Ircinals A and B from the Okinawan marine sponge Ircinia sp.: plausible biogenetic precursors of manzamine alkaloids

Kondo, Kazuyoshi; Shigemori, Hideyuki; Kikuchi, Yumiko; Ishibashi, Masami; Sasaki, Takuma; Kobayashi, Jun’ichi

doi:10.1021/jo00034a052

Cited by 159 publications

(114 citation statements)

References 1 publication

Supporting

Mentioning

105

Contrasting

Unclassified

Order By: Relevance

“…Two additional alkaloids isolated from Okinawan waters in 1992 by Kobayashi and co-workers are ircinal A (1.17) and B (1.18). 8 Interestingly, the structures of ircinal A and B are very similar to the tetracyclic aldehyde (1.13) proposed earlier by Baldwin.…”

Section: Scheme 2 Baldwin's Proposed Biosynthesis Of Manzamine B (18)supporting

confidence: 65%

Total Synthesis of (±)‐Haliclonacyclamine C

Smith

Sulikowski

2010

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Section: Scheme 2 Baldwin's Proposed Biosynthesis Of Manzamine B (18)supporting

confidence: 65%

Total Synthesis of (±)‐Haliclonacyclamine C

Smith

Sulikowski

2010

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

“…8 This completed the first total synthesis of manzamine in 33 overall steps (31 steps longest linear sequence). 50 Martin Total Synthesis of Manzamine A (1.3)…”

Section: Baldwin's Biomimetic Studiesmentioning

confidence: 99%

“…[9][10][11] They were also able to install the 8-membered ring by a lactamization and introduced the β-carboline unit using the Pictet-Spengler reaction similar to the Winkler and Martin approaches. 7,8 The Pandit synthesis began with L-Serine (2.29), which was transformed to iodide Nakagawa's Approach to Manzamine A (1.3)…”

Section: Baldwin's Biomimetic Studiesmentioning

confidence: 99%

Total Synthesis of (±)‐Haliclonacyclamine C

Smith

Sulikowski

2010

Angew Chem Int Ed

View full text Add to dashboard Cite

show abstract

“…17 The IR spectrum exhibited an absorption band at 1722 cm −1 , supporting the presence of a carbonyl functionality in 3. 18 manzamine A (1), 19 8-hydroxymanzamine A (10), 20 manzamine E (6), 21 manzamine F (8), 21 ircinol A, 22 and the new manzamine analogue, 8-hydroxymanzamine B (5).…”

mentioning

confidence: 99%

Manzamine B and E and Ircinal A Related Alkaloids from an Indonesian Acanthostrongylophora Sponge and Their Activity against Infectious, Tropical Parasitic, and Alzheimer's Diseases

et al. 2006

View full text Add to dashboard Cite

Four new manzamine-type alkaloids, 12,28-oxamanzamine E (2), 12,34-oxa-6-hydroxymanzamine E (3), 8-hydroxymanzamine B (5), and 12,28-oxaircinal A (11), were isolated from three collections of an Indonesian sponge of the genus Acanthostrongylophora together with 13 known manzamine alkaloids, ircinal A, ircinol A, xestomanzamine A, manzamines A, E, F, J, and Y, manadomanzamines A and B, neo-kauluamine, 8-hydroxymanzamine A, and manzamine A Noxide. The structures of the new compounds were elucidated by means of 1D and 2D NMR spectroscopic methods. Three of these compounds (2, 3, and 11) possess a unique manzaminetype aminal ring system generated through an ether linkage between carbons 12-28 or between carbons 12-34. In the case of manzamine B and related metabolites, carbons 11 and 12 of the typical manzamine structure have an epoxide group and add to our growing understanding of manzamine structure-activity relationships (SAR) and metabolism. The bioactivity and SAR for a number of previously reported manzamine-related metabolites against malaria, leishmania, tuberculosis, and HIV-1 are also presented. Manzamine Y (9) showed significant inhibitory activity of GSK3, an enzyme implicated in Alzheimer's disease pathology. The toxicity of manzamine A and neo-kauluamine was evaluated against both medaka fry and eggs.A common Indo-Pacific sponge, Acanthostrongylophora sp., has been shown to be a highly rich source of bioactive manzamine-related alkaloids. [1][2][3] This class of alkaloids has been reported previously to show a number of significant biological activities including cytotoxic, 4 insecticidal, 5 antibacterial, 6 anti-inflammatory, 7 anti-infective, 8 and antiparasitic 9 * To whom correspondence should be addressed. . mthamann@olemiss.edu. HHS Public AccessAuthor manuscript J Nat Prod. Author manuscript; available in PMC 2016 June 22. Author Manuscript Author ManuscriptAuthor ManuscriptAuthor Manuscript activities, with the greatest potential for possible clinical applications existing for the control of Plasmodium falciparum and Mycobacterium tuberculosis. 10 As part of our ongoing investigations to identify new manzamines and to define the SAR as well as utilize the natural products as synthetic starting materials, [1][2][3][11][12][13] extracts of the Indonesian sponge Acanthostrongylophora sp. were investigated. In an earlier investigation, this sample yielded two new manzamine alkaloids, named 12,28-oxamanzamine A and 12,28-oxa-8-hydroxymanzamine A, and a unique ircinol A analogue together with manzamines A and F and neo-kauluamine. 2 Manzamine A (1) exhibits potent in vitro bioactivity against chloroquine-sensitive (D6, Sierra Leone) and -resistant (W2, Indo-China) strains of P. falciparum. Reisolation of manzamine A for pharmacokinetic and toxicology studies as well as for preparation of analogues necessitated a major collection of Acanthostrongylophora sp., yielding four new manzamine alkaloids (2, 3, 5, and 11)together with the 13 known manzamine alkaloids, which are the subject of this re...

show abstract

Ircinals A and B from the Okinawan marine sponge Ircinia sp.: plausible biogenetic precursors of manzamine alkaloids

Cited by 159 publications

References 1 publication

Total Synthesis of (±)‐Haliclonacyclamine C

Total Synthesis of (±)‐Haliclonacyclamine C

Total Synthesis of (±)‐Haliclonacyclamine C

Manzamine B and E and Ircinal A Related Alkaloids from an Indonesian Acanthostrongylophora Sponge and Their Activity against Infectious, Tropical Parasitic, and Alzheimer's Diseases

Contact Info

Product

Resources

About