Diarylheptanoids

A group of compounds consisting of two aryl rings linked by seven carbons (HEPTANES) which may be acyclic (linear) or cyclic. It is a group of secondary metabolites in polyketide synthesis pathway best exemplified by a linear diarylheptanoid CURCUMIN.

Also Known As:

Diarylheptanones; Derivative, Diarylheptanoid; Diarylheptanoid, Cyclic; Diarylheptanoids, Acyclic; Diarylheptanoids, Cyclic; Diarylheptanoids, Linear; Heptanoids, Diaryl; Acyclic Diarylheptanoids; Curcuminoid; Curcuminoids; Cyclic Diarylheptanoid; Cyclic Diarylheptanoids; Diaryl Heptanoids; Diarylheptanoid; Diarylheptanoid Derivative; Diarylheptanoid Derivatives; Linear Diarylheptanoids

Networked: 471 relevant articles (65 outcomes, 121 trials/studies)

Relationship Network

Bio-Agent Context: Research Results

Organic Chemicals: 133
- Hydrocarbons: 1713
  - Cyclic Hydrocarbons: 97
    - Aromatic Hydrocarbons: 291
      - Diarylheptanoids: 471
        Curcumin: 10678
        bisdemethoxycurcumin: 100
        demethoxycurcumin: 89
        hirsutenone: 16
        oregonin: 15
        myricanol: 12
        gingerenone A: 6
        platyphylloside: 6
        myricanone: 5
        yakuchinone B: 5
        3,4-difluorobenzylidenecurcumin: 4
        aceroside VIII: 3
        DMC-BH: 3
        hirsutanone: 3
        IR-1048: 3
        4-methoxycarbonyl curcumin: 2
        alpinoid-C: 2
        ASPP 049: 2
        bis-dehydroxy-curcumin: 2
        calyxin Y: 2
        epicalyxin F: 2
        hirsutanonol: 2
        YPE 01: 2
        (3S)-7-(3,4-dihydroxyphenyl)-1-phenyl-(1E)-1-hepten-3-ol: 1
        1,5-bis(2-fluorophenyl)penta-1,4-dien-3-one: 1
        1-(4-hydroxy-3-methoxyphenyl)-7-(3,4-dihydroxyphenyl)-4E-en-3-heptanone: 1
        3,5-bis(3,4,5-trimethoxybenzylidene)-1-methylpiperidine-4-one: 1
        acerogenin M: 1
        alnuside B: 1
        calyxin I: 1
        calyxin J: 1
        epicalyxin J: 1
        garuganin: 1
        katsumadain A: 1
        letestuianin C: 1
        myricanol 5-fluorobenzyloxy ether: 1
        (3S)-1-(3,4-dihydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol
        1,7-bis(3,4-dihydroxyphenyl)hept-4-en-3-one oxime
        1,7-bis(3,4-dihydroxyphenyl)heptan-3-ol
        1,7-bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione
        1,7-bis(4-hydroxyphenyl)-2,4,6-heptatrienone
        1,7-bis(4-hydroxyphenyl)-3-hydroxy-1,3-heptadien-5-one
        1,7-di(1H-indol-3-yl)hepta-1,6-diene-3,5-dione
        1,7-diphenyl-4,6-heptadien-3-ol
        1,7-diphenylhept-4-en-3-one
        1,9'-didesmethylgaruganin III
        1-(2',4'-dihydroxy-3'-methoxyphenyl)-7-(4'-methoxyphenyl)-3-heptanone
        1-(3',5'-dihydroxy-4'-methoxyphenyl)-7-phenyl-3-heptanone
