Page last updated: 2024-11-08

butylidenephthalide

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Description

butylidenephthalide: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

(Z)-3-butylidenephthalide : A gamma-lactone that is phthalide substituted by a butylidene group at position 3. Isolated from Ligusticum porteri, it exhibits hypoglycemic activity. [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]

FloraRankFlora DefinitionFamilyFamily Definition
LigusticumgenusA plant genus of the family APIACEAE.[MeSH]ApiaceaeA large plant family in the order Apiales, also known as Umbelliferae. Most are aromatic herbs with alternate, feather-divided leaves that are sheathed at the base. The flowers often form a conspicuous flat-topped umbel. Each small individual flower is usually bisexual, with five sepals, five petals, and an enlarged disk at the base of the style. The fruits are ridged and are composed of two parts that split open at maturity.[MeSH]
Ligusticum porterispecies[no description available]ApiaceaeA large plant family in the order Apiales, also known as Umbelliferae. Most are aromatic herbs with alternate, feather-divided leaves that are sheathed at the base. The flowers often form a conspicuous flat-topped umbel. Each small individual flower is usually bisexual, with five sepals, five petals, and an enlarged disk at the base of the style. The fruits are ridged and are composed of two parts that split open at maturity.[MeSH]

Cross-References

ID SourceID
PubMed CID5352899
CHEMBL ID1765390
CHEBI ID196485
SCHEMBL ID290483
SCHEMBL ID783051
MeSH IDM0086097
PubMed CID642376
CHEMBL ID249592
CHEBI ID68233
SCHEMBL ID290482
MeSH IDM0086097

Synonyms (80)

Synonym
ligusticum lactone
nsc 325307
einecs 208-991-3
fema no. 3333
3-butylidene phthalide
3-butylidene-1(3h)-isobenzofuranone
ai3-37306
n-butylidene phthalide
phthalide, 3-butylidene-
butylidenephthalide
3-butylidenephthalide
1(3h)-isobenzofuranone, 3-butylidene-
3-butylidenephthalide, (e)-
3-butylidenephthalide, (z)-
(3e)-3-butylidene-2-benzofuran-1-one
(3e)-3-butylidene-2-benzouran-1-one
CHEBI:196485
CHEMBL1765390 ,
(z)-3-butylidenephthalide
bdbm50341204
76681-73-7
1(3h)-isobenzofuranone, 3-butylidene-, (3e)-
s9178g4b3f ,
unii-s9178g4b3f
(3e)-3-butylideneisobenzofuran-1-one
SCHEMBL290483
DTXSID9060281
SCHEMBL783051
lingustilide
WMBOCUXXNSOQHM-DHZHZOJOSA-N
2JL3MHX6ZE
(3e)-3-butylidene-1,3-dihydro-2-benzofuran-1-one
fema 3333
(e)-3-butylidenephthalide
3-butylidenephthalide, 8ci
3-butylidene-phthalide
AKOS032948974
Q27890207
cis-butylidenephthalide;(z)-butylidenephthalide
n-butylidenephthalide
551-08-6
bdph
nsc325307
nsc-325307
1(3h)-isobenzofuranone, 3-butylidene-, (3z)-
inchi=1/c12h12o2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-8h,2-3h2,1h3/b11-8
(3z)-3-butylidene-2-benzofuran-1(3h)-one
bdbm50241315
(z)-3-butylideneisobenzofuran-1(3h)-one
z-butylidenephthalide
CHEMBL249592 ,
chebi:68233 ,
C16924
(3z)-3-butylidene-2-benzofuran-1-one
72917-31-8
unii-6gm611h175
6gm611h175 ,
(3z)-3-butylideneisobenzofuran-1-one
S6493
SCHEMBL290482
(z)-butylidenephthalide
AKOS024286816
trans-3n-butylidenephthalide
WMBOCUXXNSOQHM-FLIBITNWSA-N
AC-34145
1(3h)-isobenzofuranone, 3-butylidene-, (z)-
butylidenephthalide, (z)-
(3z)-3-butylidene-1(3h)-isobenzofuranone
mfcd00047319
3-butylideneisobenzofuran-1(3h)-one
Q27136726
1795142-65-2
F17666
DTXSID30993698
A14633
CS-0008897
HY-N0336
BS-49282
(e)-butylidene phthalide
3-butylidenephthalide-d8

