phillygenin

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

Description

phillygenin: cytoprotective lignan from Forsythia suspensa; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Flora	Rank	Flora Definition	Family	Family Definition
Forsythia	genus	A plant genus of the family OLEACEAE. Members contain suspensaside.[MeSH]	Oleaceae	A plant family of the order Lamiales. The leaves are usually opposite and the flowers usually have four sepals, four petals, two stamens, and two fused carpels that form a single superior ovary.[MeSH]

Cross-References

ID Source	ID
PubMed CID	3083590
CHEMBL ID	2260010
SCHEMBL ID	10052265
MeSH ID	M0537666

Synonyms (33)

Synonym
phenol, 4-(4-(3,4-dimethoxyphenyl)tetrahydro-1h,3h-furo(3,4-c)furan-1-yl)-2-methoxy-, (1s-(1alpha,3aalpha,4beta,6aalpha))-
unii-886ial08gn
phillygenol
epipinoresinol methyl ether
phillygenin
487-39-8
886ial08gn ,
ACON1_001142
sylvatesmin
MEGXP0_000876
NCGC00169636-01
BRD-K69431605-001-01-7
4-[(3s,3ar,6r,6ar)-6-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
S9187
(+)-monomethylpinoresinol
(+)-phillygenin
phillyrin aglycone
phenol, 4-((1s,3ar,4r,6ar)-4-(3,4-dimethoxyphenyl)tetrahydro-1h,3h-furo(3,4-c)furan-1-yl)-2-methoxy-
CHEMBL2260010
SCHEMBL10052265
AC-34423
Q-100547
DTXSID80197588
CS-5705
HY-N0483
AKOS030524964
4-((1s,3ar,4r,6ar)-4-(3,4-dimethoxyphenyl)tetrahydro-1h,3h-furo[3,4-c]furan-1-yl)-2-methoxyphenol
mfcd01075148
forsythigenol
CCG-268325
Q27269895
(+)-sylvatesmin
AS-56623

Research Excerpts

Overview

Phillygenin (PHI) is a kind of lignans extracted and separated from Forsythiae Fructus. It has been reported to have a good anti-inflammatory effect. Phillygenin is a potential candidate in osteosarcoma therapy.

Excerpt	Reference	Relevance
"Phillygenin (PHI) is a kind of lignans extracted and separated from Forsythiae Fructus, which has been reported to have a good anti-inflammatory effect."	( Phillygenin inhibits LPS-induced activation and inflammation of LX2 cells by TLR4/MyD88/NF-κB signaling pathway. Dai, X; Gong, L; Hu, N; Li, Y; Peng, C; Wang, C; Yu, L; Zhou, M, 2020)	2.72
"Phillygenin is a potential candidate in osteosarcoma therapy."	( A natural product phillygenin suppresses osteosarcoma growth and metastasis by regulating the SHP-1/JAK2/STAT3 signaling. Ding, X; Fan, J; Lu, D, 2021)	1.68

Pharmacokinetics

Excerpt	Reference	Relevance
" In a recent study, phillygenin was found to be a potential "metabolite" of phillyrin and the effective material of phillyrin may be changed according to the in vivo pharmacokinetic process."	( Determination of phillygenin in rat plasma by high-performance liquid chromatography and its application to pharmacokinetic studies. Gong, XH; Li, YX; Peng, C; Ye, LH; Zheng, XG, 2013)	1.05

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (3)

Assay ID	Title	Year	Journal	Article
AID1371010	Anti-inflammatory activity in human neutrophils assessed as inhibition of fMLP/CB-induced superoxide anion generation by measuring superoxide dismutase SOD-inhibitable ferricytochrome c reduction incubated for 5 mins before fMLP/CB stimulation for 3 mins	2017	Journal of natural products, 04-28, Volume: 80, Issue:4	Chemical Constituents and Anti-inflammatory Principles from the Fruits of Forsythia suspensa.
AID1371011	Anti-inflammatory activity in human neutrophils assessed as inhibition of fMLP/CB-induced elastase release pre-incubated for 5 mins before fMLP/CB stimulation using MeO-Suc-Ala-Ala-Pro-Val-pnitroanilide as substrate	2017	Journal of natural products, 04-28, Volume: 80, Issue:4	Chemical Constituents and Anti-inflammatory Principles from the Fruits of Forsythia suspensa.
AID1371012	Anti-inflammatory activity in human neutrophils assessed as inhibition of fMLP/CB-induced superoxide anion generation by measuring superoxide dismutase SOD-inhibitable ferricytochrome c reduction at 10 ug/ml incubated for 5 mins before fMLP/CB stimulation	2017	Journal of natural products, 04-28, Volume: 80, Issue:4	Chemical Constituents and Anti-inflammatory Principles from the Fruits of Forsythia suspensa.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (21)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	2 (9.52)	29.6817
2010's	7 (33.33)	24.3611
2020's	12 (57.14)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.53

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.

