Firmosides A and B: two new sucrose ferulates from the aerial parts of Silene firma and evaluation of radical scavenging activities.


Journal

Journal of natural medicines
ISSN: 1861-0293
Titre abrégé: J Nat Med
Pays: Japan
ID NLM: 101518405

Informations de publication

Date de publication:
Sep 2020
Historique:
received: 16 05 2020
accepted: 23 06 2020
pubmed: 8 7 2020
medline: 2 10 2020
entrez: 8 7 2020
Statut: ppublish

Résumé

Two new tri-ferulates of sucrose, firmosides A and B (1 and 2, respectively), together with 18 known compounds (3-20), were isolated from the aerial parts of Silene firma. The structures of the isolated compounds were elucidated by various spectroscopic methods, including 1D, 2D NMR, and high-resolution electro-spray ionization-mass spectrometry (HR-ESI-MS). All the isolated compounds were evaluated for their free radical scavenging activity using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. As a result, two new compounds (1, 2) and 11 demonstrated significant radical scavenging activity, implying the usefulness as antioxidant agents.

Identifiants

pubmed: 32632912
doi: 10.1007/s11418-020-01426-5
pii: 10.1007/s11418-020-01426-5
doi:

Substances chimiques

Free Radical Scavengers 0
Plant Extracts 0
Sucrose 57-50-1

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

796-803

Subventions

Organisme : Japan Society for the Promotion of Science
ID : 17K08336

Références

Mamadalieva NZ, Lafont R, Wink M (2014) Diversity of secondary metabolites in the genus Silene L. (Caryophyllaceae)—structures, distribution, and biological properties. Diversity 6:415–499. https://doi.org/10.3390/d6030415
doi: 10.3390/d6030415
Satake Y, Ohwi J, Kitamura S, Watari S, Tominari T (eds) (1982) Wild flowers of Japan. Herbaceous plants II, Heibon-sha, p 21
Makino T (2008) New Makino’s illustrated flora of Japan. Tokyo, Hokuryukan, p 584
Perry LM, Metzger J (1980) Medical plants of east and southeast Asia. Attributed properties and uses. MIT Press, Cambridge, p 74
Cui SN (1995) Chaoyaozhi. Yanbian People’s Press, Yanji, pp 77–79
Lee MY, Shin IS, Seo CS, Lee NH, Ha HK, Son JK, Shin HK (2012) Effect of methanolic extract on testosterone-induced benign prostatic hyperplasia in Wistar rats. Asian J Androl 14:320–324
doi: 10.1038/aja.2011.166
Chang HZ, Da LY, Cheng SL, Jie L, Mei J, Ming SZ, Zhen HL, Tie FJ, Gao L (2015) Cytotoxic anthraquinone dimers from Melandrium firmum. Arch Pharmacal Res 38:1033–1037
doi: 10.1007/s12272-014-0360-2
Chang HZ, Jie L, Tian L, Yong C, Mei J, Da LY, Ming SZ, Zhen HL, Jiong MC, Gao L (2015) Chemical constituents from the aerial parts of Melandrium firmmum. Arch Pharmacal Res 38:1746–1751
doi: 10.1007/s12272-014-0545-8
Seo CS, Shin HK (2016) Simultaneous determination of the five marker compounds in Melandrium firmum using high-performance liquid chromatography with photodiode-array detection. Nat Prod Commun 11(11):1934578X1601101111. https://doi.org/10.1177/1934578x1601101111
doi: 10.1177/1934578x1601101111
Pham-Huy LA, He H, Pham-Huy C (2008) Free radicals, antioxidants in disease and health. Int J Biomed Sci 4:89–96
pubmed: 23675073 pmcid: 3614697
Bao K, Fan A, Dai Y, Zhang L, Zhang W, Cheng M, Yao X (2009) Selective demethylation and debenzylation of aryl ethers by magnesium iodide under solvent-free conditions and its application to the total synthesis of natural products. Org Biomol Chem 7(24):5084–5090
doi: 10.1039/b916969e
Peng WW, Song WW, Huang MB, Tan NH (2014) Monoterpenes and sesquiterpenes from Clausena excavate. Zhongguo Zhong Yao ZaZhi 39(9):1620–1624
Wang L, Yu MM, Chi YQ, Ouyang WB, Zang Z, Zhao Y (2014) Chemical constituents of Euphorbia dracunculoides. Zhongguo Zhong Yao ZaZhi 39(20):3969–3973
Shirahata T, Sunazuka T, Yoshida K, Yamamoto D, Harigaya Y, Kuwajima I, Nagai T, Kiyohara H, Yamada H, Omura S (2006) Total synthesis, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acids. Tetrahedron 62(40):9483–9496
doi: 10.1016/j.tet.2006.06.088
Roussel PG, Sik V, Turner NJ (1997) Dinan LN (1997) Synthesis and biological activity of side-chain analogs of ecdysone and 20-hydroxyecdysone. J Chem Soc Perkin 15:2237–2246
doi: 10.1039/a700986k
Senatore F, D’Agostino M, Dini I (2000) Flavonoid glycosides of Barbarea vulgaris L. (Brassicaceae). J Agric Food Chem 48(7):2659–2662
doi: 10.1021/jf990625k
Rayyan S, Fossen T, Nateland HS, Andersen OM (2005) Isolation and identification of flavonoids, including flavone rotamers, from the herbal drug Crataegi folium cum flore (hawthorn). Phytochem Anal 16(5):334–341
doi: 10.1002/pca.853
Nakano T, Sugimoto S, Matsunami K, Otsuka H (2011) Dianthosaponins A-F, triterpene saponins, flavonoid glycoside, aromatic amide glucoside and γ-pyrone glucoside from Dianthus japonicas. Chem Pharm Bull 59(9):1141–1148
doi: 10.1248/cpb.59.1141
Yan LL, Gao WY, Zhang YJ, Wang Y (2008) A new phenylpropanoid glycosides from Paris polyphylla var. yunnanensis. Fitoterapia 79(4):306–307
doi: 10.1016/j.fitote.2007.11.029
Odinokov VN, Galyautdinov IV, Nedopekin DV, Khalilov LM, Shashkov AS, Kachala VV, Dinan L, Lafont R (2002) Phytoecdysteroids from the juice of Serratula coronate L. (Asteraceae). Insect Biochem Mol Biol 32(2):161–165
doi: 10.1016/S0965-1748(01)00106-0
Lui S, Que S, Cheng W, Zhang Q, Liang H (2013) Chemical constituents from whole plants of Carduus acanthoides. China J Chin Materia Med 38(14):2334–2337
Chang YC, Chang FR, Wu YC (2000) The Constituents of Lindera glauca. J Chin Chem Soc 47(2):373–380
doi: 10.1002/jccs.200000050
Wang G, Zhu L, Zhao Y, Gao S, Sun D, Yuan J, Huang Y, Zhang X, Yao X (2017) A natural product from Cannabis sativa subsp. sativa inhibits homeodomain-interacting protein kinase 2 (HIPK2), attenuating MPP
doi: 10.1016/j.bioorg.2017.03.011
Kai H, Baba M, Okuyama T (2007) Two new megastigmanes from the leaves of Cucumis sativus. Chem Pharm Bull 55(1):133–136
doi: 10.1248/cpb.55.133
Kreye O, Toth T, Meier MAR (2011) Copolymers derived from rapeseed derivatives via ADMET and thiol-ene addition. Eur Polym J 47(9):1804–1816
doi: 10.1016/j.eurpolymj.2011.06.012
Rong GQ, Geng CA, Ma YB, Huang XY, Wang HL, Zhao Y, Zhang XM, Chen JJ (2014) Chemical constituents from ethyl acetate extract of flower of Albizia julibrissin. Zhongguo Zhong Yao ZaZhi 39(10):1845–1851
Ashour MA, Elkhayat ES, Ebel R, Edrada R, Proksch P (2007) Indole alkaloid from the Red Sea sponge Hyrtios erectus. ARKIVOC 15:225–231
Zou Y, Zhang L, Xu JK, Cheng Q, Ye XS, Li P, Zhang WK, Li YJ (2015) A new benzaldehyde from aerial part of Rehmannia glutinosa. Zhongguo Zhong Yao ZaZhi 40(7):1316–1319
Kuang HX, Yang BY, Xia YG, Feng WS (2008) Chemical constituents from the flower of Datura metel L. Arch Pharm Res 31(9):1094–1097
doi: 10.1007/s12272-001-1274-6
Takahira M, Kusano A, Shibano M, Kusano G, Miyase T (1998) Piscidic acid and fukiic acid esters from Cimicifuga simplex. Phytochemistry 49(7):2115–2119
doi: 10.1016/S0031-9422(98)00407-5
Chang CL, Zhang LJ, Chen RY, Kuo LMY, Huang JP, Huang HC, Lee KH, Wu YC, Kuo YH (2010) Antioxidant and anti-inflammatory phenylpropanoid derivatives from Calamus quiquesetinervius. J Nat Prod 73(9):1482–1488
doi: 10.1021/np100181c
Putt KS, Nesterenko V, Dothager RS, Hergenrother PJ (2006) The compound 13-D selectively induces apoptosis in white blood cancers versus other cancer cell types. ChemBioChem 7(12):1916–1922
doi: 10.1002/cbic.200600228
Matsunami K, Takamori I, Shinzato T, Aramoto M, Kondo K, Otsuka H, Takeda Y (2006) Radical-scavenging activities of new megastigmane glucosides from Macaranga tanarius (L.) MULL.-ARG. Chem Pharm Bull 54(10):1403–1407
doi: 10.1248/cpb.54.1403

