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Dehydrotrametenolic acid

$250

  • Brand : BIOFRON

  • Catalogue Number : BF-D4010

  • Specification : 98%(HPLC)

  • CAS number : 29220-16-4

  • Formula : C30H46O3

  • Molecular Weight : 454.69

  • PUBCHEM ID : 15391340

  • Volume : 25mg

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Catalogue Number

BF-D4010

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

454.69

Appearance

Powder

Botanical Source

Poria cocos

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(=CCCC(C1CCC2(C1(CC=C3C2=CCC4C3(CCC(C4(C)C)O)C)C)C)C(=O)O)C

Synonyms

3β-hydroxylanosta-7,9(11)24-trien-21-oic acid/3-epidehydrotrametenolic/3-epi-dehydrotrametenolic acid/3β-hydroxylanosta-7,9(11),24-trien-21-oic acid/3-epidehydrotrametenolic acid/(3β)-3-Hydroxylanosta-7,9(11),24-trien-21-oic acid/Lanosta-7,9(11),24-trien-21-oic acid, 3-hydroxy-, (3β)-/3beta-Hydroxylanosta-7,9(11),24-trien-21-oic acid

IUPAC Name

(2R)-2-[(3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid

Density

1.08±0.1 g/cm3

Solubility

Methanol

Flash Point

321.9±26.6 °C

Boiling Point

585.4±50.0 °C at 760 mmHg

Melting Point

257-259 ºC

InChl

InChI=1S/C30H46O3/c1-19(2)9-8-10-20(26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h9,11,14,20-21,24-25,31H,8,10,12-13,15-18H2,1-7H3,(H,32,33)/t20-,21-,24+,25+,28-,29-,30+/m1/s1

InChl Key

QFPLAAZRZNKRRY-GIICLEHTSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:29220-16-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

11824563

Abstract

We recently discovered that the triterpene acid compound dehydrotrametenolic acid promotes adipocyte differentiation in vitro and acts as an insulin sensitizer in vivo. This natural product has been isolated from dried sclerotia of Poria cocos WOLF (Polyporaceae), a well-known traditional Chinese medicinal plant. We examined the effects of dehydrotrametenolic acid on plasma glucose concentration in obese hyperglycemic db/db mice. Dehydrotrametenolic acid can reduce hyperglycemia in mouse models of noninsulin-dependent diabetes mellitus (NIDDM) and act as an insulin sensitizer as indicated by the results of the glucose tolerance test. These terpenoids and thiazolidine type of antidiabetic agents such as Ciglitazone, although structurally unrelated, share many biological activities: both induce adipose conversion, activate peroxisome proliferator-activated receptor gamma (PPAR gamma) in vitro, and reduce hyperglycemia in animal models of NIDDM. Dehydrotrametenolic acid is a promising candidate for a new type of insulin-sensitizing drug. This finding is very important for the development of insulin sensitizers that are not of the thiazolidine type.

Title

Dehydrotrametenolic Acid Induces Preadipocyte Differentiation and Sensitizes Animal Models of Noninsulin-Dependent Diabetes Mellitus to InsulinQ

Author

Mayumi Sato 1 , Takaaki Tai, Yoshiki Nunoura, Yukiko Yajima, Seiichi Kawashima, Keiji Tanaka

Publish date

2002 Jan

PMID

16112686

Abstract

The screening of natural products that preferentially inhibit growth of H-ras transformed rat2 cells vs. rat2 cells was performed to identify H-ras specific growth inhibitor. A lanostane-type triterpene acid, dehydrotrametenolic acid (3beta-hydroxylanosta-7,9(11),24-trien-21-oic acid), was isolated from the sclerotium of Poria cocos (Polyporaceae). Dehydrotrametenolic acid selectively inhibited the growth of H-ras transformed cells with a GI(50) value of 40 microM. FACS analysis indicated that the compound exerted its anti-proliferation effects through cell cycle arrest at G2/M phase and accumulation of sub-G1 population. Dehydrotrametenolic acid-induced apoptosis was further confirmed with chromosomal DNA fragmentation, caspase-3 activation, and degradation of PARP and Lamin A/C degradation. The compound also regulated the expression of H-ras, Akt and Erk, which are the downstream proteins of H-ras signaling pathways. The results suggest that dehydrotrametenolic acid can be a potential anticancer agent against H-ras transformed tumor. Q

Title

Dehydrotrametenolic Acid Selectively Inhibits the Growth of H-ras Transformed rat2 Cells and Induces Apoptosis Through caspase-3 Pathway

Author

Hyun-Mi Kang 1 , Su-Kyung Lee, Dae-Seop Shin, Mi-Young Lee, Dong Cho Han, Nam-In Baek, Kwang-Hee Son, Byoung-Mog Kwon

Publish date

2006 Jan 2

PMID

31847353

Abstract

Dehydrotrametenolic acid (DTA) is a lanostane-type triterpene acid isolated from Poria cocos Wolf (Polyporaceae). Several studies have reported the anti-inflammatory and antidiabetic effects of DTA; however, its effects on the skin are poorly understood. In this study, we investigated the effects of DTA on skin barrier function in vitro and its regulatory mechanism in human keratinocyte cell line HaCaT cells. DTA increased the microRNA (mRNA) expression of natural moisturizing factor-related genes, such as HAS-2, HAS-3, and AQP3 in HaCaT cells. DTA also upregulated the mRNA expression of various keratinocyte differentiation markers, including TGM-1, involucrin, and caspase-14. Moreover, the protein expression of HAS-2, HAS-3, and TGM-2 were significantly increased by DTA. To examine the regulatory mechanisms of DTA, Western blotting, luciferase-reporter assays, and RT-PCR were conducted. The phosphorylation of mitogen-activated protein kinases (MAPKs) and IκBα were increased in DTA-treated HaCaT cells. In addition, AP-1 and NF-κB transcriptional factors were dose-dependently activated by DTA. Taken together, our in vitro mechanism studies indicate that the regulatory effects of DTA on skin hydration and keratinocyte differentiation are mediated by the MAPK/AP-1 and IκBα/NF-κB pathways. In addition, DTA could be a promising ingredient in cosmetics for moisturizing and increased skin barrier function.

KEYWORDS

keratinocyte differentiation; skin barrier; skin hydration.

Title

In Vitro Effects of Dehydrotrametenolic Acid on Skin Barrier Function

Author

Eunju Choi 1 , Young-Gyu Kang 2 , So-Hyeon Hwang 1 , Jin Kyeong Kim 1 , Yong Deog Hong 2 , Won-Seok Park 2 , Donghyun Kim 2 , Eunji Kim 1 , Jae Youl Cho 1

Publish date

2019 Dec 14


Description :

3-​Dehydrotrametenolic acid, isolated from the sclerotium of Poria cocos, is a lactate dehydrogenase (LDH) inhibitor. 3-​Dehydrotrametenolic acid promotes adipocyte differentiation in vitro and acts as an insulin sensitizer in vivo. 3-​Dehydrotrametenolic acid induces apoptosis and has anticancer activity[1][2].