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Journal articles on the topic 'Arylnaphthalene lignan'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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1

Cow, Christopher, Carmen Leung, and James L. Charlton. "Antiviral activity of arylnaphthalene and aryldihydronaphthalene lignans." Canadian Journal of Chemistry 78, no. 5 (2000): 553–61. http://dx.doi.org/10.1139/v00-059.

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A practical method for large scale synthesis of 1-arylnaphthalene and 1-aryl-1,2-dihydronaphthalene lignans is described. The method makes use of the classic Stobbe condensation followed by regioselective reactions that provide access to both the common and retrolactone lignans, e.g., 2 and 3. A total of 25 compounds, many of which are known natural products, were prepared and their antiviral activity against human cytomegalovirus measured.Key words: lignan, Stobbe, arylnaphthalene, antiviral.

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2

Ivanova, Antoaneta, Bozhanka Mikhova, Tatyana Stambolijska, and Ivanka Kostova. "Lignan and Coumarin Glycosides from Haplophyllum suaveolens." Zeitschrift für Naturforschung C 56, no. 5-6 (2001): 329–33. http://dx.doi.org/10.1515/znc-2001-5-602.

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Two new lignan glycosides of dibenzylbutyrolactol type (haplomarin) and arylnaphthalene type (haploborin) were isolated from the aerial parts of Haplophyllum suaveolens together with the known arylnaphthalene lignan glycoside arabelline and hydroxycoumarin glycoside xeroboside. So far arabelline is found only in H. buxbaumii. This is the first report of the isolation of xeroboside from Haplophyllum.

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3

Meng, Jin, Liyue Du, and Liucheng Guo. "Synthesis of Arylnaphthalene Lignan Lactones." Chinese Journal of Organic Chemistry 36, no. 11 (2016): 2723. http://dx.doi.org/10.6023/cjoc201603007.

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4

Das, B., and J. Banerji. "Arylnaphthalene lignan from Jatropha gossypifolia." Phytochemistry 27, no. 11 (1988): 3684–86. http://dx.doi.org/10.1016/0031-9422(88)80799-4.

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5

Xiao, Jian, Guangming Nan, Ya-Wen Wang та Yu Peng. "Concise Synthesis of (+)-β- and γ-Apopicropodophyllins, and Dehydrodesoxypodophyllotoxin". Molecules 23, № 11 (2018): 3037. http://dx.doi.org/10.3390/molecules23113037.

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Herein, we present an expeditous synthesis of bioactive aryldihydronaphthalene lignans (+)-β- and γ-apopicropodophyllins, and arylnaphthalene lignan dehydrodesoxypodophyllotoxin. The key reaction is regiocontrolled oxidations of stereodivergent aryltetralin lactones, which were easily accessed from a nickel-catalyzed reductive cascade approach developed in our group.

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6

Al-Abed, Yousef, Musa Abu-Zarga, Salim Sabri, Atta-Ur-Rahman, and Wolfgang Voelter. "A arylnaphthalene lignan from Haplophyllum buxbaumii." Phytochemistry 49, no. 6 (1998): 1779–81. http://dx.doi.org/10.1016/s0031-9422(98)00222-2.

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7

NAVARRO, Eduardo, Simeona Josefina ALONSO, Pedro Juan ALONSO, Juan TRUJILLO, Elena JORGE, and Cirilo PEREZ. "Pharmacological Effects of Elenoside, an Arylnaphthalene Lignan." Biological & Pharmaceutical Bulletin 24, no. 3 (2001): 254–58. http://dx.doi.org/10.1248/bpb.24.254.

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8

Ogiku, Tsuyoshi, Shin-ichi Yoshida, Tooru Kuroda, Hiroshi Ohmizu, and Tameo Iwasaki. "A New Synthesis of Arylnaphthalene Lignan Lactones." Synlett 1992, no. 08 (1992): 651–52. http://dx.doi.org/10.1055/s-1992-21444.

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9

Hesse, Manfred, Belkis Gozler, Gokay Arar, and Tekant Gozler. "Isodaurinol, an arylnaphthalene lignan from Haplophyllum cappadocicum." Phytochemistry 31, no. 7 (1992): 2473–75. http://dx.doi.org/10.1016/0031-9422(92)83302-f.

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10

Rangkaew, Noppadon, Rutt Suttisri, Masataka Moriyasu, and Kazuko Kawanishi. "A new arylnaphthalene lignan from Knema furfuracea." Fitoterapia 80, no. 6 (2009): 377–79. http://dx.doi.org/10.1016/j.fitote.2009.05.005.

