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Stachybotrin B

Name: Stachybotrin B
Brand: BOC Sciences
Rating: 5 (1 reviews)

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

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

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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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