Toxicants from mangrove plant. 3. Heritol, a novel ichthyotoxin from the mangrove plant Heritiera littoralis

Miles, D. Howard; Lho, Dong Seok; Cruz, Armando A. de la; Gomez, Edgardo D.; Weeks, James A.; Atwood, Jerry L.

doi:10.1021/jo00389a053

Cited by 35 publications

(21 citation statements)

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“…This crude extract also resulted in significant antioxidant activity [34]. H. littoralis, on the other hand, has resulted in significant biochemical compounds of flavonoid and terpenoid family as well as cinnamoylglycoflavonoid, antimycobacterial and antioxidant properties [30,[35][36][37][38][39]. Despite the fact that antimicrobial, antioxidant, anticancer, antihyperglycemic and antinociceptive effects of H. fomes have already been reported, only a few studies were carried out on H. littoralis [40][41][42][43][44].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of antioxidant, anti-hemolytic, cytotoxic effects and anti-bacterial activity of selected mangrove plants (Bruguiera gymnorrhiza and Heritiera littoralis) in Bangladesh

Karim¹,

Islam²,

Islam³

et al. 2020

Clin Phytosci

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Objectives: In this present study, antioxidant, anti-hemolytic, cytotoxic and anti-bacterial activities derived from methanol extracts of Bruguiera gymnorrhiza and Heritiera littoralis were investigated in order to determine their medicinal activities.Materials and methods: Folin-Ciocalteu reagent method and aluminum chloride methods were used to determine the mangroves' total phenolics and total flavonoid content, respectively. Antioxidant capacity was assessed via the following methods: 1,1-diphenyl-2-picryl hydroxyl (DPPH), 43 mM H 2 O 2 , Fe 2+ quenching assay, and anti-hemolytic activity. Brine shrimp (Artemia salina L.) lethality assay was also carried out to determine the cytotoxic potential of the mangroves along with antibacterial activity test using five Gram-negative and another two Gram-positive bacterial strains.Results: The mangroves yielded 58.917 ± 0.601 and 36.625 ± 0.551 mg Gallic acid equivalent (GAE)/g sample and 76.417 ± 0.19 and 113.637 ± 0.17 mg quercetin equivalent (QE)/g sample in B. gymnorrhiza and H. littoralis, respectively. Methanol extracts of both mangroves exhibited high radical scavenging activity against DPPH, H 2 O 2 and Fe 2+ radicals. The reductive capacity of the extracts increased with increasing concentrations of samples, and the extracts inhibited H 2 O 2 induced hemolysis in human red blood cells (RBCs). Antioxidant properties were found to be moderately weaker than that of the reference standard, L-ascorbic acid (AA), and Gallic acid (GA). Further, brine shrimp (Artemia salina L.) lethality assay revealed significant cytotoxicity (241.4 and 272.6 μg/mL, respectively). Methanol extracts could also inhibit the growth of pathogenic bacterial strains. Conclusion: This study showed that the crude methanol extract of selected mangrove plants possesses free radical scavenging, anti-hemolytic, cytotoxic and anti-bacterial activity. The experimented plant has the potential to be used as a traditional medicine and replace synthetic drugs. Further studies are necessary to isolate active compounds responsible for the overall antioxidant activity of the crude extracts.

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Section: Introductionmentioning

confidence: 99%

Evaluation of antioxidant, anti-hemolytic, cytotoxic effects and anti-bacterial activity of selected mangrove plants (Bruguiera gymnorrhiza and Heritiera littoralis) in Bangladesh

Karim¹,

Islam²,

Islam³

et al. 2020

Clin Phytosci

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“…Compounds 25 and 26 are related to the natural product heritol25 and its derivatives,26 having identical ring systems (Figure 3). The cascade reaction observed here might make these natural products accessible.…”

