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Planta Med 2020; 86(11): 776-781
DOI: 10.1055/a-1179-1050
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

α-Glucosidase Inhibitory Depsidones from the Lichen Parmotrema tsavoense

Thuc-Huy Duong
1   Department for Management of Science and Technology Development, Ton Duc Thang University, Ho Chi Minh City, Vietnam
2   Faculty of Applied Sciences, Ton Duc Thang University, Ho Chi Minh City, Vietnam
,
Tai-Xuan-Hoa Hang
3   Department of Chemistry, Ho Chi Minh City University of Education, Ho Chi Minh City, Vietnam
,
Pierre Le Pogam
4   Équipe “Pharmacognosie-Chimie des Substances Naturelles”, BioCIS, Université Paris-Sud, CNRS, Université Paris-Saclay, Châtenay-Malabry, France
,
Thanh-Nha Tran
3   Department of Chemistry, Ho Chi Minh City University of Education, Ho Chi Minh City, Vietnam
,
Dinh-Hung Mac
5   Department of Organic Chemistry, University of Science, Vietnam National University, Ha Noi, Vietnam
,
Minh-Hiep Dinh
6   Management Board of Agricultural Hi-Tech Park, Ho Chi Minh City, Vietnam
,
Jirapast Sichaem
7   Faculty of Science and Technology, Thammasat University Lampang Campus, Lampang, Thailand
› Author Affiliations
Further Information

Publication History

received 17 January 2020
revised 01 May 2020

accepted 11 May 2020

Publication Date:
29 May 2020 (online)

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Abstract

Chemical investigation of the lichen Parmotrema tsavoense led to the isolation of 5 new depsidones, parmosidones F – J (1 – 5). These compounds were structurally elucidated using spectroscopic methods including HRESIMS and 2D NMR data. Compounds 1, 3, and 4 were evaluated for their inhibition of α-glucosidase. All exhibited potent α-glucosidase inhibitory activity with IC50 values ranging from 10.7 to 17.6 µM, which was much lower than that of the positive control acarbose (IC50 449 µM).

Key words

Parmeliaceae - Parmotrema tsavoense - lichen - parmosidones F – J - depsidone - α-glucosidase inhibition

Supporting Information

    HRESIMS and 1D, 2D-NMR spectra of compounds 1 – 5 are available as Supporting Information.