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" This abnormal proteolysis leads to the accumulation of cleaved fragments, which have been identified as toxic and further they act as a seed for more aggregate formation, thereby increasing toxicity in neuronal cells."( n-Butylidenephthalide exhibits protection against neurotoxicity through regulation of tryptophan 2, 3 dioxygenase in spinocerebellar ataxia type 3.
Chiang, IT; Chiou, TW; Harn, HJ; Hsieh, DK; Lin, SY; Lin, SZ; Liu, JW; Rajamani, K; Wu, CH; You, DH, 2017
)
0.46

Pharmacokinetics

ExcerptReferenceRelevance
" The objectives of the present study were to evaluate the pharmacokinetic comparative study of BDPH and ALI in herbal extracts and their purified forms."( Pharmacokinetic Profiling of Butylidenephthalide and Alisol B in Danggui-Shaoyao-San in Rats.
Deng, JF; Li, WR; Quan, SJ; Wang, Q; Wang, XY; Wu, HF, 2018
)
0.48
" The pharmacokinetic parameters were significantly different in herbal extracts and their purified forms."( Pharmacokinetic Profiling of Butylidenephthalide and Alisol B in Danggui-Shaoyao-San in Rats.
Deng, JF; Li, WR; Quan, SJ; Wang, Q; Wang, XY; Wu, HF, 2018
)
0.48

Compound-Compound Interactions

ExcerptReferenceRelevance
" In both HepG2 and J5 HCC cell lines, a synergistic antiproliferative effect was observed when a low dosage of BP was combined with the chemotherapeutic drug 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU)."( Extended O6-methylguanine methyltransferase promoter hypermethylation following n-butylidenephthalide combined with 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU) on inhibition of human hepatocellular carcinoma cell growth.
Chan, DC; Chen, YL; Harn, HJ; Jian, MH; Lin, CC; Lin, PC; Lin, SZ; Su, CC; Su, KJ; Tseng, IH; Wei, CW; Yu, SL; Yu, YL, 2010
)
0.36
" For our study, we chose sodium ferulate (SF) and n-butylidenephthalide (BP) combined with BMSC, and observed if the combination treatment possessed more significant effects on angiogenesis and neurogenesis post-stroke."( Sodium ferulate and n-butylidenephthalate combined with bone marrow stromal cells (BMSCs) improve the therapeutic effects of angiogenesis and neurogenesis after rat focal cerebral ischemia.
Chen, Z; Ke, C; Liu, B; Liu, N; Wu, W; Xu, Y; Zhang, Q; Zhao, Y, 2016
)
0.43
" Meanwhile, it showed that SF and BP combined with BMSC treatment notably up-regulated AKT/mTOR signal pathway compared with SF + BP group and BMSC alone post-stroke."( Sodium ferulate and n-butylidenephthalate combined with bone marrow stromal cells (BMSCs) improve the therapeutic effects of angiogenesis and neurogenesis after rat focal cerebral ischemia.
Chen, Z; Ke, C; Liu, B; Liu, N; Wu, W; Xu, Y; Zhang, Q; Zhao, Y, 2016
)
0.43
"We firstly demonstrate that SF and BP combined with BMSC can significantly improve angiogenesis and neurogenesis in IBZ following stroke."( Sodium ferulate and n-butylidenephthalate combined with bone marrow stromal cells (BMSCs) improve the therapeutic effects of angiogenesis and neurogenesis after rat focal cerebral ischemia.
Chen, Z; Ke, C; Liu, B; Liu, N; Wu, W; Xu, Y; Zhang, Q; Zhao, Y, 2016
)
0.43

