Gylongiposide I

Enzymatic Biotransformation of Gypenoside XLIX into Gylongiposide I and Their Antiviral Roles against Enterovirus 71 In Vitro.[Pubmed:35807341]

Molecules. 2022 Jun 25;27(13):4094.

Biotransformation of specific saponins in the valuable medical plants to increase their bioavailability and pharmaceutical activities has attracted more and more attention. A gene encoding a thermophilic glycoside hydrolase from Fervidobaterium pennivorans DSM9078 was cloned and expressed in Escherichia coli. The purified recombinant enzyme, exhibiting endoglucanase cellulase activity, was used to transform gypenoside XLIX into Gylongiposide I via highly selective and efficient hydrolysis of the glucose moiety linked to the C21 position in gypenoside XLIX. Under the optimal reaction conditions for large scale production of Gylongiposide I, 35 g gypenoside XLIX was transformed by using 20 g crude enzyme at pH 6.0 and 80 degrees C for 4 h with a molar yield of 100%. Finally, 11.51 g of Gylongiposide I was purified using a silica gel column with 91.84% chromatographic purity. Furthermore, inhibitory activities of gypenoside XLIX and Gylongiposide I against Enterovirus 71 (EV71) were investigated. Importantly, the EC(50) of gypenoside XLIX and Gylongiposide I calculated from viral titers in supernatants was 3.53 muM and 1.53 muM, respectively. Moreover, the transformed product Gylongiposide I has better anti-EV71 activity than the glycosylated precursor. In conclusion, this enzymatic method would be useful in the large-scale production of Gylongiposide I, which would be a novel potent anti-EV71 candidate.

Profiling and activity screening of Dammarane-type triterpen saponins from Gynostemma pentaphyllum with glucose-dependent insulin secretory activity.[Pubmed:30679754]

Sci Rep. 2019 Jan 24;9(1):627.

The global prevalence of type 2 diabetes is increasing rapidly; consequently there is great need for new and novel therapeutic options. Gynostemma pentaphyllum (GP) is a traditional medicinal plant, mainly present in Southeast Asian countries, that has been reported to exert antidiabetic effects, by stimulating insulin secretion. The specific compound responsible for this effect is however as yet unidentified. Screening for discovery and identification of bioactive compounds of an herbal GP extract, was performed in isolated pancreatic islets from spontaneously diabetic Goto-Kakizaki (GK) rats, a model of type 2 diabetes, and from non-diabetic control Wistar rats. From this herbal extract 27 dammarane-type saponins, including two novel compounds, were isolated and their structure was elucidated by mass spectrometry and NMR spectroscopy. One of the dammarane-type triterpenoid showed a glucose-dependent insulin secretion activity. This compound, Gylongiposide I, displays unique abilities to stimulate insulin release at high glucose levels (16.7 mM), but limited effects at a low glucose concentration (3.3 mM). Further studies on this compound, also in vivo, are warranted with the aim of developing a novel anti-diabetic therapeutic with glucose-dependent insulinogenic effect.

Novel dammarane-type glycosides from Gynostemma pentaphyllum.[Pubmed:15577241]

Chem Pharm Bull (Tokyo). 2004 Dec;52(12):1440-4.

Three new dammarane glycosides (1-3), together with five known compounds, gypenoside LXIX (4), Gylongiposide I (5), gypenoside XLVIII (6), allantion (7) and vitexin (8) were isolated from the MeOH extract of the aerial parts of Gynostemma pentaphyllum. Compounds 5, 7, and 8 were isolated from this plant for the first time. Their structures were elucidated by 1D and 2D NMR spectra interpretation as well as by chemical degradation.

[Studies on the chemical constituents of Gynostemma longipes C.Y. Wu].[Pubmed:11596278]

Yao Xue Xue Bao. 1997 Jul;32(7):524-9.

A new triterpenoid saponin named Gylongiposide I was isolated from the aerial parts of Gynostemma longipes C.Y. Wu. On the basis of chemical evidence and spectral data the structure of Gylongiposide I was elucidated as 19-oxo-3 beta, 20(S), 21-trihydroxydammar-24-ene-3-O-([alpha-L-rhamnopyranosy(1-->2)] [beta-D-xylpyranosyl(1-->3)]) alpha-L-arabinopyranoside (G). The known compounds were identified as gypenoside XLIX(F) and ginsenoside Rb1(A).