New triterpenoid saponins with strong α-glucosidase inhibitory activity from the roots of Gypsophila oldhamiana

Luo, Jian‐Guang; Ma, Liang; Kong, Ling–Yi

doi:10.1016/j.bmc.2007.12.053

Cited by 95 publications

(47 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…7,8) Furthermore, recent investigations have reported that the compounds with cinnamic amide unit have strong a-glucosidase inhibition activities. [9][10][11] These motivated us to carry out further structural modifications on oleanolic acid by incorporating different cinnamic amide units.…”

Section: -6)mentioning

confidence: 99%

Synthesis of New .ALPHA.-Glucosidase Inhibitors Based on Oleanolic Acid Incorporating Cinnamic Amides

Nie

Luo

Wang

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

Type II diabetes mellitus affects approximately 215 million people worldwide. It is currently clear that aggressive control of hyperglycemia in patients with type II diabetes can attenuate the development of chronic complications such as retinopathy and nephropathy.1) To date, therapy for type II diabetes relies mainly on several approaches intended to suppress the hyperglycemia, which include reducing gut glucose absorption. Therefore inhibition of a-glucosidase, an enzyme catalyzing the cleavage of glycosidic bonds in oligosaccharides or glycoconjugates, is a choice to control elevated glucose level in blood.Oleanolic acid is the hypoglycemic component in many Traditional Chinese Medicines (TCMs). In previous reports, some oleanolic acid derivatives have been designed, synthesized based on inhibitor of glycogen phosphorylase (GP). 2-6)But it was found that oleanolic acid and its derivates were used to suppress the hyperglycemia for not only inhibitor of glycogen phosphorylase but also inhibitors of a-glucosidase in our previous research. 7,8) Furthermore, recent investigations have reported that the compounds with cinnamic amide unit have strong a-glucosidase inhibition activities. [9][10][11] These motivated us to carry out further structural modifications on oleanolic acid by incorporating different cinnamic amide units.In the present paper, a series of analogues with the oleanolic acid core and different cinnamic amide ligands were designed, synthesized, and evaluated as a-glucosidase inhibitors (Fig. 1, Table 1). Their structure-activity relationships also were analyzed. Results and DiscussionWith oleanolic acid as a lead compound, we sought to identify a series of oleanolic acid derivatives as novel a-glucosidase inhibitor. Synthetic efforts were focused on structural modifications at C-3 and C-28 positions. The synthetic route of 28-substituted oleanolic acid derivatives is outlined in Chart 1. Piperazine fragment was induced in order to link cinnamic amide unit with oleanolic acid at C-28.Oleanolic acid unit and cinnamic amide unit were connected at N-1 and N-4 positions of piperazine, respectively. On basis of these, 3,28-disubstituted oleanolic acid deriva- Department of Medicinal Chemistry, China Pharmaceutical University; 24 Tongjia Xiang, Nanjing 210009, People's Republic of China. Received March 24, 2011; accepted May 24, 2011; published online May 30, 2011 A series of a a-glucosidase inhibitors with the oleanolic acid core and different cinnamic amide ligands were designed and synthesized. Their preliminary structure-activity relationships were analyzed. In general, the compounds with 3,28-disubstituted oleanolic acid exhibited stronger activity than those 28-monosubstituted analogues, and variation of cinnamic amide substitution significantly affected a a-glucosidase inhibition activities. Most of the compounds showed potent inhibitory activity against a a-glucosidase with much greater efficacy than a typical a a-glucosidase inhibitor, acarbose. Synthesis of New a a-Glucosidase Inhibitors ...

show abstract

Section: -6)mentioning

confidence: 99%

Synthesis of New .ALPHA.-Glucosidase Inhibitors Based on Oleanolic Acid Incorporating Cinnamic Amides

Nie

Luo

Wang

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

show abstract

“…Its roots have been usually used as a folk medicine to treat fever, consumptive disease, and infantile malnutrition syndrome in China. 11) Previous chemical researches on its roots have revealed the occurrence of saponins, sterols, and fatty acid, [11][12][13][14][15] and triterpenoid saponins and saponin-rich extract of its roots showed obvious anticancer activity in vitro and in vivo. [16][17][18] However, there is no report on the mechanisms responsible for the anti-proliferative effects.…”

mentioning

confidence: 99%

“…The supernatant was concentrated to 50 mL with a rotary evaporator under reduced pressure. As previously described, 11,[13][14][15] the extract was partitioned with ethyl acetate and n-butanol, respectively. The n-butanol extract was subjected to MCI column (MeOH-H 2 O 50%, 90%), and the 90% fraction was evaporated under vacuum and then lyophilized to give the TGOE.…”

mentioning

confidence: 99%

Different Apoptotic Effects of Triterpenoid Saponin-Rich <i>Gypsophila oldhamiana</i> Root Extract on Human Hepatoma SMMC-7721 and Normal Human Hepatic L02 Cells

