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Journal articles on the topic 'Phenylpropanoid glycoside'

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Author: Grafiati

Published: 11 March 2023

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1

Arnold, Ulrike W., Christian Zidorn, Ernst P. Ellmerer, and Hermann Stuppner. "Iridoid and Phenolic Glycosides from Wulfenia carinthiaca." Zeitschrift für Naturforschung C 57, no. 11-12 (December 1, 2002): 969–75. http://dx.doi.org/10.1515/znc-2002-11-1202.

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Two new phenylpropanoid glycosides (2′-O-acetylplantamajoside and 2′-O, 6″-O-diacetylplantamajoside), a new iridoid glycoside (10-O-(cinnamoyl)-6′-O-(desacetylalpinosidyl)-catalpol), the two known iridoid glycosides globularin and isoscrophularioside, and the known phenylpropanoid glycoside platamajoside were isolated from the methanolic extract of the underground parts of Wulfenia carinthiaca. Structure elucidations were based on high-resolution mass spectrometry and extensive 1-D and 2-D NMR spectroscopy.

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2

Santos, Javier de, Ana M. Díaz Lanza, Lidia Fernández, and Angel Rumbero. "Isoangoroside C, a Phenylpropanoid Glycoside from Scrophularia scorodonia Roots." Zeitschrift für Naturforschung C 55, no. 5-6 (June 1, 2000): 333–36. http://dx.doi.org/10.1515/znc-2000-5-606.

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A new phenylpropanoid glycoside isoangoroside C was isolated from the roots of Scrophularia scorodonia. Its structure was determined on the basis of spectral data as: 3-hydroxy- 4-methoxy-β-phenylethoxy-O-α-ʟ-arabinopyranosyl-(1→6)α ʟ-rhamnopyranosyl-(l→3)-4-O- Z-feruloyl-β-ᴅ -glucopyranoside. Additionally, one known phenylpropanoid, angoroside C, and five known iridoid glycosides, harpagoside, bartsioside, 8-O-acetyl-harpagide, aucuboside and harpagide were isolated and identified.

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3

Alishir, Akida, and Ki Hyun Kim. "Antioxidant Phenylpropanoid Glycosides from Ginkgo biloba Fruit and Identification of a New Phenylpropanoid Glycoside, Ginkgopanoside." Plants 10, no. 12 (December 8, 2021): 2702. http://dx.doi.org/10.3390/plants10122702.

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Ginkgo biloba (Ginkgoaceae), well-known as the oldest living plant species and often referred to as a “living fossil,” is a famous medicinal plant that has been used in multiple countries to improve numerous illnesses, including anxiety, dementia, peripheral artery disease, and eye problems. We conducted a phytochemical exploration of G. biloba fruit, commonly consumed as a functional food as part of an ongoing natural product chemical research for the discovery of bioactive phytochemicals with novel structures. The natural product chemical analysis of the methanol extract of G. biloba fruit using column chromatography and high-performance liquid chromatography separation under the guidance of a liquid chromatography–mass spectrometry (LC/MS)-based analysis identified six phenylpropanoid glycosides (1–6), including one new compound, ginkgopanoside (1). The structures of the isolated compounds were elucidated by nuclear magnetic resonance spectroscopic data and LC/MS analysis, and the absolute configuration of compound 1 was established by chemical reactions followed by the application of Snatzke’s method. The 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activities of the isolated compounds 1–6 and the aglycone 1a of 1 were evaluated, and we found that compounds 1–5 exhibited antioxidant activities with IC50 values in the range 32.75–48.20 μM, while the aglycone 1a exhibited greater radical scavenging activity (IC50 = 5.23 μM) comparable to that of ascorbic acid (IC50 = 2.54 μM), a positive control, implying that the present of glucose may decrease the DPPH scavenging activity. These findings provide experimental information that the active phenylpropanoid glycosides could represent natural antioxidants for use in pharmaceuticals and functional foods.

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4

Zhang, San-Qi, Zhong-Jun Li, An-Bang Wang, Meng-Shen Cai, and Rui Feng. "Synthesis of a phenylpropanoid glycoside, Osmanthuside B611Studies on Glycosides XXIV." Carbohydrate Research 308, no. 3-4 (April 1998): 281–85. http://dx.doi.org/10.1016/s0008-6215(98)00092-5.

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5

Seidel, Veronique, François Bailleul, Francine Libot, and François Tillequin. "A phenylpropanoid glycoside from Ballota nigra." Phytochemistry 44, no. 4 (February 1997): 691–93. http://dx.doi.org/10.1016/s0031-9422(96)00578-x.

