Page last updated: 2024-11-07

obovatol

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

Description

Obovatol is a natural product isolated from the leaves of *Olea europaea* (olive tree). It exhibits various biological activities, including anti-inflammatory, antioxidant, and anticancer properties. Its synthesis involves complex multi-step reactions starting from readily available starting materials. Obovatol is studied due to its potential therapeutic applications, particularly in the treatment of inflammatory diseases and cancer. Its antioxidant activity is attributed to its ability to scavenge free radicals and protect cells from oxidative damage. The compound's anticancer activity is associated with its ability to inhibit cell proliferation and induce apoptosis in cancer cells.'

obovatol: antineoplastic agent from Magnolis obovata; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID100771
CHEMBL ID491809
SCHEMBL ID454929
MeSH IDM0111768

Synonyms (23)

Synonym
obovatol
83864-78-2
nsc-364150
nsc364150
1,2-benzenediol, 5-(2-propenyl)-3-(4-(2-propenyl)phenoxy)-
5-prop-2-enyl-3-(4-prop-2-enylphenoxy)benzene-1,2-diol
CHEMBL491809
obovator
h6szx78nxa ,
4',5-diallyl-2,3-dihydroxybiphenyl ether
unii-h6szx78nxa
nsc 364150
SCHEMBL454929
obvatol
5-allyl-3-(4-allylphenoxy)benzene-1,2-diol
Q15634039
DTXSID601003992
5-(prop-2-en-1-yl)-3-[4-(prop-2-en-1-yl)phenoxy]benzene-1,2-diol
AC-36774
1,2-benzenediol, 5-(2-propenyl)-3-[4-(2-propenyl)phenoxy]-
5-(2-propen-1-yl)-3-[4-(2-propen-1-yl)phenoxy]-1,2-benzenediol
AKOS040760602
FS-8182

Research Excerpts

Effects

Obovatol has various biological activities, including anti-proliferative, neurotrophic, anti-fibrillogenic and anti-platelet. It also has been reported biological activities such as muscle relaxative,Anti-gastric ulcer and Anti-allergic activities.

ExcerptReferenceRelevance
"Obovatol has a potent antithrombotic effect, which may be due to antiplatelet activity. "( Antiplatelet activity of obovatol, a biphenolic component of Magnolia Obovata, in rat arterial thrombosis and rabbit platelet aggregation.
Hong, JT; Kwon, BM; Lee, SH; Lim, Y; Park, ES; Yoo, HS; Yun, YP, 2011
)
2.12
"Obovatol has a potent antithrombotic effect, which may be due to antiplatelet activity. "( Antiplatelet activity of obovatol, a biphenolic component of Magnolia Obovata, in rat arterial thrombosis and rabbit platelet aggregation.
Hong, JT; Kwon, BM; Lee, SH; Lim, Y; Park, ES; Yoo, HS; Yun, YP, 2011
)
2.12
"Obovatol has various biological activities, including anti-proliferative, neurotrophic, anti-fibrillogenic, anti-platelet, anti-fungal and anti-inflammatory activities. "( JJK694, a synthesized obovatol derivative, inhibits platelet activation by suppressing cyclooxygenase and lipoxygenase activities.
Jung, JK; Kim, TJ; Lee, JJ; Lee, MY; Ma, JY; Min, YK; Yu, JY; Yun, YP, 2012
)
2.14
"Obovatol has been reported biological activities such as muscle relaxative, anti-gastric ulcer, anti-allergic and anti-bacterial activities. "( Anti-platelet activity of diacetylated obovatol through regulating cyclooxygenase and lipoxygenase activities.
Jung, JK; Kim, TJ; Lee, JJ; Lee, MY; Ma, JY; Min, YK; Yu, JY; Yun, YP, 2012
)
2.09

Treatment

Obovatol (10, 15, 20, 25 microM) inhibits cancer cell growth in the absence or the presence of tumor necrosis factor-alpha (TNF-alpha , 10 ng/ml) and tetradecanoyl phorbol acetate (TPA 10 or 50 nM) in a concentration-dependent manner through induction of apoptotic cell death. Treatment blocked the cell cycle in G1 phase by down-regulating the expression of cyclins and CDKs.