  • Supporting Information
 

  • References

  • 1 Tabish SA. Is diabetes becoming the biggest epidemic of the twenty-first century?. Int J Health Sci (Qassim) 2007; 1: 3-8
    PubMedGoogle Scholar
  • 2 Kumar S, Narwal S, Kumar V, Prakash O. α-Glucosidase inhibitors from plants: a natural approach to treat diabetes. Pharmacogn Rev 2011; 5: 19-29
    CrossrefPubMedGoogle Scholar
  • 3 Thadhani VM, Karunaratne V. Potential of lichen compounds as antidiabetic agents with antioxidative properties: a review. Oxidative Med Cell Longev 2017; 2017: 1-10
    PubMedGoogle Scholar
  • 4 Karunaratne V, Thadhani VM, Khan SN, Choudhary MI. Potent α-glucosidase inhibitors from the lichen Cladonia species from Sri Lanka. J Natl Sci Found Sri 2014; 42: 95-98
    PubMedGoogle Scholar
  • 5 Bogner E, Wastlhuber R, Schlegl I, Loos E. Glycogen, amylase and α-glucosidase as possible components in the glucose release system of the cyanobiont of Peltigera horizontalis. Partial purification and characterization. Symbiosis 1993; 14: 485-494
    PubMedGoogle Scholar
  • 6 Duong TH, Chavasiri W, Boustie J, Nguyen KPP. New meta-depsidones and diphenyl ethers from the lichen Parmotrema tsavoense (Krog & Swinscow) Krog & Swinscow, Parmeliaceae. Tetrahedron 2015; 71: 9684-9691
    CrossrefPubMedGoogle Scholar
  • 7 Duong TH, Beniddir MA, Genta-Jouve G, Aree T, Chollet-Krugler M, Boustie J, Ferron S, Sauvager A, Nguyen HH, Chavasiri W, Le Pogam P. Tsavoenones A–C: unprecedented polyketides with a 1,7-dioxadispiro[4.0.4.4]tetradecane core from the lichen Parmotrema tsavoense. . Org Biomol Chem 2018; 16: 5913-5919
    CrossrefPubMedGoogle Scholar
  • 8 Duong TH, Beniddir MA, Boustie J, Nguyen KP, Chavasiri W, Bernadat G, Le Pogam P. DP4-assisted structure elucidation of isodemethylchodatin, a new norlichexanthone derivative meager in H-Atoms, from the lichen Parmotrema tsavoense . Molecules 2019; 24: 1527
    CrossrefPubMedGoogle Scholar
  • 9 Nguyen DM, Do LM, Nguyen VT, Chavasiri W, Mortier J, Nguyen PP. Phenolic compounds from the lichen Lobaria orientalis . J Nat Prod 2017; 80: 261-268
    CrossrefPubMedGoogle Scholar
  • 10 Gunzinger J, Tabacchi R. Isolement et identification de lʼacide furfurique, nouvelle depsidone du lichen Pseudevernia furfuracea (L.). Ach Helv Chim Acta 1985; 68: 1936-1939
    PubMedGoogle Scholar
  • 11 Kinoshita K, Takatori K, Narui T. A novel secondary metabolite from Lethariella sernanderi . Heterocycles 2004; 63: 1023-1026
    CrossrefPubMedGoogle Scholar
  • 12 Culberson CF. Chemical and botanical Guide to Lichen Products. Chapel Hill: University of North Carolina Press; 1969: 85-93
    Google Scholar
  • 13 Elix JA, Whitton AA, Sargent MV. Recent Progress in the Chemistry of Lichen Substances. Fortschritte der Chemie organischer Naturstoffe/Progress in the Chemistry of organic natural Products. Vienna: Springer; 1984: 103-234
    Google Scholar
  • 14 Elix JA, Jones AJ, Lajide L, James PW. Two new diphenyl ethers and a new depside from the lichen Micarea prasina Fr. Aust J Chem 1984; 37: 2349-2364
    CrossrefPubMedGoogle Scholar
  • 15 Elix JA, Gaul KL. The interconversion of the lichen depsides para- and meta-scrobiculin, and the biosynthetic implications. Aust J Chem 1986; 39: 613-624
    CrossrefPubMedGoogle Scholar
  • 16 Elix JA, Jenie UA, Parker JL. A novel synthesis of the lichen depsidones divaronic acid and stenosporonic acid, and the biosynthetic implications. Aust J Chem 1987; 40: 1451-1464
    CrossrefPubMedGoogle Scholar
  • 17 Elix JA, Naidu R, Thor G. Cyclographin, a new depsidone from the lichen Catarraphia dictyoplaca . Aust J Chem 1995; 48: 635-649
    CrossrefPubMedGoogle Scholar
  • 18 Huneck S. New Results on the Chemistry of Lichen Substances. Fortschritte der Chemie organischer Naturstoffe/Progress in the Chemistry of organic natural Products. Vienna: Springer; 2001: 1-276
    Google Scholar
  • 19 Boustie J, Grube M. Lichens – a promising source of bioactive secondary metabolites. Plant Genet Resour 2005; 3: 273-287
    CrossrefPubMedGoogle Scholar
  • 20 Schinkovitz A, Le Pogam P, Derbré S, Roy-Vessieres E, Blanchard P, Thirumaran SL, Breard D, Aumond MC, Zehl M, Urban E, Kaur A. Secondary metabolites from lichen as potent inhibitors of advanced glycation end products and vasodilative agents. Fitoterapia 2018; 131: 182-188
    CrossrefPubMedGoogle Scholar
  • 21 Kekuda TP, Lavanya D, Pooja R. Lichens as promising resources of enzyme inhibitors: A review. J Drug Deliv Ther 2019; 9: 665-676
    PubMedGoogle Scholar
  • 22 Kumar K, Siva B, Sarma VU, Mohabe S, Reddy AM, Boustie J, Tiwari AK, Rao NR, Babu KS. UPLC-MS/MS quantitative analysis and structural fragmentation study of five Parmotrema lichens from the Eastern Ghats. J Pharm Biomed Anal 2018; 156: 45-57
    CrossrefPubMedGoogle Scholar
  • 23 Rama Krishna B, Ramakrishna S, Rajendra S, Madhusudana K, Mallavadhani UV. Synthesis of some novel orsellinates and lecanoric acid related depsides as α-glucosidase inhibitors. J Asian Nat Prod Res 2019; 21: 1013-1027
    CrossrefPubMedGoogle Scholar
  • 24 Gómez-Serranillos MP, Fernández-Moriano C, González-Burgos E, Divakar PK, Crespo A. Parmeliaceae family: phytochemistry, pharmacological potential and phylogenetic features. RSC Adv 2014; 4: 59017-59047
    CrossrefPubMedGoogle Scholar
  • 25 Verma N, Behera BC, Sharma BO. Glucosidase inhibitory and radical scavenging properties of lichen metabolites salazinic acid, sekikaic acid and usnic acid. Hacettepe J Biol Chem 2012; 40: 7-21
    PubMedGoogle Scholar
  • 26 Nguyen TH, Um BH, Kim SM. Two unsaturated fatty acids with potent α-glucosidase inhibitory activity purified from the body wall of sea cucumber (Stichopus japonicus). J Food Sci 2011; 76: H208-H214
    CrossrefPubMedGoogle Scholar