In silico studies of bis-spiro- and Furano-Labdane diterpenoids from Rydingia persica Scheen (Otostegia persica) as α-glucosidase enzyme inhibitor

Abstract

The inhibition potential of α-glucosidase enzyme by crude- dichloromethane, methanol, and ethanol -extracts of Rydingia persica were evaluated using colorimetric method. We have isolated four labdane diterpenoids: 15, 16- epoxy-3α, 7β, 9α -trihydroxylabdan-13- (16), 14-dien-6-one (1), 15, 16- epoxy-3α, 7α, 9α -trihydroxylabdan-13- (16), 14-dien-6-one (2), 9, 13, 15, 16-diepoxy- 3α, 7β, 15α (β)- trihydroxy-labdan- 6 one (3, 4) from the most potent enzyme inhibitor fraction; the ethyl acetate soluble part of ethanol extract of the aerial parts of R. persica. The structures of the compounds were elucidated by their ¹H and¹³C NMR and ESIMS spectral data analyses. The enzyme inhibition potential of the compounds was evaluated against acetylcholine esterase (AChE) and α-glucosidase by simulation studies. The predicted binding energy of most diterpenes towards mouse AChE enzyme was low, while the binding energy of diterpenes towards α-glucosidase enzyme was moderate to potent.

Graphical Abstract

Keywords:

• α-Glucosidase
• acetylcholinesterase
• Rydingia persica
• labdane diterpene
• Lamiaceae

Acknowledgment

The authors appreciate Mr. Mehdi Zare at Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences (MNCRC), Shiraz, Iran for collection and identification of the plant.

Disclosure statement

The Authors declare no financial or ethical interests. Amir Reza Jassbi is the scientific mentor and founder of “Aryana Phytochemistry of Tirazis” a start-up company.

Additional information

Funding

Research reported in this publication was supported (ARJ) by Elite Researcher Grant Committee under award number [988197] from the National Institutes for Medical Research Development (NIMAD), Tehran, Iran as well as Golestan University. MD thanks for a PhD student position supported by Golestan University.