Aucubigenin

Characteristics, Isolation Methods, and Biological Properties of Aucubin.[Pubmed:37241895]

Molecules. 2023 May 17;28(10):4154.

Aucubin is an iridoid glycoside widely spread in the families Cornaceae, Garryaceae, Orobanchaceae, Globulariaceae, Eucommiaceae, Scrophulariaceae, Plantaginaceae, and Rubiaceae. This review is intended to provide data on the physicochemical characteristics, isolation methods, and biological activities of aucubin and its producing plants. Aucubin is unstable and can be deglycosylated into its aglycone, Aucubigenin. Various chromatographic methods (column chromatography, vacuum liquid chromatography, medium pressure liquid chromatography, and high-performance liquid chromatography) have been used together to isolate aucubin, mainly with the stationary phase C-18 and the mobile phase water-methanol solution made in gradients. In vitro and in vivo studies reveal that aucubin has a wide range of activities, including anti-inflammatory, antioxidant, anxiolytic and antidepressant, antidiabetic, antifibrotic, antimicrobial, anticancer, antihyperlipidemic, gastroprotective, cardioprotective, hepatoprotective, retinoprotective, neuroprotective, osteoprotective, and renoprotective. Even though aucubin has been extensively investigated, further research in humans is urgently needed primarily to substantiate the clinical evidence. Moreover, extensive studies on its drug delivery systems will help maximize efficacy and minimize side effects.

Aucubin and its hydrolytic derivative attenuate activation of hepatic stellate cells via modulation of TGF-beta stimulation.[Pubmed:28199906]

Environ Toxicol Pharmacol. 2017 Mar;50:234-239.

Eucommia ulmoides is an important traditional Chinese medicine and has been used as a tonic with a long history. Aucubin is an active component extracted from Eucommia ulmoides, which has liver-protection effects. However the mechanisms are still unclear. To investigate the inhibitory effects and the underlying mechanisms of aucubin on TGF-beta1-induced activation of hepatic stellate cells and ECM deposition, Human hepatic stellate cells (LX-2 cells) were incubated with TGF-beta1 to evaluate the anti-fibrotic effect of aucubin. Western blot was used to investigate the expression of alpha-SMA, Col I, Col III, MMP-2 and TIMP-1. ROS production was monitored using DCFH-DA probe, and NOX4 expression was detected by Real-time PCR. Results indicated that TGF-beta1 stimulated the activation and ECM deposition of LX-2 cells. Compared with the control group, aucubin and Aucubigenin both reduced the protein expression of alpha-SMA, Col I, Col III and MMP-2 in LX-2 cells. Aucubin and Aucubigenin also suppressed the generation of ROS and down-regulated the NOX4 mRNA expression. Taken together, aucubin and Aucubigenin both inhibit the activation and ECM deposition of LX-2 cells activated by TGF-beta1. Aucubin and Aucubigenin are potential therapeutic candidate drugs for liver fibrosis.

X-ray crystal structure of iridoid glucoside aucubin and its aglycone.[Pubmed:19762008]

Carbohydr Res. 2009 Nov 2;344(16):2270-3.

X-ray diffraction analyses of iridoid glycoside aucubin (1) and its aglycone Aucubigenin (2) are reported. It was found that crystals of 1 are orthorhombic, with P2(1)2(1)2(1) space group, both cyclopentane ring and pyran ring adopt envelope conformations, and the Glc moiety is in the (4)C(1) conformation. Crystals of 2 are monoclinic, with space group P2(1), the cyclopentane and pyran rings also adopt the envelope conformation. The absolute configurations of 1 and 2 were also determined. Intensive O-H . . . O hydrogen bonds in both crystal lattices were observed.

[Research advances in pharmacology of aucubin and aucubigenin].[Pubmed:18338591]

Zhongguo Zhong Yao Za Zhi. 2007 Dec;32(24):2585-7.

The advances in the research on pharmacological activities of aucubin have been summarized in the last ten years. Aucubin is one of active components of Chinese medicinal herbs such as Eucommia ulmoides and has been shown wide pharmacological activities including hepatoproective, antitoxicanti-inflammatory, antioxidant, antiaging, antiosteoporosis and neurotrophic and should be further researched and utilized.

Studies on the possible mechanisms of protective activity against alpha-amanitin poisoning by aucubin.[Pubmed:11235813]

Arch Pharm Res. 2001 Feb;24(1):55-63.

Aucubin, an iridoid glucoside, was investigated to determine whether it has a stimulating effect on alpha-amanitin excretion in alpha-amanitin intoxicated rats, and whether there is binding activity to calf thymus DNA. High-performance liquid chromatography (HPLC) analysis of alpha-amanitin in rat urine allowed quantitative measurement of the alpha-amanitin concentration with a detection limit of 50 ng/ml. In this system, a group treated with both alpha-amanitin and aucubin showed that alpha-amanitin was excreted about 1.4 times faster than in the alpha-amanitin only treated group. Our previous results showed that the toxicity of alpha-amanitin is due to specific inhibition of RNA polymerase activity and the resultant blockage of the synthesis of certain RNA species in the nucleus. However, no significant activity change on RNA polymerase from Hep G2 cells was observed when aucubin was treated with alpha-amanitin at any concentration tested. Nevertheless, Aucubigenin inhibited both DNA polymerase (IC50, 80.5 microg/ml) and RNA polymerase (IC50, 135.0 microg/ml) from the Hep G2 cells. The potential of both alpha-amanitin and aucubin to interact with DNA were examined by spectrophotometric analysis. Alpha-Amanitin showed no significant binding capacity to calf thymus DNA, but aucubin was found to interact with DNA, and the apparent binding constant (Kapp) and apparent number of binding sites per DNA phosphate (Bapp) were 0.45 x 10(4) M(-1) and 1.25, respectively.