VERBASCOSIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H36O15
Molecular Weight	624.5871
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]4(O[C@@H]1[C@@H](O)[C@H](OCCC2=CC(O)=C(O)C=C2)O[C@H](CO)[C@H]1OC(=O)\C=C\C3=CC=C(O)C(O)=C3)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O

InChI

InChIKey=FBSKJMQYURKNSU-ZLSOWSIRSA-N

InChI=1S/C29H36O15/c1-13-22(36)23(37)24(38)29(41-13)44-27-25(39)28(40-9-8-15-3-6-17(32)19(34)11-15)42-20(12-30)26(27)43-21(35)7-4-14-2-5-16(31)18(33)10-14/h2-7,10-11,13,20,22-34,36-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27+,28+,29-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22147269 | https://clinicaltrials.gov/ct2/show/NCT02662283 | https://www.ncbi.nlm.nih.gov/pubmed/29054705

Acteoside (verbsacoside) is the one of the main active phenylethanoid glycosides from Cistanche deserticola, Lantana camara and some others herbs. It is known to have antioxidant and neuroprotective activity, and herbs containing it are used to enhance memory and can be studied for the treatment of Alzheimer's disease. It is known, that amyloid fibrils accumulation in cerebral can easily lead to neurodegenerative disorders. Acteoside has been reported to inhibit Aβ42 aggregation by activating nuclear translocation of the transcription factor NF-E2-related factor 2 (Nrf2), increasing heme oxygenase-1 (HO-1) expression. It has also been shown that acteoside could decrease nitric oxide synthase (NOS) activity and caspase-3 expression. Acteoside is a natural antioxidant product unlike other anti-tumor compounds, is an inhibitor of protein kinase C (PKC). In addition Reh-acteoside, a general acteoside of Rehmannia leaves was studied in phase 2/3 clinical trials for patients with IgA nephropathy.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Protein kinase C (PKC) 44 Target ID: CHEMBL2094266 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1812212	Inhibitor 8297		25.0 µM [Ki]
Nuclear factor erythroid 2-related factor 2 20 Target ID: Q16236 Gene ID: 4780.0 Gene Symbol: NFE2L2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22147269	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
IGA nephropathy 1 Sources: https://clinicaltrials.gov/ct2/show/NCT02662283	Primary		Phase III 656	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587		inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
mCYP2E1 1 CYP2A6 707 CYP1A1 110 CYP19A1 60 CYP1A2 1524 CYP1B1 19	CYPs 33 Methyl conjugation 1 Sulfonation conjugation 1 UGT1A7 236 UGT1A8 283 BCRP 561 P-gp 1537 UGT1A10 291 MRP2 205	rGST-alpha 1

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/31212689/	moderate [IC50 24 uM]
CYP19A1 60	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/31212689/	no
CYP1A1 218	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/31212689/	unlikely [IC50 350 uM]
CYP2A6 739	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/31212689/	weak [IC50 135 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/31212689/	weak [IC50 76 uM]
CYP1B1 67	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/31212689/	weak [IC50 86 uM]
CYP2D6 1891	inhibitor 3277	weak [IC50 96 uM]
CYP2C19 1553	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/31212689/	weak
mCYP2E1 2	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/14672760/	yes
rGST-alpha 1	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/16649555/	yes

Drug as victim

Target	Modality	Activity
UGT1A10 291	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/31212689/	likely
UGT1A7 236	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/31212689/	likely
UGT1A8 283	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/31212689/	likely
BCRP 561	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29687721/	no
CYPs 33	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/31212689/	no
MRP2 205	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29687721/	no
Methyl conjugation 1	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/31212689/	yes
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/33184029/ \| https://pubmed.ncbi.nlm.nih.gov/29687721/	yes
Sulfonation conjugation 1	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/31212689/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/720551#sid=85201029