Bioavailability

ExcerptReferenceRelevance
" It was found that BDPH and ALI had higher bioavailability in the DSS extract compared with their purified forms."( Pharmacokinetic Profiling of Butylidenephthalide and Alisol B in Danggui-Shaoyao-San in Rats.
Deng, JF; Li, WR; Quan, SJ; Wang, Q; Wang, XY; Wu, HF, 2018
)
0.48
"Although butylidenephthalide (BP) is an efficient anticancer drug, its poor bioavailability renders it ineffective for treating drug-resistant brain tumors."( Liposome Consolidated with Cyclodextrin Provides Prolonged Drug Retention Resulting in Increased Drug Bioavailability in Brain.
Chen, SR; Chen, YS; Chiou, TW; Chuang, HM; Harn, HJ; Huang, MH; Lee, CH; Li, YS; Lin, EY; Lin, SZ; Tai, DF; Yang, HH, 2020
)
0.56

Dosage Studied

ExcerptRelevanceReference
" In both HepG2 and J5 HCC cell lines, a synergistic antiproliferative effect was observed when a low dosage of BP was combined with the chemotherapeutic drug 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU)."( Extended O6-methylguanine methyltransferase promoter hypermethylation following n-butylidenephthalide combined with 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU) on inhibition of human hepatocellular carcinoma cell growth.
Chan, DC; Chen, YL; Harn, HJ; Jian, MH; Lin, CC; Lin, PC; Lin, SZ; Su, CC; Su, KJ; Tseng, IH; Wei, CW; Yu, SL; Yu, YL, 2010
)
0.36
" Because of the limitation of the blood-brain barrier, the Bdph dosage required for treatment of glioma is relatively high."( Local interstitial delivery of z-butylidenephthalide by polymer wafers against malignant human gliomas.
Chang, LF; Chiou, TW; Harn, HJ; Hsieh, DK; Lin, PC; Lin, SZ; Liu, CY; Liu, FC; Liu, PY; Tai, DF; Yen, SY, 2011
)
0.37
") also did not affect log dose-response curves of prazosin, clonidine and Bay K 8644, a Ca(2+) channel activator, in normotensive rats."( Butylidenephthalide antagonizes cromakalim-induced systolic pressure reduction in conscious normotensive rats.
Chen, CM; Ko, WC; Lin, YJ; Shih, CH, 2015
)
0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
hypoglycemic agentA drug which lowers the blood glucose level.
EC 3.2.1.20 (alpha-glucosidase) inhibitorAn EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-glucosidase (EC 3.2.1.20).
[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 (3)

ClassDescription
isobenzofuranoneA 2-benzofuran containing one or more oxo groups.
2-benzofurans
gamma-lactoneA lactone having a five-membered lactone ring.
[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]

Protein Targets (8)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Alpha-glucosidase MAL62Saccharomyces cerevisiae (brewer's yeast)IC50 (µMol)2,350.00000.84001.42002.0000AID592240
Oligo-1,6-glucosidase IMA1Saccharomyces cerevisiae S288CIC50 (µMol)2,350.00009.37009.37009.3700AID735123
Oligo-1,6-glucosidase IMA1Saccharomyces cerevisiae S288CKi4.86004.86004.86004.8600AID735122
Tissue alpha-L-fucosidaseBos taurus (cattle)IC50 (µMol)82.00000.00500.05750.1100AID1688689
Transient receptor potential cation channel subfamily A member 1Homo sapiens (human)IC50 (µMol)23.00000.05102.47257.5000AID772958
5-hydroxytryptamine receptor 7Homo sapiens (human)IC50 (µMol)126.60000.00050.45464.7640AID380792
Transient receptor potential cation channel subfamily A member 1Rattus norvegicus (Norway rat)IC50 (µMol)44.50000.45003.42437.5000AID772955
Transient receptor potential cation channel subfamily M member 8Rattus norvegicus (Norway rat)IC50 (µMol)147.00000.05802.65048.3000AID772951; AID772952
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (25)