        1-(4-hydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-one
        2,3-digalloyl oregonin
        3,5-dihydroxy-1,7-bis(3,4-dihydroxyphenyl)heptane
        3,5-dihydroxy-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)heptane
        3,5-dihydroxy-1-(4'-hydroxy-3',5'-dimethoxyphenyl)-7-(4''-hydroxy-3''-methoxyphenyl)heptane
        3-hydroxy-1,7-bis(4-hydroxyphenyl)-6-hepten-1,5-dione
        4-(4-hydroxy-3-methoxyphenylmethyl)curcumin
        4-dihydroxyphenyl)-1-phenyl-3-heptanone (5S)-5-hydroxy-7-(3
        5-1,7-di(4-hydroxyphenyl)-5-O-(6-(p-coumaroylglucopyranosyl))heptane-3-one
        5-dihydroxyphenyl)-1-phenyl-3-heptanone (5R)-5-hydroxy-7-(3-methoxy-4
        5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-1-hepten-3-one
        5-hydroxy-1-(3'-methoxy-4'-hydroxyphenyl)-7-phenyl-4,6-heptadien-3-one
        5-O-methyl-4-desmethyl-myricanol
        5-O-methylhirsutanonol
        7-(4-hydroxy-3-methoxyphenyl)-1-phenyl-4-hepten-3-one
        acerogenin A
        acerogenin L
        aceroketoside
        aceroside B1
        aceroside B2
        alnuheptanoid A
        Alpinin C
        Alpinin D
        alpinnanin A
        alpinnanin B
        alpinnanin C
        diarylheptanone glucoside I
        epihirsutanonol
        galeon
        garugamblin
        garugamblin-3
        giffonin J
        giffonin K
        giffonin T
        giffonin U
        hirustenone
        jugcathanin
        juglanin B 11-sulfate
        juglanin D
        katsumadain B
        katsumadain C
        letestuianin A
        letestuianin B
        muricarpone A
        muricarpone B
        musellarin A
        musellarin B
        musellarin C
        myricanol 11-sulfate
        myricanol-15-glucoside
        myricanone 5-O-(6'-O-galloyl)glucoside
        myricatomentogenin
  - Acyclic Hydrocarbons
    - Alkanes: 241
      - Heptanes: 70
        Diarylheptanoids: 471
        Curcumin: 10678
        bisdemethoxycurcumin: 100
        demethoxycurcumin: 89
        hirsutenone: 16
        oregonin: 15
        myricanol: 12
        gingerenone A: 6
        platyphylloside: 6
        myricanone: 5
        yakuchinone B: 5
        3,4-difluorobenzylidenecurcumin: 4
        aceroside VIII: 3
        DMC-BH: 3
        hirsutanone: 3
        IR-1048: 3
        4-methoxycarbonyl curcumin: 2
        alpinoid-C: 2
        ASPP 049: 2
        bis-dehydroxy-curcumin: 2
        calyxin Y: 2
        epicalyxin F: 2
        hirsutanonol: 2
        YPE 01: 2
        (3S)-7-(3,4-dihydroxyphenyl)-1-phenyl-(1E)-1-hepten-3-ol: 1
        1,5-bis(2-fluorophenyl)penta-1,4-dien-3-one: 1
        1-(4-hydroxy-3-methoxyphenyl)-7-(3,4-dihydroxyphenyl)-4E-en-3-heptanone: 1
        3,5-bis(3,4,5-trimethoxybenzylidene)-1-methylpiperidine-4-one: 1
