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Planta Med 2019; 85(11/12): 1034-1039
DOI: 10.1055/a-0889-0412
Biological and Pharmacological Activities
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Antiangiogenic Iridoids from Stachys ocymastrum and Premna resinosa [*]

Anna Maria Iannuzzi   **
1   Dipartimento di Farmacia, Università di Pisa, Pisa, Italy
,
César Muñoz Camero   **
1   Dipartimento di Farmacia, Università di Pisa, Pisa, Italy
,
Massimiliano DʼAmbola
2   Dipartimento di Farmacia, Università di Salerno, Fisciano (SA), Italy
,
Valeria DʼAngelo
3   Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche e Ambientali, Università degli Studi di Messina, Messina, Italy
,
Smain Amira
4   Department of Animal Biology and Physiology, University of Setif, Setif, Algeria
,
Ammar Bader
5   Department of Pharmacognosy, Faculty of Pharmacy, Umm Al-Qura University, Makkah, Saudi Arabia
,
Alessandra Braca
1   Dipartimento di Farmacia, Università di Pisa, Pisa, Italy
6   Centro Interdipartimentale di Ricerca “Nutraceutica e Alimentazione per la Salute”, Università di Pisa, Pisa, Italy
,
Nunziatina De Tommasi
2   Dipartimento di Farmacia, Università di Salerno, Fisciano (SA), Italy
,
Maria Paola Germanò
3   Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche e Ambientali, Università degli Studi di Messina, Messina, Italy
› Institutsangaben
Weitere Informationen

Publikationsverlauf

received 07. Februar 2019
revised 18. März 2019

accepted 26. März 2019

Publikationsdatum:
09. April 2019 (online)

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Abstract

In this paper, the isolation of one new iridoid glucoside, 6β-acetoxyipolamiide (1), and thirteen (2 – 14) known congeners from two Lamiaceae species, Stachys ocymastrum and Premna resinosa, leaf extracts is reported. The structural determination of the isolated compounds was performed by mono- and bidimensional NMR spectroscopic analysis as well as MS experiments. The isolates were assayed for their antiangiogenic activity by two in vivo models, zebrafish embryos and chick chorioallantoic membrane assays. The compounds with a significant antiangiogenic activity in both assays were β-hydroxyipolamiide (2), ipolamiide (3), and buddlejoside A5 (8). 6-O-α-l-(3″-O-p-Methoxycinnamoyl-4″-O-acetyl)rhamnopyranosyl catalpol (13) and 6-O-α-l-(2″-trans-caffeoyl)rhamnopyranosyl catalpol (6) showed the best antiangiogenic response on blood vessel growth in zebrafish embryos, whereas saccatoside (10) and 6-O-α-l-(2″-O - p-methoxycinnamoyl-3″-O-acetyl)rhamnopyranosyl catalpol (14) resulted in a strong reduction of capillary formation in the chorioallantoic membrane assay.

Key words

Stachys ocymastrum - Premna resinosa - Lamiaceae - iridoids - antiangiogenic activity - chick chorioallantoic membrane - zebrafish

* Dedicated to Professor Dr. Cosimo Pizza 70th birthday in recognition of his outstanding contribution to natural product research.


** These two authors contributed equally to this work.


Supporting Information

 

