A new feruloylfriedelinol from the stems of Bridelia stipularis and its a-glucosidase inhibition

被引：0

作者：

Limtragool, Oue-artorn ^{[1
,2
]}

Pitchuanchom, Siripit ^{[1
,2
]}

Saensouk, Surapon ^{[3
]}

Poopasit, Kitisak ^{[4
,5
]}

Kanokmedhakul, Kwanjai ^{[4
,5
]}

Kanokmedhakul, Somdej ^{[4
,5
]}

机构：

[1] Mahasarakham Univ, Fac Sci, Dept Chem, Multidisciplinary Res Unit Pure & Appl Chem, Maha Sarakham, Thailand

[2] Mahasarakham Univ, Fac Sci, Ctr Excellence Innovat Chem, Maha Sarakham, Thailand

[3] Mahasarakham Univ, Walai Rukhavej Bot Res Inst, Divers Family Zingiberaceae & Vasc Plant Its Appli, Maha Sarakham, Thailand

[4] Khon Kaen Univ, Fac Sci, Dept Chem, Nat Prod Res Unit, Khon Kaen, Thailand

[5] Khon Kaen Univ, Fac Sci, Ctr Excellence Innovat Chem, Khon Kaen, Thailand

来源：

NATURAL PRODUCT RESEARCH | 2024年 / 38卷 / 18期

关键词：

Bridelia stipularis; Phyllanthaceae; alpha-glucosidase inhibition; triterpene; molecular docking; CONSTITUENTS; TRITERPENES; BARK;

D O I：

10.1080/14786419.2023.2222218

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Phytochemical investigation of the stems of Bridelia stipularis led to the isolation of a new triterpene, 3 beta-O-trans-feruloylfriedelinol (1), together with five known compounds, friedelin (2), 3 beta-friedelinol (3), lupeol (4), stigmasterol (5), and 4-(1,5-dimethyl-3-oxo-4-hexenyl) benzoic acid (6). Their structures were identified by intensive spectroscopic analysis including 1D and 2D nuclear magnetic resonance, infrared, and mass spectrometry. Compound 1 showed significant alpha-glucosidase inhibitory activity (IC50 = 337.49 +/- 0.59 mu M) close to the standard, acarbose. Furthermore, the structure activity relationship of 1 was analyzed by molecular docking studies. In addition, the molecular docking results showed that the interaction between 1 and the active site occurred through hydrophobic forces and hydrogen bonds. [GRAPHICS] .

引用

页码：3269 / 3274

页数：6

共 30 条

[1] Abbas G, 2017, NAT PROD DRUG DISC, P251, DOI 10.1016/B978-0-12-809450-1.00009-0
[2] Chemical and biological studies on Bridelia ferruginea grown in Nigeria
Afolayan, Michael
Srivedavyasasri, Radhakrishnan
Asekun, Olayinka T.
Familoni, Oluwole B.
Ross, Samir A.
[J]. NATURAL PRODUCT RESEARCH, 2019, 33 (02) : 287 - 291
[3] Anjum A., 2013, J SCI RES, V5, P343
[4] α-glucosidase inhibitory activity of triterpenoids from Cichorium intybus
Atta-Ur-Rahman
Zareen, Seema
Choudhary, M. Iqbal
Akhtar, M. Nadeern
Khan, Shamsun Nahar
[J]. JOURNAL OF NATURAL PRODUCTS, 2008, 71 (05): : 910 - 913
[5] Isolation and structure elucidation of acetylcholinesterase lipophilic lupeol derivatives inhibitors from the latex of the Tunisian Periploca laevigata
Ben Nejma, Aymen
Besbes, Malek
Guerineau, Vincent
Touboul, David
Ben Jannet, Hichem
Hamza, M'hamed Ali
[J]. ARABIAN JOURNAL OF CHEMISTRY, 2017, 10 : S2767 - S2772
[6] A NEW TRITERPENOID FROM BRIDELIA-TOMENTOSA
BOONYARATAVEJ, S
BATES, RB
CALDERA, S
SUVANNACHUT, K
[J]. JOURNAL OF NATURAL PRODUCTS, 1990, 53 (01): : 209 - 211
[7] Gallocatechin-(4′→O→7)-epigallocatechin, a new biflavonoid isolated from Bridelia ferruginea.
De Bruyne, T
Cimanga, K
Pieters, L
Claeys, M
Dommisse, R
Vlietinck, A
[J]. NATURAL PRODUCT LETTERS, 1997, 11 (01): : 47 - 52
[8] Bidesmosidic saponins from the fruits of Diploclisia glaucescens
Jayasinghe, L
Hara, N
Fujimoto, Y
[J]. PHYTOCHEMISTRY, 2003, 62 (04) : 563 - 567
[9] Kamboj A., 2011, Int. J. Pharm. Pharm. Sci, V3, P94
[10] Khan AS., 2018, J ADV MED PHARM SCI, V18, P1, DOI DOI 10.9734/JAMPS/2018/45396

← 1 2 3 →