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Prenylated Coumarins from the Fruits of Manilkara zapota with Potential Anti-inflammatory Effects and Anti-HIV Activities
journal contribution
posted on 2019-10-17, 15:55 authored by Yan-Ping Liu, Gui Yan, Jia-Ming Guo, Yun-Yao Liu, Yu-Jie Li, Ying-Ying Zhao, Lei Qiang, Yan-Hui FuManilkara
zapota, usually known as Sapodilla,
is a fairly slow-growing evergreen tropical tree which belongs to
the genus Manilkara (Sapotaceae), indigenous to Central
America, southern Mexico, and the Caribbean. The ripe fruits of M. zapota have been widely consumed as an uniquely flavored
tropical fruit and verified to hold a variety of health benefits.
In order to investigate the potential health-promoting chemical compositions
from the fruits of M. zapota cultivated in Hainan
Island of China, a systematic and in-depth phytochemical study on
this fruit was accordingly implemented. In our current study, three
new prenylated coumarins, manizapotins A–C (1–3), together with seven known prenylated coumarins (4–10), were separated from the fruits
of M. zapota. The chemical structures of new prenylated
coumarins 1–3 were unambiguously
established by means of comprehensive spectroscopic analyses, and
the known compounds 4–10 were determined
by comparing their experimental spectral data with those described
data in the literature. This is the first time to discover prenylated
coumarins occurring in M. zapota. The potential anti-inflammatory
effects and anti-HIV (human immunodeficiency virus) activities of
all these separated prenylated coumarins were assessed. Prenylated
coumarins 1–10 dispalyed remarkable
inhibitory effects against nitric oxide production induced by lipopolysaccharide
in mouse macrophage RAW 264.7 cells with the IC50 values
equivalent to that of hydrocortisone in vitro. Meanwhile, prenylated
coumarins 1–10 exhibited pronounced
anti-HIV-1 reverse transcriptase activities with the EC50 values in range of 0.12–8.69 μM. These results suggest
that appropriate and reasonable consumption of the fruits of M. zapota might assist people to prevent and reduce the
occurrence of inflammatory diseases together with the infection of
HIV. Furthermore, the discovery of these prenylated coumarins from
the fruits of M. zapota holding pronounced anti-inflammatory
effects along with anti-HIV activities could be of great significance
to the research and development of new natural anti-inflammatory and
anti-HIV agents.