New α-Glucosidase Inhibitory Triterpenic Acid from Marine Macro Green Alga Codium dwarkense Boergs

Abstract

The marine ecosystem has been a key resource for secondary metabolites with promising biological roles. In the current study, bioassay-guided phytochemical investigations were carried out to assess the presence of enzyme inhibitory chemical constituents from the methanolic extract of marine green alga—Codium dwarkense. The bioactive fractions were further subjected to chromatographic separations, which resulted in the isolation of a new triterpenic acid; dwarkenoic acid (1) and the known sterols; androst-5-en-3β-ol (2), stigmasta-5,25-dien-3β,7α-diol (3), ergosta-5,25-dien-3β-ol (4), 7-hydroxystigmasta-4,25-dien-3-one-7-O-β-d-fucopyranoside (5), 7-hydroxystigmasta-4,25-dien-3-one (6), and stigmasta-5,25-dien-3β-ol (7). The structure elucidation of the new compound was carried out by combined mass spectrometry and 1D (1H and 13C) and 2D (HSQC, HMBC, COSY, and NOESY) NMR spectroscopic data. The sub-fractions and pure constituents were assayed for enzymatic inhibition of alpha-glucosidase. Compound 1 showed significant inhibition at all concentrations. Compounds 2, 3, 5, and 7 exhibited a dose-dependent response, whereas compounds 4–6 showed moderate inhibition. Utilizing such marine-derived biological resources could lead to drug discoveries related to anti-diabetics.

Screening of Ulva rigida, Gracilaria sp., Fucus vesiculosus and Saccharina latissima as Functional Ingredients

“…Our results are in accordance with previous studies that analyzed the effect on α-glucosidase of F. vesiculosus ’ fucoidans [ 22 ] with an IC 50 > 50 mg/mL and commercially-available polyphenol extracts [ 49 , 50 ], with IC 50 of 0.604 µg/mL and 5 µg/mL, respectively, when obtained with hot water but further purified with ultrafiltration. Certain molecules from other seaweed species have also been studied for their ability to inhibit α-glucosidase, particularly, a triterpenoid from Padina boergesenii [ 51 ], a triterpenic acid from Codium dwarkense [ 52 ], octaphlorethol A from Ishige foliacea [ 53 ] and crude extracts from Grateloupia elliptica [ 54 ], with IC 50 ’s of <100 µg/mL, 3.31 µg/mL, 109 µg/mL and 20 µg/mL, respectively. However, these compounds were again obtained through extensive purification procedures with organic solvent extraction and column fractionation.…”

Marine natural products

“…Also reported were diterpenoids, 731-733, an a-tocopheroid 734, a sterol 735 along with 12 known compounds from Caulerpa racemosa 504 and a triterpene acid 736 from Codium dwarkense. 505 The diterpenoid 733 and the a-tocopheroid 734 are the rst natural products to contain the haematinic acid and 3,5dimethylphenoxy motifs respectively.…”

New Enzyme-Inhibitory Triterpenoid from Marine Macro Brown Alga Padina boergesenii Allender & Kraft

“…In this regard, prospects have shown that various terrestrial and aquatic plants possess novel chemical constituents, which could help in inhibiting α-glucosidase activity in diabetic conditions [ 17 ]. Previously, aquatic- and/or marine-derived plants have been reported to provide potent resources for finding α-glucosidase inhibitors, as described by one of our previous communications [ 18 ] and those by other researchers [ 19 ].…”