Elucidation of a new oleanane glycoside from Barringtonia asiatica

Burton, Robert P.; Wood, Steve; Owen, Noel L.

doi:10.3998/ark.5550190.0004.d14

Cited by 14 publications

(3 citation statements)

References 9 publications

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“…Barrigenol-like triterpenoids are a small group of olean-12enes hydroxylated at the C-3, C-15, and/or C-16, C-22 and/or C-21, and C-28 positions, 31 occurring mainly in the families Apocynaceae (Gymnema sylvestre), 33 Lecythidaceae (Barringtonia acutangula 18 and Barringtonia asiatica), 19 Pittosporaceae (Pittosporum tobira), 34 Sapindaceae (Aesculus hippocastanum, 6 Aesculus pavia, 21 Harpullia pendula, 8 and Xanthoceras sorbifolium), 22,25 and Theaceae (Camellia sinensis). 35 Some of these compounds were identified as the main active components of Barringtonia asiatica, for which the seeds have been used as fish poison by indigenous Polynesian populations, 36 and of Gymnema sylvestre, with its leaves having been found to have sweetness inhibitory properties. 33 All chromatographically and spectroscopically pure compounds (purity >95%) isolated from C. racemif lora in the present study were tested in terms of their cytotoxicity against the HT-29 human colon cancer cell line, using paclitaxel as the positive control.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Cytotoxic Barrigenol-like Triterpenoids from an Extract of Cyrilla racemiflora Housed in a Repository

Ren¹,

VanSchoiack²,

Chai³

et al. 2015

J. Nat. Prod.

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Two new [(+)-cyrillins A (1) and B (2)] and four known barrigenol-like triterpenoids (3–6), along with betulinic acid and (+)-3β-O-trans-feruloylbetulinic acid, were isolated from a sample-restricted CH2Cl2-soluble extract of the bark of Cyrilla racemiflora, collected in Dominica. The structures of the new compounds were elucidated by interpretation of their spectroscopic data, and the absolute configuration of the cyclic 1,2-diol unit of (+)-cyrillin A (1) was ascertained by analysis of the electronic circular dichroism (ECD) spectrum induced with [Mo2(OAc)4]. In the case of (+)-cyrillin B (2), which was found to contain a di-angeloylated glucose residue, the structure proposed was supported by analysis of its MS2 and MS3 spectra. All compounds isolated were evaluated for their cytotoxicity against HT-29 human colon cancer cells, and the known compound, (+)-barringtogenol B (3), was found to be the most potent, exhibiting an IC50 value of 1.7 µM. This compound also showed inhibitory activity toward the CCD-112CoN human normal colon cell line, with an IC50 value of 5.9 µM, indicating a lack of cytotoxic selectivity.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Cytotoxic Barrigenol-like Triterpenoids from an Extract of Cyrilla racemiflora Housed in a Repository

Ren¹,

VanSchoiack²,

Chai³

et al. 2015

J. Nat. Prod.

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“…The crude extract of barringtonia asiatica seeds exhibited high biological activity in the brine shrimp hatchability and lethality assay and the fractions of the extract of leaves, stem-bark and roots exhibited a broad spectrum antibacterial and fungal activity [25]. The hexane leaf extract as reported by [26], in their studies on the antibacterial and cytotoxicity test showed the potential of Barringtonia asiatica extract as lead agent in the development of new drugs for pathogens. The seed was reported to have piscidal activity and the oleanane glycoside ranuncoside was elucidated as the principal compound responsible for the activity [27].…”

Section: Pharmacological Potentialsmentioning

confidence: 99%

“…According to their research the toxicity criteria, based on Australian Petroleum Energy Association, the concentration of 35.572ppm of seeds hutun methanol extract or (LC50 = 35.572ppm) at 24 hours of observation is included in the criteria for Toxic Toxicity. Isaac et al [26] in their studies of toxicity reported the toxicity of the plant.…”

Section: Cytotoxicity and Safetymentioning

confidence: 99%

A Review on The Phytochemical and Pharmacological Properties Barringtonia Asiatica

Umaru

2018

DDIPIJ

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Barringtonia asiatica is a species of Barringtonia native to mangrove habitats on the tropical, it is a common plant in the Malaysian Mangroves and wetlands such as the Kuching wetlands Sarawak and Bako National Park, it is also found in tropical Africa, Nigeria and Madagascar. Its large pinkish-white, pompon flowers give off a sickly-sweet smell to attract bats and moths which pollinate the flowers at night. It is grown along streets for decorative and shade purposes among Sarawakian houses in Malaysia and it's also known as Box Fruit due to the distinct box-shaped of the fruit, it is a medium-sized tree growing to 7-25m tall [1]. The leaves are narrow obovate, 20-40cm in length and 10-20cm in width matured foliage colour is green, smooth glossy shiny leathery thick simple and evergreen. It is used as sausage food among the native of sarawakian in the kampong as well as a medicinal plant, inhabitants of several West African countries, Nigeria and the Polynesian Islands use liquid from the crushed bark of Barringtonia asiatica to treat stomach-aches, the top leaves from this tree are squeezed into water and the liquid taken orally. The stem bark of the plant is pinkish grey [2]. The plant when mature the bark texture is smooth and woody. The root type is fibrous and has pronounced tap root.The Fruit, due to its distinct square like diagonals jutting out from the cross section, it gives a semi spherical shape form from stem altering to a sub pyramidal shape at its base. The fruit measures 9-11cm in diameter, where a thick spongy fibrous layer covers up to 4-5cm diameter. The fruit is dispersed in the same way as a coconut by ocean current and is extremely water-resistant and buoyant [3].It can survive afloat for up to fifteen years [1]. When washed ashore and soaked by rainwater then the seeds germinate.All parts of the tree are Poisonous, and the active poisons include saponins. The box fruits are potent enough to be used as a fish poison. This Angiosperm of a flowering seed plant has a perennial life span with an autotrophic mode of nutrition, the seeds have been used when ground to a powder form to stun or kill fish for easy capture, it suffocates the fish living no effect on the flesh [4]. The active components may be found in the root, bark, stem, and leaves of the identified plant [2]. The seeds of Barringtonia asiatica are used in the Pacific Islands by scraping the seeds on lavarocks by shallow tidal pools and washing the scrapings into the water. This method and the methods described above result in dead or stunned fish rising to the surface in a short time where they are

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