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

Sianne L. Schwikkard, Hannah Whitmore, Timothy Corson, Kamakshi Sishtla, Moses K. Langat, Mark Carew, Dulcie A. Mulholland

Research output: Contribution to journalArticle

3 Citations (Scopus)

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 )-17 α ,23-epoxy-3 β ,22 β ,29-trihydroxylanost-8-en-27,23-olide 5 , and ( 17S, 23S )-17 α ,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.

Original languageEnglish (US)
JournalPlanta Medica
DOIs
StateAccepted/In press - Feb 28 2018

Fingerprint

Cytotoxicity
Neutral Red
Middle East
Caco-2 Cells
Far East
Methylene Chloride
Endothelial cells
Traditional Medicine
Human Activities
Medicine
4-chromanone
Assays
Cell Survival
Endothelial Cells
Cells
Derivatives

Keywords

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

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

Antiangiogenic Activity and Cytotoxicity of Triterpenoids and Homoisoflavonoids from Massonia pustulata and Massonia bifolia . / Schwikkard, Sianne L.; Whitmore, Hannah; Corson, Timothy; Sishtla, Kamakshi; Langat, Moses K.; Carew, Mark; Mulholland, Dulcie A.

In: Planta Medica, 28.02.2018.

Research output: Contribution to journalArticle

Schwikkard, Sianne L. ; Whitmore, Hannah ; Corson, Timothy ; Sishtla, Kamakshi ; Langat, Moses K. ; Carew, Mark ; Mulholland, Dulcie A. / Antiangiogenic Activity and Cytotoxicity of Triterpenoids and Homoisoflavonoids from Massonia pustulata and Massonia bifolia . In: Planta Medica. 2018.
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AU - Corson, Timothy

AU - Sishtla, Kamakshi

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AU - Carew, Mark

AU - Mulholland, Dulcie A.

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