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11

Sağlam, H., T. Gözler, and B. Gözler. "A new prenylated arylnaphthalene lignan from Haplophyllum myrtifolium." Fitoterapia 74, no. 6 (2003): 564–69. http://dx.doi.org/10.1016/s0367-326x(03)00147-3.

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12

Ren, Yulin, Daniel D. Lantvit, Youcai Deng, et al. "Potent Cytotoxic Arylnaphthalene Lignan Lactones from Phyllanthus poilanei." Journal of Natural Products 77, no. 6 (2014): 1494–504. http://dx.doi.org/10.1021/np5002785.

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13

Ma, Jian-Xiong, Ming-Sheng Lan, Shi-Jin Qu, et al. "Arylnaphthalene lignan glycosides and other constituents fromPhyllanthus reticulatus." Journal of Asian Natural Products Research 14, no. 11 (2012): 1073–77. http://dx.doi.org/10.1080/10286020.2012.712040.

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14

Boluda, Carlos José, José Piñero, Marialina Romero, et al. "Anti-leishmanial Activity of Justicidone and its Synthetic Precursors." Natural Product Communications 2, no. 2 (2007): 1934578X0700200. http://dx.doi.org/10.1177/1934578x0700200212.

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Justicidone, a C-5, C-8 dioxo-lignan of the arylnaphthalene type isolated from Justicia hyssopifolia, and its synthetic precursors were tested for the activity against Leishmania braziliensis and Leishmania amazonensis promastigotes in vitro. Justicidone showed activity against L. braziliensis with an IC50 of 181.90 μM, while, the diasteromeric mixture of one of its synthetic precursors exhibited activity against both parasite strains with an IC50 of 99.27 μM (L. braziliensis) and 181.75 μM (L. amazonensis). This activity has not previously been reported for dibenzylbutyrolactones and dioxo-li

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15

Boluda, Carlos J., Juan M. Trujillo, José A. Pérez, Hermelo López, Zulma Aragón, and Raquel G. Díaz. "Semisynthesis of Justicidone and a 1,2-Quinone Lignan. Cytotoxic Activity of Some Natural and Synthetic Lignans." Natural Product Communications 4, no. 2 (2009): 1934578X0900400. http://dx.doi.org/10.1177/1934578x0900400214.

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The dioxo-lignans of the arylnaphthalene-type named justicidone (2) and elenodione (3) were obtained from elenoside (1) through a short and efficient semisynthetic process. Justicidone (2), one of its synthetic precursors, 4-(benzo[d][1,3]dioxol-5-yl)-5,6,8-trimethoxy-3a,4-dihydronaphtho[2,3-c]furan-1(3H)-one (9), and the aglycone of elenoside (5) showed cytotoxic activity towards the HL-60 cell line (IC50 = 7.25 μM, 5.41 μM and 2.06 μM, respectively).

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16

Siani, Antonio C., M. das G. B. Zoghbi, Esther L. A. Wolter, and Ivo Vencato. "5-Methoxyjusticidin A, a New Arylnaphthalene Lignan fromProtium unifoliolatum." Journal of Natural Products 61, no. 6 (1998): 796–97. http://dx.doi.org/10.1021/np9702291.

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17

Anastas, Paul T., and Robert Stevenson. "Synthesis of Natural Lignan Arylnaphthalene Lactones, Daurinol and Retrochinensin." Journal of Natural Products 54, no. 6 (1991): 1687–91. http://dx.doi.org/10.1021/np50078a035.

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18

Mohagheghzadeh, Abdolali, Shadab Dehshahri, and Shiva Hemmati. "Accumulation of Lignans by in vitro Cultures of Three Linum Species." Zeitschrift für Naturforschung C 64, no. 1-2 (2009): 73–76. http://dx.doi.org/10.1515/znc-2009-1-213.

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Justicidin B, an arylnaphthalene lignan, has strong cytotoxicity on chronic myeloid and chronic lymphoid leukemia cell lines. The first report of the production of justicidin B in a Linum species concerned in vitro culture of Linum austriacum. Therefore, culture characterization and presence of arylnaphthalene-type lignans in calli and plantlets of Linum tenuifolium from section Linastrum, Linum bienne, and Linum glaucum from section Linum were studied. Seed germination of L. tenuifolium in the light and darkness was significantly higher (p < 0.05) than of L. bienne in the light and L. glau

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19

Silva, Sâmia Andrícia Souza da, Augusto Lopes Souto, Maria de Fátima Agra, et al. "A new arylnaphthalene type lignan from Cordia rufescens A. DC. (Boraginaceae)." Arkivoc 2004, no. 6 (2004): 54–58. http://dx.doi.org/10.3998/ark.5550190.0005.607.

