Tirucallane triterpenes from the leaf extract of Entandrophragma angolense

Orisadipe, A.; Adesomoju, Akinbobola; D’Ambrosio, Michele; Guerriero, Antonio; Okogun, Joseph I.

doi:10.1016/j.phytochem.2005.07.017

Cited by 19 publications

(14 citation statements)

References 13 publications

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“…Aphanamgrandin H and I (60 and 61) are methyl ester and ∆ 24,25 analogs of Aphanamgrandin G (59) respectively. Aphanamgrandin J (62) is C21 methyl analog of 3,4secotirucalla-23-oxo-4(28), 7,24-trien-21-al-3-oic acid reported previously 81 . Compounds (63,64) contain A ring with ether linkage and compounds (65,66) contain both ether linkage and lactone moiety in A ring.…”

Section: Ring A-seco Protolimonoidmentioning

confidence: 88%

Chemistry and Biology of Novel Meliaceae Limonoids

Mulani

Nandikol

Thulasiram

2022

Preprint

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Nature has bestowed us with abundant bioactive/drug molecules for various uses in our everyday life. One such group of plant specialized molecules is limonoids, which are structurally characterized as 4,4,8-trimethyl-17-furanyl steroidal skeleton. Limonoids are well known for their various biological activities such as potent anti-feedent, anti-cancer, anti-inflammatory, insecticidal, anti-diabetic, anti-viral, anti-microbial etc. These tetranortriterpenes are highly oxygenated and structurally diversified molecules majorly found in Meliaceae and Rutaceae and less frequently in the Cneoraceae families in the plant kingdom. Many of these plants have been used in traditional medicine from ages. One of the well-known limonoid, azadirachtin A is highly valued and widely popular for its outstanding insecticidal properties. Till date, nearly 2500 limonoids with over 35 unique carbon frameworks have been observed. In recent times, these molecules have dig a great interest among researchers due to their myriad biological properties. With the advancement of analytical techniques, the limonoid research is aced to explore more different molecules from their sources. In our review we cover all the Meliaceous limonoids isolated during July 2010 to Dec 2020. We found over 1502 new limonoids, which are reported from various Meliaceae plants after Jun 2010. We have classified them based on their skeletal structure rearrangements and functional groups into various classes such as protolimonoids, Apoprotolionoid, Azadirone, Vilasinin, Cedrelone, Havanensin, Trichilin, Nimbin, Salannin, Azadirachtin, Nimbolidin, Nimbolinin, Obacunol, Evodulone, Trijugin, Cipadesin, Andirobin, Mexicanolide, Phragmalin, Khayanolide, Preieurianin, Aphanamixoid, Nor Limonoid and N-containing derivatives. Further we have discussed their biological activities in detail.

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Section: Ring A-seco Protolimonoidmentioning

confidence: 88%

Chemistry and Biology of Novel Meliaceae Limonoids

Mulani

Nandikol

Thulasiram

2022

Preprint

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“…170 Eight new tirucallanes 249-256 have been found in the roots of Ozoroa insignis. 171 Other new tirucallanes include 257 from Boswellia serrata 172 (reported as a euphane derivative), 258-260 from Entandrophragma angolense 173 and 261 from Amoora dasyclada. 174 The unusual 3-deoxyeuphane structure 262 has been proposed for a constituent of Boswellia serrata.…”

Section: The Dammarane Groupmentioning

confidence: 99%

Triterpenoids

Connolly

Hill

2008

Nat. Prod. Rep.

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This review covers the isolation and structure determination of triterpenoids including squalene derivatives, protostanes, lanostanes, holostanes, cycloartanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, quassinoids, lupanes, oleananes, friedelanes, ursanes, hopanes, isomalabaricanes and saponins. The literature from January 2005 to December 2006 is reviewed and 478 references are cited.

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“…The tirucallane-type triterpenoids isolated from Entandrophragma displayed some changes in their structure ranging from intact or seco-ring A, as well as having a side chain which can be linear or cyclic (containing a 5-, 6-, or 7-membered ring) with different levels of oxidation. 3,4-Secotirucalla-21-formyl-23-oxo-4(28),7,24-trien-3-oic acid (94) was firstly isolated from the leave extract of E. angolense [45] and was recently reported in 2018 from the root extract of E. congo€ ense [31] can be formed through Bayer-Villiger oxidation followed by hydrolysis of congoensin B (97) obtained as a minor compound from the bark extract of E. congo€ ense. [44] In the same manner, formation of seco-tiaminic acid A (95) obtained from the previously mentioned bark extract can be comprehensively correlated to piscidinol A (98) also isolated from the root extract of the same plant E. congo€ ense.…”

Section: Protolimonoidsmentioning

confidence: 99%

“…Sapelin F E. cylindricum [127] 86 Melianone R = O E. caudatum [128] 87 3a-turreanthin R = OAc E. caudatum [128] 88 Epoxytriol E. utile [126] 89 3,23-dioxoturucalla-7,24dien-21-al [45] 90…”

Section: Toxicity Of Entandrophragmamentioning

confidence: 99%