(Z)-6,6',7,3'a-Diligustilide

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

Description

(Z)-6,6',7,3'a-Diligustilide is a **natural product** isolated from the *Ligusticum lucidum* plant. It is a **lignan**, a class of organic compounds characterized by the presence of two phenylpropanoid units linked through a **dibenzyl ether** bridge.

Here's why it's important for research:

* **Pharmacological Activity:**
* (Z)-6,6',7,3'a-Diligustilide has demonstrated a variety of **pharmacological activities**, including:
* **Antioxidant:** It exhibits strong antioxidant properties, which can help protect cells from damage caused by free radicals.
* **Anti-inflammatory:** It has been shown to reduce inflammation in animal models.
* **Neuroprotective:** Studies suggest it may protect against neuronal damage and have potential for treating neurodegenerative diseases.
* **Anticancer:** Some research indicates it could possess anti-cancer activity by inhibiting cancer cell growth.

* **Chemical Structure and Synthesis:**
* The unique structure of (Z)-6,6',7,3'a-Diligustilide, particularly the presence of the **dibenzyl ether** bridge and the **stereochemistry** of the molecule, has sparked interest in understanding its **biosynthetic pathways** and exploring potential **synthetic strategies**.

* **Potential for Drug Development:**
* The promising pharmacological activities of (Z)-6,6',7,3'a-Diligustilide make it a potential candidate for developing new drugs. Researchers are currently investigating its therapeutic potential and exploring its safety and efficacy in clinical trials.

**In summary, (Z)-6,6',7,3'a-Diligustilide is a naturally occurring compound with significant pharmacological potential. Its antioxidant, anti-inflammatory, neuroprotective, and anticancer properties make it a promising lead compound for drug development. Further research is ongoing to understand its mechanisms of action and explore its therapeutic applications.**

levistilide A: isolated from Angelica sinensis, inhibits hepatic stellate cell proliferation; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	70698035
CHEBI ID	68231

Synonyms (27)

Synonym
CHEBI:68231
(z)-6,6',7,3'a-diligustilide
S9201
(z,z)-di(butylidene)[?]dione
1h-5,10c-ethanonaphtho(1,2-c:7,8-c')difuran-3,10-dione, 1,8-dibutylidene-5,5a,6,7,8,10b-hexahydro-, (5s,8z,10cs)-
levistolide a
e,z'-6,6',7,3'a-diligustilide
88182-33-6
diligustilide
29mrt0h4ce ,
levistolid a
unii-29mrt0h4ce
1h-5,10c-ethanonaphtho(1,2-c:7,8-c')difuran-3,10-dione, 1,8-dibutylidene-5,5a,6,7,8,10b-hexahydro-, (1z,5s,5as,8z,10bs,10cs)-
z,z'-6,6',7,3'a-diligustilide
(z,z)-diligustilide
levistilide a
levistilide-a
levistolide a [inci]
142797-35-1
senkyunolide o
AKOS037514718
Q27136724
HY-N1472
(1s,2s,6z,10s,11s,16z)-6,16-di(butylidene)-5,15-dioxapentacyclo[9.5.2.01,13.02,10.03,7]octadeca-3(7),12-diene-4,14-dione
CS-0016970
DTXSID601317628
levistilidea

Research Excerpts

Pharmacokinetics

Excerpt	Reference	Relevance
" In this study, the developed method is successfully applied to the comparative pharmacokinetic study of LA in rats after oral administration of LA alone, Rhizoma Chuanxiong, and Danggui-Shaoyao-San along with the bioavailability study of LA in rats."	( Study on Pharmacokinetics of Three Preparations from Levistolide A by LC-MS-MS. He, WQ; Huang, XT; Li, WR; Liu, CH; Lv, WS; Qu, Z; Wang, Q; Wei, RR; Zhang, L; Zhang, Y; Zhou, XX, 2015)	0.42

Bioavailability

Excerpt	Reference	Relevance
" In this study, the developed method is successfully applied to the comparative pharmacokinetic study of LA in rats after oral administration of LA alone, Rhizoma Chuanxiong, and Danggui-Shaoyao-San along with the bioavailability study of LA in rats."	( Study on Pharmacokinetics of Three Preparations from Levistolide A by LC-MS-MS. He, WQ; Huang, XT; Li, WR; Liu, CH; Lv, WS; Qu, Z; Wang, Q; Wei, RR; Zhang, L; Zhang, Y; Zhou, XX, 2015)	0.42

