Antidiabetic Principles of Natural Medicines. III. Structure-Related Inhibitory Activity and Action Mode of Oleanolic Acid Glycosides on Hypoglycemic Activity.

The peptides from the ranacyclin family share similar active disulphide loop with plant-derived Bowman–Birk type inhibitors, some of which have the dual activities of trypsin inhibition and antimicrobial. Herein, a novel Bowman–Birk type trypsin inhibitor of the ranacyclin family was identified from the skin secretion of broad-folded frog (Sylvirana latouchii) by molecular cloning method and named as SL-BBI. After chemical synthesis, it was proved to be a potent inhibitor of trypsin with a Ki value of 230.5 nM and showed weak antimicrobial activity against tested microorganisms. Modified analogue K-SL maintains the original inhibitory activity with a Ki value of 77.27 nM while enhancing the antimicrobial activity. After the substitution of active P1 site to phenylalanine and P2′ site to isoleucine, F-SL regenerated its inhibitory activity on chymotrypsin with a Ki value of 309.3 nM and exhibited antiproliferative effects on PC-3, MCF-7 and a series of non-small cell lung cancer cell lines without cell membrane damage. The affinity of F-SL for the β subunits in the yeast 20S proteasome showed by molecular docking simulations enriched the understanding of the possible action mode of Bowman–Birk type inhibitors. Further mechanistic studies have shown that F-SL can activate caspase 3/7 in H157 cells and induce apoptosis, which means it has the potential to become an anticancer agent.

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Synthesis and Anti-Fungal Activity of Seven Oleanolic Acid Glycosides

Molecules ◽

10.3390/molecules16021113 ◽

2011 ◽

Vol 16 (2) ◽

pp. 1113-1128 ◽

Cited By ~ 6

Author(s):

Hanqing Zhao ◽

Guanghui Zong ◽

Jianjun Zhang ◽

Daoquan Wang ◽

Xiaomei Liang

Keyword(s):

Oleanolic Acid ◽

Fungal Activity ◽

Oleanolic Acid Glycosides ◽

Anti Fungal

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Synthesis and α-glucosidase inhibitory activity of oleanolic acid derivatives

Journal of Asian Natural Products Research ◽

10.1080/10286020903405456 ◽

2010 ◽

Vol 12 (1) ◽

pp. 20-29 ◽

Cited By ~ 5

Author(s):

Shan Qian ◽

Jiao Hai Li ◽

Yu Wei Zhang ◽

Xin Chen ◽

Yong Wu

Keyword(s):

Oleanolic Acid ◽

Inhibitory Activity

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Phytochemical Studies of Seeds of Medicinal Plants. III. Ursolic Acid and Oleanolic Acid Glycosides from Seeds of Patrinia scabiosaefolia Fischer.

Chemical and Pharmaceutical Bulletin ◽

10.1248/cpb.41.183 ◽

1993 ◽

Vol 41 (1) ◽

pp. 183-186 ◽

Cited By ~ 19

Author(s):

Tsutomu NAKANISHI ◽

Keishi TANAKA ◽

Hiroko MURATA ◽

Midori SOMEKAWA ◽

Akira INADA

Keyword(s):

Medicinal Plants ◽

Ursolic Acid ◽

Oleanolic Acid ◽

Oleanolic Acid Glycosides ◽

Patrinia Scabiosaefolia ◽

Phytochemical Studies

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The Potential Angiotensin-Converting Enzyme Inhibitory Activity of Oleanolic Acid in the Hydroethanolic Extract of Crataegus monogyna Jacq

Natural Product Communications ◽

10.1177/1934578x0600100507 ◽

2006 ◽

Vol 1 (5) ◽

pp. 1934578X0600100 ◽

Cited By ~ 4

Author(s):

Everaldo Attard ◽

Henrietta Attard

Keyword(s):

Angiotensin Converting Enzyme ◽

Oleanolic Acid ◽

Inhibitory Activity ◽

Acid Group ◽

Converting Enzyme ◽

Ace Inhibitory Activity ◽

Crataegus Monogyna ◽

Triterpenic Acids ◽

Hydroethanolic Extract ◽

Ace Inhibitory

The hydroethanolic extract of Crataegus monogyna was studied for its chemical constitution and angiotensin-converting enzyme (ACE) inhibitory activity. The extract contained triterpenic acids, flavonoids and coumarins. The ACE inhibitory activity was studied using captropril, as a control drug, and oleanolic acid, as a constituent of the hydroethanolic extract and a member of the triterpenic acid group. The hydroethanolic extract and oleanolic acid showed higher IC50 values (335.00 μg/mL and 3.61 μM, respectively) in comparison to captopril (46.9 nM). However, these results indicate the anti-ACE activity of oleanolic acid and the triterpenic acids, which has not been demonstrated earlier for hawthorn extracts. In previous studies, the ACE inhibitory activity of C. monogyna extracts was always attributed to flavonoids and proanthocyanidins.

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LC-MS- and NMR-Guided Isolation of Monoterpene Dimers from Cultivated Thymus vulgaris Varico 3 Hybrid and Their Antityrosinase Activity

Planta Medica ◽

10.1055/a-0927-7041 ◽

2019 ◽

Vol 85 (11/12) ◽

pp. 941-946 ◽

Cited By ~ 1

Author(s):

Ilias Stefanis ◽

Dimitra Hadjipavlou-Litina ◽

Anna-Rita Bilia ◽

Anastasia Karioti

Keyword(s):

Ursolic Acid ◽

Oleanolic Acid ◽

Inhibitory Activity ◽

Kojic Acid ◽

2D Nmr ◽

Thymus Vulgaris ◽

Reference Compound ◽

Aerial Parts ◽

Spectroscopic Analyses ◽

Antityrosinase Activity

AbstractTargeted isolation based on a combination of NMR and HPLC-PDA-MS of a dichloromethane extract of Thymus vulgaris Varico 3 aerial parts afforded one new p-cymene dimer, 6,3′,4′-trihydroxy-5,5′-diisopropyl-2,2′-dimethylbiphenyl (1), together with two known p-cymene derivatives (2 and 3), as well as five known compounds, namely, thymol (4), oleanolic acid (5), ursolic acid (6), cirsimaritin (7), and xanthomicrol (8). The structural elucidation of all compounds was performed by spectroscopic analyses, including 1D and 2D NMR, and HRESIMS experiments. The biphenyls were assayed for their inhibitory activity on tyrosinase. Compounds 2 and 3 showed negligible activity on tyrosinase, while compound 1 effectively inhibited the enzyme with 35% (± 0.3) inhibitory activity, higher than the inhibition of the reference compound kojic acid (18.6 ± 0.02).

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