472-15-1Relevant articles and documents
A SAPONIN FROM ASPARAGUS GONOCLADUS
Mandloi, Dilip,Sant, P. G.
, p. 1687 - 1688 (1981)
The ethanolic extract of the aerial part of Asparagus gonocladus yielded a new saponin.It was identified as lup-20(29)-en-28-oic-3-O-α-L-rhamnopyranosyl-(2->1)-O-β-D-glucopyranoside. - Keywords: Asparagus gonocladus; Liliaceae; lup-20(29)-en-28-oic-3-O-α-L-rhamnopyranosyl-(2->1)-O-β-D-glucopyranoside.
α-L-RHAMNOPYRANOSYL-3β-HYDROXY-LUP-20(29)-EN-28-OIC ACID FROM THE STEM OF DILLENIA PENTAGYNA
Tiwari, Kamala P.,Srivastava, Savitri D.,Srivastava, Santosh K.
, p. 980 - 981 (1980)
Key Word Index: Dillenia pentagyna; Dilleniaceae; α-L-rhamnopyranosyl-3β-hydroxy-lup-20(29)-en-28-oic acid; a new saponin.
Design, synthesis and evaluation of antiproliferative activity of fluorinated betulinic acid
Li, Jizhen,Chang, Ling-Chu,Hsieh, Kan-Yen,Hsu, Pei-Ling,Capuzzi, Stephen J.,Zhang, Ying-Chao,Li, Kang-Po,Morris-Natschke, Susan L.,Goto, Masuo,Lee, Kuo-Hsiung
, p. 2871 - 2882 (2019)
Betulinic acid (BA), a pentacyclic triterpenoid, exhibits broad spectrum antiproliferative activity, but generally with only modest potency. To improve BA's pharmacological properties, fluorine was introduced as a single atom at C-2, creating two diastereomers, or in a trifluoromethyl group at C-3. We evaluated the impact of these groups on antiproliferative activity against five human tumor cell lines. A racemic 2-F-BA (compound 6) showed significantly improved antiproliferative activity, while each diastereomer exhibited similar effects. We also demonstrated that 2-F-BA is a topoisomerase (Topo) I and IIα dual inhibitor in cell-based and cell-free assays. A hypothetical mode of binding to the Topo I-DNA suggested a difference between the hydrogen bonding of BA and 2-F-BA to DNA, which may account for the difference in bioactivity against Topo I.
A BETULINIC ACID GLYCOSIDE FROM SCHEFFLERA VENULOSA
Purohit, M. C.,Pant, G.,Rawat, M. S. M.
, p. 2419 (1991)
A new betulinic acid glycoside, lup-20(29)-en-28-oic-3-O-β-D-glucopyranosyl (2->1)-O-β-D-glucopyranoside has been characterized from the leaves of Schefflera venulosa.
Genotoxic and mutagenic properties of synthetic betulinic acid and betulonic acid
Frolova,Kukina,Sinitsyna
, p. 409 - 413 (2015)
Abstract Betulinic acid was synthesized from birch bark extract (Betula pendula), with betulonic acid being an intermediate of the synthesis. Both compounds were isolated with a purity of 95%. Genotoxicity and mutagenicity of the prepared compounds was analyzed by the Ames test and SOS chromotest and it was found that the substances show no mutagenic and genotoxic activity.
The Effect of Experimental BCG Antigen–Betulin-Derived Conjugates on the Guinea Pig Immunological Response
Koshkin, I. N.,Kulakov, I. V.,Vlasenko, V. S.
, p. 837 - 844 (2021/08/25)
Abstract: The immunopotentiating properties of BCG vaccine strain antigen conjugated with betulin derivatives have been evaluated. The experiments were carried out on agouti guinea pigs (n = 20). The animals of the experimental groups (n = 5) were immunized with the following antituberculosis drugs: group 1, with antigens of the BCG vaccine strain conjugated with betulinic acid; group 2, with BCG antigens conjugated with betulonic acid; and group 3, with the BCG vaccine. The animals of the control group (n = 5) were injected with a saline solution. All the animals were infected with a virulent culture of Mycobacterium bovis (strain 8) on day 30 after the administration of antituberculosis drugs. The blood sampling for the assessment of the immune status was conducted on day 30 after the administration of drugs and day 30 after the infection with M. bovis. The designed conjugates were found to display immunopotentiating activity characterized by a 1.7–3.8-fold increase in the number of immunocompetent cells and an increase in the neutrophil functional activity observed to a greater degree in the guinea pig group 2. After infection with M. bovis some key parameters of the immune system, such as a T-lymphocyte count and the activity of enzymatic (myeloperoxidase) and nonenzymatic (cationic proteins) bactericidal systems of neutrophilic granulocytes significantly increased in groups 2 and 3, which implied the highest antituberculosis activity of the agents administered to these animals. The guinea pigs were euthanized 45 days after the infection with M. bovis. The next pathoanatomical experiments proved that the vaccine strain conjugates with betulonic acid and the BCG vaccine induced marked resistance against the pathogenic mycobacteria. The protection indexes for these agents were approximately the same and achieved 66 and 71%, respectively.
Synthesis of a Hexavalent Betulinic Acid Derivative as a Hemagglutinin-Targeted Influenza Virus Entry Inhibitor
Chen, Yingying,Si, Longlong,Wang, Xinchen,Xiao, Sulong,Zhang, Bo,Zhang, Lihe,Zhang, Yongmin,Zhou, Demin,Zhu, Yinbiao
, p. 2546 - 2554 (2020/08/14)
Naturally occurring pentacyclic triterpenes, such as betulinic acid (BA) and its derivatives, exhibit various pharmaceutical activities and have been the subject of great interest, in particular for their antiviral properties. Here, we found a new anti-influenza virus conjugate, hexakis 6-deoxy-6-[4-N-(3β-hydroxy-lup-20(29)-en-28-oate)aminomethyl-1H-1,2,3-triazol-1-yl]-2,3-di-O-acetyl-α-cyclodextrin (CYY1-11, 1), in a mini library of pentacyclic triterpene-cyclodextrin conjugates by performing a cell-based screening assay and then exploring the underlying mechanisms. Our results showed that conjugate 1 possessed a high-level activity against the influenza virus A/WSN/33 with an IC50 value of 5.20 μM (SI > 38.4). The study of the mechanism of action indicated that conjugate 1 inhibited viral replication by directly targeting the influenza hemagglutinin protein (KD = 1.50 μM), thus efficiently preventing the attachment of the virion to its receptors on host cells and subsequent infection. This study suggests that multivalent BA derivatives have possible use as a new class of influenza virus entry inhibitors.