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Stachybotrin B

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Category Bioactive by-products
Catalog number BBF-02954
CAS 144385-02-4
Molecular Weight 385.50
Molecular Formula C23H31NO4

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is produced by the strain of Stachyborrys sp. It has antimicrobial and antifungal activity.

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Synonyms (+)-Stachybotrin B
IUPAC Name (2S,3S)-2-[(3E)-4,8-dimethylnona-3,7-dienyl]-3,5-dihydroxy-2-methyl-3,4,8,9-tetrahydropyrano[2,3-e]isoindol-7-one
Canonical SMILES CC(=CCCC(=CCCC1(C(CC2=C(C=C3C(=C2O1)CNC3=O)O)O)C)C)C
InChI InChI=1S/C23H31NO4/c1-14(2)7-5-8-15(3)9-6-10-23(4)20(26)12-17-19(25)11-16-18(21(17)28-23)13-24-22(16)27/h7,9,11,20,25-26H,5-6,8,10,12-13H2,1-4H3,(H,24,27)/b15-9+/t20-,23-/m0/s1
InChI Key XGUHYRYUXUVLOK-BHNVPJQESA-N
Antibiotic Activity Spectrum Fungi
Melting Point 178-180°C
Solubility Soluble in Methanol, Chloroform, Ethyl Acetate
1. Synthesis of tricyclic pyrano[2,3-e]isoindolin-3-ones as the core structure of stachybotrin A, B, and C
Seiichi Inoue, Riyoung Kim, Yujiro Hoshino, Kiyoshi Honda Chem Commun (Camb). 2006 May 14;(18):1974-6. doi: 10.1039/b601433j. Epub 2006 Apr 3.
The substituted tricyclic pyrano[2,3-e]isoindolin-3-ones and , as the core structure of stachybotrin A, B, and C (), have been regioselectively synthesized for the first time by a short route which involved Mannich reaction and Claisen rearrangement.
2. Isolation and absolute configuration of SMTP-0, a simplest congener of the SMTP family nonlysine-analog plasminogen modulators
Keiji Hasumi, Keiko Hasegawa, Yoshikazu Kitano J Antibiot (Tokyo). 2007 Jul;60(7):463-8. doi: 10.1038/ja.2007.60.
SMTP-0, a new simple congener of the SMTP nonlysine-analog plasminogen modulators, was isolated from a culture of Stachybotrys microspora. Based on the physico-chemical data, SMTP-0 was shown to be an enantiomer of the antimicrobial compound stachybotrin B. The absolute configuration of SMTP-0 was determined by the modified Mosher method. The stereochemistry was further confirmed using an epimer of SMTP-0. Unlike most SMTPs with an amino acid side chain linked to the nitrogen atom of the lactam moiety, SMTP-0, which lacks the N-linked side chain, showed no plasminogen modulator activity.

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