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

Roles (1)

Role	Description
metabolite	Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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 (1)

Class	Description
butenolide	A gamma-lactone that consists of a 2-furanone skeleton and its substituted derivatives.
[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]

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	5 (23.81)	29.6817
2010's	10 (47.62)	24.3611
2020's	6 (28.57)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	22 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	2.03	1	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	2.04	1	aromatic ether; nitrile; polyether; tertiary amino compound
hydroxyproline Hydroxyproline: A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.. hydroxyproline : A proline derivative that is proline substituted by at least one hydroxy group.	2.17	1	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
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.	2.25	1	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	2.05	1	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
phthalide 2-benzofuran-1(3H)-one : A gamma-lactone that is 1,3-dihydro-2-benzofuran in which the hydrogens at position 1 are replaced by an oxo group.. isobenzofuranone : A 2-benzofuran containing one or more oxo groups.	2.07	1	2-benzofurans; gamma-lactone
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	2.43	2	butan-4-olide	metabolite; neurotoxin
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.41	1	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
3-n-butylphthalide 3-n-butylphthalide: isolated from phenolic part of Ligusticum wallichii Franch; structure given in first source	2.06	1	benzofurans
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	2.25	1	amino acid zwitterion; angiotensin II	human metabolite
3-n-butyl-4,5-dihydrophthalide 3-N-butyl-4,5-dihydrophthalide: from seeds of Apium graveolens Linn.; RN given refers to (-)-isomer; structure given in first source	2.47	2
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	4.23	16
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	2.44	2	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.05	1
7,3'-dihydroxy-4'-methoxyisoflavone 7,3'-dihydroxy-4'-methoxyisoflavone: isolated from Astragali radix; structure in first source. calycosin : A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at the 3' position and a methoxy group at the 4' position.	2.17	1	4'-methoxyisoflavones; 7-hydroxyisoflavones	antioxidant; metabolite
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	2.05	1	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
ligustilide ligustilide: found in Umbelliferae plants; RN given refers to cpd without isomeric designation; structure in first source	2.51	2	butenolide	metabolite
beta-escin [no description available]	2.17	1
(3z,6alpha,7alpha)-isomer of 3-butylidene-4,5,6,7-tetrahydro-6,7-dihydroxy-1(3h)-isobenzofuranone senkyunolide H: from Ligusticum chuanxiong; structure nin first source	2.1	1	2-benzofurans
lyoniside lyoniside: see also eleutherosides & syringin for eleutheroside B: 118-34-3; RN given refers to (3beta)-isomer	2.05	1
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2.15	1	benzenes; hydroxycoumarin; methyl ketone
senkyunolide i senkyunolide I: has antioxidant and anti-migraine activities; isolated from Ligusticum chuanxiong; structure in first source	2.1	1

Condition	Relationship Strength	Studies
Chronic Kidney Diseases [description not available]	2.6	1
Cirrhosis [description not available]	2.6	1
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	2.6	1
Renal Insufficiency, Chronic Conditions in which the KIDNEYS perform below the normal level for more than three months. Chronic kidney insufficiency is classified by five stages according to the decline in GLOMERULAR FILTRATION RATE and the degree of kidney damage (as measured by the level of PROTEINURIA). The most severe form is the end-stage renal disease (CHRONIC KIDNEY FAILURE). (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002)	2.6	1
Cognitive Decline [description not available]	2.31	1
Acute Confusional Senile Dementia [description not available]	2.31	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.69	2
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	2.31	1
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	2.31	1
Diabetic Glomerulosclerosis [description not available]	2.31	1
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	2.31	1
Cancer of Colon [description not available]	2.15	1
Colonic Neoplasms Tumors or cancer of the COLON.	2.15	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.11	1
Gastric Ulcer [description not available]	2.11	1
Stomach Ulcer Ulceration of the GASTRIC MUCOSA due to contact with GASTRIC JUICE. It is often associated with HELICOBACTER PYLORI infection or consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	2.11	1
Breast Cancer [description not available]	2.52	2
Breast Neoplasms Tumors or cancer of the human BREAST.	2.52	2
Cirrhosis, Liver [description not available]	2.61	2
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.	2.61	2
Buerger Disease [description not available]	2.17	1

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