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6

Sang, Shengmin, Aina Lao, Hongcheng Wang, Zhongliang Chen, Jun Uzawa, and Yasuo Fujimoto. "A phenylpropanoid glycoside from Vaccaria segetalis." Phytochemistry 48, no. 3 (June 1998): 569–71. http://dx.doi.org/10.1016/s0031-9422(97)00896-0.

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7

Huong, Nguyen Thi Hong, Nguyen Khac Quynh Cu, Trinh Van Quy, Christian Zidorn, Markus Ganzera, and Hermann Stuppner. "A new phenylpropanoid glycoside fromJasminum subtriplinerveBlume." Journal of Asian Natural Products Research 10, no. 11 (November 2008): 1035–38. http://dx.doi.org/10.1080/10286020802320897.

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8

Khan, I., C. Erdelmeier, and O. Sticher. "A New Phenylpropanoid Glycoside fromEurya tigang." Planta Medica 56, no. 06 (December 1990): 573. http://dx.doi.org/10.1055/s-2006-961170.

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9

Lahloub, M., G. A. Gross, O. Sticher, T. Winkler, and H. R. Schulten. "Ehrenoside, a New Phenylpropanoid Glycoside fromVeronica bellidioides1." Planta Medica 52, no. 05 (October 1986): 352–55. http://dx.doi.org/10.1055/s-2007-969182.

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10

Afifi, M., M. Lahloub, S. El-Khayaat, C. Anklin, H. Rüegger, and O. Sticher. "Crenatoside: A Novel Phenylpropanoid Glycoside fromOrobanche crenata1." Planta Medica 59, no. 04 (August 1993): 359–62. http://dx.doi.org/10.1055/s-2006-959701.

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11

Kawada, Toshinari, Ryuji Asano, Shiho Hayashida, and Tomoyasu Sakuno. "Total Synthesis of the Phenylpropanoid Glycoside, Acteoside." Journal of Organic Chemistry 64, no. 25 (December 1999): 9268–71. http://dx.doi.org/10.1021/jo9906983.

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12

Çaliş, İ., D. Taşdemir, and O. Sticher. "Lagotoside: A New Phenylpropanoid Glycoside fromLagotis stolonifera." Planta Medica 56, no. 06 (December 1990): 574. http://dx.doi.org/10.1055/s-2006-961173.

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13

Lahloub, M., H. Rüegger, S. El-Khayaat, M. Affifi, and O. Sticher. "Crenatoside, a Novel Phenylpropanoid Glycoside fromOrobanche crenata." Planta Medica 55, no. 07 (December 1989): 612–13. http://dx.doi.org/10.1055/s-2006-962164.

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14

Baudouin, Geneviève, Alexios-Léandros Skaltsounis, François Tillequin, and Michel Koch. "Lugrandoside: A New Phenylpropanoid Glycoside from VariousDigitalisSpecies." Planta Medica 54, no. 04 (August 1988): 321–23. http://dx.doi.org/10.1055/s-2006-962445.

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15

Gross, G. A., M. F. Lahloub, C. Anklin, H. R. Schulten, and O. Sticher. "Teucrioside, a phenylpropanoid glycoside from Teucrium chamaedrys." Phytochemistry 27, no. 5 (January 1988): 1459–63. http://dx.doi.org/10.1016/0031-9422(88)80215-2.

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16

Zheng-Dan, He, and Yang Chong-Ren. "Brandioside, a phenylpropanoid glycoside from Brandisia hancei." Phytochemistry 30, no. 2 (January 1991): 701–2. http://dx.doi.org/10.1016/0031-9422(91)83759-e.

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17

Başaran, Arif Ahmet, İhsan Çaliş, Clemens Anklin, Sansei Nishibe, and Otto Sticher. "Lavandulifolioside: A New Phenylpropanoid Glycoside fromStachys lavandulifolia." Helvetica Chimica Acta 71, no. 6 (September 28, 1988): 1483–90. http://dx.doi.org/10.1002/hlca.19880710612.

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18

Çaliş, İhsan, Deniz Taşdemir, Anthony D. Wright, and Otto Sticher. "Lagotoside: A New Phenylpropanoid Glycoside fromLagotis stolonifera." Helvetica Chimica Acta 74, no. 6 (September 18, 1991): 1273–77. http://dx.doi.org/10.1002/hlca.19910740615.