        acerogenin M: 1
        alnuside B: 1
        calyxin I: 1
        calyxin J: 1
        epicalyxin J: 1
        garuganin: 1
        katsumadain A: 1
        letestuianin C: 1
        myricanol 5-fluorobenzyloxy ether: 1
        (3S)-1-(3,4-dihydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol
        1,7-bis(3,4-dihydroxyphenyl)hept-4-en-3-one oxime
        1,7-bis(3,4-dihydroxyphenyl)heptan-3-ol
        1,7-bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione
        1,7-bis(4-hydroxyphenyl)-2,4,6-heptatrienone
        1,7-bis(4-hydroxyphenyl)-3-hydroxy-1,3-heptadien-5-one
        1,7-di(1H-indol-3-yl)hepta-1,6-diene-3,5-dione
        1,7-diphenyl-4,6-heptadien-3-ol
        1,7-diphenylhept-4-en-3-one
        1,9'-didesmethylgaruganin III
        1-(2',4'-dihydroxy-3'-methoxyphenyl)-7-(4'-methoxyphenyl)-3-heptanone
        1-(3',5'-dihydroxy-4'-methoxyphenyl)-7-phenyl-3-heptanone
        1-(4-hydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-one
        2,3-digalloyl oregonin
        3,5-dihydroxy-1,7-bis(3,4-dihydroxyphenyl)heptane
        3,5-dihydroxy-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)heptane
        3,5-dihydroxy-1-(4'-hydroxy-3',5'-dimethoxyphenyl)-7-(4''-hydroxy-3''-methoxyphenyl)heptane
        3-hydroxy-1,7-bis(4-hydroxyphenyl)-6-hepten-1,5-dione
        4-(4-hydroxy-3-methoxyphenylmethyl)curcumin
        4-dihydroxyphenyl)-1-phenyl-3-heptanone (5S)-5-hydroxy-7-(3
        5-1,7-di(4-hydroxyphenyl)-5-O-(6-(p-coumaroylglucopyranosyl))heptane-3-one
        5-dihydroxyphenyl)-1-phenyl-3-heptanone (5R)-5-hydroxy-7-(3-methoxy-4
        5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-1-hepten-3-one
        5-hydroxy-1-(3'-methoxy-4'-hydroxyphenyl)-7-phenyl-4,6-heptadien-3-one
        5-O-methyl-4-desmethyl-myricanol
        5-O-methylhirsutanonol
        7-(4-hydroxy-3-methoxyphenyl)-1-phenyl-4-hepten-3-one
        acerogenin A
        acerogenin L
        aceroketoside
        aceroside B1
        aceroside B2
        alnuheptanoid A
        Alpinin C
        Alpinin D
        alpinnanin A
        alpinnanin B
        alpinnanin C
        diarylheptanone glucoside I
        epihirsutanonol
        galeon
        garugamblin
        garugamblin-3
        giffonin J
        giffonin K
        giffonin T
        giffonin U
        hirustenone
        jugcathanin
        juglanin B 11-sulfate
        juglanin D
        katsumadain B
        katsumadain C
        letestuianin A
        letestuianin B
        muricarpone A
        muricarpone B
        musellarin A
        musellarin B
        musellarin C
        myricanol 11-sulfate
        myricanol-15-glucoside
        myricanone 5-O-(6'-O-galloyl)glucoside
        myricatomentogenin