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P003ARN	https://www.1pchem.com/search?query=1P003ARN
A2B Chem	AB53123	http://a2bchem.com/prod/AB53123
AK Scientific	V1534	https://aksci.com/item_detail.php?cat=V1534
Alfa Chemistry	ACM22323520	http://www.alfa-chemistry.com/search.aspx?q=ACM22323520
Ambeed	A119193	http://www.ambeed.com/search/Search.html?keyword=A119193
AstaTech	41627	http://astatechinc.com/CPSResult.php?CRNO=41627
AstaTech	44132	http://astatechinc.com/CPSResult.php?CRNO=44132
BLD Pharm	BD134970	http://www.bldpharm.com/search/Search.html?keyword=BD134970
BOC Sciences	22323-52-0	http://www.bocsci.com/description.asp?cas=22323-52-0
Biopurify Phytochemicals	BP0124	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP0124&searchhtmp=simplesearch&t=1
Chem Scene	CS-2624	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-2624
Combi-Blocks	QV-0462	http://www.combi-blocks.com/cgi-bin/find.cgi?QV-0462
KeyOrganics	AS-75167	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-75167
MedChem Express	HY-N0021	https://www.medchemexpress.com/search.html?q=HY-N0021&ft=&fa=&fp=
MolPort	MolPort-001-740-227	https://www.molport.com/shop/molecule-link/MolPort-001-740-227
MolPort	MolPort-006-069-350	https://www.molport.com/shop/molecule-link/MolPort-006-069-350
Molnova	M18894	https://www.molnova.com/en/serch-list.html?keywords=M18894
TargetMol	BBP00491	https://www.targetmol.com/search?keyword=BBP00491
TargetMol	T3375	https://www.targetmol.com/search?keyword=T3375
W&J PharmaChem	50A169811	http://wjpharmachem.com/new/searcht.php?keyword=50A169811
eMolecules	30512773	https://orderbb.emolecules.com/search/#?query=30512773
eMolecules	43445639	https://orderbb.emolecules.com/search/#?query=43445639
eMolecules	50894955	https://orderbb.emolecules.com/search/#?query=50894955
eMolecules	95715841	https://orderbb.emolecules.com/search/#?query=95715841
mcule	MCULE-6138465280	https://mcule.com/MCULE-6138465280/

PubMed

Title	Date	PubMed
HIV-1 integrase inhibitory phenylpropanoid glycosides from Clerodendron trichotomum.	2001 Aug	11534758
HIV gp41 binding phenolic components from Fraxinus sieboldiana var. angustata.	2002 Nov	12451497
Protective effect of acteoside on carbon tetrachloride-induced hepatotoxicity.	2004 Jan 9	14672760
The inhibitory effect of phenylpropanoid glycosides and iridoid glucosides on free radical production and beta2 integrin expression in human leucocytes.	2006 Jan	16393473
Acteoside inhibits human promyelocytic HL-60 leukemia cell proliferation via inducing cell cycle arrest at G0/G1 phase and differentiation into monocyte.	2007 Sep	17634406
Natural antioxidants synergistically enhance the anticancer potential of AP9-cd, a novel lignan composition from Cedrus deodara in human leukemia HL-60 cells.	2010 Dec 5	20932957
Antioxidant and signal modulation properties of plant polyphenols in controlling vascular inflammation.	2011 May 11	21371465
In vitro antifungal activities of amphotericin B in combination with acteoside, a phenylethanoid glycoside from Colebrookea oppositifolia.	2011 Sep	21474610
Plant polyphenols differentially modulate inflammatory responses of human keratinocytes by interfering with activation of transcription factors NFκB and AhR and EGFR-ERK pathway.	2011 Sep 1	21756928
Plant polyphenols regulate chemokine expression and tissue repair in human keratinocytes through interaction with cytoplasmic and nuclear components of epidermal growth factor receptor system.	2012 Feb 15	21967610
Resveratrol induces long-lasting IL-8 expression and peculiar EGFR activation/distribution in human keratinocytes: mechanisms and implications for skin administration.	2013	23527233
Modulation of human keratinocyte responses to solar UV by plant polyphenols as a basis for chemoprevention of non-melanoma skin cancers.	2013	23210792

Patents

Sample Use Guides

In Vivo Use Guide

Oral take reh-acteoside (0.4g bid) for 8 weeks

Route of Administration: Oral

In Vitro Use Guide

Acteoside treatment resulted in nuclear translocation of the transcription factor NF-E2-related factor 2 (Nrf2). Acteoside activated both ERK and PI3 K/Akt, and treatments with the specific ERK inhibitor PD98059, the PI3 K inhibitor LY294002, and the specific Nrf2 siRNA suppressed the acteoside-induced HO-1 expression. The PC12 cells transfected with Nrf2-siRNA (siNrf2) were treated with acteoside (30 uM), and the level of Nrf2 protein was then determined by Western blotting. Acteoside induced the accumulation of Nrf2 in the nuclei.

Name

Type

Language

VERBASCOSIDE

Official Name

English

TJC-160

Code

English

RUSSETINOL

Common Name

English

KUSAGININ

Common Name

English

VERBASCOSIDE [INCI]

Common Name

English

STEREOSPERMIN

Common Name

English

VERBASCOSIDE [USP-RS]

Common Name

English

.BETA.-D-GLUCOPYRANOSIDE, 2-(3,4-DIHYDROXYPHENYL)ETHYL 3-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-, 4-((2E)-3-(3,4-DIHYDROXYPHENYL)-2-PROPENOATE)

Systematic Name

English

NSC-603831

Code

English

ACTEOSIDE

Common Name

English

Classification Tree Code System Code

DSLD

3474 (Number of products:7)