Processvia Protein(s)Taxonomy
glycolipid catabolic processTissue alpha-L-fucosidaseBos taurus (cattle)
monoatomic ion transportTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
intracellular calcium ion homeostasisTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
cell surface receptor signaling pathwayTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
response to coldTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
response to xenobiotic stimulusTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
response to organic substanceTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
response to organic cyclic compoundTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
sensory perception of painTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
calcium-mediated signalingTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
response to painTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
thermoceptionTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
detection of mechanical stimulus involved in sensory perception of painTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
detection of chemical stimulus involved in sensory perception of painTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
protein homotetramerizationTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
cellular response to hydrogen peroxideTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
calcium ion transmembrane transportTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
cellular response to organic substanceTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
smooth muscle contraction5-hydroxytryptamine receptor 7Homo sapiens (human)
circadian rhythm5-hydroxytryptamine receptor 7Homo sapiens (human)
blood circulation5-hydroxytryptamine receptor 7Homo sapiens (human)
vasoconstriction5-hydroxytryptamine receptor 7Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathway5-hydroxytryptamine receptor 7Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 7Homo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 7Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
alpha-L-fucosidase activityTissue alpha-L-fucosidaseBos taurus (cattle)
calcium channel activityTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
channel activityTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
intracellularly gated calcium channel activityTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
identical protein bindingTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
temperature-gated cation channel activityTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
protein binding5-hydroxytryptamine receptor 7Homo sapiens (human)
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 7Homo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 7Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
plasma membraneTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
stereocilium bundleTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 7Homo sapiens (human)
trans-Golgi network membrane5-hydroxytryptamine receptor 7Homo sapiens (human)
synapse5-hydroxytryptamine receptor 7Homo sapiens (human)
dendrite5-hydroxytryptamine receptor 7Homo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 7Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (88)

