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Militarine

$225

  • Brand : BIOFRON

  • Catalogue Number : BF-M4003

  • Specification : 98%(HPLC)

  • CAS number : 58139-23-4

  • Formula : C34H46O17

  • Molecular Weight : 726.73

  • PUBCHEM ID : 171638

  • Volume : 25mg

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Catalogue Number

BF-M4003

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

726.73

Appearance

Powder

Botanical Source

Bletilla striata

Structure Type

Others

Category

SMILES

CC(C)CC(CC(=O)OCC1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O)(C(=O)OCC3=CC=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)O

Synonyms

bis[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl] (2R)-2-hydroxy-2-(2-methylpropyl)butanedioate

IUPAC Name

bis[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl] (2R)-2-hydroxy-2-(2-methylpropyl)butanedioate

Applications

Density

1.5±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

296.0±27.8 °C

Boiling Point

954.0±65.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C34H46O17/c1-17(2)11-34(45,33(44)47-16-19-5-9-21(10-6-19)49-32-30(43)28(41)26(39)23(14-36)51-32)12-24(37)46-15-18-3-7-20(8-4-18)48-31-29(42)27(40)25(38)22(13-35)50-31/h3-10,17,22-23,25-32,35-36,38-43,45H,11-16H2,1-2H3/t22-,23-,25-,26-,27+,28+,29-,30-,31-,32-,34-/m1/s1

InChl Key

GQNUDXCKVPLQBI-KIQVUASESA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:58139-23-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

24161344

Abstract

A synthetic Militarin analog-1[(2R,3R,4R,5R)-1,6-bis(4-(2,4,4-trimethylpentan-2-yl)phenoxy) hexane-2,3,4,5-tetraol] is a novel derivative of constituents from Cordyceps militaris, which has been used to treat a variety of chronic diseases including inflammation, diabetes, hyperglycemia and cancers. Here, we report for the first time the synthesis of Militarin analog-1 (MA-1) and the apoptotic mechanism of MA-1 against human lung cancer cell lines. Treatment with MA-1 significantly inhibited the viability of 3 human lung cancer cell lines. The inhibition of viability and growth in MA-1-treated A549 cells with an IC50 of 5μM were mediated through apoptosis induction, as demonstrated by an increase in DNA fragmentation, sub-G0/G1-DNA fraction, nuclear condensation, and phosphatidylserine exposure. The apoptotic cell death caused mitochondrial membrane permeabilization through regulation of expression of the Bcl-2 family proteins, leading to cytochrome c release in a time-dependent manner. Subsequently, the final stage of apoptosis, activation of caspase-9/-3 and cleavage of poly (ADP ribose) polymerase, was induced. Furthermore, A549 lung cancer cells were more responsive to MA-1 than a bronchial epithelial cell line (BEAS-2B), involving the rapid generation of reactive oxygen species (ROS), c-Jun N-terminal kinase (JNK) and p38 mitogen-activated protein kinase (MAPK) activation. The pharmacological inhibition of ROS generation and JNK/p38 MAPK exhibited attenuated DNA fragmentation in MA-1-induced apoptosis. Oral administration of MA-1 also retarded growth of A549 orthotopic xenografts. In conclusion, the present study indicates that the new synthetic derivative MA-1 triggers mitochondrial apoptosis through ROS generation and regulation of MAPKs and may be a potent therapeutic agent against human lung cancer.

KEYWORDS

Human lung cancer cells; JNK/p38 MAPK; Militarin analog-1 (MA-1); Mitochondria mediated apoptosis; Orthotopic xenograft; Reactive oxygen species.

Title

A novel synthetic analog of Militarin, MA-1 induces mitochondrial dependent apoptosis by ROS generation in human lung cancer cells

Author

Deok Hyo Yoon 1, Mi-Hee Lim, Yu Ran Lee, Gi-Ho Sung, Tae-Ho Lee, Byeong Hwa Jeon, Jae Youl Cho, Won O Song, Haeil Park, Sunga Choi, Tae Woong Kim

Publish date

2013 Dec 15

PMID

8009989

Abstract

Eight phenolic derivatives, p-hydroxybenzaldehyde (I), 4,4′-dihydroxy-diphenyl methane(II), 2,4-bis(4-hydroxybenzyl) phenol (III), 5-methoxy-3-(2-phenyl-E-ethenyl)-2,4-bis (4-hydroxybenzyl) phenol (IV), p-hydroxybenzyl alcohol (V), 4-(beta-D-glucopyranosyloxy) benzyl alcohol (gastrodin) (VI), bis[4-(beta-D-glucopyranosyloxy) benzyl] (S)-2-isopropylmalate (VII), bis [4-(beta-D-glucopyranosyloxy) benzyl] (S)-2-sec-butylmalate (VIII) were isolated from the rhizome of Galeola faberi Rolfe for the first time. IV and VIII are new compounds. III is a new natural compound.

Title

[Studies on the phenolic derivatives from Galeola faberi Rolfe]

Author

Y M Li 1, Z L Zhou, Y F Hong

Publish date

1993;

PMID

32074105

Abstract

Bletilla striata is an endangered traditional Chinese medicinal plant with multiple uses and a slow regeneration rate of its germplasm resources. To evaluate the callus growth kinetics and accumulation of secondary metabolites (SMs), a callus suspension culture was proven to be a valuable approach for acquiring high yields of medicinal compounds. An effective callus suspension culture for obtaining B. striata callus growth and its SMs was achieved with the in vitro induction of calluses from B. striata seeds. The callus growth kinetics and accumulation of SMs were analyzed using a mathematical model. The resulting callus growth kinetic model revealed that the growth curves of B. striata suspension-cultured calluses were sigmoidal, indicating changes in the growth of the suspension-cultured calluses. Improved Murashige and Skoog callus growth medium was the most favorable medium for B. striata callus formation, with the highest callus growth occurring during the stationary phase of the cultivation period. Callus growth acceleration started after 7 days and thereafter gradually decreased until day 24 of the cultivation period and reached its highest at day 36 period in both the dry weight and fresh weight analyses. The coelonin concentration peaked during the exponential growth stage and decreased afterward during the stationary stage of the callus suspension culture. The maximum content of coelonin (approximately 0.3323 mg/g callus dry weight) was observed on the 18th day of the cultivation cycle, while dactylorhin A and militarine reached the highest concentrations at day 24, and p-hydroxybenzyl alcohol at day 39. This investigation also laid a foundation for a multimathematical model to better describe the accumulation variation of SMs. The production of SMs showed great specificity during callus growth and development. This research provided a well-organized way to increase the accumulation and production of SMs during the scaled-up biosynthesis of calluses in B. striata callus suspension cultures.

Title

Callus growth kinetics and accumulation of secondary metabolites of Bletilla striata Rchb.f. using a callus suspension culture

Author

Yinchi Pan, Writing - original draft,#1,2 Lin Li, Project administration, Supervision,#1 Shiji Xiao, Data curation, Formal analysis,3 Zhongjie Chen, Writing - original draft,1 Surendra Sarsaiya, Writing - review & editing,4 Shebo Zhang, Investigation,1 Yanni ShangGuan, Data curation,1 Houbo Liu, Methodology,1 and Delin Xu, Conceptualization, Funding acquisition, Project administration, Supervision, Writing - original draft, Writing - review & editing1,*

Publish date

2020;