Drimentine B

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Drimentine B
Category Antibiotics
Catalog number BBF-04228
CAS 204398-91-4
Molecular Weight 485.66
Molecular Formula C31H39N3O2
Purity >98% by HPLC

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Description

It is produced by the strain of Actinomycete strain MST-8651. It belongs to a novel class of antibiotics, possessing a new terpenylated diketopiperazine structure, with antibacterial, antifungal and anthelmintic activity.

Specification

Synonyms [5aS-[5aα,6aβ(1R*,4aR*,8aR*),11aβ]]-6a-[(Decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl)methyl]-6,6a,11,11a-tetrahydro-3H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-5,13(2H,5aH)-dione
Storage Store at -20°C
IUPAC Name (1S,10S,12S)-12-[[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-2,8,19-triazapentacyclo[10.7.0.02,10.04,8.013,18]nonadeca-4,13,15,17-tetraene-3,9-dione
Canonical SMILES CC1(CCCC2(C1CCC(=C)C2CC34CC5C(=O)N6CCC=C6C(=O)N5C3NC7=CC=CC=C47)C)C
InChI InChI=1S/C31H39N3O2/c1-19-12-13-25-29(2,3)14-8-15-30(25,4)21(19)17-31-18-24-26(35)33-16-7-11-23(33)27(36)34(24)28(31)32-22-10-6-5-9-20(22)31/h5-6,9-11,21,24-25,28,32H,1,7-8,12-18H2,2-4H3/t21-,24-,25-,28-,30+,31-/m0/s1
InChI Key SUUCBHITXBJOGT-JMGSXGSMSA-N
Source Streptomyces sp.

Properties

Appearance White Crystal
Antibiotic Activity Spectrum Fungi; Parasites; Bacterial
Boiling Point 691.1±55.0°C at 760 mmHg
Melting Point 158-160°C
Density 1.2±0.1 g/cm3
Solubility Soluble in Ethanol, Methanol, DMF, DMSO, Chloroform

Reference Reading

1. Polycyclic hybrid isoprenoids from a reed rhizosphere soil derived Streptomyces sp. CHQ-64
Tianjiao Zhu, Qianqun Gu, Qian Che, Jing Li, Dehai Li, Robert A Keyzers, Xiaofang Liu J Nat Prod . 2013 Apr 26;76(4):759-63. doi: 10.1021/np3008864.
Two new hybrid isoprenoids, named indotertine B (2) and drimentine H (3), along with the known analogue drimentine C (4), were isolated from the reed rhizosphere soil derived actinomycete Streptomyces sp. CHQ-64. The structures of these compounds, including absolute configurations, were elucidated by extensive NMR, MS, and CD analyses. Indotertine B (2) exists as a pair of rotamers about the N-C(O) bond with a 2:1 ratio and displays activities against HCT-8 and A549 tumor cell lines with IC50 values of 6.96 and 4.88 μM, respectively.

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