Assay IDTitleYearJournalArticle
AID1688689Inhibition of bovine kidney alpha-fucosidase using PNPG as substrate incubated for 10 mins by spectrophotometric method2020European journal of medicinal chemistry, Feb-15, Volume: 188Discovery of novel pyrido-pyrrolidine hybrid compounds as alpha-glucosidase inhibitors and alternative agent for control of type 1 diabetes.
AID592339Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 56.2 mg/kg after 2 hrs by oral glucose tolerance test (RVb= -12.9 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID592249Antihyperglycemic activity in ICR mouse assessed as change in blood glucose level at 10 mg/kg after 1.5 hrs by oral glucose tolerance test (RVb= 2.5 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID1103607Ratio of rotenone LD50 to compound LD50 for adult Drosophila melanogaster2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID592333Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 56.2 mg/kg after 1 hr by oral glucose tolerance test (RVb= 10.3 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID592329Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 31.2 mg/kg after 0.5 hr by oral glucose tolerance test (RVb= 51.9 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID592240Inhibition of yeast alpha-glucosidase assessed as inhibition of p-nitrophenyl-alpha-D-glucopyranoside substrate hydrolysis after 35 mins by spectroscopy2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID592343Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 56.2 mg/kg after 0.5 hr by oral sucrose tolerance test (RVb= 56 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID1103589Ratio of N,N-diethyl-m-toulamide (DEET) LC50 to compound LC50 for Tyrophagus putrescentiae2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID592410Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 10 mg/kg after 2 hrs by oral sucrose tolerance test (RVb= -4.3 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID1103609Ratio of rotenone LC50 to compound LC50 for Drosophila melanogaster larvae2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID592337Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 10 mg/kg after 2 hrs by oral glucose tolerance test (RVb= -12.9 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID592251Antihyperglycemic activity in ICR mouse assessed as change in blood glucose level at 20 mg/kg after 0.5 hr by oral glucose tolerance test (RVb= 59 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID592252Antihyperglycemic activity in ICR mouse assessed as change in blood glucose level at 20 mg/kg after 1 hr by oral glucose tolerance test (RVb= 1.5 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID592338Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 31.2 mg/kg after 2 hrs by oral glucose tolerance test (RVb= -12.9 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID1103608Adulticidal activity against Drosophila melanogaster larvae assessed as mortality measured per adult2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103601Acaricidal activity against Dermatophagoides farinae assessed as mortality at 10 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103598Acaricidal activity against Dermatophagoides farinae assessed as mortality after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID592247Antihyperglycemic activity in ICR mouse assessed as change in blood glucose level at 10 mg/kg after 0.5 hr by oral glucose tolerance test (RVb= 59 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID592335Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 31.2 mg/kg after 1.5 hrs by oral glucose tolerance test (RVb= 0.005 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID592332Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 31.2 mg/kg after 1 hr by oral glucose tolerance test (RVb= 10.3 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID592407Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 10 mg/kg after 1.5 hrs by oral sucrose tolerance test (RVb= 6.1 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID1103599Acaricidal activity against Dermatophagoides farinae assessed as mortality at 2.5 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103596Acaricidal activity against Tyrophagus putrescentiae assessed as mortality at 50 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID592239Inhibition of alpha-glucosidase in streptozotocin-induced diabetic ICR mouse intestine assessed as lowering of blood glucose levels2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID592345Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 10 mg/kg after 1 hr by oral sucrose tolerance test (RVb= 11.4 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID1103602Acaricidal activity against Dermatophagoides farinae assessed as mortality at 20 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID592408Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 56.2 mg/kg after 1.5 hrs by oral sucrose tolerance test (RVb= 6.1 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID1103590Acaricidal activity against Tyrophagus putrescentiae assessed as mortality after 24 hr2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID592346Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 56.2 mg/kg after 1 hr by oral sucrose tolerance test (RVb= 11.4 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID592254Antihyperglycemic activity in ICR mouse assessed as change in blood glucose level at 20 mg/kg after 2 hrs by oral glucose tolerance test (RVb= -12 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID1103588Insecticidal activity against adult Ctenocephalides felis at 200 ug/cm22006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID592342Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 10 mg/kg after 0.5 hr by oral sucrose tolerance test (RVb= 56 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID1688691Inhibition of jack bean alpha-mannosidase using PNPG as substrate incubated for 10 mins by spectrophotometric method2020European journal of medicinal chemistry, Feb-15, Volume: 188Discovery of novel pyrido-pyrrolidine hybrid compounds as alpha-glucosidase inhibitors and alternative agent for control of type 1 diabetes.
