Match!

Molecular Docking and Inhibition Kinetics of α-glucosidase Activity by Labdane Diterpenes Isolated from Tora Seeds (Alpinia nigra B.L. Burtt.)

Published on Feb 1, 2015in Applied Biochemistry and Biotechnology2.14
· DOI :10.1007/s12010-014-1366-4
Sudipta Ghosh6
Estimated H-index: 6
(Indian Institute of Science Education and Research, Bhopal),
Latha Rangan15
Estimated H-index: 15
(IITG: Indian Institute of Technology Guwahati)
Abstract
Current approach against type 2 diabetes involves α-glucosidase inhibitors like acarbose associated with many side effects. Therefore, as an alternative to the existing drug, many natural products mainly from plant sources have been investigated which inhibit α-glucosidase. Here, we have selected medicinally important Alpinia nigra to explore its α-glucosidase inhibitory activity. Organic extracts of seeds and two purified natural diterpenes I: (E)-labda-8(17), 12-diene-15, 16-dial and II: (E)-8β, 17-epoxylabd-12-ene-15, 16-dial from A. nigra were investigated towards inhibition of α-glucosidase activity. Dose-dependant inhibition pattern were observed for seed extracts and both the compounds. Further, inhibition kinetics studies of the diterpenes indicated a non-competitive type of inhibition against α-glucosidase. Docking studies were carried out which revealed that both the diterpenes interacted within the active site of N-terminal and C-terminal domain of human maltase-glucoamylase enzyme, respectively. This is the first report of α-glucosidase inhibitory activity of these isolated diterpenes and their higher inhibitory potential than any terpenoids studied till date against α-glucosidase.
  • References (40)
  • Citations (9)
📖 Papers frequently viewed together
8 Citations
1 Citations
7 Authors (Feng Guo, ..., Zhiguo Yu)
1 Citations
78% of Scinapse members use related papers. After signing in, all features are FREE.
References40
Newest
#1Sudipta Ghosh (IITG: Indian Institute of Technology Guwahati)H-Index: 6
Last. Latha Rangan (IITG: Indian Institute of Technology Guwahati)H-Index: 15
view all 3 authors...
Abstract The radical scavenging activity and the antibacterial properties of different solvent (hexane, ethyl acetate and methanol) extracts of Alpinia nigra seeds were investigated in the present study. All the extracts were used to assess their potential antioxidant activities using methods for scavenging of 2,2-diphenyl-1-picrylhydrazyl radical. Ethyl acetate and methanol extracts exhibited effective free radical scavenging activities compared to the standard antioxidant butylated hydroxyl to...
6 CitationsSource
#1Sudipta Ghosh (IITG: Indian Institute of Technology Guwahati)H-Index: 6
#2Kiran Indukuri (IITG: Indian Institute of Technology Guwahati)H-Index: 9
Last. Latha Rangan (IITG: Indian Institute of Technology Guwahati)H-Index: 15
view all 5 authors...
The labdane diterpene, (E)-labda-8(17), 12-diene-15, 16-dial (compound A) and its epoxide analogue, (E)-8β, 17-Epoxylabd-12-ene-15, 16-dial (compound B) were isolated from the seeds of Alpinia nigra for the first time. The antibacterial activities of both compounds were evaluated against three Gram-positive and four Gram-negative bacteria, and flow cytometric analysis revealed that these compounds caused significant damage to the bacterial cell membranes. Further, field emission scanning electro...
28 CitationsSource
#1Prinya Wongsa (MFU: Mae Fah Luang University)H-Index: 2
#2Jiranun Chaiwarit (MFU: Mae Fah Luang University)H-Index: 1
Last. Anis Zamaludien (MFU: Mae Fah Luang University)H-Index: 1
view all 3 authors...
Herbs that are commonly used in Thai dishes were selected for evaluation in order to determine their phenolic compounds, antioxidant activity, and in vitro potential inhibition against a-amylase and a-glu- cosidase. The total phenolic content ranged from 2.89 to 75.26 mg GAE/g dw. The three aqueous herb extracts with the highest total phenolic content were yellow-berried nightshade (Solanum xanthocar- pum), holy basil (Ocimum sanctum) and acacia (Acacia pennata). The antioxidant activity was exp...
42 CitationsSource
#1Jamnian Chompoo (Kadai: Kagoshima University)H-Index: 9
#2Atul Upadhyay (Kadai: Kagoshima University)H-Index: 9
Last. Shinkichi Tawata (University of the Ryukyus)H-Index: 25
view all 5 authors...
Advanced glycation end products (AGEs) are major factors responsible for the complication of diabetes. The present study was carried out to investigate the inhibitory activities on fructosamine adduct and a- dicarbonyl formations by hexane extracts of various parts of Alpinia zerumbet. Furthermore, we isolated two previously known compounds, namely 5,6-dehydrokawain (DK) and dihydro-5,6-dehydrokawain (DDK). 8(17),12-Labdadiene-15,16-dial (labdadiene) was isolated for the first time from the rhiz...