  • References

  • 1 Dinda B, Debnath S, Harigaya Y. Naturally occurring iridoids. A review, part 1. Chem Pharm Bull 2007; 55: 159-222
    CrossrefPubMedGoogle Scholar
  • 2 Tundis R, Loizzo MR, Menichini F, Statti GA, Menichini F. Biological and pharmacological activities of iridoids: recent developments. Mini Rev Med Chem 2008; 8: 399-420
    CrossrefPubMedGoogle Scholar
  • 3 Camero CM, Germanò MP, Rapisarda A, DʼAngelo V, Amira S, Benchikh F, Braca A, De Leo M. Anti-angiogenic activity of iridoids from Galium tunetanum . Rev Bras Farmacogn 2018; 28: 374-377
    PubMedGoogle Scholar
  • 4 Beladjila KA, Kabouche Z, Germanò MP, DʼAngelo V, De Tommasi N, DʼAndrea F, Braca A, De Leo M. Antiangiogenic Activity of Compounds from Anarrhinum pedatum . J Nat Prod 2019; 82: 510-519
    CrossrefPubMedGoogle Scholar
  • 5 Laszczyk MN. Pentacyclic triterpenes of the lupane, oleanane and ursane group as tools in cancer therapy. Planta Med 2009; 75: 1549-1560
    Artikel in Thieme ConnectPubMedGoogle Scholar
  • 6 Lay IS, Chiu JH, Shiao MS, Lui WY, Wu CW. Crude extract of Salvia miltiorrhiza and salvianolic acid B enhance in vitro angiogenesis in murine SVR endothelial cell line. Planta Med 2003; 69: 26-32
    Artikel in Thieme ConnectPubMedGoogle Scholar
  • 7 Dadach M, Mehdadi Z, Adjouj AL. Evaluation of the tolerance to temperature and salinity on seed germination of three Lamiaceae from Algerian Scrubland. Adv Res Life Sci 2018; 2: 11-15
    PubMedGoogle Scholar
  • 8 Adema F. Iridoid glucosides of species of Lamium and some related genera. Acta Bot Neerl 1968; 17: 423-430
    CrossrefPubMedGoogle Scholar
  • 9 Lakhal H, Boudiar T, Kabouche A, Laggoune S, Kabouche Z, Topcu G. Antioxidant activity and flavonoids of Stachys ocymastrum . Chem Nat Compd 2011; 46: 964-965
    CrossrefPubMedGoogle Scholar
  • 10 El-Gazzar A, Hammouda AA. Nine revived records to the Flora of Egypt. Egypt J Biol 2006; 8: 74-80
    PubMedGoogle Scholar
  • 11 Albadawi DA, Mothana RA, Khaled JM, Ashour AE, Kumar A, Ahmad SF, Al-Said MS, Al-Rehaily AJ, Almusayeib NM. Antimicrobial, anticancer, and antioxidant compounds from Premna resinosa growing in Saudi Arabia. Pharm Biol 2017; 55: 1759-1766
    CrossrefPubMedGoogle Scholar
  • 12 Rekha K, Richa PK, Babu S, Rao M. A phytochemistry of the genus Premna: a review. Int J Pharm Chem Sci 2015; 4: 317-325
    PubMedGoogle Scholar
  • 13 Njeru SN, Obonyo MA, Nyambati SO, Ngari SM. Antimicrobial and cytotoxicity properties of the crude extracts and fractions of Premna resinosa (Hochst.) Schauer (Compositae): Kenyan traditional medicinal plant. BMC Complement Altern Med 2015; 15: 295
    CrossrefPubMedGoogle Scholar
  • 14 Abdallah Q, Al-Deeb I, Bader A, Hamam F, Saleh K, Abdulmajid A. Anti-angiogenic activity of Middle East medicinal plants of the Lamiaceae family. Mol Med Rep 2018; 18: 2441-2448
    PubMedGoogle Scholar
  • 15 Frezza C, Venditti A, Matrone G, Serafini I, Foddai S, Bianco A, Serafini M. Iridoid glycosides and polyphenolic compounds from Teucrium chamaedrys L. Nat Prod Res 2018; 32: 1583-1589
    CrossrefPubMedGoogle Scholar
  • 16 De Luca C, Guiso M, Martino C. 6β-Hydroxyipolamiide, an iridoid glucoside from Stachytarpheta mutabilis . Phytochemistry 1983; 22: 1185-1187
    CrossrefPubMedGoogle Scholar
  • 17 Tasdemir D, Scapozza L, Zerbe O, Linden A, Çalis I, Sticher O. Iridoid glycosides of Leonurus persicus . J Nat Prod 1999; 62: 811-816