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19

Liu, Shi-Qiao, Li-Ping Kang, Jie Zhang, Yi-Xun Liu, Yang Zhao, Bin Liu, and Bai-Ping Ma. "New sesquiterpenoid glycoside and phenylpropanoid glycosides from the tuber of Ophiopogon japonicus." Journal of Asian Natural Products Research 18, no. 6 (December 23, 2015): 520–27. http://dx.doi.org/10.1080/10286020.2015.1121996.

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20

Ahn, Jong Hoon, Se Hwan Ryu, Solip Lee, Sang Won Yeon, Ayman Turk, Yoo Kyong Han, Ki Yong Lee, Bang Yeon Hwang, and Mi Kyeong Lee. "Aromatic Constituents from the Leaves of Actinidia arguta with Antioxidant and α-Glucosidase Inhibitory Activity." Antioxidants 10, no. 12 (November 26, 2021): 1896. http://dx.doi.org/10.3390/antiox10121896.

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As the leaf of Actinidia arguta has shown antioxidant activity, a study was conducted to identify the active ingredients. Forty-eight compounds were isolated from the leaves of A. arguta through various chromatographic techniques. Further characterization of the structures on the basis of 1D and 2D NMR and MS data identified several aromatic compounds, including phenylpropanoid derivatives, phenolics, coumarins, flavonoids and lignans. Among them, five compounds were newly reported, naturally occurring, and named argutosides A–D (1–4), which consist of phenylpropanoid glycosides that are conjugated with a phenolic moiety, and argutoside E (5), which is a coumarin glycoside that is conjugated with a phenylpropanoid unit. The isolated compounds showed good antioxidant and α-glucosidase inhibitory activity with differences in activity depending on the structures. Molecular docking analysis demonstrated the interaction between the hydroxyl and carbonyl groups of compounds 1 and 5 with α-glucosidase. Taken together, the leaves of A. arguta are rich in aromatic compounds with diverse structures. Therefore, the leaves of A. arguta and their aromatic components might be beneficial for oxidative stress and glucose-related diseases.

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21

Chu, Hong-Biao, Ning-Hua Tan, and Yu-Mei Zhanga. "Chemical Constituents from Pedicularis rex C. B. Clarke." Zeitschrift für Naturforschung B 62, no. 11 (November 1, 2007): 1465–70. http://dx.doi.org/10.1515/znb-2007-1117.

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One new ionone glycoside, pedicurexoside (1), one new flavonoid, 5, 4′-dihydroxy-3′-methoxyflavone- 7-O-6″-n-butyryl-β -D-glucopyranoside (2), two new iridoid glycosides, 6-O-ethyl-aucubin (7), 6-O-ethyl-epiaucubin (8), and one new phenylpropanoid glycoside, 4-hydroxy-phenylpropenyl- α-L-rhamnopyranosyl-(1→3)-4-O- feruloyl-β -D-glucopyranoside (13), together with eleven known compounds, apigenin (3), luteolin (4), chrysoeriol (5), luteolin-7-O-β -D-glucopyranoside (6), aucubin (9), yuheinoside (10), euphroside (11), mussaenoside (12), verbascoside (14), martynoside (15) and isomartynoside (16), were isolated from Pedicularis rex. The structures of 1 - 16 were elucidated mainly by 1D and 2D NMR techniques, MS evidence and chemical methods. The ionone derivative with thirteen carbon atoms was found in Pedicularis plants for the first time.

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22

Liu, Yong, Otto Seligmann, Hildebert Wagner, and Rudolf Bauer. "Paucifloside, A New Phenylpropanoid Glycoside from Lysionotus pauciflorus." Natural Product Letters 7, no. 1 (August 1995): 23–28. http://dx.doi.org/10.1080/10575639508043182.

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23

INOUE, Makoto, Mari UEDA, Yukio OGIHARA, and Iclal SARACOGLU. "Induction of Cytokines by a Phenylpropanoid Glycoside Acteoside." Biological & Pharmaceutical Bulletin 21, no. 12 (1998): 1394–95. http://dx.doi.org/10.1248/bpb.21.1394.

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24

Kellam, Stephen J., Kevin A. Mitchell, John W. Blunt, Bruce M. Clark, Murray H. G. Munro, and John R. L. Walker. "Phenylpropanoid Glycoside Esters: Leucine Aminopeptidase Inhibitors fromHebe strictavar.Atkinsonii." Natural Product Letters 3, no. 2 (September 1993): 87–94. http://dx.doi.org/10.1080/10575639308043843.