Section: Resultsmentioning

confidence: 99%

Structure Elucidation and Total Synthesis of Altenuic Acid III and Studies towards the Total Synthesis of Altenuic Acid II

et al. 2013

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The structure of the Alternaria mycotoxin altenuic acid III was elucidated by NMR spectroscopic analysis of an authentic sample, and was confirmed by total synthesis. This compound is not a resorcylic acid lactone but a resorcylic acid substituted with a butenolide, and thus is the first member of a new class of alternaria toxins. For the total synthesis, a short and efficient access to halogenated butenolides bearing acetal‐protected side‐chains was carried out. Suzuki coupling of these butenolides with a highly functionalized boronate gave rise to a precursor of the natural product in high yield. The side‐chain was completed by deprotection and subsequent oxidation. An unexpected cascade reaction leading to tricyclic butenolides was discovered during optimization of the deprotection protocol. Cleavage of the acetal protecting group gave altenuic acid III. Furthermore, a synthetic study towards altenuic acid II, a compound with a characteristic spirolactone structure, is described. It was planned to construct the spirocyclic lactone by using an intramolecular Michael‐type addition of an aromatic carboxylate group to a butenolide moiety, but this approach was not successful. While testing the feasibility of this concept, a new and mild protocol for the well‐known Pinner reaction in the presence of Lewis acids was discovered.

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“…In addition, they have been used to control mosquitos and as a piscicide [65,66,67]. The sap is reported to be a fish poison and arrowhead and spearhead poison [64,68]. The seeds and leaves are, however, regarded as edible in the Andaman and Nicobar islands [69].…”

Section: Traditional Antidiarrhoeal Plants From Bangladeshmentioning

confidence: 99%

“…Roots : Sesquiterpenes : heritol, heritonin, heritianin, vallapin, vallapianin [68,76,77,78]; Triterpenoid : friedelin [77]. …”

Section: Traditional Antidiarrhoeal Plants From Bangladeshmentioning

confidence: 99%

Can Scientific Evidence Support Using Bangladeshi Traditional Medicinal Plants in the Treatment of Diarrhoea? A Review on Seven Plants

et al. 2013

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Diarrhoea is a common disease which causes pain and may be deadly, especially in developing countries. In Bangladesh, diarrhoeal diseases affect thousands of people every year, and children are especially vulnerable. Bacterial toxins or viral infections are the most common cause of the disease. The diarrhoea outbreaks are often associated with flood affected areas with contaminated drinking water and an increased risk of spreading the water-borne disease. Not surprisingly, plants found in the near surroundings have been taken into use by the local community as medicine to treat diarrhoeal symptoms. These plants are cheaper and more easily available than conventional medicine. Our question is: What is the level of documentation supporting the use of these plants against diarrhoea and is their consumption safe? Do any of these plants have potential for further exploration? In this review, we have choosen seven plant species that are used in the treatment of diarrhoea; Diospyros peregrina, Heritiera littoralis, Ixora coccinea, Pongamia pinnata, Rhizophora mucronata, Xylocarpus granatum, and Xylocarpus moluccensis. Appearance and geographical distribution, traditional uses, chemical composition, and biological studies related to antidiarrhoeal activity will be presented. This review reveals that there is limited scientific evidence supporting the traditional use of these plants. Most promising are the barks from D. peregrina, X. granatum and X. moluccensis which contain tannins and have shown promising results in antidiarrhoeal mice models. The leaves of P. pinnata also show potential. We suggest these plants should be exploited further as possible traditional herbal remedies against diarrhoea including studies on efficacy, optimal dosage and safety.

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Toxicants from mangrove plant. 3. Heritol, a novel ichthyotoxin from the mangrove plant Heritiera littoralis

Cited by 35 publications

References 0 publications

Evaluation of antioxidant, anti-hemolytic, cytotoxic effects and anti-bacterial activity of selected mangrove plants (Bruguiera gymnorrhiza and Heritiera littoralis) in Bangladesh

Evaluation of antioxidant, anti-hemolytic, cytotoxic effects and anti-bacterial activity of selected mangrove plants (Bruguiera gymnorrhiza and Heritiera littoralis) in Bangladesh

Structure Elucidation and Total Synthesis of Altenuic Acid III and Studies towards the Total Synthesis of Altenuic Acid II

Can Scientific Evidence Support Using Bangladeshi Traditional Medicinal Plants in the Treatment of Diarrhoea? A Review on Seven Plants

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