First report of antioxidative abeo-oleanenes from red seaweed Gracilaria salicornia as dual inhibitors of starch digestive enzymes
- 31 Downloads
Carbolytic enzyme-associated cascades have been considered as potential curative target in attenuating diabetic mellitus pathogenesis. Two oleanene class of triterpenoids characterised as 24(4 → 23), 27(8 → 26), 30(20 → 29)-tris-abeo-olean-(12-oxo)-1,15,22-triene-methyl hept-5-enoate (1) and 24(4 → 23)-abeo-olean-(12-oxo)-3,5-diene-deconoate (2) with potential inhibitory activities against the starch digestive enzymes α-glucosidase and α-amylase, were purified from the organic extract of intertidal red seaweed Gracilaria salicornia (family Gracilariaceae). Structural interpretation of compounds was carried out by detailed spectroscopic analysis, and their antioxidant/anti-diabetic potentials were assessed. Inhibitory potential of abeo-oleanene derivative (2) towards the starch digestive enzymes, α-glucosidase (IC50 0.29 mM) and α-amylase (IC50 0.32 mM) were greater than those displayed by its abeo-oleanene chemotype 1 (IC50 0.34–0.40 mM). The molecular modelling studies were performed to designate the α-amylase and α-glucosidase inhibitory mechanism of oleanene analogues, and the comparison of docking parameters suggested that compound 2 exhibited least binding energy of −10.04 and −9.84 kcal mol−1 towards α-amylase and α-glucosidase respectively, and those results were corroborated with its greater inhibition potential against carbolytic enzymes. These results demonstrated that abeo-oleanene derivative (2) might constitute prospective anti-hyperglycaemic pharmaceutical candidate to moderate the likelihood of type-II diabetes.
KeywordsGracilaria salicornia Gracilariaceae Abeo-oleanenes Anti-diabetic Starch digestive enzymes Biosynthetic pathway
The present work was supported by Science and Engineering Research Board (SERB) (grant number SR/S1/OC-96A/2012) of Department of Science and Technology, New Delhi, India. The authors thank the Director, Indian Council of Agricultural Research-Central Marine Fisheries Research Institute (ICAR-CMFRI), and Head, Marine Biotechnology Division, ICAR-CMFRI for guidance and support.
Compliance with ethical standards
Conflict of interest
The authors declare that they have no conflict of interest.
This article does not contain any studies with human participants or animals performed by any of the authors.
- Antony T, Chakraborty K (2018) First report of antioxidant abeo-labdane type diterpenoid from intertidal red seaweed Gracilaria salicornia with 5-lipoxygenase inhibitory potential. Nat Prod Res https://doi.org/10.1080/14786419.2018.1508150
- Da Rocha CQ, Vilela FC, Santa-Cecilia FV, Cavalcante GP, Vilegas W, Giusti-Paiva A, Dos Santos MH (2015) Oleanane-type triterpenoid: an anti-inflammatory compound of the roots Arrabidaea brachypoda. Rev Bras Farmacogn 25:228–232Google Scholar
- Goldstein BJ, Ahmad F, Ding W, Li PM, Zhang WR (1998) Regulation of the insulin signaling pathway by cellular protein-tyrosine phosphatases. Mol Cell Biol 182:91–99Google Scholar
- Hamdan II, Afifi FU (2004) Studies on the in vitro and in vivo hypoglycemic activities of some medicinal plants used in treatment of diabetes in Jordanian traditional medicine. J Ethanopharmacol 93:117–121Google Scholar
- Hassan EM, Mohammed MMD, Mohamed SM (2012) Two new phorbol-type diterpene esters from Synadenium grantii Hook F. leaves. Rec Nat Prod 6:255–262Google Scholar
- Hyun TK, Eom SH, Kim J-S (2014) Molecular docking studies for discovery of plant-derived α-glucosidase inhibitors. POJ 7:166–170Google Scholar
- Koay YC, Wong KC, Osman H, Eldeen IMS, Asmawi MZ (2013) Chemical constituents and biological activities of Strobilanthes crispus L. Rec Nat Prod 7:59–64Google Scholar
- Kwon YI, Apostolidis E, Kim YC, Shetty K (2007) Health benefits of traditional corn, beans and pumpkin: in vitro studies for hyperglycemia and hypertension management. J Med Food 10:266–275Google Scholar
- Perera PRD, Ekanayake S, Ranaweera KKDS (2013) In vitro study on antiglycation activity, antioxidant activity and phenolic content of Osbeckia octandra L. leaf decoction. J Pharmacogn. Phytochem 2:198–201Google Scholar
- Sekar S, Viswanathan KP, Kishnan B, Ganesan KK (2015) Evaluation of anti-hyperglycemic effect of Gracilaria corticata extract in normal and streptozotocin-induced diabetic rats. Chem. Biol Lett 2:6–11Google Scholar