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20

Ukita, Tatsuzo, Yoshinori Nakamura, Akira Kubo, et al. "1-Arylnaphthalene Lignan: A Novel Scaffold for Type 5 Phosphodiesterase Inhibitor." Journal of Medicinal Chemistry 42, no. 7 (1999): 1293–305. http://dx.doi.org/10.1021/jm9807048.

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21

Mori, Sachio, Shozo Takechi, Sumio Shimizu, Shiro Kida, Hikozo Iwakura, and Makoto Hajima. "Convergent synthesis of S-8921, a new potent hypocholesterolemic arylnaphthalene lignan analog." Tetrahedron Letters 40, no. 6 (1999): 1165–68. http://dx.doi.org/10.1016/s0040-4039(98)02554-4.

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22

Ogiku, Tsuyoshi, Sin-ich Yoshida, Hiroshi Ohmizu, and Tameo Iwasaki. "Efficient Syntheses of 1-Arylnaphthalene Lignan Lactones and Related Compounds from Cyanohydrins." Journal of Organic Chemistry 60, no. 14 (1995): 4585–90. http://dx.doi.org/10.1021/jo00119a041.

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23

Stevenson, Robert, and James V. Weber. "Improved Methods of Synthesis of Lignan Arylnaphthalene Lactones via Arylpropargyl Arylpropiolate Esters." Journal of Natural Products 52, no. 2 (1989): 367–75. http://dx.doi.org/10.1021/np50062a024.

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24

Innocenti, Gabbriella, Lucia Puricelli, Sonia Piacente, Rosy Caniato, Raffaella Filippini, and Elsa Mariella Cappelletti. "Patavine, a New Arylnaphthalene Lignan Glycoside from Shoot Cultures of Haplophyllum patavinum." CHEMICAL & PHARMACEUTICAL BULLETIN 50, no. 6 (2002): 844–46. http://dx.doi.org/10.1248/cpb.50.844.

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25

Liu, Guorui, Jun Wu, Jianyong Si, Junmei Wang, and Meihua Yang. "Complete assignments of1H and13C NMR data for three new arylnaphthalene lignan fromJusticia procumbens." Magnetic Resonance in Chemistry 46, no. 3 (2008): 283–86. http://dx.doi.org/10.1002/mrc.2175.

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26

KURODA, Tooru, Kazuhiko KONDO, Tameo IWASAKI, Akio OHTANI, and Kohki TAKASHIMA. "Synthesis and Hypolipidemic Activity of Diesters of Arylnaphthalene Lignan and Their Heteroaromatic Analogs." CHEMICAL & PHARMACEUTICAL BULLETIN 45, no. 4 (1997): 678–84. http://dx.doi.org/10.1248/cpb.45.678.

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27

Hayat, Faisal, Lien Kang, Chang-Yong Lee, and Dongyun Shin. "Synthesis of arylnaphthalene lignan lactone using benzoin condensation, intramolecular thermal cyclization and Suzuki coupling." Tetrahedron 71, no. 19 (2015): 2945–50. http://dx.doi.org/10.1016/j.tet.2015.03.023.

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28

Gudla, Vanajakshi, and Rengarajan Balamurugan. "Synthesis of Arylnaphthalene Lignan Scaffold by Gold-Catalyzed Intramolecular Sequential Electrophilic Addition and Benzannulation." Journal of Organic Chemistry 76, no. 24 (2011): 9919–33. http://dx.doi.org/10.1021/jo201918d.

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29

Mori, Sachio, Shozo Takechi, Sumio Shimizu, Shiro Kida, Hikozo Iwakura, and Makoto Hajima. "ChemInform Abstract: Convergent Synthesis of S-8921, a New Potent Hypocholesterolemic Arylnaphthalene Lignan Analogue." ChemInform 30, no. 21 (2010): no. http://dx.doi.org/10.1002/chin.199921106.

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30

Innocenti, Gabbriella, Lucia Puricelli, Sonia Piacente, Rosy Caniato, Raffaella Filippini, and Elsa Mariella Cappelletti. "ChemInform Abstract: Patavine, a New Arylnaphthalene Lignan Glycoside from Shoot Cultures of Haplophyllum patavinum." ChemInform 33, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.200248197.

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31

OGIKU, T., S. YOSHIDA, H. OHMIZU, and T. IWASAKI. "ChemInform Abstract: Efficient Syntheses of 1-Arylnaphthalene Lignan Lactones and Related Compounds from Cyanohydrins." ChemInform 26, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199548242.

