Valepotriate

CAS# 18296-44-1

Valepotriate

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Quality Control of Valepotriate

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Chemical structure

Valepotriate

3D structure

Chemical Properties of Valepotriate

Cas No. 18296-44-1 SDF Download SDF
PubChem ID 442436 Appearance Oil
Formula C22H30NO8 M.Wt 436.5
Type of Compound Iridoids Storage Desiccate at -20°C
Synonyms Halazuchrome B; Valepotriate; Valtratum
Solubility Soluble in chloroform; slightly soluble in water
Chemical Name [(1S,6S,7R,7aS)-4-(acetyloxymethyl)-1-(3-methylbutanoyloxy)spiro[6,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-oxirane]-6-yl] 3-methylbutanoate
SMILES CC(C)CC(=O)OC1C=C2C(C13CO3)C(OC=C2COC(=O)C)OC(=O)CC(C)C
Standard InChIKey BDIAUFOIMFAIPU-KVJIRVJXSA-N
Standard InChI InChI=1S/C22H30O8/c1-12(2)6-18(24)29-17-8-16-15(9-26-14(5)23)10-27-21(20(16)22(17)11-28-22)30-19(25)7-13(3)4/h8,10,12-13,17,20-21H,6-7,9,11H2,1-5H3/t17-,20+,21-,22+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Valepotriate

The roots of Valeriana officinalis L.

Biological Activity of Valepotriate

DescriptionValepotriates, a new class of cytotoxic and antitumor agents, they are very potent cytotoxic agents for the HTC hepatoma cells. Valepotriates may have a potential anxiolytic effect on the psychic symptoms of anxiety. Valepotriate fraction can have sedative effects and affect behavioral parameters related to recognition memory.
In vitro

Valepotriates, a new class of cytotoxic and antitumor agents.[Pubmed: 7232547 ]

Planta Med. 1981 Jan;41(1):21-8.


METHODS AND RESULTS:
The following Valepotriates: valtrate and didrovaltrate, isolated from the roots of VALERIANA WALLICHII D. C., as well as baldrinal, a degradation product of the valtrate, were tested for their cytotoxic and antitumor activities, respectively IN VITRO on cultured rat hepatoma cells (HTC line), and IN VIVO, on female mice KREBS II ascitic tumors.
CONCLUSIONS:
It appears that the three Valepotriates are very potent cytotoxic agents for the HTC hepatoma cells, and that the didrovaltrate induces a perceptible high per cent definitive remissions of the KREBS II ascitic tumors.

In vivo

A Valepotriate Fraction of Valeriana glechomifolia Shows Sedative and Anxiolytic Properties and Impairs Recognition But Not Aversive Memory in Mice.[Pubmed: 20047889]

Evid Based Complement Alternat Med. 2010 Jan 4.

Plants of the genus Valeriana (Valerianaceae) are used in traditional medicine as a mild sedative, antispasmodic and tranquilizer in many countries.
METHODS AND RESULTS:
This study was undertaken to explore the neurobehavioral effects of systemic administration of a Valepotriate extract fraction of known quantitative composition of Valeriana glechomifolia (endemic of southern Brazil) in mice. Adult animals were treated with a single intraperitoneal injection of Valepotriate fraction (VF) in the concentrations of 1, 3 or 10 mg kg(-1), or with vehicle in the pre-training period before each behavioral test. During the exploration of an open field, mice treated with 10 mg kg(-1) of Valepotriate fraction showed reduced locomotion and exploratory behavior. Although overall habituation sessions for locomotion and exploratory behavior among vehicle control and doses of Valepotriate fraction were not affected, comparison between open-field and habituation sessions within each treatment showed that Valepotriate fraction administration at 1 and 10 mg kg(-1) impaired habituation. In the elevated plus-maze test, mice treated with Valepotriate fraction (10 mg kg(-1)) showed a significant increase in the percentage of time spent in the open arms without significant effects in the number of total arm entries. Valepotriate fraction at 3 mg kg(-1) produced an impairment of novel-object recognition memory. In contrast, Valepotriate fraction did not affect fear-related memory assessed in an inhibitory avoidance task.
CONCLUSIONS:
The results indicate that Valepotriate fraction can have sedative effects and affect behavioral parameters related to recognition memory.

