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Two rare antioxidative prenylated terpenoids from loop-root Asiatic mangrove Rhizophora mucronata (Family Rhizophoraceae) and their activity against pro-inflammatory cyclooxygenases and lipoxidase

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Relation http://eprints.cmfri.org.in/11345/
http://www.tandfonline.com/doi/abs/10.1080/14786419.2016.1174232?journalCode=gnpl20
 
Title Two rare antioxidative prenylated terpenoids from
loop-root Asiatic mangrove Rhizophora mucronata (Family
Rhizophoraceae) and their activity against pro-inflammatory
cyclooxygenases and lipoxidase
 
Creator Raola, Vamshi Krishna
Chakraborty, Kajal
 
Subject Bioactive compound
Fish Biotechnology
 
Description Two new biogenic prenylated terpenoids were isolated from the methanol
extract of Rhizophora mucronata. The extended C20 sesquiterpenoid
with prenylated guaiane framework was characterised as (4E, 8Z)-3,
3a, 6, 7-tetrahydro-3, 9-dimethyl-5-(6-methylheptan-2-yl) cycloocta[b]
furan-2-(9aH)-one (1). (35E)-1,2,3,5,6,6-icosahydro-4,4,8b,10,14,17,20,20-
octamethylpicen-3-yl-34,35-dimethyloct-31-enoate (2) represents
the first example of naturally occurring C40 prenylated oleanane-type
triterpenoid, whereas one 4,5-dimethyloct-5-enoate side chain remains
attached at C-3 position of the oleanane framework formed by the E-ring
closure of C30 saccharide moiety. The structures of the compounds were
elucidated using NMR and mass spectrometric analysis. Compound 1 was
found to have significantly greater antioxidant activities (IC50 ~ 0.75 mg/
mL) compared to 2 (IC50 > 0.80 mg/mL). No significant differences in
anti-cyclooxygenase-2 of these compounds were discernable (IC50
0.8 – 0.9 mg/mL), whilst compound 1 showed greater anti-5-lipoxidase
activities (IC50 ~ 0.8 mg/mL) those that of 2 (IC50 0.96 mg/mL). Bioactivities
of the prenylated terpenoids were inversely proportional to lipophilic
and bulk descriptors.
 
Publisher Taylor and Francis
 
Date 2016
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/11345/1/Two%20rare%20antioxidative%20prenylated%20terpenoids%20from_Natural%20Product%20Research_Kajal%20Chakraborty_2016.pdf
Raola, Vamshi Krishna and Chakraborty, Kajal (2016) Two rare antioxidative prenylated terpenoids from loop-root Asiatic mangrove Rhizophora mucronata (Family Rhizophoraceae) and their activity against pro-inflammatory cyclooxygenases and lipoxidase. Natural Product Research. pp. 1-10. ISSN 1478-6427 (Online)