Metric	This Compound (vs All)
Research Demand Index	23.53 (24.57)
Research Supply Index	3.14 (2.92)
Research Growth Index	5.02 (4.65)
Search Engine Demand Index	23.28 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (23.53)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (4.55%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	21 (95.45%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
molsidomine Molsidomine: A morpholinyl sydnone imine ethyl ester, having a nitrogen in place of the keto oxygen. It acts as NITRIC OXIDE DONORS and is a vasodilator that has been used in ANGINA PECTORIS.. molsidomine : A member of the class of oxadiazoles that is 1,2,3-oxadiazole substituted by morpholin-4-yl and (ethoxycarbonyl)azanidyl groups at positions 3 and 5, respectively. It is used as a vasodilator drug for the treatment of myocardial ischemic syndrome and congestive heart failure.	2.05	1	ethyl ester; morpholines; oxadiazole; zwitterion	antioxidant; apoptosis inhibitor; cardioprotective agent; nitric oxide donor; vasodilator agent
linsidomine linsidomine: RN given refers to parent cpd; structure	2.05	1	morpholines
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	7.41	1	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
diquat Diquat: A contact herbicide used also to produce desiccation and defoliation. (From Merck Index, 11th ed). diquat : The organic cation formed formally by addition of an ethylene bridge between the nitrogen atoms of 2,2'-bipyridine. Most often available as the dibromide.	2.05	1	organic cation	defoliant; herbicide
furaldehyde Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.	2.05	1	aldehyde; furans	Maillard reaction product; metabolite
diethylhexyl phthalate Diethylhexyl Phthalate: An ester of phthalic acid. It appears as a light-colored, odorless liquid and is used as a plasticizer for many resins and elastomers.. bis(2-ethylhexyl) phthalate : A phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	2.05	1	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
podophyllotoxin Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.	3.35	1	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	2.49	2	D-glucopyranose	epitope; mouse metabolite
ursolic acid [no description available]	2.15	1	hydroxy monocarboxylic acid; pentacyclic triterpenoid	geroprotector; plant metabolite
masoprocol Masoprocol: A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.. masoprocol : The meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase.	3.35	1	nordihydroguaiaretic acid	antineoplastic agent; hypoglycemic agent; lipoxygenase inhibitor; metabolite
pinoresinol (+)-pinoresinol : An enantiomer of pinoresinol having (+)-1S,3aR,4S,6aR-configuration.	2.15	1	pinoresinol	hypoglycemic agent; phytoestrogen; plant metabolite
diphyllin diphyllin: extract of Cleistanthus collinus (Roxb), a highly poisonous plant; do not confuse with diphyllin or diphylline which is the main heading AMINOPHYLLINE; do not confuse with the theophylline derivative DYPHYLLINE	3.35	1	lignan
matairesinol matairesinol: lignan that is a central precursor in plants in the biosynthesis of numerous lignans (coordinate with specific); RN refers to (3R-trans)-isomer. (-)-matairesinol : A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).	2.15	1	gamma-lactone; lignan; polyphenol	angiogenesis inhibitor; anti-asthmatic agent; phytoestrogen; plant metabolite
peroxynitrous acid Peroxynitrous Acid: A potent oxidant synthesized by the cell during its normal metabolism. Peroxynitrite is formed from the reaction of two free radicals, NITRIC OXIDE and the superoxide anion (SUPEROXIDES).	2.05	1	nitrogen oxoacid
oleanolic acid 3-acetate oleanolic acid 3-acetate: from Gardenia jasminoides; RN given for (3beta)-isomer	2.15	1
sorafenib [no description available]	2.15	1	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; phenylureas; pyridinecarboxamide	angiogenesis inhibitor; anticoronaviral agent; antineoplastic agent; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; ferroptosis inducer; tyrosine kinase inhibitor
5-hydroxymethylfurfural 5-hydroxymethylfurfural: has antisickling activity; HMF is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo. 5-hydroxymethylfurfural : A member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and hydroxymethyl substituents, respectively. Virtually absent from fresh foods, it is naturally generated in sugar-containing foods during storage, and especially by drying or cooking. It is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo.	2.05	1	arenecarbaldehyde; furans; primary alcohol	indicator; Maillard reaction product
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	5.45	17
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	2.05	1	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
terameprocol [no description available]	3.35	1	lignan
glycosides [no description available]	2.46	2
epipinoresinol epipinoresinol : An enantiomer of pinoresinol having (+)-(1R,3aR,4S,6aR)-configuration.	2.15	1	pinoresinol	marine metabolite; plant metabolite
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.05	1
8-hydroxypinoresinol 8-hydroxypinoresinol: cytoprotective lignan from Forsythia suspensa; structure in first source	2.05	1	lignan
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.05	1
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.31	1	prostaglandins E	human metabolite; mouse metabolite; oxytocic
stigmasterol stigmasta-5,22-dien-3-ol: isolated from freeze-dried powder of Blackberries (Rubus ursinus L.) which showed an activity on inhibition of chemocarcinogen. stigmasterol : A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions.	2.05	1	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols; stigmastane sterol	plant metabolite
forsythiaside forsythiaside: RN given refers to (E)-isomer; structure given in first source; from the unripe fruit of Forsythia suspensa (qinglianquiao)	2.77	3	hydroxycinnamic acid
suspensaside suspensaside: from fruit of Forsythia suspensa Vahl (Oleaceae); structure given in first source	2.15	1
acteoside acteoside: a protein kinase C inhibitor with hepatoprotective, anti-asthmatic, and analgesic activities; a phenylethanoid glycoside related to isoacteoside; from leaves of Lippia multiflora (Verbenaceae). acteoside : A glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid.	2.15	1	catechols; cinnamate ester; disaccharide derivative; glycoside; polyphenol	anti-inflammatory agent; antibacterial agent; antileishmanial agent; neuroprotective agent; plant metabolite
bicyclol bicyclol: an antihepatitis drug, on the metabolism and hepatotoxicity of aflatoxin B1 (AFB1) in rats.	3.35	1
phillyrin [no description available]	2.05	1
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.05	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent

