Compounds > 3-o-(alpha-l-arabinopyranosyl)hederagenin
Page last updated: 2024-12-08

3-o-(alpha-l-arabinopyranosyl)hederagenin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Akebia saponin PA: isolated from Dipsacus asperoides; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

hederagenin 3-O-arabinoside : A triterpenoid saponin that is hederagenin attached to an alpha-L-arabinopyranosyl residue at position 3 via a glycosidic linkage. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID441928
CHEBI ID5634
MeSH IDM0110945

Synonyms (41)

Synonym
17184-21-3
C08953
cauloside a
hederagenin 3-o-arabinoside
leontoside a
chebi:5634 ,
delta-hederin
(4as,6ar,6as,6br,8ar,9r,10s,12ar,14bs)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
3-o-(alpha-l-arabinopyranosyl)hederagenin
qw2x5b5l5w ,
fj-2 acid
3-o-arabinopyranosylhederagenin
olean-12-en-28-oic acid, 3-(alpha-l-arabinopyranosyloxy)-23-hydroxy-, (3beta,4alpha)-
3-(alpha-l-arabinopyransoyloxy)-23-hydroxy-olean-12-en-28-oic acid
3beta-(alpha-l-arabinopyranosyloxy)-23-hydroxyolean-12-en-28-oic acid
3beta-o-alpha-l-arabinopyranosyl hederagenin
AKOS032949072
DTXSID80938054
23-hydroxy-3-(pentopyranosyloxy)olean-12-en-28-oic acid
Q27106835
HY-N3557
CS-0023837
MS-30661
E88796
akeboside stb
akebia saponin pa
hederoside a3
3.beta.-(.alpha.-l-arabinopyranosyloxy)-23-hydroxyolean-12-en-28-oic acid
prosapogenin cp1
saponin k3
kizuta saponin k3
glycoside l-b2
(4as,6ar,6as,6br,8ar,9r,10s,12ar,14bs)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-((2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl)oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
olean-12-en-28-oic acid, 3-(alpha-l-arabinopyranosyloxy)-23-hydroxy-, (3.beta.,4.alpha.)-
fatsiaside b1
nepalin 1
.beta.2-fatsin
tauroside b
scabioside a
hederagenin 3-o-.alpha.-l-arabinopyranoside
beta2-fatsin

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Consequently, the validated method could be successfully and precisely applied to the pharmacokinetic study of asperosaponin VI and its metabolites."( Pharmacokinetics study of asperosaponin VI and its metabolites cauloside A, HN saponin F and hederagenin.
Chang, YX; Gao, XM; Han, LF; Huo, Y; Liu, EW; Wang, JL; Wang, L; Wang, T, 2014)		0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (5)