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32

Vasilev, Nikolay, Elfahmi, Rein Bos, et al. "Production of Justicidin B, a Cytotoxic Arylnaphthalene Lignan from Genetically Transformed Root Cultures ofLinumleonii." Journal of Natural Products 69, no. 7 (2006): 1014–17. http://dx.doi.org/10.1021/np060022k.

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33

Woodard, John L., Andrew C. Huntsman, Pratiq A. Patel, et al. "Synthesis and antiproliferative activity of derivatives of the phyllanthusmin class of arylnaphthalene lignan lactones." Bioorganic & Medicinal Chemistry 26, no. 9 (2018): 2354–64. http://dx.doi.org/10.1016/j.bmc.2018.03.033.

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34

D’Urso, Gilda, Milena Masullo, Jacqueline Seigner, et al. "LC–ESI–FT–MSn Metabolite Profiling of Symphytum officinale L. Roots Leads to Isolation of Comfreyn A, an Unusual Arylnaphthalene Lignan." International Journal of Molecular Sciences 21, no. 13 (2020): 4671. http://dx.doi.org/10.3390/ijms21134671.

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Preparations of comfrey (Symphytum officinale L.) roots are used topically to reduce inflammation. Comfrey anti-inflammatory and analgesic properties have been proven in clinical studies. However, the bioactive compounds associated with these therapeutic activities are yet to be identified. An LC–ESI–Orbitrap–MSn metabolite profile of a hydroalcoholic extract of comfrey root guided the identification of 20 compounds, including a new arylnaphthalene lignan bearing a rare δ-lactone ring, named comfreyn A. Its structure was determined using extensive 2D NMR and ESI–MS experiments. Additionally, t

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35

da Silva, Rosangela, Marcelo Maia Ruas, and Paulo Marcos Donate. "Complete assignments of 1 H and 13 C NMR spectral data for arylnaphthalene lignan lactones." Magnetic Resonance in Chemistry 45, no. 10 (2007): 902–4. http://dx.doi.org/10.1002/mrc.2065.

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36

KURODA, T., K. KONDO, T. IWASAKI, A. OHTANI, and K. TAKASHIMA. "ChemInform Abstract: Synthesis and Hypolipidemic Activity of Diesters of Arylnaphthalene Lignan and Their Heteroaromatic Analogues." ChemInform 28, no. 43 (2010): no. http://dx.doi.org/10.1002/chin.199743108.

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37

Zhao, Yang, Chuen-Fai Ku, Xin-Ya Xu, et al. "Stable Axially Chiral Isomers of Arylnaphthalene Lignan Glycosides with Antiviral Potential Discovered from Justicia procumbens." Journal of Organic Chemistry 86, no. 8 (2021): 5568–83. http://dx.doi.org/10.1021/acs.joc.1c00068.

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38

Navarro, Eduardo, S. J. Alonso, and R. Navarro. "Toxicity and Neuropharmacological Effects of Elenine." Evidence-Based Complementary and Alternative Medicine 2011 (2011): 1–10. http://dx.doi.org/10.1155/2011/312524.

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Elenine is the aglycone of elenoside, a cytotoxic arylnaphthalene lignan (NSC 644013-W/1) derived fromJusticia hyssopifolia. (Family: Acanthaceae). Elenoside is a β-D-glucoside, with a similar chemical structure to etoposide, exhibiting central depressant activity. In the present study, elenine was given to mice and rats at doses of 10, 20, and 40 mg/kg. Acute toxicity (24 h) and general behaviour in mice was studied as well as its effects on muscular relaxant activity, locomotor activity (Varimex test), and the open-field test and were compared with 10 mg/kg of chlorpromazine. Elenine produce

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39

Mizufune, Hideya, Minoru Nakamura та Hiroyuki Mitsudera. "Process research on arylnaphthalene lignan aza-analogues: a new palladium-catalyzed benzannulation of α,β-bisbenzylidenesuccinic acid derivatives". Tetrahedron 62, № 36 (2006): 8539–49. http://dx.doi.org/10.1016/j.tet.2006.06.090.

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40

Al-Abed, Yousef, Salim Sabri, Musa Abu Zarga, Zahir Shah, and Atta-ur-Rahman. "Chemical Constituents of the Flora of Jordan, Part V-B. Three New Arylnaphthalene Lignan Glucosides from Haplophyllum buxbaumii." Journal of Natural Products 53, no. 5 (1990): 1152–61. http://dx.doi.org/10.1021/np50071a003.

