehmannia glutinosa. Similar iridoids possessing a cage-like skeleton have been isolated from Picrorhiza kurroa, 41 Catalpa bignonioides, 42 and Rehmannia glutinosa 43 and also obtained through bromination and dehydration of the catalposide extracted from the roots of Picrorhiza kurroa.…”

Section: Resultsmentioning

confidence: 99%

Chemical components from the seeds of Catalpa bungei and their inhibitions of soluble epoxide hydrolase, cholinesterase and nuclear factor kappa B activities

et al. 2016

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Two new chlorinated iridoids, named bungosides A (1) and B (2), were isolated from the seeds of Catalpa bungei (family Bignoniaceae). Their structures were elucidated on the basis of NMR analysis. Twenty known compounds (3-22) were also characterized, including in one case (6-O-phydroxybenzoylglutinoside, 3) the assignment of the absolute configuration by employing electronic circular dichroism (CD) and time-dependent density functional theory (TDDFT) calculations. Compounds 1-3 were unusual cage-like iridoids with an oxygen bridge between C-3 and C-10. Among the isolates, ursolic acid lactone (14) was the most active soluble epoxide hydrolase (sEH) inhibitor with an IC 50 19.1 AE 0.8 mM. In addition, D-pinoresinol (19) and ladanein (21) displayed selectively inhibitory effects on butyrylcholinesterase (BChE) with IC 50 of 31.5 AE 0.4 mM and 33.0 AE 2.3 mM, respectively, but not acetylcholinesterase (AChE) activity, and only compound 18 suppressed NF-kB activity in HepG2 cells (IC 50 21.53 AE 2.37 mM).

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“…The n-BuOH portion was chromatographed repeatedly on silica gel, C 18 , and Sephadex LH-20 to afford compounds 1-10. The other nine known glycosides were subsequently identified as 2- 9) scroside B (4), 7) hemiphroside A (5), 9) plantainoside D (6), 10) scroside A (7), 7) androsin (8), 6) piceoside (9), 11) and 6-O-feruloyl-b-D-glucopyranoside (10), 12) by comparison of spectral data with the data reported in the lit-erature. The purity of these compounds was confirmed by TLC and HPLC (purity Ͼ90% for all compounds).…”

Section: Resultsmentioning

confidence: 99%

Antioxidative Phenylethanoid and Phenolic Glycosides from Picrorhiza scrophulariiflora

Wang

Sun

et al. 2004

Chem. Pharm. Bull.

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The plant Picrorhiza scrophulariiflora PENNELL (Scrophulariaceae) grows in high-altitude regions (above 4400 m) in southeast Tibet and northwest Yunnan province in China. The root of this plant is used in traditional Chinese medicine for the treatment of damp-heat dysentery, jaundice, and steaming of bone.1) Picrorhiza kurrooa, the other unique species of the same genus, is also widely utilized in India for the treatment of jaundice, indigestion, common fever, acute viral hepatitis, and bronchial asthma.2) The hepatoprotective action of P. kurrooa is not fully understood but may be attributed to inhibition of the generation of oxygen anions and scavenging of free radicals.3) Picroside I and kutkoside, iridoid glycosides obtained from P. kurrooa, were reported to be scavengers of superoxide anion radicals.4) Iridoid glycosides, triterpenoids, phenolic glycosides, and phenylethanoid glycosides have been isolated from the roots of P. scrophulariiflora. 5-7)In our screening program searching for antioxidative natural substances from traditional Chinese medicine, the nBuOH portion from the ethanol extract of P. scrophulariiflora showed potent antioxidative activity evaluated based on its scavenging effects on hydroxyl radicals and superoxide anion radicals, with the concentrations exhibiting 50% inhibition (IC 50 ) being 2.82 and 1.98 mg/ml, respectively. Further bioassay-guided analysis led to the isolation of 10 phenylethanoid and phenolic glycosides from the active n-BuOH fraction from P. scrophulariiflora. In this paper, we describe the isolation and structure elucidation of a new phenylethanoid glycoside, scroside D (2), along with nine known glycosides obtained from this plant. The antioxidative activities of these 10 glycosides were evaluated based on their scavenging effects on hydroxyl radicals produced by H 2 O 2 /Fe 2ϩ , and superoxide anion radicals produced by xathine/xanthine oxidase systems. Results and DiscussionThe ethanol extract of the plant was suspended in water and then successively extracted with petroleum ether (60-90°C), EtOAc, and n-BuOH. The n-BuOH portion was chromatographed repeatedly on silica gel, C 18 , and Sephadex LH-20 to afford compounds 1-10. The other nine known glycosides were subsequently identified as 2-(3,4-dihydroxy-plantainoside D (6), 10) scroside A (7), 7) androsin (8) Medicine and Natural Products, Jinan University; Guangzhou 510632, P. R. China. Received November 11, 2003; accepted January 20, 2004 One new phenylenthanoid glycoside, scroside D (2), was isolated from the roots of Picrorhiza scrophulariiflora ( The structures of these compounds were elucidated using spectroscopic methods. The antioxidative activities of these isolated compounds were evaluated based on their scavenging effects on hydroxyl radicals and superoxide anion radicals, respectively. Compounds 1, 2, and 6 showed potent antioxidative effects as those of ascorbic acid and the structure-activity relationship is discussed.

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Naturstoffe aus Arzneipflanzen, XXV Isolierung und Strukturaufklärung neuer Inhaltsstoffe aus dem sodaalkalischen Extrakt von Picrorhiza kurrooa

Cited by 13 publications

References 18 publications

Pikuroside: A Novel Iridoid from Picrorhiza kurroa

Pikuroside: A Novel Iridoid from Picrorhiza kurroa

Chemical components from the seeds of Catalpa bungei and their inhibitions of soluble epoxide hydrolase, cholinesterase and nuclear factor kappa B activities

Antioxidative Phenylethanoid and Phenolic Glycosides from Picrorhiza scrophulariiflora

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