AID1103594Acaricidal activity against Tyrophagus putrescentiae assessed as mortality at 20 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID592334Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 10 mg/kg after 1.5 hrs by oral glucose tolerance test (RVb= 0.005 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID735123Inhibition of baker's yeast alpha-glucosidase2013Journal of natural products, Mar-22, Volume: 76, Issue:3
Mexican antidiabetic herbs: valuable sources of inhibitors of α-glucosidases.
AID1688686Non-competitive inhibition of rat intestinal alpha-glucosidase2020European journal of medicinal chemistry, Feb-15, Volume: 188Discovery of novel pyrido-pyrrolidine hybrid compounds as alpha-glucosidase inhibitors and alternative agent for control of type 1 diabetes.
AID735122Mixed type inhibition of baker's yeast alpha-glucosidase by Dixon plot analysis2013Journal of natural products, Mar-22, Volume: 76, Issue:3
Mexican antidiabetic herbs: valuable sources of inhibitors of α-glucosidases.
AID1103605Acaricidal activity against Dermatophagoides farinae assessed as mortality at 50 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103600Acaricidal activity against Dermatophagoides farinae assessed as mortality at 5 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID592330Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 56.2 mg/kg after 0.5 hr by oral glucose tolerance test (RVb= 51.9 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID1103593Acaricidal activity against Tyrophagus putrescentiae assessed as mortality at 10 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID592250Antihyperglycemic activity in ICR mouse assessed as change in blood glucose level at 10 mg/kg after 2 hrs by oral glucose tolerance test (RVb= -12 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID592253Antihyperglycemic activity in ICR mouse assessed as change in blood glucose level at 20 mg/kg after 1.5 hrs by oral glucose tolerance test (RVb= 2.5 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID1103597Ratio of N,N-diethyl-m-toulamide (DEET) LC50 to compound LC50 for Dermatophagoides farinae2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103610Larvicidal activity against Drosophila melanogaster larvae assessed as mortality administered through diet after 8 days2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID592411Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 56.2 mg/kg after 2 hrs by oral sucrose tolerance test (RVb= -4.3 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID592328Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 10 mg/kg after 0.5 hr by oral glucose tolerance test (RVb= 51.9 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID592248Antihyperglycemic activity in ICR mouse assessed as change in blood glucose level at 10 mg/kg after 1 hr by oral glucose tolerance test (RVb= 1.5 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID1103591Acaricidal activity against Tyrophagus putrescentiae assessed as mortality at 2.5 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1688687Inhibition of Saccharomyces cerevisiae alpha-glucosidase using PNPG as substrate incubated for 10 mins by spectrophotometric method2020European journal of medicinal chemistry, Feb-15, Volume: 188Discovery of novel pyrido-pyrrolidine hybrid compounds as alpha-glucosidase inhibitors and alternative agent for control of type 1 diabetes.
AID592336Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 56.2 mg/kg after 1.5 hrs by oral glucose tolerance test (RVb= 0.005 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID592331Antidiabetic activity in streptozotocin-induced diabetic ICR mouse assessed as change in blood glucose level at 10 mg/kg after 1 hr by oral glucose tolerance test (RVb= 10.3 %)2011Journal of natural products, Mar-25, Volume: 74, Issue:3
(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
AID308997Antiplatelet activity in human platelet rich plasma assessed as inhibition of ADP-induced platelet aggregation2007Bioorganic & medicinal chemistry letters, Sep-15, Volume: 17, Issue:18
Synthesis, resolution, and antiplatelet activity of 3-substituted 1(3H)-isobenzofuranone.
AID1103590Acaricidal activity against Tyrophagus putrescentiae assessed as mortality after 24 hr2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID772951Antagonist activity at rat recombinant TRPM8 overexpressed in HEK293 cells assessed as inhibition of menthol-induced intracellular calcium influx preincubated for 5 mins followed by menthol challenge by Fluo-4-AM dye-based spectrofluorimetric analysis2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators.
AID1103608Adulticidal activity against Drosophila melanogaster larvae assessed as mortality measured per adult2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID772956Agonist activity at rat recombinant TRPA1 overexpressed in HEK293 cells assessed as induction of intracellular calcium influx by Fluo-4-AM dye-based spectrofluorimetric analysis2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators.
AID1103591Acaricidal activity against Tyrophagus putrescentiae assessed as mortality at 2.5 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103593Acaricidal activity against Tyrophagus putrescentiae assessed as mortality at 10 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103599Acaricidal activity against Dermatophagoides farinae assessed as mortality at 2.5 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103588Insecticidal activity against adult Ctenocephalides felis at 200 ug/cm22006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1082320Adulticidal activity against female Bemisia tabaci biotype B (sweet potato whitefly) in cucumber leaves assessed as residual contact toxicity treated for 30 secs before adult insect infestation measured after 24 hr by leaf dip bioassay2011Journal of agricultural and food chemistry, Aug-10, Volume: 59, Issue:15
Adulticidal activity of phthalides identified in Cnidium officinale rhizome to B- and Q-biotypes of Bemisia tabaci.
