Isolation of Guttiferones from Renewable Parts of Symphonia globulifera by Centrifugal Partition Chromatography

Abstract

The aim of this study was to investigate the species Symphonia globulifera, a source of polycyclic polyprenylated acyl phloroglucinols such as guttiferone A, which is known to exhibit a variety of biological activities including noticeable antileishmanial properties. Our goal was the identification and the quantification of guttiferone A in different renewable parts of S. globulifera and its preparative isolation. To the best of our knowledge, there is no data concerning its mechanism of action. Consequently, it is particularly interesting to isolate it in gram quantities in order to establish structure activity relationship studies. After performing high-performance liquid chromatography profiles detecting the presence of guttiferone A and proceeding to its quantification, a centrifugal partition chromatography methodology using a two-phase solvent system of cyclohexane/ethyl acetate/methanol/water (20 : 1 : 20 : 1, v/v/v/v) was applied to each extract. In conclusion, a centrifugal partition chromatography system has been developed to ensure a fast, reliable, and scalable way to isolate, with a high level of purity, guttiferone A from five renewable parts of S. globulifera. Moreover, this methodology can be extended to the isolation of other polycyclic polyprenylated acyl phloroglucinols such as guttiferones B, C, and D.

Biotransformation of guttiferones, Symphonia globulifera metabolites, by Bipolaris cactivora, an endophytic fungus isolated from its leaves

“…Guttiferones A (1) and C (6) were obtained as described. 24 Trifluoroacetic acid and formic acid were of reagent grade from Fluka. Gradient grade HiPersSolv acetonitrile from VWR was used.…”

“…1 Guttiferone A and oxy-guttiferones, the xanthone derivatives guttiferone A (1) shows a broad spectrum of activity, such as anti-HIV, 18 cytotoxic, 19 trypanocidal, 20 antiplasmodial, 21 leishmanicidal, 22 and antibacterial 23 effects, and can be extracted on a gram scale. 24 It belongs to the polycyclic polyprenyl acyl phloroglucinol family (PPAPs) which has been exclusively isolated from the plants of family Guttiferae. Some semisynthetic derivatives has been synthetized through the modification of catechol moiety and the phloroglucinol ring in order to reduce its toxicity and increase its antiparasitic activity.…”

Guttiferone A Aggregates Modulate Silent Information Regulator 1 (SIRT1) Activity

“…Guttiferone A ( 2 ) was extracted from Symphonia globulifera extract following a reported procedure . Hyperforin ( 3 ) was extracted from a petroleum ether extract of Hypericum perforatum following a reported procedure .…”

“…The results showed that renewable organs/tissues could be used as starting material for the production of PPAPs, thereby reducing the impact on the biodiversity. We also succeeded in isolating the guttiferone A ( 2 , Chart ) from the latex in large quantity, permitting its use in biological research. , Therefore, we decided to test the guttiferone A ( 2 ), structurally close to the guttiferone G, on SIRT1, and to carry out subsequent structure–activity relationship studies. Other PPAPs such as hyperforin ( 3 ) and its derivative aristoforin ( 4 , Chart ) were also included in the study to serve as positive control.…”