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Literature DB >> 20806908

Caylobolide B, a macrolactone from symplostatin 1-producing marine cyanobacteria Phormidium spp. from Florida.

Lilibeth A Salvador¹, Valerie J Paul, Hendrik Luesch.

Abstract

A Phormidium spp. collection from Key West, Florida, afforded caylobolide B (1), an analogue of the known macrolactone caylobolide A, previously isolated from a Lyngbya majuscula collection from the Bahamas. The planar structure of 1 was determined using NMR and MS experiments. The relative configuration for subunits C7-C9 and C25-C29 was assigned using Kishi's Universal NMR Database. Caylobolide B (1) displayed cytotoxic activity against HT29 colorectal adenocarcinoma and HeLa cervical carcinoma cells with IC(50) values of 4.5 and 12.2 μM, respectively.

Entities: CellLine Chemical Disease Gene Species

Mesh：

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Year: 2010 PMID： 20806908 PMCID： PMC2965599 DOI： 10.1021/np100467d

Source DB: PubMed Journal: J Nat Prod ISSN： 0163-3864 Impact factor: 4.050

12 in total

1. Toward creation of a universal NMR database for stereochemical assignment: complete structure of the desertomycin/oasomycin class of natural products.

Authors: Y Kobayashi; C H Tan; Y Kishi
Journal: J Am Chem Soc Date: 2001-03-07 Impact factor: 15.419

2. Isolation of dolastatin 10 from the marine cyanobacterium Symploca species VP642 and total stereochemistry and biological evaluation of its analogue symplostatin 1.

Authors: H Luesch; R E Moore; V J Paul; S L Mooberry; T H Corbett
Journal: J Nat Prod Date: 2001-07 Impact factor: 4.050

3. Structure and absolute stereochemistry of phormidolide, a new toxic metabolite from the marine cyanobacterium Phormidium sp.

Authors: R Thomas Williamson; Anna Boulanger; Alexandra Vulpanovici; Mary A Roberts; William H Gerwick
Journal: J Org Chem Date: 2002-11-15 Impact factor: 4.354

4. Tolytoxin and new scytophycins from three species of Scytonema.

Authors: S Carmeli; R E Moore; G M Patterson
Journal: J Nat Prod Date: 1990 Nov-Dec Impact factor: 4.050

5. The molecular pharmacology of symplostatin 1: a new antimitotic dolastatin 10 analog.

Authors: Susan L Mooberry; Rachel M Leal; Tina L Tinley; Hendrik Luesch; Richard E Moore; Thomas H Corbett
Journal: Int J Cancer Date: 2003-04-20 Impact factor: 7.396

Review 6. Bioactive natural products from marine cyanobacteria for drug discovery.

Authors: Lik Tong Tan
Journal: Phytochemistry Date: 2007-03-02 Impact factor: 4.072

7. Caylobolide A, a unique 36-membered macrolactone from a Bahamian Lyngbya majuscula.

Authors: John B MacMillan; Tadeusz F Molinski
Journal: Org Lett Date: 2002-05-02 Impact factor: 6.005

Review 8. New peptides isolated from Lyngbya species: a review.

Authors: Li Liu; Kathleen S Rein
Journal: Mar Drugs Date: 2010-06-09 Impact factor: 5.118

9. Symplostatin 1: A dolastatin 10 analogue from the marine cyanobacterium Symploca hydnoides.

Authors: G G Harrigan; H Luesch; W Y Yoshida; R E Moore; D G Nagle; V J Paul; S L Mooberry; T H Corbett; F A Valeriote
Journal: J Nat Prod Date: 1998-09 Impact factor: 4.050

10. Long-range stereo-relay: relative and absolute configuration of 1,n-glycols from circular dichroism of liposomal porphyrin esters.

Authors: John B MacMillan; Tadeusz F Molinski
Journal: J Am Chem Soc Date: 2004-08-18 Impact factor: 15.419

17 in total

1. Targeted natural products discovery from marine cyanobacteria using combined phylogenetic and mass spectrometric evaluation.

Authors: Lilibeth A Salvador-Reyes; Niclas Engene; Valerie J Paul; Hendrik Luesch
Journal: J Nat Prod Date: 2015-01-30 Impact factor: 4.050

2. Amantelides A and B, Polyhydroxylated Macrolides with Differential Broad-Spectrum Cytotoxicity from a Guamanian Marine Cyanobacterium.

Authors: Lilibeth A Salvador-Reyes; Jennifer Sneed; Valerie J Paul; Hendrik Luesch
Journal: J Nat Prod Date: 2015-07-23 Impact factor: 4.050

Caylobolide B, a macrolactone from symplostatin 1-producing marine cyanobacteria Phormidium spp. from Florida.

1. Toward creation of a universal NMR database for stereochemical assignment: complete structure of the desertomycin/oasomycin class of natural products.

2. Isolation of dolastatin 10 from the marine cyanobacterium Symploca species VP642 and total stereochemistry and biological evaluation of its analogue symplostatin 1.

3. Structure and absolute stereochemistry of phormidolide, a new toxic metabolite from the marine cyanobacterium Phormidium sp.

4. Tolytoxin and new scytophycins from three species of Scytonema.

5. The molecular pharmacology of symplostatin 1: a new antimitotic dolastatin 10 analog.

Review 6. Bioactive natural products from marine cyanobacteria for drug discovery.

7. Caylobolide A, a unique 36-membered macrolactone from a Bahamian Lyngbya majuscula.

Review 8. New peptides isolated from Lyngbya species: a review.

9. Symplostatin 1: A dolastatin 10 analogue from the marine cyanobacterium Symploca hydnoides.

10. Long-range stereo-relay: relative and absolute configuration of 1,n-glycols from circular dichroism of liposomal porphyrin esters.

1. Targeted natural products discovery from marine cyanobacteria using combined phylogenetic and mass spectrometric evaluation.

2. Amantelides A and B, Polyhydroxylated Macrolides with Differential Broad-Spectrum Cytotoxicity from a Guamanian Marine Cyanobacterium.

Review 3. Therapeutic potential of marine peptides in cervical and ovarian cancers.

Review 4. Marine natural products targeting the eukaryotic cell membrane.

5. Total Synthesis of (-)-Bastimolide A: A Showcase for Type I Anion Relay Chemistry.

6. The Phormidolide Biosynthetic Gene Cluster: A trans-AT PKS Pathway Encoding a Toxic Macrocyclic Polyketide.

Review 7. Recent advances and applications of experimental technologies in marine natural product research.

8. Macrolactone Nuiapolide, Isolated from a Hawaiian Marine Cyanobacterium, Exhibits Anti-Chemotactic Activity.

Review 9. Marine cyanobacteria compounds with anticancer properties: a review on the implication of apoptosis.

10. Fresh Water Cyanobacteria Geitlerinema sp. CCC728 and Arthrospira sp. CCC729 as an Anticancer Drug Resource.