Effect of valepotriates (valerian extract) in generalized anxiety disorder: a randomized placebo-controlled pilot study.[Pubmed: 12410546]

Phytother Res. 2002 Nov;16(7):650-4.

The aim of the present study was to carry out a controlled pilot study on the putative anxiolytic effect of Valepotriates.
METHODS AND RESULTS:
Thirty-six outpatients with generalized anxiety disorder (DSM III-R), after a 2-week wash-out, were randomized to one of the following three treatments for 4 weeks (n = 12 per group): Valepotriates (mean daily dose: 81.3 mg), diazepam (mean daily dose: 6.5 mg), or placebo. A parallel, double-blind, flexible-dose, placebo-controlled design was employed. No significant difference was observed among the three groups at baseline or in the change from baseline on the Hamilton anxiety scale (HAM-A) or in the trait part of the state-trait anxiety inventory (STAI-trait). Moreover, the three groups presented a significant reduction in the total HAM-A scores. On the other hand, only the diazepam and Valepotriates groups showed a significant reduction in the psychic factor of HAM-A. The diazepam group also presented a significant reduction of the STAI-trait.
CONCLUSIONS:
Although the principal analysis (HAM-A between group comparison) found negative results (probably due to the small sample size in each group), the preliminary data obtained in the present study suggest that the Valepotriates may have a potential anxiolytic effect on the psychic symptoms of anxiety. However, since the number of subjects per group was very small, the present results must be viewed as preliminary. Thus, further studies addressing this issue are warranted.

Protocol of Valepotriate

Cell Research

Valepotriate production of normal and colchicine-treated cell suspension cultures of Valeriana wallichii.[Pubmed: 4009183]

J Nat Prod. 1985 Jan-Feb;48(1):17-21.

Colchicine-treated suspension cultures of Valeriana wallichii produce higher amounts of Valepotriates than did the respective untreated cultures.
METHODS AND RESULTS:
The ability to produce Valepotriates in the treated culture remains in the absence of colchicine even if the chromosome status returns to normal. When the colchicine treatment is repeated, a further increase in Valepotriate production can be obtained. Besides known Valepotriates, a series of fourteen new compounds, hitherto not described for the parent plant, were isolated from the cell suspension culture.
CONCLUSIONS:
Eight of them are also found in plant parts in minor amounts, but six seem to be present only in tissue cultures of V. wallichii.

Valepotriate Dilution Calculator

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Preparing Stock Solutions of Valepotriate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.291 mL 11.4548 mL 22.9095 mL 45.819 mL 57.2738 mL
5 mM 0.4582 mL 2.291 mL 4.5819 mL 9.1638 mL 11.4548 mL
10 mM 0.2291 mL 1.1455 mL 2.291 mL 4.5819 mL 5.7274 mL
50 mM 0.0458 mL 0.2291 mL 0.4582 mL 0.9164 mL 1.1455 mL
100 mM 0.0229 mL 0.1145 mL 0.2291 mL 0.4582 mL 0.5727 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Valepotriate

Effect of valepotriates (valerian extract) in generalized anxiety disorder: a randomized placebo-controlled pilot study.[Pubmed:12410546]

Phytother Res. 2002 Nov;16(7):650-4.

The aim of the present study was to carry out a controlled pilot study on the putative anxiolytic effect of Valepotriates. Thirty-six outpatients with generalized anxiety disorder (DSM III-R), after a 2-week wash-out, were randomized to one of the following three treatments for 4 weeks (n = 12 per group): Valepotriates (mean daily dose: 81.3 mg), diazepam (mean daily dose: 6.5 mg), or placebo. A parallel, double-blind, flexible-dose, placebo-controlled design was employed. No significant difference was observed among the three groups at baseline or in the change from baseline on the Hamilton anxiety scale (HAM-A) or in the trait part of the state-trait anxiety inventory (STAI-trait). Moreover, the three groups presented a significant reduction in the total HAM-A scores. On the other hand, only the diazepam and Valepotriates groups showed a significant reduction in the psychic factor of HAM-A. The diazepam group also presented a significant reduction of the STAI-trait. Although the principal analysis (HAM-A between group comparison) found negative results (probably due to the small sample size in each group), the preliminary data obtained in the present study suggest that the Valepotriates may have a potential anxiolytic effect on the psychic symptoms of anxiety. However, since the number of subjects per group was very small, the present results must be viewed as preliminary. Thus, further studies addressing this issue are warranted.