ExcerptReferenceRelevance
"Obovatol was treated to macrophages with inflammasome triggers, and secretions of interleukin (IL)-1β, IL-18, and caspase-1 were measured as readouts of inflammasome activation. "( Obovatol inhibits NLRP3, AIM2, and non-canonical inflammasome activation.
Ahn, H; Han, BC; Jung, EM; Kang, SG; Kim, J; Kim, JC; Lee, GS; Lee, J; Lee, SH; Shin, H; Yang, H, 2019
)
3.4
"The obovatol-treated groups (100 microg and 1mg: 0.14+/-0.04 and 0.09+/-0.03 mm2, respectively) showed significant reduction in neointimal formation versus the control group (0.17+/-0.02 mm2)."( Obovatol from Magnolia obovata inhibits vascular smooth muscle cell proliferation and intimal hyperplasia by inducing p21Cip1.
Hong, JT; Kim, DW; Kwon, BM; Kwon, JS; Lee, JJ; Lee, SH; Lim, Y; Park, RK; Yoo, HS; Yun, YP, 2010
)
2.28
"Treatment with obovatol blocked the cell cycle in G1 phase by down-regulating the expression of cyclins and CDKs, and selectively up-regulating the expression of p21Cip1, a well-known CDK inhibitor."( Obovatol from Magnolia obovata inhibits vascular smooth muscle cell proliferation and intimal hyperplasia by inducing p21Cip1.
Hong, JT; Kim, DW; Kwon, BM; Kwon, JS; Lee, JJ; Lee, SH; Lim, Y; Park, RK; Yoo, HS; Yun, YP, 2010
)
2.14
"Treatment of obovatol (10, 15, 20, 25 microM) inhibits cancer cell growth in the absence or the presence of tumor necrosis factor-alpha (TNF-alpha , 10 ng/ml) and tetradecanoyl phorbol acetate (TPA 10 or 50 nM) in a concentration-dependent manner through induction of apoptotic cell death."( Growth inhibitory effects of obovatol through induction of apoptotic cell death in prostate and colon cancer by blocking of NF-kappaB.
Hong, JT; Jung, JK; Lee, BS; Lee, SY; Moon, DC; Song, HS; Yoon, DY; Yuk, DY, 2008
)
0.99

Toxicity

ExcerptReferenceRelevance
" Their conditioned media were toxic to SH-SY5Y cells."( Effects of obovatol on GSH depleted glia-mediated neurotoxicity and oxidative damage.
Kwon, BM; Lee, M; McGeer, E; McGeer, PL; Suk, K, 2012
)
0.77

Pharmacokinetics

ExcerptReferenceRelevance
" On this basis, the chemical components of XECQ were targeted and enriched by network pharmacology, to screen the main pharmacodynamic substances of XECQ in the treatment of acute upper respiratory tract infection in children and discuss the mechanism of action."( [Pharmacodynamic substances and mechanism of action of Xiaoer Chiqiao Qingre Granules in treatment of acute upper respiratory tract infection in children].
Feng, L; Jia, XB; Liu, J; Lu, GZ; Yang, YJ; Zhao, J; Zhu, MM; Zhu, XJ, 2022
)
0.72
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pathways (1)

PathwayProteinsCompounds
chitin biosynthesis1640

Bioassays (41)

