Unusual ent-isopimarane-type diterpenoids from the wood of Excoecaria agallocha

Ponnapalli, Mangala Gowri; Ankireddy, Madhu; Annam, Suresh; Ravirala, Saidulu; Sukki, Sushma; Tuniki, Venugopal Raju

doi:10.1016/j.tetlet.2013.03.105

Cited by 17 publications

(9 citation statements)

References 14 publications

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“…The poisonous milky latex, exuded from the bark of this plant, can cause blistering of the skin and temporary blindness [12,13,14,15,16]. Previous chemical investigation of this plant resulted in the isolation and identification of diterpenoid, triterpenoid, tanninoid, and flavonoid natural compounds [10,17,18,19,20,21]. To date, only 18 triterpenoid compounds, including types of cycloartane, friedelane, lupane, oleanane, and taraxerane, have been reported from this plant [17].…”

Section: Introductionmentioning

confidence: 99%

Mangrove Tirucallane- and Apotirucallane-Type Triterpenoids: Structure Diversity of the C-17 Side-Chain and Natural Agonists of Human Farnesoid/Pregnane–X–Receptor

et al. 2018

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Ten new triterpenoid compounds with structure diversity of the C-17 side-chain, including nine tirucallanes, named xylocarpols A–E (1–5) and agallochols A–D (6–9), and an apotirucallane, named 25-dehydroxy protoxylogranatin B (10), were isolated from the mangrove plants Xylocarpus granatum, Xylocarpus moluccensis, and Excoecaria agallocha. The structures of these compounds were established by HR-ESIMS and extensive one-dimensional (1D) and two-dimensional (2D) NMR investigations. The absolute configurations of 1 and 2 were unequivocally determined by single-crystal X-ray diffraction analyses, conducted with Cu Kα radiation; whereas those of 4, 6–8 were assigned by a modified Mosher’s method and the comparison of experimental electronic circular dichroism (ECD) spectra. Most notably, 5, 6, 7, and 9 displayed potent activation effects on farnesoid–X–receptor (FXR) at the concentration of 10.0 μM; 10 exhibited very significant agonistic effects on pregnane–X–receptor (PXR) at the concentration of 10.0 nM.

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Section: Introductionmentioning

confidence: 99%

Mangrove Tirucallane- and Apotirucallane-Type Triterpenoids: Structure Diversity of the C-17 Side-Chain and Natural Agonists of Human Farnesoid/Pregnane–X–Receptor

et al. 2018

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“…Compounds 77 and 78 represent a kind of ent-isopimaranetype diterpenoids with unusual seven membered lactone moiety. [31] Besides, the marine-derived ent-isopimarane diterpenes of compounds 71 -80 were collected in Table 1.…”

Section: Ent-isopimaranesmentioning

confidence: 99%

Bioactive Pimarane‐Type Diterpenes from Marine Organisms

Wang

Zhang

et al. 2017

Chemistry & Biodiversity

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Marine organisms represent an abundant sources of bioactive natural products with unique chemical structure. Pimarane diterpenes are a structurally diverse family of natural products with various biological activities and pharmacological properties. A prolific source of new marine-derived pimarane diterpenes have attracted considerable interest because of their unique structural diversity and varied biological activities, including antimicrobial, antitumor, and antiproliferative activities. This review provides a comprehensive overview of the structures, names, bioactivities, and references of 80 marine-derived pimarane-type natural products for the first time.

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“…More than 72 cytotoxic diterpenoids have been identified from E . agallocha , structurally belonging to labdane (Konishi et al, 1999 , 2003 ; Anjaneyulu and Rao, 2000 ; Annam et al, 2015 ), isopimarane/ ent -isopimarane (Anjaneyulu et al, 2003 ; Wang and Guo, 2004 ; Kang et al, 2005 ; Wang et al, 2005 ; Gowri Ponnapalli et al, 2013 ), atisane/ ent -atisane (Konishi et al, 2000 ; Wang et al, 2009 ), ent -kaurane (Anjaneyulu et al, 2002 ; Li et al, 2010 ), and beyerane-type (Anjaneyulu et al, 2002 ).…”

Section: Introductionmentioning

confidence: 99%

Polyketides From the Endophytic Fungus Cladosporium sp. Isolated From the Mangrove Plant Excoecaria agallocha

et al. 2018

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Five new polyketides (2–6) and ten known compounds (1 and 7–15) were obtained from the fermentation products of the endophytic fungus Cladosporium sp. OUCMDZ-302 with the mangrove plant, Excoecaria agallocha (Euphorbiaceae). The new structures of 2–6 were established on the basis of ECD, specific rotation and spectroscopic data as well as the chemical calculation. Compound 7 showed cytotoxicity against H1975 cell line with an IC50 value of 10.0 μM. Compounds 4 and 8–10 showed radical scavenging activity against DPPH with the IC50 values of 2.65, 0.24, 5.66, and 6.67 μM, respectively. In addition, the absolute configuration of compound 1 was solidly determined by X-ray and sugar analysis of the acidic hydrolysates for the first time as well as those of compounds 8–10 in this paper.

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Unusual ent-isopimarane-type diterpenoids from the wood of Excoecaria agallocha

Cited by 17 publications

References 14 publications

Mangrove Tirucallane- and Apotirucallane-Type Triterpenoids: Structure Diversity of the C-17 Side-Chain and Natural Agonists of Human Farnesoid/Pregnane–X–Receptor

Mangrove Tirucallane- and Apotirucallane-Type Triterpenoids: Structure Diversity of the C-17 Side-Chain and Natural Agonists of Human Farnesoid/Pregnane–X–Receptor

Bioactive Pimarane‐Type Diterpenes from Marine Organisms

Polyketides From the Endophytic Fungus Cladosporium sp. Isolated From the Mangrove Plant Excoecaria agallocha

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