glandicoline B

naturalproductmech:mibig-7a476dbad3 MINTED SEEDED

Grounding review: No 3-star ChEBI entry shares this structure, so the record keeps a content-hashed identifier.

What these status tags mean

Curation status describes a workflow state. SEEDED means the record entered through the source-seeding workflow; it does not imply that no later curation occurred. PROPOSED marks an addition awaiting review; REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record. These are workflow decisions, not independently verified human review. Agent-assisted contributions may appear in the record history.

Grounding describes the identifier mapping: EXACT uses an ontology identity asserted by the source; MINTED keeps a local identifier when no defensible ontology identity is available; REVIEW_NEEDED flags an exact structure whose ontology identity needs adjudication. The grounding note retains any unresolved alternatives. These tags do not establish the strength of producer or activity evidence.

Structure

Standard InChIKey	YEVSOYBNHBOQJZ-CXUHLZMHSA-N
SMILES	CC(C)(C=C)C12C=C(C(=O)N\3C1(NC(=O)/C3=C\C4=CN=CN4)N(C5=CC=CC=C25)O)O
Stereochemistry	undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers
Cross-references	pubchem:91820473

Filing pathway

Alkaloids — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is nrps, from MIBiG.

Producer organisms 1

A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.

Taxon	Basis	Cluster	Evidence
Penicillium rubens Wisconsin 54-1255 NCBITaxon:500485	BGC_CHARACTERIZED	mibig:BGC0000420	DOI:10.1371/journal.pone.0065328

Occurrences 0

None cited.

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000420	Penicillium rubens Wisconsin 54-1255 NCBITaxon:500485	CLUSTER_DEMONSTRATED	genbank:AM920436.1

A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.

Biosynthesis curated

Written by a curator with claim-level evidence on each step; not derived from a source. This is what the rest of the record exists to support.

Step	Enzyme	Reaction	Substrate → product	Evidence
7	RoqN glandicoline B O-methyltransferase UniProtKB:B6HJU2	RHEA:51732	naturalproductmech:mibig-7a476dbad3 → CHEBI:70399	DOI:10.1039/c8ob01565a

Step 7: This curates the Penicillium rubens Wisconsin 54-1255 BGC0000420 terminal O-methylation of glandicoline B to meleagrin. RHEA:51732 uses CHEBI:134347 for glandicoline B; this corpus keeps the exact BGC0000420 glandicoline B structure as naturalproductmech:mibig-7a476dbad3 because its stereochemical representation is not an exact ChEBI match.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Penicillium rubens Wisconsin 54-1255 BGC0000420 O-methyltransferase RoqN (Pc21g15440) methylates glandicoline B into meleagrin in the terminal step of the roquefortine/meleagrin pathway.

Subject	Predicate	Object	Notes	Evidence
glandicoline B	is O-methylated by	RoqN	RoqN uses SAM to methylate the hydroxylamine oxygen of glandicoline B in the roquefortine/meleagrin branch.	DOI:10.1039/c8ob01565a DOI:10.1371/journal.pone.0065328 https://www.uniprot.org/uniprotkb/B6HJU2 https://www.rhea-db.org/rhea/51732 reference DOI:10.1039/c8ob01565a evidence type PRIMARY_EXPERIMENT snippet The homologous enzymes OxaG and RoqN were shown to catalyze penultimate hydroxylamine O-methylation to generate meleagrin in vitro. notes Murray et al. directly assayed RoqN-catalyzed O-methylation of glandicoline B to meleagrin and OxaG, its Penicillium oxalicum homolog, with SAM as methyl donor. reference DOI:10.1371/journal.pone.0065328 evidence type PRIMARY_EXPERIMENT snippet Eventually, meleagrin is produced from glandicoline B involving a methyltransferase (RoqN). notes Ali et al. assigned roqN in Penicillium rubens / P. chrysogenum by profiling BGC0000420 deletion strains in the branched roquefortine/meleagrin pathway. reference https://www.uniprot.org/uniprotkb/B6HJU2 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes Reviewed UniProtKB:B6HJU2 is the 288 aa Penicillium rubens Wisconsin 54-1255 RoqN/gmt/Pc21g15440 glandicoline B O-methyltransferase and cross-references EMBL AM920436 protein CAP96441.1. reference https://www.rhea-db.org/rhea/51732 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes RHEA:51732 is the glandicoline B plus S-adenosyl-L-methionine to meleagrin plus S-adenosyl-L-homocysteine plus proton reaction; Rhea maps the master reaction to UniProtKB:B6HJU2 in Swiss-Prot.
RoqN	forms	meleagrin	RoqN is the Pc21g15440/gmt methyltransferase that forms meleagrin from glandicoline B as the terminal BGC0000420 tailoring reaction.	DOI:10.1039/c8ob01565a DOI:10.1371/journal.pone.0065328 https://www.uniprot.org/uniprotkb/B6HJU2 https://www.rhea-db.org/rhea/51732 reference DOI:10.1039/c8ob01565a evidence type PRIMARY_EXPERIMENT snippet The homologous enzymes OxaG and RoqN were shown to catalyze penultimate hydroxylamine O-methylation to generate meleagrin in vitro. notes Murray et al. directly assayed RoqN-catalyzed O-methylation of glandicoline B to meleagrin and OxaG, its Penicillium oxalicum homolog, with SAM as methyl donor. reference DOI:10.1371/journal.pone.0065328 evidence type PRIMARY_EXPERIMENT snippet Eventually, meleagrin is produced from glandicoline B involving a methyltransferase (RoqN). notes Ali et al. assigned roqN in Penicillium rubens / P. chrysogenum by profiling BGC0000420 deletion strains in the branched roquefortine/meleagrin pathway. reference https://www.uniprot.org/uniprotkb/B6HJU2 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes Reviewed UniProtKB:B6HJU2 is the 288 aa Penicillium rubens Wisconsin 54-1255 RoqN/gmt/Pc21g15440 glandicoline B O-methyltransferase and cross-references EMBL AM920436 protein CAP96441.1. reference https://www.rhea-db.org/rhea/51732 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes RHEA:51732 is the glandicoline B plus S-adenosyl-L-methionine to meleagrin plus S-adenosyl-L-homocysteine plus proton reaction; Rhea maps the master reaction to UniProtKB:B6HJU2 in Swiss-Prot.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Explore across X-Mech

AntibioticMech (glandicoline B) ↗ MediaIngredientMech (naturalproductmech:mibig-7a476dbad3) ↗ TaxonMech: Penicillium rubens Wisconsin 54-1255 (NCBITaxon:500485) ↗ PathwayMech (mibig:BGC0000420) ↗

Provenance

Source concept	Source	Version
BGC0000420	MIBIG	5

This page is generated from data/natural_products/alkaloids/glandicoline-b.yaml, which is generated from the committed inventories. Neither is edited by hand.