34 CitationsSource
#1Limei Ren (NKU: Nankai University)H-Index: 4
#2Xiaohong Qin (NKU: Nankai University)H-Index: 6
Last. Yuequan Shen (NKU: Nankai University)H-Index: 23
view all 7 authors...
Human maltase-glucoamylase (MGAM) hydrolyzes linear alpha-1,4-linked oligosaccharide substrates, playing a crucial role in the production of glucose in the human lumen and acting as an efficient drug target for type 2 diabetes and obesity. The amino- and carboxyl-terminal portions of MGAM (MGAM-N and MGAM-C) carry out the same catalytic reaction but have different substrate specificities. In this study, we report crystal structures of MGAM-C alone at a resolution of 3.1 A, and in complex with it...
78 CitationsSource
#1Sri Nurestri Abd Malek (UM: University of Malaya)H-Index: 17
#2Guan Serm Lee (UM: University of Malaya)H-Index: 5
Last. Syed Adnan Ali ShahH-Index: 16
view all 7 authors...
Investigations on the cytotoxic effects of the crude methanol and fractionated extracts (hexane, ethyl acetate) C. mangga against six human cancer cell lines, namely the hormone-dependent breast cell line (MCF-7), nasopharyngeal epidermoid cell line (KB), lung cell line (A549), cervical cell line (Ca Ski), colon cell lines (HCT 116 and HT-29), and one non-cancer human fibroblast cell line (MRC-5) were conducted using an in-vitro neutral red cytotoxicity assay. The crude methanol and fractionated...
36 CitationsSource
Diabetes is known as a multifactorial disease. The treatment of diabetes (Type II) is complicated due to the inherent patho-physiological factors related to this disease. One of the complications of diabetes is post-prandial hyperglycemia (PPHG). Glucosidase inhibitors, particularly α-amylase inhibitors are a class of compounds that helps in managing PPHG. Six ethno-botanically known plants having antidiabetic property namely, Azadirachta indica Adr. Juss.; Murraya koenigii (L.) Sprengel; Ocimum...
95 CitationsSource
AIDS and influenza are viral pandemics and remain one of the leading causes of human deaths worldwide. The increasing resistance of these diseases to synthetic drugs demands the search for novel compounds from plant-based sources. In this regard, the leaves and rhizomes of Alpinia zerumbet, a traditionally important economic plant in Okinawa, were investigated for activity against HIV-1 integrase (IN) and neuraminidase (NA). The aqueous extracts of leaves and rhizomes had IN inhibitory activity ...
34 CitationsSource
#1Kunga Mohan Ramkumar (Anna University)H-Index: 17
#2Balsamy Thayumanavan (TNAU: Tamil Nadu Agricultural University)H-Index: 3
Last. P. Rajaguru (Anna University)H-Index: 19
view all 4 authors...
The present study was attempted to investigate the effect of G. montanum leaf extract on inhibition of α-glucosidase and α-amylase activity. The ethanol extract of G. montanum (GLEt) at various concentrations (1–10 μg/ml) was tested for its inhibition pattern against α-glucosidase and α-amylase activity in vitro and compared with the commercially available α-glucosidase inhibitor, acarbose. The GLEt showed competitive inhibition against yeast α-glucosidase and noncompetitive inhibition against s...
38 CitationsSource
#1Tushar (IITG: Indian Institute of Technology Guwahati)H-Index: 3
#2Supriyo Basak (IITG: Indian Institute of Technology Guwahati)H-Index: 5
Last. Latha Rangan (IITG: Indian Institute of Technology Guwahati)H-Index: 15
view all 4 authors...
Abstract Aim of the study Family Zingiberaceae consists of large number of medicinal plants and is well known for its use in ethnomedicine. The objective of this study is to systematically analyse and document the traditional knowledge regarding the use of Zingiberaceous plants for the treatment of various human ailments from NE India, adding information to the valuation of biodiversity and, to forward suggestions for its sustainable use, conservation and for future pharmacological studies. Mate...
93 CitationsSource
Cited By9
Newest
#1Tahani Awin (UPM: Universiti Putra Malaysia)H-Index: 1
#2Ahmed Mediani (UiTM: Universiti Teknologi MARA)H-Index: 13
Last. Faridah Abas (UPM: Universiti Putra Malaysia)H-Index: 26
view all 7 authors...
ABSTRACTCurcuma mangga is a medicinal plant, and its rhizomes are often used to treat various conditions, such as fever, thorax pain, itching, stomachaches, skin diseases, gout, and asthma. Althoug...
1 CitationsSource
#1Mohammad Hossein Mehraban (UI: University of Isfahan)H-Index: 4
Last. Younes Ghasemi (Shiraz University of Medical Sciences)H-Index: 30
view all 8 authors...
