Cyclo(L-Leu-trans-4-hydroxy-L-Pro)

* Please be kindly noted products are not for therapeutic use. We do not sell to patients.

Cyclo(L-Leu-trans-4-hydroxy-L-Pro)
Category Others
Catalog number BBF-04458
CAS 115006-86-5
Molecular Weight 226.27
Molecular Formula C11H18N2O3
Purity ≥95%

Online Inquiry

Description

Cyclo(L-Leu-trans-4-hydroxy-L-Pro) is a natural compound isolated from Phellinus igniarius. It is a plant growth regulator.

Specification

Synonyms Cyclo(L-leucyl-trans-4-hydroxy-L-proline); Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-7-hydroxy-3-(2-methylpropyl)-, (3S,7R,8aS)-; L-hydroxyprolyl-L-leucine anhydride; cyclo[L-(4-hydroxyprolinyl)-L-leucine]; 7-Hydroxygancidin W
Storage Store at -20°C
IUPAC Name (3S,7R,8aS)-7-hydroxy-3-(2-methylpropyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Canonical SMILES CC(C)CC1C(=O)N2CC(CC2C(=O)N1)O
InChI InChI=1S/C11H18N2O3/c1-6(2)3-8-11(16)13-5-7(14)4-9(13)10(15)12-8/h6-9,14H,3-5H2,1-2H3,(H,12,15)/t7-,8+,9+/m1/s1
InChI Key YEHIUWVXPQQDMC-VGMNWLOBSA-N

Properties

Appearance Powder
Boiling Point 486.9±45.0°C (Predicted)
Melting Point 178-179°C
Density 1.24±0.1 g/cm3 (Predicted)
Solubility Soluble in Methanol, Water

Reference Reading

1. Streptomyces nigra sp. nov. Is a Novel Actinobacterium Isolated From Mangrove Soil and Exerts a Potent Antitumor Activity in Vitro
Can Chen, Yanghui Ye, Ruijun Wang, Yinglao Zhang, Chen Wu, Sanjit C Debnath, Zhongjun Ma, Jidong Wang, Min Wu Front Microbiol. 2018 Jul 18;9:1587. doi: 10.3389/fmicb.2018.01587. eCollection 2018.
A new bacterial strain, designated 452T, was isolated from the rhizosphere soil of the mangrove Avicennia marina in China. As determined, its cell wall peptidoglycan contained LL-diaminopimelic acid; MK-9(H8) and MK-9(H6) were the major isoprenoid quinones; and iso-C16:0 (31.3%), anteiso-C15:0 (16.9%), and iso-C15:0 (12.5%) were the major cellular fatty acids (>10.0%). Phylogenetic analysis based on the 16S rRNA gene sequence revealed that strain 452T formed a distinct lineage in the clade of the genus Streptomyces, and was closely related to S. coerulescens DSM 40146T (99.6% sequence identity), S. bellus DSM 40185T (99.5%), and S. coeruleorubidus DSM 41172T (99.3%). The DNA-DNA relatedness between strain 452T and these type strains ranged between 29.3 and 42.3%. Based on the phenotypic, chemotaxonomic, and phylogenetic features, the strain 452T is considered to represent a novel species of the genus Streptomyces, for which the name Streptomyces nigra sp. nov. is proposed. The type strain is 452T (=KCTC 39960T = MCCC 1K03346T). Further, strain 452T extracts exhibited a pronounced antitumor activity against human cancer cell lines A549, HCT-116, and HepG2, but not against normal human colon cells CCD-18Co. Active substances in the fermentation broth of strain 452T were isolated by bioassay-guided analysis, and then purified using a macroporous resin, silica gel, sephadex LX-20 column, and semi-preparative high-performance liquid chromatography (HPLC). Eight proline-containing diketopiperazines, namely, cyclo(Pro-Ala), cyclo(Pro-Gly), cyclo(Pro-Phe), cyclo(Pro-Met), cyclo(Pro-Val), cyclo(Pro-Leu), cyclo(Pro-Tyr), and cyclo(L-Leu-trans-4-hydroxy-L-Pro), were identified by electrospray ionization mass spectrometry (MS) and nuclear magnetic resonance (NMR). The compounds displayed different levels of cytotoxicity. The highest cytotoxicity was exhibited by cyclo(Pro-Ala) and cyclo(Pro-Met) against A549 cells, and cyclo(Phe-Pro) and cyclo(Pro-Ala) against HCT-116 cells, with average IC50 values equal to 18.5, 27.3, 32.3, and 47.6 μg/mL, respectively. The diversity of diketopiperazines and other chemicals produced by 452T was further investigated using gas chromatography (GC)-MS and liquid chromatography (LC)-MS. The analysis revealed 16 types of metabolites with antitumor activity and 16 other types of diketopiperazines. Hence, extracts of the newly identified strain may be used a starting material for the development of antitumor agents.

Recommended Products

Bio Calculators

Stock concentration: *
Desired final volume: *
Desired concentration: *

L

* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
g/mol
g

Recently viewed products

Online Inquiry

Verification code

Copyright © 2024 BOC Sciences. All rights reserved.

cartIcon
Inquiry Basket