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41

Luo, Jiaoyang, Weijun Kong, and Meihua Yang. "HJC, a New Arylnaphthalene Lignan Isolated From Justicia procumbens, Causes Apoptosis and Caspase Activation in K562 Leukemia Cells." Journal of Pharmacological Sciences 125, no. 4 (2014): 355–63. http://dx.doi.org/10.1254/jphs.13211fp.

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42

Barker, David, Lisa Pilkington, Soo Song, and Bruno Fedrizzi. "Efficient Total Synthesis of (±)-Isoguaiacin and (±)-Isogalbulin." Synlett 28, no. 12 (2017): 1449–52. http://dx.doi.org/10.1055/s-0036-1588788.

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1-Arylnaphthalene lignans such as (–)-isoguaiacin and (–)-isogalbulin have been reported to exhibit notable biological properties. While (–)-isoguaiacin has not been previously synthesized, syntheses of (–)-isogalbulin are generally long and produce a mixture of stereoisomers. We herein present the efficient total synthesis of (±)-isoguaiacin and (±)-isogalbulin in seven and eight steps with an overall yield of 46% and 36%, respectively. The reported approach harnesses a hydrogenolysis reaction in acidic conditions, to convert a furan into an arylnaphthalen structure.

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43

Nukul, Ghada S., Musa H. Abu Zarga, Salim S. Sabri, and Dawud M. Al-Eisawi. "Chemical Constituents of the Flora of Jordan, Part III. Mono-O-acetyl Diphyllin Apioside, a New Arylnaphthalene Lignan from Haplophyllum buxbaumii." Journal of Natural Products 50, no. 4 (1987): 748–50. http://dx.doi.org/10.1021/np50052a032.

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44

He, Yan, Xinying Zhang, and Xuesen Fan. "Synthesis of naphthalene amino esters and arylnaphthalene lactone lignans through tandem reactions of 2-alkynylbenzonitriles." Chem. Commun. 50, no. 42 (2014): 5641–43. http://dx.doi.org/10.1039/c4cc01738b.

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45

Charlton, James L., Curtis J. Oleschuk, and Gaik-Lean Chee. "Hindered Rotation in Arylnaphthalene Lignans." Journal of Organic Chemistry 61, no. 10 (1996): 3452–57. http://dx.doi.org/10.1021/jo952048e.

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46

Wu, Shwu-Jen, and Tian-Shung Wu. "Cytotoxic Arylnaphthalene Lignans from Phyllanthus oligospermus." CHEMICAL & PHARMACEUTICAL BULLETIN 54, no. 8 (2006): 1223–25. http://dx.doi.org/10.1248/cpb.54.1223.

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47

Al-Abed, Yousef, Salim Sabri, Musa Abu Zarga, Zahir Shah, and Atta-Ur-Rahman. "Two arylnaphthalene lignans from Haplophyllum buxbaumii." Phytochemistry 29, no. 8 (1990): 2659–61. http://dx.doi.org/10.1016/0031-9422(90)85207-v.

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48

Abdullaev, N. D., M. R. Yagudaev, �. Kh Batirov, and V. M. Malikov. "13C NMR spectra of arylnaphthalene lignans." Chemistry of Natural Compounds 23, no. 1 (1987): 63–74. http://dx.doi.org/10.1007/bf00602461.

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49

Zhang, Bao, Li Jiang, Xue Ma, et al. "A New Arylnaphthalide Lignan From Oxalis corniculata." Natural Product Communications 14, no. 9 (2019): 1934578X1987588. http://dx.doi.org/10.1177/1934578x19875885.

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A new arylnaphthalide lignan, corniculin (1), was isolated from 75% EtOH extract of Oxalis corniculata. Its chemical structure was determined by mass spectrometric analysis as well as 1D and 2D nuclear magnetic resonance (NMR).

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50

Tsao, Nai-Wen, Ying-Hsuan Sun, Shih-Chang Chien, et al. "Content and distribution of lignans in Taiwania cryptomerioides Hayata." Holzforschung 70, no. 6 (2016): 511–18. http://dx.doi.org/10.1515/hf-2015-0154.

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Abstract Taiwania (Taiwania cryptomerioides Hayata) is one of the economically important tree species indigenous to Taiwan. Hundreds of secondary metabolites have been identified from its wood, bark, root, and needles with lignans as the dominant ones. This substance group contributes a lot to the color, durability, and bioactivities of Taiwaniana. The present paper is dedicated to the quantification of radial and longitudinal lignan distribution. The extractives begin to accumulate largely in the transition zone (TZ), and reach a maximum after finishing the heartwood (hW) formation. Both dibe

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