Haploscleridamine, a novel tryptamine-derived alkaloid from a sponge of the order Haploselerida: An inhibitor of cathepsin K

As part of a search for novel inhibitors of cathepsin K, the MeOH extract of a Micronesian sponge of the order Haplosclerida was shown to be active. Bioassay-guided fractionation of the extract yielded hahtoxins, tryptamine, and a novel tryptamine-derived alkaloid, haploscleridamine (1). The tetrahy...

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Published inJournal of natural products (Washington, D.C.) Vol. 65; no. 4; pp. 628 - 629
Main Authors Patil, AD, Freyer, AJ, Carte, B, Taylor, PB, Johnson, RK, Faulkner, DJ
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 01.04.2002
Subjects
Chemistry, Medicinal
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Plant Sciences
Science & Technology
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Abstract As part of a search for novel inhibitors of cathepsin K, the MeOH extract of a Micronesian sponge of the order Haplosclerida was shown to be active. Bioassay-guided fractionation of the extract yielded hahtoxins, tryptamine, and a novel tryptamine-derived alkaloid, haploscleridamine (1). The tetrahydro-beta-carboline structure of haploscleridamine (1) was elucidated through spectral techniques. Haploscleridamine (1) was found to be an inhibitor of cathepsin K with an IC50 of 26 muM.
AbstractList As part of a search for novel inhibitors of cathepsin K, the MeOH extract of a Micronesian sponge of the order Haplosclerida was shown to be active. Bioassay-guided fractionation of the extract yielded hahtoxins, tryptamine, and a novel tryptamine-derived alkaloid, haploscleridamine (1). The tetrahydro-beta-carboline structure of haploscleridamine (1) was elucidated through spectral techniques. Haploscleridamine (1) was found to be an inhibitor of cathepsin K with an IC50 of 26 muM.
Author Freyer, AJ
Taylor, PB
Faulkner, DJ
Patil, AD
Carte, B
Johnson, RK
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References DELAISSE, JM (WOS:A1980KM07200043) 1980; 192
BROMME, D (WOS:A1989CC89100020) 1989; 264
Carte, BK (WOS:A1996UB24700008) 1996; 46
SEARLE, PA (WOS:A1994PQ52200018) 1994; 59
CHRISEY, LA (WOS:A1990CQ80700016) 1990; 30
SCHMITZ, FJ (WOS:A1978FR28500026) 1978; 43
KREBS HC (WOS:000175327700047.6) 1986; 49
Faulkner, DJ (WOS:000166564400001) 2001; 18
References_xml – volume: 49
  start-page: 152
  year: 1986
  ident: WOS:000175327700047.6
  publication-title: FORTSCHR CHEM ORG NA
  contributor:
    fullname: KREBS HC
– volume: 43
  start-page: 3916
  year: 1978
  ident: WOS:A1978FR28500026
  article-title: MARINE NATURAL-PRODUCTS - HALITOXIN, TOXIC COMPLEX OF SEVERAL MARINE SPONGES OF GENUS HALICLONA
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: SCHMITZ, FJ
– volume: 30
  start-page: 267
  year: 1990
  ident: WOS:A1990CQ80700016
  article-title: R-(+)-TETRAHYDROHARMINE AND S-(-)-TETRAHYDROHARMINE - PREPARATION OF OPTICALLY PURE ALKALOIDS AND ACID-CATALYZED RACEMIZATION
  publication-title: HETEROCYCLES
  contributor:
    fullname: CHRISEY, LA
– volume: 59
  start-page: 6600
  year: 1994
  ident: WOS:A1994PQ52200018
  article-title: 5 NEW ALKALOIDS FROM THE TROPICAL ASCIDIAN, LISSOCLINUM SP - LISSOCLINOTOXIN-A IS CHIRAL
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: SEARLE, PA
– volume: 18
  start-page: 1
  year: 2001
  ident: WOS:000166564400001
  article-title: Marine natural products
  publication-title: NATURAL PRODUCT REPORTS
  doi: 10.1039/b006897g
  contributor:
    fullname: Faulkner, DJ
– volume: 264
  start-page: 475
  year: 1989
  ident: WOS:A1989CC89100020
  article-title: THE SPECIFICITY OF BOVINE SPLEEN CATHEPSIN-S - A COMPARISON WITH RAT-LIVER CATHEPSIN-L AND CATHEPSIN-B
  publication-title: BIOCHEMICAL JOURNAL
  contributor:
    fullname: BROMME, D
– volume: 46
  start-page: 271
  year: 1996
  ident: WOS:A1996UB24700008
  article-title: Biomedical potential of marine natural products
  publication-title: BIOSCIENCE
  contributor:
    fullname: Carte, BK
– volume: 192
  start-page: 365
  year: 1980
  ident: WOS:A1980KM07200043
  article-title: INHIBITION OF BONE-RESORPTION IN CULTURE BY INHIBITORS OF THIOL PROTEINASES
  publication-title: BIOCHEMICAL JOURNAL
  contributor:
    fullname: DELAISSE, JM
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SubjectTerms Chemistry, Medicinal
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Plant Sciences
Science & Technology
Title Haploscleridamine, a novel tryptamine-derived alkaloid from a sponge of the order Haploselerida: An inhibitor of cathepsin K
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