Assay IDTitleYearJournalArticle
AID387407Antitumor activity in human SW620 cells xenografted nude mouse assessed as decrease in tumor volume at 5 mg/kg/day, ip after 21 days2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387419Antitumor activity against human SW620 cells at 30 uM after 96 hrs2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387431Antiproliferative activity against human DLD1 cells after 48 hrs by MTS assay2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387438Cell cycle arrest in human SW620 cells assessed as accumulation at S phase at 50 uM after 72 hrs by FACS analysis2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387428Toxicity in SW480 cells xenografted nude mouse assessed as change in body weight 5 mg/kg/day, ip after 21 days2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387435Antiproliferative activity against human PC-3 cells after 48 hrs by MTS assay2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387447Induction of apoptosis in human SW620 cells assessed as necrosis relative to control2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387426Antitumor activity against human SW620 cells at 100 uM after 72 hrs2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387439Cell cycle arrest in human SW620 cells assessed as accumulation at G2/M phase at 50 uM after 72 hrs by FACS analysis2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387411Antitumor activity in human SW620 cells xenografted nude mouse assessed as decrease in tumor volume at 5 mg/kg/day, po after 5 days2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID1279207Antiinflammatory activity in human neutrophils assessed as inhibition of FMLP/CB-induced elastase release using MeO-Suc-Ala-Ala-Pro-Val-p-nitroanilide as substrate incubated for 5 mins by spectrophotometric analysis2016Bioorganic & medicinal chemistry, Apr-01, Volume: 24, Issue:7
Anti-inflammatory neolignans from the roots of Magnolia officinalis.
AID387433Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTS assay2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387418Antitumor activity against human SW620 cells at 30 uM after 72 hrs2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387429Antiproliferative activity against human HCT 116 cells after 48 hrs by MTS assay2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387442Induction of apoptosis in human MDA-MB-231 cells assessed as morphological changes in presence of N-acetyl-cysteine after 24 hrs2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387423Antitumor activity against human SW620 cells at 50 uM after 96 hrs2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387424Antitumor activity against human SW620 cells at 100 uM after 24 hrs2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387425Antitumor activity against human SW620 cells at 100 uM after 48 hrs2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387412Antitumor activity in human SW620 cells xenografted nude mouse assessed as decrease in tumor volume at 5 mg/kg/day, po after 10 days2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387446Induction of apoptosis in human SW620 cells assessed as apoptotic cell form at 50 uM relative to control2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387422Antitumor activity against human SW620 cells at 50 uM after 72 hrs2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387413Antitumor activity in human SW620 cells xenografted nude mouse assessed as decrease in tumor volume at 5 mg/kg/day, po after 16 days2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID1279204Antiinflammatory activity in human neutrophils assessed as inhibition of FMLP/CB-induced superoxide anion generation by measuring superoxide dismutase-inhibitable reduction of ferricytochrome c by spectrophotometric analysis2016Bioorganic & medicinal chemistry, Apr-01, Volume: 24, Issue:7
Anti-inflammatory neolignans from the roots of Magnolia officinalis.
AID387437Cell cycle arrest in human SW620 cells assessed as accumulation at G1 phase at 50 uM after 72 hrs by FACS analysis2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387441Induction of apoptosis in human MDA-MB-231 cells assessed as ROS production after 24 hrs2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387417Antitumor activity against human SW620 cells at 30 uM after 48 hrs2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387432Antiproliferative activity against human MCF7 cells after 48 hrs by MTS assay2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387416Antitumor activity against human SW620 cells at 30 uM after 24 hrs2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387427Antitumor activity against human SW620 cells at 100 uM after 96 hrs2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387436Antiproliferative activity against human K-562 cells after 48 hrs by MTS assay2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387430Antiproliferative activity against human HT-29 cells after 48 hrs by MTS assay2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387443Cell cycle arrest in human SW620 cells assessed as accumulation at subG1 phase at 50 uM after 72 hrs by FACS analysis2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387421Antitumor activity against human SW620 cells at 50 uM after 48 hrs2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387414Antitumor activity in human SW620 cells xenografted nude mouse assessed as decrease in tumor volume at 5 mg/kg/day, po after 23 days2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387420Antitumor activity against human SW620 cells at 50 uM after 24 hrs2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387440Induction of apoptosis in human SW620 cells assessed as chromosomal DNA fragmentation at 50 mM after 48 hrs by FACS analysis2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387683Antiproliferative activity against human DU145 cells after 48 hrs by MTS assay2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387445Effect on apoptosis-mediated morphological changes in human SW620 cells assessed as round cell formation2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387408Antitumor activity in human SW620 cells xenografted nude mouse assessed as decrease in tumor weight at 5 mg/kg/day, ip after 21 days2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID387415Antitumor activity in human SW620 cells xenografted nude mouse assessed as decrease in tumor volume at 5 mg/kg/day, po after 27 days2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and inducing apoptosis.
AID1279208Induction of ferricytochrome c reduction in human neutrophils by spectrophotometric analysis2016Bioorganic & medicinal chemistry, Apr-01, Volume: 24, Issue:7
Anti-inflammatory neolignans from the roots of Magnolia officinalis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (39)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (2.56)18.7374
1990's0 (0.00)18.2507
2000's11 (28.21)29.6817
2010's22 (56.41)24.3611
2020's5 (12.82)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.37

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 Index21.37 (24.57)
Research Supply Index3.69 (2.92)
Research Growth Index4.47 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.37)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (5.13%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other37 (94.87%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]