ClassDescription
triterpenoid saponinA terpene glycoside in which the terpene moiety is a triterpenoid.
monosaccharide derivativeA carbohydrate derivative that is formally obtained from a monosaccharide.
pentacyclic triterpenoid
hydroxy monocarboxylic acidAny monocarboxylic acid which also contains a separate (alcoholic or phenolic) hydroxy substituent.
alpha-L-arabinopyranoside
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID393223Cell membrane permeabilization in human DLD1 cells assessed as drug level causing decrease in calcein fluorescence2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural lupane- and oleanane-type saponins.
AID772917Cytotoxicity against human HL60 cells assessed as cell viability after 72 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis.
AID393221Cytotoxicity against human WS1 cells after 48 hrs by resazurin reduction test2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural lupane- and oleanane-type saponins.
AID772915Cytotoxicity against human U87MG cells assessed as cell viability after 72 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis.
AID402638Cytotoxicity against human KB cells by colorimetric method2005Journal of natural products, Jul, Volume: 68, Issue:7
Bioactive constituents of the leaves of Phyllanthus polyphyllus var. siamensis.
AID393218Toxicity in sheep erythrocytes assessed as induction of hemolysis2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural lupane- and oleanane-type saponins.
AID393220Cytotoxicity against human DLD1 cells after 48 hrs by resazurin reduction test2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural lupane- and oleanane-type saponins.
AID1591909Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitirc oxide production preincubated for 1 hr followed by LPS-stimulation and measured after 18 hrs by Griess assay2019Bioorganic & medicinal chemistry letters, 08-15, Volume: 29, Issue:16
Bioactive triterpene glycosides from the fruit of Stauntonia hexaphylla and insights into the molecular mechanism of its inflammatory effects.
AID402640Cytotoxicity against human NCI-H187 cells by colorimetric method2005Journal of natural products, Jul, Volume: 68, Issue:7
Bioactive constituents of the leaves of Phyllanthus polyphyllus var. siamensis.
AID393219Cytotoxicity against human A549 cells after 48 hrs by resazurin reduction test2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural lupane- and oleanane-type saponins.
AID772916Cytotoxicity against human A549 cells assessed as cell viability after 72 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis.
AID772914Cytotoxicity against human HeLa cells assessed as cell viability after 72 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis.
AID393224Cell membrane permeabilization in human WS1 cells assessed as drug level causing decrease in calcein fluorescence2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural lupane- and oleanane-type saponins.
AID772918Cytotoxicity against human HepG2 cells assessed as cell viability after 72 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis.
AID1678889Antileishmanial activity against axenic amastigote stage of Leishmania mexicana (MNYC/BZ/62/M379) assessed as inhibition of parasite proliferation at 50 uM incubated for 24 hrs by alamar blue dye based fluorescence analysis2020RSC medicinal chemistry, Jul-01, Volume: 11, Issue:7
An investigation of the antileishmanial properties of semi-synthetic saponins.
AID1678888Antileishmanial activity against axenic amastigote stage of Leishmania mexicana (MNYC/BZ/62/M379) assessed as induction of parasite killing incubated for 24 hrs by alamar blue dye based fluorescence analysis2020RSC medicinal chemistry, Jul-01, Volume: 11, Issue:7
An investigation of the antileishmanial properties of semi-synthetic saponins.
AID393222Cell membrane permeabilization in human A549 cells assessed as drug level causing decrease in calcein fluorescence2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural lupane- and oleanane-type saponins.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (23.08)18.2507
2000's2 (15.38)29.6817
2010's7 (53.85)24.3611
2020's1 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.33

