Iridoid glucosides in Avicennia marina

doi:10.1016/S0031-9422(00)81110-3

Phytochemistry

Volume 24, Issue 6, 1985, Pages 1245-1248

https://doi.org/10.1016/S0031-9422(00)81110-3 Get rights and content

Abstract

2′-Cinnamoyl-mussaenoside, 10-O-(5-phenyl-2,4-pentadienoyl)-geniposide, 7-O-(5-phenyl-2,4-pentadienoyl)-8-epiloganin, and the known iridoids geniposide and mussaenoside have been isolated from a methylated extract of the leaves of Avicennia marina. Evidence is presented that the iridoids occur as the free acids in the plant. The taxonomic significance of these findings is discussed.

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Cited by (44)

Anti-leishmanial activity of Avicennia marina (Avicenniaceae family) leaves hydroalcoholic extract and its possible cellular mechanisms
2022, Parasite Epidemiology and Control
Citation Excerpt :
A. marina (Avicenniaceae family) is one of the mangrove species that grows along the coast of Persian Gulf in Iran. A few chemical analyses have been conducted on A. marina leaf, which identified different compounds of iridoid glucosides, naphthoquinone derivatives, hydrocarbons and triterpenes (König and Rimpler, 1985; Sharaf et al., 2000; Orhan et al., 2012). This unique plant has been used far and wide in traditional medicine for the treatment of ulcers, skin diseases, smallpox and rheumatism (Namazi et al., 2013; Vinoth et al., 2019).
Natural products are the main source of potent antioxidants and anti-leishmanial agents. This study was aimed to evaluate Avicennia marina (Avicenniaceae family) extract inhibitory effect against Leishmania tropica by accessing apoptotic markers and arginase activity. The A. marina were extracted and phytochemical analysis conducted. The inhibitory effect of A. marina was evaluated on L. tropica promastigote and amastigote forms, compared to meglumine antimoniate (Glucantime, MA) as standard drug. The level of apoptosis, Reactive Oxygen Species (ROS) production and arginase activity was assessed in A. marina-treated cells compared to control group. Phytochemical screening of A. marina extract showed strong presence of tannins and saponins. We demonstrated the inhibitory effect of A. marina on promastigote stages in a dose dependent manner. Also, lower 50% inhibitory concentration (IC₅₀) value of amastigotes was indicated in A. marina group compared with the standard group of Glucantime (60.57 ± 1.46 vs. 73.19 ± 10.12 μg/mL, respectively, P < 0.05). Besides, A. marina represented no cytotoxicity as the selectivity index (SI) was 10.7. Also, it showed the potential to induce early apoptosis of 46.5% in promastigotes at 125 μg/mL concentration. Significant reduction of arginase level was observed in both A. marina-treated cells and promastigotes. The promising results indicated higher effectiveness of A. marina in decreasing parasite growth, inducing apoptosis in promastigotes, increasing ROS production and decreasing arginase level. So, A. marina can be a native plant candidate for anti-leishmanial drug in tropical regions with cutaneous leishmaniasis due to L. tropica.
Antibacterial and antioxidant potential of GC-MS analysis of crude ethyl acetate extract from the tropical mangrove plant Avicennia officinalis L.
2021, South African Journal of Botany
Citation Excerpt :
The Avicennia genus mangrove plants are reported to be widely used in ethnomedicinal applications for treatment of various diseases such as astringent, aphrodisiac, asthma, antiulcer, antitumor, bronchial boils, cancer, contraceptive, diabetes, diarrhea, diuretic, HIV, hepatitis, gastroprotective, inflammation, leprosy, malaria, rheumatism, small pox, treatment for snake bites, skin diseases, oxidative stress-related diseases, tooth brush and ulcer (Rege et al 2010; Sumithra et al., 2011; Thirunavukkarasu et al., 2011; Ramanjaneyulu et al., 2015; Sachithanandam et al., 2019; Sachithanandam et al., 2020). The vast healing property of Avicennia species are evidenced by its high number of phytochemicals like terpenoids, glucosides and naphthalene derivatives (Konig and Rimpler 1985; Sutton et al., 1985; Shaker et al., 2001; Han et al., 2007; Sachithanandam et al., 2019). Few studies have characterized and identified theses bioactive compounds and antimicrobial activity in Avicennia plants (Han et al., 2007; Subrahmanyam et al., 2006; Chinnappan et al., 2013; Thu et al., 2019).
