ChemInform Abstract: MARINE NATURAL PRODUCTS PART 10, ELATOL, A HALOGENATED SESQUITERPENE ALCOHOL FROM THE RED ALGA LAURENCIA ELATA

Carrageenophyte farming is an expanding economical activity in North Borneo Island, Malaysia. During routine monitoring of "ice-ice" disease and epiphyte outbreak at commercial farms, it was apparent that culture lines were heavily (60-80%) infested with biofoulers, particularly Acanthophora spp. and Laurencia majuscula. However, only L. majuscula showed dominance and flourished even during "ice-ice" disease outbreak. Presence of chemical defense against seaweed pathogens was investigated in two populations of L. majuscula collected from three major carrageenophyte farms in two districts; (A) Lohok Butun, Selakan Island, and Bum-Bum Island, in Semporna district, and (B) Telutuh, Carrington Reef, and Balambangan Island, in Kudat district. The first population contained elatol (1), and iso-obtusol (2), and, second population contained (Z)-10,15-dibromo-9-hydroxy-chamigra-1,3(15),7(14)-triene (3) and (E)-10-15-dibromo-9-hydroxy-chamigra-1,3(15),7(14)-triene (4), as their antibacterial metabolites. All four metabolites showed highly selective inhibition against "ice-ice" disease bacteria compared to human pathogens at 30µg disk −1 . In addition, seasonal variation of these compounds at two representative farms (Selakan Island [P-1] and Balambangan Island [P-2]) revealed a 120-170% increase in concentration during "ice-ice" disease outbreak. Microscopy of fresh specimens showed the presence of corps en cerise, which is the synthesis and storage site of halogenated metabolites at superficial cortical cells, branch tips, and trichoblasts. This suggests the importance of these metabolites as defense chemicals against "ice-ice" disease bacteria in L. majuscula that grows on seaweed culture lines.

show abstract

“…1 H and 13 C-NMR spectra were identical to that of the authentic samples (Sims et al 1974;González et al 1979).…”

Section: Resultsmentioning

confidence: 98%

Role of secondary metabolites as defense chemicals against ice-ice disease bacteria in biofouler at carrageenophyte farms

et al. 2009

View full text Add to dashboard Cite

show abstract

“…The likelihood of development of an invasive SCC from a single AK lesion is around 0.075-0.096% per lesion per year, meaning that for an individual with an average of 7.7 lesions, the probability of at least one transforming into SCC, within a ten-year period, is almost 10% [174]. Before the introduction of 5 the pharmacological treatment was based on 5-fluorouracil, imiquimod, retinoids, or diclofenac [174]. The topical treatment of multiple actinic keratosis lesions by application of a pharmaceutical product to a specific area of the skin is referred to in medical terminology as "field therapy", and, before the introduction of 5, required weeks or months of treatment, alone or in association with surgical operations like laser removal, cryosurgery, electrodesiccation, shave excision, or laser ablation.…”

Section: Molecular and Clinical Pharmacology Of Picato ®mentioning

confidence: 99%

Progress in the Chemistry of Organic Natural Products 102

Kinghorn¹,

Falk²,

Gibbons³

et al. 2016

Progress in the Chemistry of Organic Natural Products

View full text Add to dashboard Cite

show abstract

“…Developing new methods for the efficient synthesis of highly substituted chiral molecules is of great importance in pharmaceuticals and agrochemicals. A cyclohexane having a chiral quaternary carbon center is a common substructure in natural products with significant biological and medicinal activities such as alkaloids and sesquiterpenoids [1][2][3][4][5] (Figure 1). Various efforts have therefore been devoted to developing new methods to synthesize these frameworks; however, the efficient formation of cyclohexanes bearing an all-carbon quaternary stereogenic center still remains as a challenging task in the field of chiral synthesis.…”

Section: Introductionmentioning

confidence: 99%

New entry to the enantioselective formation of substituted cyclohexenes bearing an all‐carbon quaternary stereogenic center

et al. 2020

View full text Add to dashboard Cite

Enantioselective formation of cyclohexene derivatives bearing an all‐carbon quaternary stereogenic center is described. The racemic cyclohexenes are readily transformed to chiral substituted cyclohexenes in good yield with excellent enantioselectivity and diastereoselectivity by a palladium‐mediated deracemization. The resulting products are promising synthetic intermediates of biologically active natural products. This protocol provides us with a new entry to the concise and scalable synthesis of multifunctionalized compounds.

show abstract

ChemInform Abstract: MARINE NATURAL PRODUCTS PART 10, ELATOL, A HALOGENATED SESQUITERPENE ALCOHOL FROM THE RED ALGA LAURENCIA ELATA

Abstract: Das aus obiger Spezies isolierfe Elatol besitzt die Struktur (I).

Cited by 17 publications

References 1 publication

Role of secondary metabolites as defense chemicals against ice-ice disease bacteria in biofouler at carrageenophyte farms

Role of secondary metabolites as defense chemicals against ice-ice disease bacteria in biofouler at carrageenophyte farms

Progress in the Chemistry of Organic Natural Products 102

New entry to the enantioselective formation of substituted cyclohexenes bearing an all‐carbon quaternary stereogenic center

Contact Info

Product

Resources

About