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.33 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index5.04 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.33)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
ellipticine
ellipticine : A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.		2.0210indole alkaloid;
organic heterotetracyclic compound;
organonitrogen heterocyclic compound;
polycyclic heteroarene		antineoplastic agent;
plant metabolite
oleanolic acid
[no description available]		3.6490hydroxy monocarboxylic acid;
pentacyclic triterpenoid		plant metabolite
dihydroferulic acid
dihydroferulic acid: structure in first source. dihydroferulic acid : A monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 3 has been replaced by a 4-hydroxy-3-methoxyphenyl group.		2.2110guaiacols;
monocarboxylic acid;
phenylpropanoid		antioxidant;
human xenobiotic metabolite;
mouse metabolite;
plant metabolite
betulinic acid
[no description available]		2.0510hydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-HIV agent;
anti-inflammatory agent;
antimalarial;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
plant metabolite
secoisolariciresinol
secoisolariciresinol: RN given refers to ((R-(R*,R*))-isomer); RN for cpd without isomeric designation not available 8/89; precursor of lignans found in human urine; structure given in first source. secoisolariciresinol : A lignan that is butane-1,4-diol in which the 2 and 3 positions are substituted by 4-hydroxy-3-methoxybenzyl groups. (-)-secoisolariciresinol : An enantiomer of secoisolariciresinol having (-)-(2R,3R)-configuration.		2.0210secoisolariciresinolantidepressant;
phytoestrogen;
plant metabolite
betulin
betulin: isolated from various white birch bark (BETULA). betulin : A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents.		2.0510diol;
pentacyclic triterpenoid		analgesic;
anti-inflammatory agent;
antineoplastic agent;
antiviral agent;
metabolite
pulsatilla saponin a
Pulsatilla saponin A: has antineoplastic activity; isolated from Pulsatilla chinensis; structure in first source. kalopanaxsaponin A : A triterpenoid saponin that is hederagenin attached to a 2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl residue at position 3 via a glycosidic linkage. It has been isolated from the stem bark of Kalopanax pictus.		3.0340disaccharide derivative;
hydroxy monocarboxylic acid;
pentacyclic triterpenoid;
triterpenoid saponin		anti-inflammatory agent;
plant metabolite
hederagenin
[no description available]		3.1650dihydroxy monocarboxylic acid;
pentacyclic triterpenoid;
sapogenin		plant metabolite
arjunolic acid
arjunolic acid: oleanane type; isol from Cochlospermum tinctorium (Bixaceae); structure given in first source; RN given refers to (2alpha,3beta,4alpha)-isomer; RN for cpd without isomeric designation not avail 12/89. arjunolic acid : A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 23 (the 2alpha,3beta stereoisomer). Isolated from Symplocos lancifolia and Juglans sinensis, it exhibits antioxidant and antimicrobial activities.		2.2110hydroxy monocarboxylic acid;
pentacyclic triterpenoid		antibacterial agent;
antifungal agent;
antioxidant;
metabolite
nimustine
nimustine hydrochloride : A hydrochloride obtained by combining nimustine with one equivalent of hydrochloric acid. An antineoplastic agent especially effective against malignant brain tumors.		2.0810hydrochlorideantineoplastic agent
gypsogenin
gypsogenin: originally from Gypsophila species; structure in first source. gypsogenin : A sapogenin that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3 and an oxo group at position 23.		2.2510aldehyde;
monocarboxylic acid;
pentacyclic triterpenoid;
sapogenin
menisdaurilide
menisdaurilide: from Ouratea reticulata structure in first source		2.0210benzofurans
cussonoside b
cussonoside B: triterpene saponin from Cussonia barteri bark; structure given in first source		2.0810
cussonoside a
cussonoside A: triterpene saponin from Cussonia barteri (Araliaceae) with sedative effect;		2.2110
campesterol
campesterol: RN refers to (3beta,24R)-isomer; structure		2.15103beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
C28-steroid;
phytosterols		mouse metabolite
dihydrocubebin
dihydrocubebin: extract of leaves of Piper guineense Schum. & Thonn.; structure. dihydrocubebin : A glycol that is butane-1,4-diol substituted at the 2- and 3-positions by (1,3-benzodioxol-5-yl)methyl groups (the R,R-configuration).		2.0210benzodioxoles;
butanediols;
glycol;
lignan
beta-hederin
beta-hederin: derived from beta-amyrin; other hederigenin based saponins are available		2.520triterpenoid
gamma-sitosterol
clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.		2.15103beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
phytosterols		marine metabolite;
plant metabolite
cytellin
cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982		2.1510
beta-escin
[no description available]		3.5480
kalopanax saponin b
kalopanax saponin B: isolated from Kalopanax septemlobus; structure given in first source. kalopanaxsaponin B : A triterpenoid saponin with hederagenin as the aglycone part. It has been isolated from the stem bark of Kalopanax pictus.		2.2110carboxylic ester;
pentacyclic triterpenoid;
triterpenoid saponin		anti-inflammatory agent;
plant metabolite
pulsatilla saponin d
[no description available]		2.0510triterpenoidmetabolite
phytosterols
Phytosterols: A class of organic compounds known as sterols or STEROIDS derived from plants.. phytosterols : Sterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond.		2.1510
cauloside c
[no description available]		2.110triterpenoid
cauloside D
[no description available]		2.2110carboxylic ester;
pentacyclic triterpenoid;
triterpenoid saponin		anti-inflammatory agent;
plant metabolite
akebia saponin d
akebia saponin D: isolated from Dipsacus asper; structure in first source. akebia saponin D : A triterpenoid saponin that is hederagenin attached to a alpha-L-arabinopyranosyl residue at position 3 via a glycosidic linkage and a 6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl residue at position 28 via an ester linkage. It is the active ingredient found in the traditional Chinese herb Radix Dipsaci.		2.110
ConditionIndicatedRelationship StrengthStudiesTrials
Extravascular Hemolysis
[description not available]		02.0510
Hemolysis
The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.		02.0510
Cancer of Stomach
[description not available]		02.0810
Stomach Neoplasms
Tumors or cancer of the STOMACH.		02.0810