Avicennia officinalis L. is an important mangrove plant used in traditional medicine to treat various diseases like asthma, dyspepsia, paralysis, tumor and rheumatism in aboriginal peoples in Andaman and Nicobar Islands (ANI). The study analyzed and separated bioactive speciation of ethyl acetate leaves extract of A. officinalis from tropical mangrove plants by Gas Chromatography-Mass Spectrometry (GC-MS) and further antimicrobial and antioxidant potential assay. GC-MS results of A. officinalis identified eight different bioactive compounds namely Trans-cinnamic acid, 2,4-Di-tert-butyl phenol, Phenol, 3-(2-phenylethyl, n-hexadecanoic acid, Dibutyl phthalate, Phytol, β – Sitosterol, Androst-7-ene-6, 17-dione and 2,3,14-trihydroxy. The natural products present in A. officinalis showed strong antibacterial activity against different bacteria like gram-positive strain: Streptococcus mutans (19 mm maximum zone of inhibition), Bacillus subtilis (17 mm), Pseudomonas aeruginosa (16 mm), and gram-negative: Klebsiella pneumonia (22 mm) and Enterobacter aerohenes (14 mm). Further, this crude extract showed good antioxidant activity with IC50 values of 23.60±0.43 µg/ml measured using the DPPH method. Thus, the study put forth the promising role of ethyl acetate leaves extract of A. officinalis in the formulation of therapeutic drugs against bacterial infections, antioxidants and cancer.
Physicochemical properties, preliminary characterization, and assessment of potential bioactivities of polysaccharide purified from the leaves of Avicennia marina
2021, Biocatalysis and Agricultural Biotechnology
Citation Excerpt :
The extracts of various parts (leaf, stem, and bark, etc.) of the mangrove plants have been used for the cure of several diseases (Shilpi et al., 2012; Simlai and Roy, 2013). The medicinally important chemical compounds such as terpenoids, glucosides, and naphthalene derivatives have been reported in the mangroves (Han et al., 2007; König and Rimpler, 1985; Shaker et al., 2001; Suiton et al., 1985). Marine plants are the potential source of bioactive compounds therefore, they have been studied as valuable biocidal and therapeutic agents (Kumar et al., 2009).
A low molecular weight polysaccharide, the AMLP was isolated from the leaves of Avicennia marina and sequentially purified using DEAE-Sepharose fast flow and size exclusion chromatography. Monosaccharide analysis suggested that AMLP is mainly composed of fucose (38.34 %), galactose (30.16 %), mannose (13.32 %), and rhamnose (18.18 %). IR spectroscopy and High-performance size-exclusion chromatography (HPSEC) analysis revealed that AMLP was a sulfated homogenous heteropolysaccharide, and their molecular weight observed was 1.31 kDa. The Spectroscopic analysis of AMLP comprised of (1,2)- α-L-Fucp, (1,6)-β-D-linked galactan, α-rhamnose, and (1,4)-β-D mannose residues. AMLP has a loosely arranged granular bead-like appearance present on the surface and also with the presence of some porous structures. The rheological properties of AMLP exhibited pseudoplastic properties with shear-thinning flow behavior. Congo red test and X-ray diffraction (XRD) results indicated the semi-crystalline nature of AMLP with a triple-helical structure. Thermogravimetric and Differential scanning calorimetry (TGA-DSC) analysis of AMLP found was thermally stable and its degradation temperature observed was 280 °C. Furthermore, AMLP exhibited potential antibacterial and antibiofilm properties against bacterial pathogens such as Listeria monocytogenes, Escherichia coli, Klebsiella pneumonia, Salmonella typhimurium, and Staphylococcus aureus. The In vitro antioxidant activities such as DPPH scavenging, Superoxide radical scavenging, OH radical scavenging, and reducing power activities of AMLP were evaluated and the results revealed that the tested antioxidant activities of AMLP were significantly (P < 0.05) increased with increasing the concentrations. Overall, these findings suggested that AMLP could be used as a potential candidate in pharmaceutical, cosmetics, and food industry applications.
Avicennia marina a natural reservoir of phytopharmaceuticals: Curative power and platform of medicines
2020, Journal of Ethnopharmacology
Avicennia marina (Forssk.) Vierh. is a historic plant, well-known for many centuries in traditional and folk use medicine. A. marina is an evergreen tree belongs to Acanthaceae family. The plant is the most widespread mangrove in the tropical and subtropical regions of Indo-West-Pacific area. Current scientific data confirmed the medicinal values of A. marina. The pharmacological activity of the plant is attributed to the presence of several phytochemical classes.
To evaluate the link between the traditional use of the plant and the scientific data accumulated over time including both the phytochemical analysis and therapeutic activities. Additionally, to evaluate the usage of obtained data for further development of the plant and its products in the pharmaceutical market.
The data related to traditional medicine, therapeutic uses, phytochemical analysis and market availability of A. marina and its products from different geographical regions were collected. The collected data was compared and the research gaps were identified in order to highlight areas that can be employed to improve plant-based research and development.