    CrossrefPubMedGoogle Scholar
  • 18 Yalçın FN, Ersöz T, Avcı K, Gotfredsen CH, Jensen SR, Çalış İ. New iridoid glycosides from Lamium eriocephalum subsp. eriocephalum . Helv Chim Acta 2007; 90: 332-336
    CrossrefPubMedGoogle Scholar
  • 19 Güvenalp Z, Özbek H, Ünsalar T, Kazaz C, Demirezer LÖ. Iridoid, flavonoid, and phenylethanoid glycosides from Wiedemannia orientalis . Turk J Chem 2006; 30: 391-400
    PubMedGoogle Scholar
  • 20 Otsuka H, Kubo N, Yamasaki K, Padolina WG. Two iridoid glycoside caffeoyl esters from Premna odorata . Phytochemistry 1989; 28: 513-515
    CrossrefPubMedGoogle Scholar
  • 21 Otsuka H, Sasaky Y, Kubo N, Yamasaki K, Takeda Y, Seki T. Isolation and structure elucidation of mono-and diacyl-iridoid diglycosides from leaves of Premna japonica . J Nat Prod 1991; 54: 547-553
    CrossrefPubMedGoogle Scholar
  • 22 Miyase T, Akahori C, Kohsaka H, Ueno A. Acylated Iridoid Glycosides from Buddleja japonica HEMSL. Chem Pharm Bull 1991; 39: 2944-2951
    CrossrefPubMedGoogle Scholar
  • 23 Warashina T, Miyase T, Ueno A. Iridoid glycosides from Verbascum thapsus L. Chem Pharm Bull 1991; 39: 3261-3264
    CrossrefPubMedGoogle Scholar
  • 24 Otsuka H, Sasaki Y, Yamasaki K, Takeda Y, Seki T. Iridoid diglycoside monoacyl esters from the leaves of Premna japonica . J Nat Prod 1990; 53: 107-111
    CrossrefPubMedGoogle Scholar
  • 25 Calis I, Gross GA, Winkler T, Sticher O. Isolation and structure elucidation of two highly acylated iridoid diglycosides from Scrophularia scopolii . Planta Med 1988; 54: 168-170
    Artikel in Thieme ConnectPubMedGoogle Scholar
  • 26 Falsone G, Laryea MD, Crea AEG, Finner E. Iridoide aus Verbascum sinuatum . Planta Med 1982; 44: 150-153
    Artikel in Thieme ConnectPubMedGoogle Scholar
  • 27 Quezada M, Alvarez M, Peña OA, Henŕiquez S, dʼ Alençon CA, Lange S, Oliva B, Owen GI, Allende ML. Antiangiogenic, antimigratory and antiinflammatory effects of 2-methoxyestradiol in zebrafish larvae. Comp Biochem Phys C 2013; 157: 141-149
    PubMedGoogle Scholar
  • 28 Han Y, Shen M, Tang LY, Tan G, Yang QC, Ye L, Ye LH, Jiang N, Gao GP, Shao Y. Antiangiogenic effects of catalpol on rat corneal neovascularization. Mol Med Rep 2018; 17: 2187-2194
    PubMedGoogle Scholar
  • 29 Widyowati R, Tezuka Y, Miyahara T, Awale S, Kadota S. Alkaline phosphatase (ALP) enhancing iridoid glucosides from the Indonesian medicinal plant Barleria lupulina . Nat Prod Comm 2010; 5: 1711-1716
    PubMedGoogle Scholar
  • 30 De Leo M, Peruzzi L, Granchi C, Tuccinardi T, Minutolo F, De Tommasi N, Braca A. Constituents of Polygala flavescens ssp. flavescens and their activity as inhibitors of human lactate dehydrogenase. J Nat Prod 2017; 80: 2077-2087
    CrossrefPubMedGoogle Scholar
  • 31 Kimmel CB, Ballard WW, Kimmel SR, Wullmann B, Schilling TF. Stages of embryonic development of zebrafish. Develop Dynam 1995; 203: 253-310
    CrossrefPubMedGoogle Scholar
  • 32 Germanò MP, Certo G, DʼAngelo V, Sanogo R, Malafronte N, De Tommasi N, Rapisarda A. Anti-angiogenic activity of Entada africana root. Nat Prod Res 2015; 29: 1551-1556
    CrossrefPubMedGoogle Scholar
  • 33 Certo G, Costa R, DʼAngelo V, Russo M, Albergamo A, Dugo G, Germanò MP. Anti-angiogenic activity and phytochemical screening of fruit fractions from Vitex agnus castus . Nat Prod Res 2017; 31: 2850-2856
    CrossrefPubMedGoogle Scholar