Condition	Relationship Strength	Studies
Lung Injury, Acute [description not available]	2.31	1
Innate Inflammatory Response [description not available]	3.49	5
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	3.49	5
Acute Lung Injury A condition of lung damage that is characterized by bilateral pulmonary infiltrates (PULMONARY EDEMA) rich in NEUTROPHILS, and in the absence of clinical HEART FAILURE. This can represent a spectrum of pulmonary lesions, endothelial and epithelial, due to numerous factors (physical, chemical, or biological).	2.31	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.41	1
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	7.9	2
Infections, Coronavirus [description not available]	2.41	1
Poultry Diseases Diseases of birds which are raised as a source of meat or eggs for human consumption and are usually found in barnyards, hatcheries, etc. The concept is differentiated from BIRD DISEASES which is for diseases of birds not considered poultry and usually found in zoos, parks, and the wild.	2.41	1
Coronavirus Infections Virus diseases caused by the CORONAVIRUS genus. Some specifics include transmissible enteritis of turkeys (ENTERITIS, TRANSMISSIBLE, OF TURKEYS); FELINE INFECTIOUS PERITONITIS; and transmissible gastroenteritis of swine (GASTROENTERITIS, TRANSMISSIBLE, OF SWINE).	2.41	1
Fatty Liver, Nonalcoholic [description not available]	2.41	1
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	7.41	1
Cirrhosis, Liver [description not available]	3.07	3
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	3.07	3
Anasarca [description not available]	2.41	1
Ache [description not available]	2.41	1
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	7.41	1
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2.41	1
Colitis Gravis [description not available]	2.6	1
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	2.6	1
Hepatitis INFLAMMATION of the LIVER.	2.25	1
Metastase [description not available]	2.31	1
Osteogenic Sarcoma [description not available]	2.31	1
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.31	1
Osteosarcoma A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)	7.31	1
Cancer of Esophagus [description not available]	2.21	1
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	2.21	1

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