Although the wide geographical distribution of the plant, its historic traditional use, richness of phytochemicals and diverse pharmacological activities, the utilization of these data has never been exploited for human health and several gaps were identified. These gaps include the lack of phyto-geographical comparison of the plant, the lack of proper mapping of traditional use to the scientific data and inadequate exploration of plant phytochemicals by researchers.
A. marina is an old tree that has evolved over centuries and adapted diverse climates. It contains a pool of potential phytochemicals that can be employed for the discovery of drugs after careful studies. Scientists are required to invest money and time to explore these renewable and natural sources of drugs and design drug formulations to overcome current difficult to treat health issues and fight against the era of drug resistant.
Bioactivity guided isolation and structural characterization of the antidiabetic and antioxidant compound from bark extract of Avicennia officinalis L
2019, South African Journal of Botany
Citation Excerpt :
Previous studies have demonstrated that A. officinalis is rich in several phytochemicals such as carbohydrate, proteins, glycosides, tannins, alkaloids, phenolics, terpenoids, saponins, sterols, flavonoids (Khushi et al., 2010; Thatoi et al., 2016). Compounds such as iridoids avicennioside and 7-cinnamoyl-8 epiloganic acid, geniposidic acid and 2’cinnamoyl mussaenosidic acid, 3a,6-methano-3ah-inden-5-ol, octahydro and 26,27-Di (nor)-cholest-5,7,23-trien-22-ol,3-methoxy have also been reported in the leaf extracts of A. officinalis (Konig et al., 1987; Ganesh and Jannet-Vennila, 2011). The ethanol bark extract of A. officinalis was fractionated on silica gel column chromatography using petroleum ether, chloroform and methanol gradient elution system.
The present study was aimed at evaluating the antidiabetic activity of the ethanol bark extract of a mangrove plant Avicennia officinalis (AOEB) in streptozotocin (STZ)-induced diabetic mice. The study revealed AOEB could lower the blood glucose level significantly (p < .05) in diabetic mice at dose of 200 mg/kg b.w. The elevated total cholesterol, triglyceride, liver toxicity makers (SGOT and SGPT) and urea level were found to be ameliorated. The in vitro bioactivity-guided assay of AOEB led to isolation of a bioactive compound that inhibits the carbohydrate metabolizing enzymes (α-amylase and α-glucosidase) and also scavenging the DPPH, ABTS and superoxide radicals. The structure of the isolated compound was analyzed by different spectral techniques as FT-IR, CHNS, ¹H NMR, ¹³C NMR, MS. Further, the isolated compound was analyzed by HPLC. However, further studies are required to elucidate the exact structure of the isolated compound.
Evaluation of anti-HIV-1 activity of a new iridoid glycoside isolated from Avicenna marina, in vitro
2014, International Immunopharmacology
Citation Excerpt :
It is usually used to treat some diseases such as ulcers, rheumatism and small pox [6]. Through extracting natural compounds from A. marina leaf in recent decades, a number of iridoid glucosides, fatty acids, sterols and hydrocarbons have been isolated [7,8]. We previously reported that luteolin derivatives isolated from A. marina leaf exhibited significant anti-HSV-2 activity [9].
This study was carried out to check the efficacy of methanol seed extract of Avicenna marina and its column chromatographic fractions on Peripheral Blood Mono nuclear Cells (PBMCs) toxicity and HIV-1 replication. The anti-HIV-1 activities of crude methanol extract and its fractions were performed by use of real-time polymerase chain reaction (PCR) assay and HIV-1 p24 antigen kit. A time of drug addiction approach was also done to identify target of anti-HIV compound. The activity of the extracts on CD4, CD3, CD19 and CD45 expression in lymphocytes population was performed by use of flow cytometry. The most active anti-HIV agent was detected by spectroscopic analysis as 2′-O-(4-methoxycinnamoyl) mussaenosidic acid. The apparent effective concentrations for 50% virus replication (EC50) of methanol extract and iridoid glycoside were 45 and 0.1 μg/ml respectively. The iridoid glycoside also did not have any observable effect on the proportion of CD4, CD3, CD19 and CD45 cells or on the intensity of their expressions on PBMCs. In addition, the expression level of C-C chemokine receptor type 5 (CCR5) and chemokine receptor type 4 (CXCR4) on CD4⁺ T cells were decreased in cells treated with this iridoid glycoside. The reduction of these two HIV coreceptors and the result of time of addition study demonstrated that this iridoid glycoside restricts HIV-1 replication on the early stage of HIV infection.

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Iridoid glucosides in Avicennia marina

Abstract

Tetrahedron Letters

Tetrahedron

Phytochemistry

Phytochemistry

Phytochemistry

Phytochemistry

Phytochemistry

Tetrahedron

Evolution und Ausbreitung der Blütenpflanzen

Symb. Bot. Upsal.