Iridoid glycosides from Phlomis younghusbandii roots

Kasai, Ryoji; Katagiri, Michiko; Ohtani, Kazuhiro; Yamasaki, Kazuo; Yang, Chong‐Ren; Tanaka, Osamu

doi:10.1016/s0031-9422(00)90473-4

Cited by 40 publications

(35 citation statements)

References 9 publications

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“…EI-MS m/z: 429.2 [M + Na] + , 445.2 [M + K] + . The 1 H NMR and 13 C NMR data were consistent with the literature [3,9].…”

supporting

confidence: 87%

“…Iridoid glycosides and phenylethanoids with antinociceptive and anti-inflammatory activities have been isolated from several plants of the genus Phlomis [2]. As to P. younghusbandii, only several iridoid glycosides and diterpenoid glycosyl esters have been reported [3][4][5]. In this paper, six iridoid glycosides, shanzhiside methyl ester (1), sesamoside (2), 7,8-dehydropenstemoside (3), penstemoside (4), 8-O-acetylshanzhiside methyl ester (5), and phlomiol (6), and three phenylethanoid glycosides, acteoside (7), alyssonoside (8), and isoacteoside (9), were isolated and identified from P. younghusbandii by comparing the spectral data with those in the literature.…”

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confidence: 99%

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Iridoid glycosides and phenylethanoid glycosides from Phlomis younghusbandii roots

Huang

Zhang

et al. 2011

Chem Nat Compd

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Phlomis younghusbandii is a perennial herb (family Labiatae) and grows wildly in the Qinghai-Tibet Plateau in northwestern China. For thousands years, P. younghusbandii has been widely used to treat colds, coughs, sore ulceration, rheumatoid arthritis, pneumonia, bronchitis, and other diseases [1]. Iridoid glycosides and phenylethanoids with antinociceptive and anti-inflammatory activities have been isolated from several plants of the genus Phlomis [2]. As to P. younghusbandii, only several iridoid glycosides and diterpenoid glycosyl esters have been reported [3][4][5]. In this paper, six iridoid glycosides, shanzhiside methyl ester (1), sesamoside (2), 7,8-dehydropenstemoside (3), penstemoside (4), 8-O-acetylshanzhiside methyl ester (5), and phlomiol (6), and three phenylethanoid glycosides, acteoside (7), alyssonoside (8), and isoacteoside (9), were isolated and identified from P. younghusbandii by comparing the spectral data with those in the literature. Compound 3 and three phenylethanoid glycosides, 7, 8, and 9, were isolated from this plant for the first time.Roots of P. younghusbandii were collect from Tibet Province of China in July 2009 and identified by Prof. Zhigang Ma, College of Pharmacy, Lanzhou University.Air-dried roots were soaked with 50% EtOH at 50qC for 3 days, three times, and then concentrated. The combined extract was dissolved in distilled water and then subjected to D101 macroporous adsorptive resin column chromatography. Alcohol (50%) was used to elute the column after it had been eluted with distilled water till the Molisch reaction became negative. The iridoid glycoside fraction was obtained after the alcohol eluate was vacuum-dried at 60qC. This fraction was further purified by reversed-phase preparative liquid chromatography with 30% methanol as the solvent system. Finally, six iridoid glycosides and three phenylethanoid glycosides were obtained, and their chemical structures were identified by spectral analysis using MS, NMR, and other spectrometers.Shanzhiside methyl ester (1) white powder. C 17 H 26 O 11 , mp 110-112qC; [D] 25 D -130.4q (c 0.44, MeOH). UV (MeOH, O max , nm) (log H): 235 (4.31). IR (KBr, Q max , cm -1 ): 3408, 1693 (C=O), 1640 (C=C), 1186, 1078, 995. EI-MS m/z: 429.2 [M + Na] + , 445 [M + K] + . The 1 H NMR and 13 C NMR data were consistent with the literature [3, 6, 7]. Sesamoside (2) white powder. C 17 H 24 O 12 , mp 206-208qC; [D] 25 D -79.5q (c 0.5, MeOH). UV (MeOH, O max , nm) (log H): 230 (4.21). IR (KBr, Q max , cm -1 ): 3423, 1693 (C =O), 1635 (C=C), 1194, 1076, 947. EI-MS m/z: 443 [M + Na] + , 459 [M + K] + . The 1 H NMR and 13 C NMR data were consistent with the literature [3, 7]. 7,8-Dehydropenstemoside (3) white powder. C 17 H 24 O 11 , mp 119-120qC; [D] 20 D -78.1q (c 0.48, MeOH). UV (MeOH, O max , nm) (log H): 234.2 (5.82). IR (KBr, Q max , cm -1 ): 3400, 1709 (C=O), 1633 (C=C), 1294, 940. EI-MS m/z: 427.2 [M + Na] + , 443.2 [M + K] + . 1 H NMR (400 MHz, D 2 O, G, ppm, J/Hz): 5.94 (1H, d, J = 2, H-1), 7.59 Penstemoside (4) white powder. C 17 H 26 O 11...

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“…EI-MS m/z: 429.2 [M + Na] + , 445.2 [M + K] + . The 1 H NMR and 13 C NMR data were consistent with the literature [3,9].…”

supporting

confidence: 87%

mentioning

confidence: 99%

Iridoid glycosides and phenylethanoid glycosides from Phlomis younghusbandii roots

Huang

Zhang

et al. 2011

Chem Nat Compd

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“…For example, geniposide, an iridoid glycoside was found in P. younghusbandii (26) enhanced melanogenesis by activating extracellular signal-regulated kinase 1/2 kinase, a downstream kinase of c-kit signaling and stimulation of stem cell factor/c-kit signaling in norepinephrineexposed normal human epidermal melanocyte (13). On the other hand, another iridoid glycoside, named shanzhiside methyl ester, has been isolated from some species of Phlomis such as, P. younghusbandii (27) and P. rigida (28), and has shown an anti-melanogenic activity near 53.7 ± 0.41% reduction of melanin content at 100 µM in the α-MSHstimulated B16 melanoma cells with almost no toxicity to the cells (14).…”

Section: Mpc Groupmentioning

confidence: 99%

Evaluation of Anti-Melanogenic and Cytotoxic Activities of Phlomis caucasica on Human Melanoma SKMEL-3 Cells

et al. 2017

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Background: Under normal physiological condition, melanosomal melanin acts as a natural UV photoprotective filter. However, after long exposure to UV radiation, melanin has shown to involve in reactive oxygen species (ROS) generation and increases the risk of developing ageing, melasma and melanoma skin cancers. A number of plant polyphenols influenced the melanin biosynthesis and growth of various melanoma cells through their anti-tyrosinase activity as well as antioxidant effect.

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“…There are a number of literature reports on flavonoids, iridoids, phenylpropanoid glycosides and essential oils from some Phlomis species. 3,[5][6][7][8][9][10][11] As a part of our continuing interest in the essential oils of Greek native Labiatae plants, we analyzed the oil of P. cretica. We found no reports on the chemical analysis of the essential oil of this species.…”

Section: Introductionmentioning

confidence: 99%