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Herquline A Sale

(Synonyms: 梅花青霉素A,Herqueline A) 目录号 : GC43818

An alkaloid fungal metabolite

Herquline A Chemical Structure

Cas No.:71812-08-3

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500μg
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产品描述

Herquline A is an alkaloid fungal metabolite originally isolated from P. herquei. It inhibits cell death induced by influenza A strain A/PR/8/34 in MDCK cells with an IC50 value of 10 μg/ml and inhibits viral replication in a plaque assay in a concentration-dependent manner. Herquline A also inhibits platelet aggregation induced by ADP and platelet-activating factor (PAF) in vitro (IC50s = 180 and 240 μM, respectively).

Chemical Properties

Cas No. 71812-08-3 SDF
别名 梅花青霉素A,Herqueline A
Canonical SMILES O=C(CCC1=C2)[C@@]2([H])[C@@]3([H])C(CC[C@@]4([H])[C@]3([H])N(C[C@@](C1)([H])N(C)C5)[C@@]5([H])C4)=O
分子式 C19H26N2O2 分子量 314.4
溶解度 DMSO: soluble,Ethanol: soluble,Methanol: soluble 储存条件 Store at -20°C
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1 mM 3.1807 mL 15.9033 mL 31.8066 mL
5 mM 0.6361 mL 3.1807 mL 6.3613 mL
10 mM 0.3181 mL 1.5903 mL 3.1807 mL
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Research Update

Synthesis of Pentacyclic Framework of Herquline A

Chem Asian J 2021 Dec 1;16(23):3882-3885.PMID:34591372DOI:10.1002/asia.202101004.

The highly strained bowl-shaped pentacyclic structure of Herquline A has rendered it one of the most difficult problems in organic synthesis yet to be solved. The challenges associated with the synthesis of Herquline A have been well documented in four Ph.D. dissertations and in multiple reports regarding syntheses of its structurally simpler congeners. Herein, we report the construction of the pentacyclic core of Herquline A that contains both N10-C2 and C3-C3' bonds. The key for success was the development of the tandem aza-Michael addition/enolate capture protocol that set the stage for subsequent palladium catalyzed C3(sp2 )-C3'(sp2 ) coupling reaction. Ensuing oxidative dearomatization of the left aryl ring allowed the formation of the pentacyclic diketone core of Herquline A.

Herquline A, produced by Penicillium herquei FKI-7215, exhibits anti-influenza virus properties

Biosci Biotechnol Biochem 2017 Jan;81(1):59-62.PMID:26999706DOI:10.1080/09168451.2016.1162084.

In the course of screening for new anti-influenza virus antibiotics, we isolated Herquline A from a culture broth of the fungus, Penicillium herquei FKI-7215. Herquline A inhibited replication of influenza virus A/PR/8/34 strain in a dose-dependent manner without exhibiting cytotoxicity against several human cell lines. It did not inhibit the viral neuraminidase.

Synthesis and Reactivity of 1-Hydroxyherquline A

Org Lett 2022 Mar 18;24(10):1964-1968.PMID:35244406DOI:10.1021/acs.orglett.2c00379.

Herein, we present the synthesis of 1-hydroxyherquline A and describe its reactivity discovered during its attempted conversion to Herquline A, a long-sought natural product target in the synthetic chemical community. The strategic installation of the C1 hydroxyl group enabled the key aza-Michael addition-mediated N10-C2 bond formation and eventually access to 1-hydroxyherquline A, the most advanced Herquline A congener reported to date. Our attempted reductive transformation of 1-hydroxyherquline A to Herquline A was challenged by the extremely strained bowl-shaped pentacyclic structures of key precursors that prevented either radical formation at C1 or protonation (or hydrogenation) from the desired face. These discoveries regarding the innate chemical reactivities of advanced intermediates toward Herquline A may prove useful in efforts toward this formidable target.

Herquline B, a new platelet aggregation inhibitor produced by Penicillium herquei Fg-372

J Antibiot (Tokyo) 1996 Jan;49(1):50-3.PMID:8609085DOI:10.7164/antibiotics.49.50.

A new herquline analog, herquline B was isolated from the culture broth of Penicillium herquei Fg372. Herquline B contains one piperazine and two cyclohexenones. The pyrrolidine ring of Herquline A was cleaved to yield herquline B. The IC50 value of herquline B against platelet aggregation induced by ADP and platelet-activating factor were 1.6 and 5.0 microM, respectively.

Biosynthesis of Strained Piperazine Alkaloids: Uncovering the Concise Pathway of Herquline A

J Am Chem Soc 2016 Oct 19;138(41):13529-13532.PMID:27690412DOI:10.1021/jacs.6b09464.

Nature synthesizes many strained natural products that have diverse biological activities. Uncovering these biosynthetic pathways may lead to biomimetic strategies for organic synthesis of such compounds. In this work, we elucidated the concise biosynthetic pathway of Herquline A, a highly strained and reduced fungal piperazine alkaloid. The pathway builds on a nonribosomal peptide synthetase derived dityrosine piperazine intermediate. Following enzymatic reduction of the P450-cross-linked dicyclohexadienone, N-methylation of the piperazine serves as a trigger that leads to a cascade of stereoselective and nonenzymatic transformations. Computational analysis of key steps in the pathway rationalizes the observed reactivities.