A Valepotriate Fraction of Valeriana glechomifolia Shows Sedative and Anxiolytic Properties and Impairs Recognition But Not Aversive Memory in Mice.[Pubmed:20047889]

Evid Based Complement Alternat Med. 2011;2011:720853.

Plants of the genus Valeriana (Valerianaceae) are used in traditional medicine as a mild sedative, antispasmodic and tranquilizer in many countries. This study was undertaken to explore the neurobehavioral effects of systemic administration of a Valepotriate extract fraction of known quantitative composition of Valeriana glechomifolia (endemic of southern Brazil) in mice. Adult animals were treated with a single intraperitoneal injection of Valepotriate fraction (VF) in the concentrations of 1, 3 or 10 mg kg(-1), or with vehicle in the pre-training period before each behavioral test. During the exploration of an open field, mice treated with 10 mg kg(-1) of VF showed reduced locomotion and exploratory behavior. Although overall habituation sessions for locomotion and exploratory behavior among vehicle control and doses of VF were not affected, comparison between open-field and habituation sessions within each treatment showed that VF administration at 1 and 10 mg kg(-1) impaired habituation. In the elevated plus-maze test, mice treated with VF (10 mg kg(-1)) showed a significant increase in the percentage of time spent in the open arms without significant effects in the number of total arm entries. VF at 3 mg kg(-1) produced an impairment of novel-object recognition memory. In contrast, VF did not affect fear-related memory assessed in an inhibitory avoidance task. The results indicate that VF can have sedative effects and affect behavioral parameters related to recognition memory.

Valepotriate content in different in vitro cultures of Valerianaceae and characterization of Valeriana officinalis L. callus during a growth period.[Pubmed:6646985]

Pharm Weekbl Sci. 1983 Oct 21;5(5):205-9.

Different in vitro cultures of Valerianaceae were analysed for Valepotriate content [(iso)valtrate, acevaltrate, didrovaltrate] in a study on properties of production in vitro (plant species, growth conditions, differentiation level, Valepotriate content of the medium after growth). The in vitro cultures were: callus cultures of Valeriana officinalis L., Valerianella locusta L. and Centranthus ruber L.DC.; a suspension culture of Valeriana officinalis L. and a root organ culture of Centranthus ruber L.DC. All of the cultures produced Valepotriates in vitro in different amounts. None of the media that had served for growth contained any Valepotriates. In order to characterize the in vitro growth more precisely different parameters were analysed at different time intervals during a growth period in one of the cultures (callus culture of Valeriana officinalis L.). These different parameters were: fresh and dry weight, lipid and nitrogen content and (iso)valtrate content. This study during a growth period was performed on two media differing in plant hormone content.

Valepotriate production of normal and colchicine-treated cell suspension cultures of Valeriana wallichii.[Pubmed:4009183]

J Nat Prod. 1985 Jan-Feb;48(1):17-21.

Colchicine-treated suspension cultures of Valeriana wallichii produce higher amounts of Valepotriates than did the respective untreated cultures. The ability to produce Valepotriates in the treated culture remains in the absence of colchicine even if the chromosome status returns to normal. When the colchicine treatment is repeated, a further increase in Valepotriate production can be obtained. Besides known Valepotriates, a series of fourteen new compounds, hitherto not described for the parent plant, were isolated from the cell suspension culture. Eight of them are also found in plant parts in minor amounts, but six seem to be present only in tissue cultures of V. wallichii.

Description

Valepotriate, isolated from Valeriana jatamansi Jones, has anti-epileptic and anti-cancer activities.

Keywords:

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