AID772954Agonist activity at rat recombinant TRPM8 overexpressed in HEK293 cells assessed as induction of intracellular calcium influx by Fluo-4-AM dye-based spectrofluorimetric analysis relative to ionomycin2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators.
AID308998Antiplatelet activity in human platelet rich plasma assessed as inhibition of arachidonic acid-induced platelet aggregation2007Bioorganic & medicinal chemistry letters, Sep-15, Volume: 17, Issue:18
Synthesis, resolution, and antiplatelet activity of 3-substituted 1(3H)-isobenzofuranone.
AID380793Displacement of [3H]LSD from human recombinant 5HT7 receptor expressed in CHO cells at 100 uM by liquid scintillation counting relative to control2006Journal of natural products, Apr, Volume: 69, Issue:4
Serotonergic activity-guided phytochemical investigation of the roots of Angelica sinensis.
AID772953Agonist activity at rat recombinant TRPM8 overexpressed in HEK293 cells assessed as induction of intracellular calcium influx by Fluo-4-AM dye-based spectrofluorimetric analysis2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators.
AID1103605Acaricidal activity against Dermatophagoides farinae assessed as mortality at 50 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103609Ratio of rotenone LC50 to compound LC50 for Drosophila melanogaster larvae2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103610Larvicidal activity against Drosophila melanogaster larvae assessed as mortality administered through diet after 8 days2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103596Acaricidal activity against Tyrophagus putrescentiae assessed as mortality at 50 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103600Acaricidal activity against Dermatophagoides farinae assessed as mortality at 5 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103602Acaricidal activity against Dermatophagoides farinae assessed as mortality at 20 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103601Acaricidal activity against Dermatophagoides farinae assessed as mortality at 10 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103589Ratio of N,N-diethyl-m-toulamide (DEET) LC50 to compound LC50 for Tyrophagus putrescentiae2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103597Ratio of N,N-diethyl-m-toulamide (DEET) LC50 to compound LC50 for Dermatophagoides farinae2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID772952Antagonist activity at rat recombinant TRPM8 overexpressed in HEK293 cells assessed as inhibition of icilin-induced intracellular calcium influx preincubated for 5 mins followed by icilin challenge by Fluo-4-AM dye-based spectrofluorimetric analysis2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators.
AID1103594Acaricidal activity against Tyrophagus putrescentiae assessed as mortality at 20 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1103607Ratio of rotenone LD50 to compound LD50 for adult Drosophila melanogaster2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID380792Displacement of [3H]LSD from human recombinant 5HT7 receptor expressed in CHO cells by liquid scintillation counting2006Journal of natural products, Apr, Volume: 69, Issue:4
Serotonergic activity-guided phytochemical investigation of the roots of Angelica sinensis.
AID1103598Acaricidal activity against Dermatophagoides farinae assessed as mortality after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID1082321Biotype susceptibility ratio, ratio of LC50 for female adult Bemisia tabaci biotype Q (sweet potato whitefly) to LC50 for female adult Bemisia tabaci biotype B2011Journal of agricultural and food chemistry, Aug-10, Volume: 59, Issue:15
Adulticidal activity of phthalides identified in Cnidium officinale rhizome to B- and Q-biotypes of Bemisia tabaci.
AID772955Antagonist activity at rat recombinant TRPA1 overexpressed in HEK293 cells assessed as inhibition of allyl isothiocyanate-induced intracellular calcium influx preincubated for 5 mins followed by allyl isothiocyanate challenge by Fluo-4-AM dye-based spectr2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators.
AID772957Agonist activity at rat recombinant TRPA1 overexpressed in HEK293 cells assessed as induction of intracellular calcium influx by Fluo-4-AM dye-based spectrofluorimetric analysis relative to allyl isothiocyanate2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators.
AID1103592Acaricidal activity against Tyrophagus putrescentiae assessed as mortality at 5 ug/cm2 after 24 hr relative to control2006Biological & pharmaceutical bulletin, Mar, Volume: 29, Issue:3
Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.
AID772958Antagonist activity at TRPA1 (unknown origin) assessed as inhibition of mustard oil-activated current2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators.
AID1082322Adulticidal activity against female Bemisia tabaci biotype Q (sweet potato whitefly) in cucumber leaves assessed as residual contact toxicity treated for 30 secs before adult insect infestation measured after 24 hr by leaf dip bioassay2011Journal of agricultural and food chemistry, Aug-10, Volume: 59, Issue:15
Adulticidal activity of phthalides identified in Cnidium officinale rhizome to B- and Q-biotypes of Bemisia tabaci.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (112)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (2.68)18.7374
1990's8 (7.14)18.2507
2000's23 (20.54)29.6817
2010's63 (56.25)24.3611
2020's15 (13.39)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.39

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index32.39 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.42 (4.65)
Search Engine Demand Index36.43 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (32.39)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.93%)5.53%
Trials0 (0.00%)5.53%
Reviews2 (1.85%)6.00%
Reviews0 (0.00%)6.00%
Case Studies2 (1.85%)4.05%
Case Studies0 (0.00%)4.05%
Observational1 (0.93%)0.25%
Observational0 (0.00%)0.25%
Other102 (94.44%)84.16%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]