Abstract The prevalence of diabetes mellitus has been incremented in the current century and the need for novel therapeutic compounds to treat this disease has been significantly increased. One of the most promising approaches is to inhibit intestinal alpha glucosidases. Based on our previous studies, four pyrimidine-fused heterocycles (PFH) were selected as they revealed satisfactory inhibitory action against mammalian α-glucosidase. The interaction of these compounds with both active domains o...
Source
#1Zhihua LiuH-Index: 1
#2Ying YangH-Index: 3
Last. Yuling LiuH-Index: 10
view all 12 authors...
α-glucosidase inhibitors (AGIs) have been an important category of oral antidiabetic drugs being widely exploited for the effective management of type 2 diabetes mellitus. However, the marketed AGIs not only inhibited the disaccharidases, but also exhibited an excessive inhibitory effect on α-amylase, resulting in undesirable gastrointestinal side effects. Compared to these agents, Ramulus Mori alkaloids (SZ-A), was a group of effective alkaloids from natural Morus alba L., and showed excellent ...
Source
#1Anusree Maneesh (CMFRI: Central Marine Fisheries Research Institute)H-Index: 4
#2Kajal Chakraborty (CMFRI: Central Marine Fisheries Research Institute)H-Index: 18
Abstract Previously undescribed frido oleanene triterpenoids 2 α -hydroxy-(28,29)- frido -olean-12(13), 21(22)-dien-20-propyl-21-hex-4′( Z ) - enoate, 2 α -hydroxy-(28,29)- frido -olean-12(13), 21(22)-dien-20-prop-2( E )-en-21-butanoate and oxygenated labdane diterpenoids 2 α -hydroxy-8(17), (12 E ), 14-labdatriene, 3 β , 6 β , 13 α -tri hydroxy 8(17), 12 E , 14-labdatriene were purified from the ethyl acetate-methanol and dichloromethane fractions of the air-dried thalli of Sargassum wightii (S...
4 CitationsSource
#1Aicha LaoudH-Index: 1
#2Fouad FerkousH-Index: 5
Last. Khaireddine Kraim ('ENS Paris': École Normale Supérieure)H-Index: 1
view all 6 authors...
Abstract In this study, a virtual screening procedure was applied to identify new potential nt-MGAM inhibitors as a possible medication for type 2 diabetes. To this aim, a series of salacinol analogues were first investigated by docking analysis for their binding to the X-ray structure of the biological target nt-MGAM. Key interactions for ligand binding into the receptor active site were identified which shared common features to those found for other known inhibitors, which strengthen the resu...
1 CitationsSource
#1Jiang Liu (Chongqing University)H-Index: 1
#2Xiansheng WangH-Index: 1
Last. Guizhao Liang (Chongqing University)H-Index: 15
view all 5 authors...
Source
A dried infusion prepared from the aerial parts of Salvia circinata did not provoke acute toxicity in mice (LD50 > 5 g/kg). This infusion showed poor hypoglycemic and antihyperglycemic effects (100–570 mg/kg) when tested in normal and hyperglycemic mice using acute and oral glucose tolerance tests, respectively. However, this infusion possessed antihyperglycemic action in vivo during an oral sucrose tolerance test (31.6–316 mg/kg), suggesting the presence of α-glucosidase inhibitors in S. circin...
12 CitationsSource
#1Xiao-Ni Ma (SOA: State Oceanic Administration)H-Index: 2
#2Chun-Lan Xie (SOA: State Oceanic Administration)H-Index: 7
Last. Xian-Wen Yang (SOA: State Oceanic Administration)H-Index: 26
view all 5 authors...
Alpinia species is one of the most important genera of the Zingiberaceae family. In Asia, they have been widely used as food and traditional medicines for centuries. This review focuses on their chemical constituents and their relevant biological activities with 252 references covering from 1955 to 2015. In total, 544 compounds were isolated from 35 Alpinia species. The major ones are terpenoids (207) and diarylheptanoids (143). The crude extracts and identified compounds exhibited a broad spect...
5 CitationsSource
From an extract prepared from the grain-based culture of Malbranchea flavorosea two new polyketides, namely, 8-chloroxylarinol A (1) and flavoroseoside (2), along with the known compounds xylarinol A (3), xylarinol B (4), massarigenins B and C (5 and 6), and clavatol (7), were isolated. The structures of 1 and 2 were elucidated using spectroscopic methods and corroborated by single-crystal X-ray diffraction analysis. In the case of compound 2 the absolute configuration at the stereogenic centers...
3 CitationsSource
Abstract Treatment of diabetes mellitus by oral α-glucosidase inhibitors is currently confined to acarbose, miglitol and voglibose marred by efficacy problems and unwanted side effects. Since the discovery of the drugs more than three decades ago, no significant progress has been made in the drug development area of anti-diabetic α-glucosidase inhibitors. Despite existence of a wide chemical diversity of α-glucosidase inhibitors identified to date, majority of them are simply piled up in publica...
64 CitationsSource