Auteurs

Nguyen Hoang Uyen (NH)

Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima, 734-8553, Japan.

Retno Widyowati (R)

Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima, 734-8553, Japan.
Department of Pharmacognosy and Phytochemistry, Faculty of Pharmacy, Universitas Airlangga, Gedung Nanizar Zaman Joenoes, Kampus C Unair, Surabaya, 60115, Indonesia.

Melanny Ika Sulistyowaty (MI)

Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima, 734-8553, Japan.
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Universitas Airlangga, Gedung Nanizar Zaman Joenoes, Kampus C Unair, Surabaya, 60115, Indonesia.

Sachiko Sugimoto (S)

Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima, 734-8553, Japan.

Yoshi Yamano (Y)

Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima, 734-8553, Japan.

Susumu Kawakami (S)

Faculty of Pharmacy, Yasuda Women's University, 6-13-1 Yasuhigashi, Asaminami-ku, Hiroshima, 731-0153, Japan.

Hideaki Otsuka (H)

Faculty of Pharmacy, Yasuda Women's University, 6-13-1 Yasuhigashi, Asaminami-ku, Hiroshima, 731-0153, Japan.

Katsuyoshi Matsunami (K)

Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima, 734-8553, Japan. matunami@hiroshima-u.ac.jp.

Articles similaires

Humans Citrus Female Male Aged
Humans Pisum sativum Breast Neoplasms Tandem Mass Spectrometry Plant Extracts
Animals Rumen Methane Fermentation Cannabis

Classifications MeSH