Antioxidative dolabellanes and dolastanes from brown seaweed Padina tetrastromatica as dual inhibitors of starch digestive enzymes

Antony, Tima and Chakraborty, Kajal and Joy, Minju (2021) Antioxidative dolabellanes and dolastanes from brown seaweed Padina tetrastromatica as dual inhibitors of starch digestive enzymes. Natural Product Research, 35 (4). pp. 614-626. ISSN 1478-6427 (Online)

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Abstract

New dolabellanes {6-methoxy-dolabella-8(17),12-diene-10β,18-diol (1), 3-methoxy-dolabella-12(18)-ene-4β-ol (2), 3-methoxy-dolabella-10,18(19)-diene-5α,8β-diol (3)} and dolastanes {2,7-dimethoxy-14α-hydroxy-dolasta-1(15),9-diene (4) and 4,7-dimethoxy-9β,14α-dihydroxy-dolasta-1-ene (5)} were identified from brown seaweed Padina tetrastromatica (family Dictyotaceae), collected from the southeast coast of India. Compounds 1–3 were found to possess dolabellane skeleton with [9.3.0] cyclotetradecane framework whereas, 4–5 were composed of tricyclic diterpenes with linear arrangement of six-seven-five fused alicyclic rings. Compounds 3 and 5 registered greater antioxidative activities (IC50 ≤0.63 mg/mL) than other analogues (IC50 ≥0.65 mg/mL), whereas their attenuating potentials against carbolytics α-amylase and α-glucosidase (IC50 ∼0.12–0.14 mg/mL) were comparable with those displayed by acarbose (IC50 0.14-0.12 mg/mL). Bioactive potentials of titled compounds were assessed by electronic and lipophilic parameters. The lesser binding energies of 3 (−9.71 kcal/mol) and 5 (−8.59 kcal/mol) through molecular docking demonstrated their effective hydrogen bonding interactions with α-amylase. Thus, dolabellanes and dolastanes might be used as anti-diabetic and antioxidant leads to reduce the risk of hyperglycaemia.

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