Zhang

Luo

Zhang

et al. 2013

Biological & Pharmaceutical Bulletin

Self Cite

View full text Add to dashboard Cite

The roots of Gypsophila oldhamiana are rich in triterpenoid saponins with antitumor properties. Although previous reports have revealed the anticancer potency of some Gypsophila species, the underlying molecular mechanisms of this activity have not been studied in detail. The purpose of the present study was to prepare a triterpenoid saponin-rich G. oldhamiana root extract (TGOE) determined by LC-electrospray ionization (ESI)-MS n for biological studies and to evaluate the different anti-proliferative activities and apoptotic effects of TGOE on human hepatoma SMMC-7721 and normal human hepatic L02 cells.

show abstract

“…Compound 1 was obtained as a white amorphous powder, and its molecular formula, C 36 H 54 O 12 , was deduced from the high resolution-electrospray ionization-mass spectra (HR-ESI-MS): m/z 679.3675 [MϩH] ϩ (Calcd 679.3694), indicating the presence of ten unsaturation degrees. There were 36 carbon signals in 13 C-NMR, among which 30 carbon signals were assigned to the aglycone, and 6 carbon signals to the saccharide moiety.…”

Section: Resultsmentioning

confidence: 99%

Triterpenoid Saponins from the Seeds of Celosia argentea and Their Anti-inflammatory and Antitumor Activities

Wang

Guo

2011

Chem. Pharm. Bull.

View full text Add to dashboard Cite

Celosia L., one category of Amaranthaceae, is widely distributed in Africa, America, the subtropical zone and temperate zone of Asia. 1) There are three species in China. They are Celosia argentea L., Celosia cristata L. and Celosia taitoensis HAYATA. We have been studying for the seeds of two species C. argentea and C. cristata in our laboratory. Semen celosiae, the seeds of C. argentea, has been traditionally used for treatment of hepatitis, caligo corneae, hypertention and sarcoptidosis.2) The crude EtOH extract of Semen celosiae possesses antipyretic, antispasmodic, anticancer, diuretic, anti-inflammatory and antibacterial activities. 3) However, there wasn't any report about the seeds of C. cristata. In our laboratory research for bioactive compounds from Semen celosiae and the seeds of C. cristata, b-sitosterol, palmitic 666 Vol. 59, No. 5 Note Triterpenoid Saponins from the Seeds of Celosia argentea and Their Anti-inflammatory and Antitumor ActivitiesQingbin WU, Yan WANG, and Meili GUO* Department of Pharmacognosy, School of Pharmacy, Second Military Medical University; No. 325 Guohe Road, Yangpu District, Shanghai 200433, P. R. China. Received December 3, 2010; accepted February 1, 2011; published online February 22, 2011 Three new triterpenoid saponins, named celosin E (1), celosin F (2) and celosin G (3), together with a known compound cristatain (4), were isolated from the seeds of Celosia argentea L. (Amaranthaceae). All the isolated compounds were obtained for the first time from this plant. The structures of new compounds were characterized on the basis of extensive NMR experiments and mass spectrometry data. The antitumor and anti-inflammatory activities of the four compounds were tested in vitro.

show abstract

New triterpenoid saponins with strong α-glucosidase inhibitory activity from the roots of Gypsophila oldhamiana

Cited by 95 publications

References 15 publications

Synthesis of New .ALPHA.-Glucosidase Inhibitors Based on Oleanolic Acid Incorporating Cinnamic Amides

Synthesis of New .ALPHA.-Glucosidase Inhibitors Based on Oleanolic Acid Incorporating Cinnamic Amides

Different Apoptotic Effects of Triterpenoid Saponin-Rich <i>Gypsophila oldhamiana</i> Root Extract on Human Hepatoma SMMC-7721 and Normal Human Hepatic L02 Cells

Triterpenoid Saponins from the Seeds of Celosia argentea and Their Anti-inflammatory and Antitumor Activities

Contact Info

Product

Resources

About