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25

Mostafa, M., Nasim Sultana, Nilufar Nahar, M. Mosihuzzaman, and M. Iqbal Choudhary. "A new phenylpropanoid glycoside from Leucas indica Linn." Journal of Asian Natural Products Research 11, no. 1 (January 1, 2009): 29–32. http://dx.doi.org/10.1080/10286020802513848.

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26

Zhang, San-Qi, Zhong-Jun Li, An-Bang Wang, Meng-Shen Cai, and Rui Feng. "Total synthesis of the phenylpropanoid glycoside, grayanoside A." Carbohydrate Research 299, no. 4 (April 1997): 281–85. http://dx.doi.org/10.1016/s0008-6215(97)00032-3.

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27

Lira-Rocha, Alfonso, Raul Diaz, and Manuel Jimenez. "Iridoids and a Phenylpropanoid Glycoside from Penstemon rosseus." Journal of Natural Products 50, no. 2 (March 1987): 331–32. http://dx.doi.org/10.1021/np50050a060.

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28

Xie, Er Lei, Guo Ping Zhou, Teng Fei Ji, Jun Wu, and Gui Ping Yuan. "A novel phenylpropanoid glycoside from Callicarpa kwangtungensis Chun." Chinese Chemical Letters 20, no. 7 (July 2009): 827–29. http://dx.doi.org/10.1016/j.cclet.2009.03.022.

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29

Li, Qing, Shu-Chun Li, Hui Li, Meng-Shen Cai, and Zhong-Jun Li. "Total synthesis of syringalide B, a phenylpropanoid glycoside." Carbohydrate Research 340, no. 9 (July 2005): 1601–4. http://dx.doi.org/10.1016/j.carres.2005.04.011.

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30

de Santos Gal�ndez, J., A. M. Diaz-Lanza, L. Fern�ndez Matellano, and A. Rumbero S�nchez. "A new phenylpropanoid glycoside isolated fromScrophularia scorodonia L." Magnetic Resonance in Chemistry 38, no. 8 (2000): 688–91. http://dx.doi.org/10.1002/1097-458x(200008)38:8<688::aid-mrc714>3.0.co;2-5.

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31

Chae, Sungwook, Kyoung Ah Kang, Ju Sun Kim, Jin Won Hyun, and Sam Sik Kang. "Trichotomoside: A New Antioxidative Phenylpropanoid Glycoside fromClerodendron trichotomum." Chemistry & Biodiversity 3, no. 1 (January 2006): 41–48. http://dx.doi.org/10.1002/cbdv.200690005.

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32

Song, Xun, Jiang He, Hong Xu, Xiao-Peng Hu, Xu-Li Wu, Hai-Qiang Wu, Li-Zhong Liu, et al. "The antiviral effects of acteoside and the underlying IFN-γ-inducing action." Food & Function 7, no. 7 (2016): 3017–30. http://dx.doi.org/10.1039/c6fo00335d.

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33

Khong, Duc Thinh, and Zaher M. A. Judeh. "Short synthesis of phenylpropanoid glycoside grayanoside-A and analogues." Carbohydrate Research 436 (December 2016): 50–53. http://dx.doi.org/10.1016/j.carres.2016.11.010.

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34

Lahloub, M., A. Zaghloul, S. El-Khayaat, M. Afifi, and O. Sticher. "2′-O-Acetylpoliumoside: A New Phenylpropanoid Glycoside fromOrobanche ramosa." Planta Medica 57, no. 05 (October 1991): 481–85. http://dx.doi.org/10.1055/s-2006-960177.

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35

Lahloub, M., A. Zaghloul, S. El-Khayaat, M. Affifi, and O. Sticher. "2′-O-Acetylpoliumoside, a New Phenylpropanoid Glycoside fromOrobanche ramosa." Planta Medica 55, no. 07 (December 1989): 613. http://dx.doi.org/10.1055/s-2006-962165.

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36

Kawada, Toshinari, Ryuji Asano, Shiho Hayashida, and Tomoyasu Sakuno. "ChemInform Abstract: Total Synthesis of the Phenylpropanoid Glycoside, Acteoside." ChemInform 31, no. 11 (June 10, 2010): no. http://dx.doi.org/10.1002/chin.200011216.

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37

ZHANG, S. Q., Z. J. LI, A. B. WANG, M. S. CAI, and R. FENG. "ChemInform Abstract: Studies on Glycosides. Part 24. Synthesis of a Phenylpropanoid Glycoside, Osmanthuside B6." ChemInform 29, no. 46 (June 19, 2010): no. http://dx.doi.org/10.1002/chin.199846236.

