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
› Author Affiliations
Further Information

Publication History

received 07 February 2019
revised 18 March 2019

accepted 26 March 2019

Publication Date:
09 April 2019 (online)


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.

* 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

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