Planta Med 2018; 84(09/10): 638-644
DOI: 10.1055/a-0577-5322
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Antiangiogenic Activity and Cytotoxicity of Triterpenoids and Homoisoflavonoids from Massonia pustulata and Massonia bifolia

Sianne L. Schwikkard
1   School of Life Sciences, Pharmacy and Chemistry, Kingston University, Kingston-upon-Thames, United Kingdom
2   Natural Products Research Group, Department of Chemistry, Faculty of Engineering and Physical Sciences, University of Surrey, Guildford, United Kingdom
,
Hannah Whitmore
2   Natural Products Research Group, Department of Chemistry, Faculty of Engineering and Physical Sciences, University of Surrey, Guildford, United Kingdom
,
Timothy W. Corson
3   Eugene and Marilyn Glick Eye Institute, Department of Ophthalmology, Indiana University School of Medicine, Indianapolis, U. S. A.
,
Kamakshi Sishtla
3   Eugene and Marilyn Glick Eye Institute, Department of Ophthalmology, Indiana University School of Medicine, Indianapolis, U. S. A.
,
Moses K. Langat
2   Natural Products Research Group, Department of Chemistry, Faculty of Engineering and Physical Sciences, University of Surrey, Guildford, United Kingdom
4   School of Chemistry and Physics, University of KwaZulu-Natal, Durban, South Africa
,
Mark Carew
1   School of Life Sciences, Pharmacy and Chemistry, Kingston University, Kingston-upon-Thames, United Kingdom
,
Dulcie A. Mulholland
3   Eugene and Marilyn Glick Eye Institute, Department of Ophthalmology, Indiana University School of Medicine, Indianapolis, U. S. A.
4   School of Chemistry and Physics, University of KwaZulu-Natal, Durban, South Africa
› Author Affiliations
Further Information

Publication History

received 01 December 2017
revised 06 February 2018

accepted 08 February 2018

Publication Date:
28 February 2018 (online)

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Abstract

The Hyacinthaceae family (sensu APGII), with approximately 900 species in around 70 genera, plays a significant role in traditional medicine in Africa as well as across Europe and the Middle and Far East. The dichloromethane extract of the bulbs of Massonia pustulata (Hyacinthaceae sensu APGII) yielded two known homoisoflavonoids, (R)-5-hydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 1 and 5-hydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromone 2 and four spirocyclic nortriterpenoids, eucosterol 3, 28-hydroxyeucosterol 4 and two previously unreported triterpenoid derivatives, (17S,23S)-17α,23-epoxy-3β,22β,29-trihydroxylanost-8-en-27,23-olide 5, and (17S, 23S)-17α,23-epoxy-28,29-dihydroxylanost-8-en-3-on-27,23-olide 6. Compounds 1, 2, 3, and 5 were assessed for cytotoxicity against CaCo-2 cells using a neutral red uptake assay. Compounds 1, 2, and 5 reduced cell viability by 70% at concentrations of 30, 100, and 100 µM, respectively. Massonia bifolia yielded three known homoisoflavonoids, (R)-(4′-hydroxy)-5-hydroxy-7-methoxy-4-chromanone 1, (R)-(4′-hydroxy)-5,7-dihydroxy-4-chromanone 7 and (R)-(3′-hydroxy-4′-methoxy)-5,7-dihydroxy-4-chromanone 9, two previously unreported homoisoflavonoids, (E)-3-benzylidene-(3′,4′-dihydroxy)-5-hydroxy-7-methoxy-4-chromanone 8 and (R)-(3′,4′-dihydroxy)-5-hydroxy-7-methoxy-4-chromanone 10, and a spirocyclic nortriterpenoid, 15-deoxoeucosterol 11. Compounds 1, 1Ac, 7, 8, 9, and 10 were screened for antiangiogenic activity against human retinal microvascular endothelial cells. Some compounds showed dose-dependent antiproliferative activity and blocked endothelial tube formation, suggestive of antiangiogenic activity.

Key words

Massonia species - Hyacinthaceae - homoisoflavonoids - spirocyclic nortriterpenoids - cytotoxicity - angiogenesis

Supporting Information

    Photographs of plant material (1S), spectra for compounds 5, 6, 8, and 10 (2S), and results of HREC cell proliferation studies (3S) are available as Supporting Information.

  • Supporting Information
 

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