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38

Luo, Wei, Yaya Wen, Yanbei Tu, Hongjian Du, Qin Li, Chao Zhu, and Yanfang Li. "A New Flavonoid Glycoside from Lysionotus pauciflorus." Natural Product Communications 11, no. 5 (May 2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100516.

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Ten flavonoids (1–10), including a new glycoside (nevadensin-7-sambubioside, 7), together with a phenylpropanoid glycoside (11) were isolated from Lysionotus pauciflorus. Their structures were elucidated by a combination of spectroscopic methods and comparing with literature data. Five compounds (1, 3, 4, 8, and 9) were obtained from the family Gesneriaceae for the first time. The new compound was evaluated in vitro for anticholinesterase activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), but was found to be inactive.

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39

Trinh, Pham Thi Nhat, Nguyen Cong Hao, Phan Thanh Thao, and Le Tien Dung. "Chemical components of the rhizomes of Drynaria fortunei (KUNZE) J. Sm. (polypodiaceae) in Vietnam." Collection of Czechoslovak Chemical Communications 76, no. 9 (2011): 1133–39. http://dx.doi.org/10.1135/cccc2010098.

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From the ethanol extract of Drynaria fortunei (KUNZE) J. Sm., a new phenylpropanoid glycoside, fortunamide (1), was isolated and characterized by spectroscopic methods. Together with a new glycoside, 9 known compounds, including three curcuminoids (2–4), two isoprenylated flavonoids (5, 6), two flavonoids (7, 8), one monoterpenoid (9) and one phenolic acid (10) were isolated and identified by spectral data analysis from the rhizomes of Drynaria fortunei (KUNZE) J. Sm. Eight of them were isolated from Drynaria fortunei (KUNZE) J. Sm. for the first time.

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40

Ono, Masateru, Yoshie Takatsu, Tetsuya Ochiai, Shin Yasuda, Yoichiro Nishida, Toshiharu Tanaka, Masafumi Okawa, Junei Kinjo, Hitoshi Yoshimitsu, and Toshihiro Nohara. "Two New Nortriterpenoid Glycosides and a New Phenylpropanoid Glycoside from the Bulbs of Scilla scilloides." Chemical and Pharmaceutical Bulletin 60, no. 10 (2012): 1314–19. http://dx.doi.org/10.1248/cpb.c12-00457.

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41

ZHANG, S. Q., Z. J. LI, A. B. WANG, M. S. CAI, and R. FENG. "ChemInform Abstract: Studies on Glycosides. Part 20. Total Synthesis of the Phenylpropanoid Glycoside, Grayanoside A." ChemInform 28, no. 34 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199734250.

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42

WEI, Dan-Dan, Jun-Song WANG, Yao ZHANG, and Ling-Yi KONG. "A new phenylpropanoid glycoside from the fruits of Illicium simonsii." Chinese Journal of Natural Medicines 10, no. 1 (January 2012): 20–23. http://dx.doi.org/10.1016/s1875-5364(12)60004-1.

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43

Shen, Hai-yan, Hui Wang, Wen-jian Zuo, You-xing Zhao, Ying Luo, Wen-li Mei, and Hao-fu Dai. "A new phenylpropanoid glycoside from dragon’s blood of Dracaena cambodiana." Chemical Research in Chinese Universities 29, no. 3 (March 25, 2013): 483–86. http://dx.doi.org/10.1007/s40242-013-2296-3.

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44

Thuan, Nguyen Duy, Do Thi Ha, Phuong Thien Thuong, Min Kyun Na, KiHwan Bae, Jong Pill Lee, Jeong-Hun Lee, Hyo-Won Seo, Byung-Sun Min, and Jin-Cheol Kim. "A phenylpropanoid glycoside with antioxidant activity from picria tel-ferae." Archives of Pharmacal Research 30, no. 9 (September 2007): 1062–66. http://dx.doi.org/10.1007/bf02980238.

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45

Potterat, Olivier, Jerome D. Msonthi, and Kurt Hostettmann. "Four iridoid glucosides and a phenylpropanoid glycoside from Sesamum angolense." Phytochemistry 27, no. 8 (1988): 2677–79. http://dx.doi.org/10.1016/0031-9422(88)87042-0.

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46

Dai, Hao Fu, and Wen Li Mei. "Ophiopojaponin D, a new phenylpropanoid glycoside fromOphiopogon Japonicus Ker-Gawl." Archives of Pharmacal Research 28, no. 11 (November 2005): 1236–38. http://dx.doi.org/10.1007/bf02978205.