Experts

1.	Sahebkar, Amirhossein: 23 articles (03/2022 - 03/2013)
2.	Suksamrarn, Apichart: 13 articles (06/2022 - 07/2009)
3.	Majeed, Muhammed: 13 articles (01/2022 - 02/2013)
4.	Panahi, Yunes: 13 articles (01/2022 - 10/2014)
5.	Ferrari, Erika: 7 articles (02/2019 - 10/2009)
6.	Funk, Janet L: 7 articles (08/2013 - 03/2006)
7.	Piyachaturawat, Pawinee: 6 articles (06/2022 - 07/2009)
8.	Khalili, Nahid: 6 articles (07/2018 - 10/2014)
9.	Fiala, Milan: 6 articles (02/2015 - 09/2006)
10.	Yasukawa, Ken: 6 articles (10/2013 - 05/2006)

Related Diseases

1.	Neoplasms (Cancer) 05/01/2018 - "Synthesis of Novel Aza-aromatic Curcuminoids with Improved Biological Activities towards Various Cancer Cell Lines." 07/11/2023 - "Hence, promising new clues for the development of efficient and superior curcuminoids as valuable treatment options for one of the most lethal cancer diseases were discovered in this study." 06/01/2023 - "In the present study, diarylheptanoids (garuganins 1, 3, 4 and 5) isolated from Garuga pinnata stem bark were evaluated for cytotoxic activity against MCF-7 and HCT15 cancer cell lines. " 11/01/2021 - "Various studies demonstrated that curcuminoids, the most important active phenolic compounds of turmeric (Curcuma longa), have anti-tumor activities in a wide range of human malignant cell lines. " 09/01/2021 - "Our studies not only enrich the structural diversity of diarylheptanoids in nature, but also discover several natural compounds for anti-tumor agents."
2.	Inflammation (Inflammations) 12/01/2012 - "The objective of this study was to examine the protective effects of standardized curcuminoid extract (SCE) in vascular inflammation of human umbilical vein endothelial cells (HUVEC) and the potential involvement of miRNA-126 and miRNA-146a. " 04/01/2013 - "Standardized liposomal curcuminoids have potential as an effective and safe topical formulation for the treatment of vaginal inflammation in early pregnancy." 12/01/2015 - "To study the effectiveness of supplementation with a bioavailable curcuminoid preparation on measures of oxidative stress and inflammation in patients with MetS. " 04/02/2023 - "The anti-inflammatory activity of the curcuminoids was evaluated in vivo using a xylol-induced inflammation model in rats. " 11/01/2018 - "Taken together, these findings demonstrated that HA/CNP for the delivery of curcuminoid may suppress inflammation and chondrocyte apoptosis in knee OA via repression of the NF‑κB pathway."
3.	Pain (Aches) 12/01/2018 - "Both curcuminoid and boswellia formulations were statistically significantly more effective than placebo for pain relief and functional improvement. " 04/01/2017 - "Compared with placebo, curcuminoids significantly reduced knee pain (visual analogue scale): (standardized mean difference: -3.45; 95% CI: -5.52 to -1.38; I2 = 95% P = 0.001), and improved quality of life (Lequesne pain-function index): (mean difference: -2.69; 95% CI: -3.48 to -1.90; I2 = 0% P < 0.00001). " 01/01/2016 - "Curcuminoids supplements may be a safe and effective strategy to improve pain severity, by warranting further rigorously conducted studies to define the long-term efficacy and safety." 12/01/2021 - "The results of our meta-analysis suggest that low- and high-dose curcuminoids have similar pain relief effects and AEs in knee OA. " 12/01/2021 - "However, no significant difference in pain relief or AEs between the high-dose (daily dose ≥1000 mg or total dose ≥42 gm) and low-dose (daily dose <1000 mg or total dose <42 gm) curcuminoid treatments was observed. "
4.	Oral Lichen Planus 04/01/2017 - "Evaluation of Efficacy of 1% Curcuminoids as Local Application in Management of Oral Lichen Planus - Interventional Study." 05/01/2012 - "We sought to study the efficacy of curcuminoids in controlling the signs and symptoms of oral lichen planus, at doses of 6000 mg/d (3 divided doses), and their safety at this dose. " 03/15/2012 - "To summarize long-term open-label use of curcuminoids and experience of side-effects in 53 patients with the autoimmune condition oral lichen planus (OLP) who had previously participated in randomized controlled trials (RCTs) of curcuminoids at UCSF. " 05/01/2012 - "Curcuminoids at doses of 6000 mg/d in 3 divided doses are well tolerated and may prove efficacious in controlling signs and symptoms of oral lichen planus." 05/01/2012 - "High-dose curcuminoids are efficacious in the reduction in symptoms and signs of oral lichen planus."
5.	Postoperative Pain 01/01/2022 - "Efficacy of Curcuminoids in Managing Postoperative Pain after Total Laparoscopic Hysterectomy: A Randomized Controlled, Open-Label Trial." 05/30/2019 - "Efficacy of curcuminoids for reducing postoperative pain after laparoscopic gynecologic surgery: A pilot randomized trial." 01/01/2022 - "The conclusion from this study is that curcuminoids may be an effective supplement to reduce postoperative pain following laparoscopic hysterectomy. " 05/30/2019 - "This study aimed to evaluate the clinical efficacy of curcuminoids for reducing postoperative pain in patients who undergo laparoscopic gynecologic surgery. " 09/01/2018 - "The aim of the current study was to evaluate the efficacy of curcuminoid in treating acute inflammation post-operative pain in the post-surgical removal of impacted third molars patients. "

Related Drugs and Biologics

1.	Curcumin
2.	Antioxidants
3.	Diarylheptanoids
4.	bisdemethoxycurcumin
5.	Biomarkers (Surrogate Marker)
6.	Polyphenols
7.	Glucose (Dextrose)
8.	turmeric extract
9.	demethoxycurcumin
10.	piperine

Related Therapies and Procedures

1.	Therapeutics
2.	Gynecologic Surgical Procedures (Gynecologic Surgery)
3.	Hysterectomy
4.	Immunomodulation
5.	Aftercare (After-Treatment)