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47

CALIS, I., D. TASDEMIR, A. D. WRIGHT, and O. STICHER. "ChemInform Abstract: Lagotoside: A New Phenylpropanoid Glycoside from Lagotis stolonifera." ChemInform 22, no. 48 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199148245.

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48

Youssef, Diaa T. A., Lamiaa A. Shaala, and Ahmed E. Altyar. "Cytotoxic Phenylpropanoid Derivatives and Alkaloids from the Flowers of Pancratium maritimum L." Plants 11, no. 4 (February 9, 2022): 476. http://dx.doi.org/10.3390/plants11040476.

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Regarding our growing interest in identifying biologically active leads from Amaryllidaceous plants, the flowers of Pancratium maritimum L. (Amaryllidaceae) were investigated. Purification of the cytotoxic fractions of the alcoholic extract of the flowers gave a new glycoside, 3-[4-(β-D-glucopyranosyloxy)phenyl]-2-(Z)-propenoic acid methyl ester (1), together with the previously reported compounds 3-methoxy-4-(β-D-glucopyranosyloxy)benzoic acid methyl ester (2), 3-(4-methoxyphenyl)propan-1-ol-1-O-β-D-glucopyranoside (3), (E)-3-(4-hydroxyphenyl)acrylic acid methyl ester (4), caffeic acid (5), dihydrocaffeic acid methyl ester (6), and pancratistatin (7). Interestingly, compounds 1 and 2 are phenolic-O-glycosides, while the glucose moiety in 3 is attached to the propanol side chain. This is the first report about the existence of 1–6 in the genus Pancratium. Further, glycosides 1–3 from the Amaryllidaceae family are reported on here for the first time. The structures of 1–7 were determined by analyses of their 1D (1H and 13C) and 2D (COSY, HMQC, HMBC) NMR spectra, and by high-resolution mass spectral measurements. Pancratistatin displayed potent and selective growth inhibitory effects against MDA-MB-231, HeLa, and HCT 116 cells with an IC50 value down to 0.058 µM, while it possessed lower selectivity towards the normal human dermal fibroblasts with IC50 of 6.6 µM.

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49

Wang, Yu, Wen Yuan Gao, Tie Jun Zhang, and Yuan Qiang Guo. "A novel phenylpropanoid glycosides and a new derivation of phenolic glycoside from Paris Polyphylla var. yunnanensis." Chinese Chemical Letters 18, no. 5 (May 2007): 548–50. http://dx.doi.org/10.1016/j.cclet.2007.03.011.

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50

Pieretti, Stefano, Anella Saviano, Adriano Mollica, Azzurra Stefanucci, Anna Maria Aloisi, and Marcello Nicoletti. "Calceolarioside A, a Phenylpropanoid Glycoside from Calceolaria spp., Displays Antinociceptive and Anti-Inflammatory Properties." Molecules 27, no. 7 (March 28, 2022): 2183. http://dx.doi.org/10.3390/molecules27072183.

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Abstract:

Phenylpropanoid glycosides are a class of natural substances of plant origin with interesting biological activities and pharmacological properties. This study reports the antinociceptive and anti-inflammatory effects of calceolarioside A, a phenylpropanoid glycoside previously isolated from various Calceolaria species. In models of acute nociception induced by thermal stimuli, such as the hot plate and tail flick test, calceolarioside administered at doses of 1, 5, and 10 μg in the left cerebral ventricles did not modify the behavioral response of mice. In an inflammatory based persistent pain model as the formalin test, calceolarioside A at the high dose tested (100 μg/paw) reduced the licking activity induced by formalin by 35% in the first phase and by 75% in the second phase of the test. In carrageenan-induced thermal hyperalgesia, calceolarioside A (50 and 100 μg/paw) was able to significantly reverse thermal hyperalgesia induced by carrageenan. The anti-inflammatory activity of calceolarioside A was then assessed using the zymosan-induced paw edema model. Calceolarioside A (50 and 100 μg/paw) induced a significant reduction in the edema from 1 to 4 h after zymosan administration. Measuring IL-6, TNFα, and IL-1β pro-inflammatory cytokines released from LPS-stimulated THP-1 cells, calceolarioside A in a concentration-dependent manner reduced the release of these cytokines from THP-1 cells. Taken together, our results highlight, for the first time, the potential and selective anti-inflammatory properties of this natural-derived compound, prompting its rationale use for further investigations.

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