Studies in the Chemical Constituents of<i>Azadirachta indica</i>Part II: Isolation and Structure of the New Triterpenoid Azadirachtol

Siddiqui, Salimuzzaman; Siddiqui, Bina Shaheen; Faizi, Shaheen

doi:10.1055/s-2007-969567

Cited by 19 publications

(11 citation statements)

References 9 publications

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“…It may be noted that epoxyazadiradione (36) appears to be identical with nimbinin [2] isolated in 1942 ( 7) and the structure established in 1967-68 (41,42), although their specific rotations differ widely. oxygenated derivatives of azadirone such as meldenin [19] (42), vepinin [20] (43), isomeldenin [21] (44), meldenin diol [22] (44), nimocinol [23] (45), and 4a,6a-dihydroxy-A-homoazadirone [24] (46) have also been reported from different parts of the tree. The latter is worth mentioning as it has a seven-membered ring A with a new bond between C-3 and C-28.…”

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confidence: 99%

Tetracyclic Triterpenoids and Their Derivatives from Azadirachta indica

Siddiqui¹,

Siddiqui²,

Faizi³

et al. 1988

J. Nat. Prod.

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Studies on the chemical constituents of Azadirachta indica (neem) are reviewed. The isolation, unique features of the structures, biosynthetic aspects, and biological activities of these constituents are discussed.Azadirachta indica Juss. (syn. Melia azadirachta L., Melia indica, Margosa), known in the vernacular as "neem" and "nimba," belongs to the family Meliaceae and is widely distributed in Asia, Africa, and other tropical parts of the world (1-5). Almost every part of the tree has long been used in folkloric and traditional systems of medicine for the treatment of a variety of human ailments, particularly against diseases of bacterial and fungal origin (l^í). The chemical and therapeutic studies undertaken since about the beginning of this century were initially concerned with the fatty acid components and amorphous bitter substances of the oil (6). It was in 1942 that the first two crystalline constituents, nimbin [1] and nimbinin [2], were isolated from the oil along with an amorphous bitter principle, nimbidin, through solvent partitioning of the oil avoiding its prior saponification (7). Nimbidin is antiarthritic and anti-inflammatory (8) in

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confidence: 99%

Tetracyclic Triterpenoids and Their Derivatives from Azadirachta indica

Siddiqui¹,

Siddiqui²,

Faizi³

et al. 1988

J. Nat. Prod.

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“…As such, 1 represents the first side chain in the biosynthesis of apotirucallane apoeuphane triterpenoids from tirucallanes (euphanes), since prior to this the isolation of such an apotirucallane apoeuphane derivative has not been reported. Subsequently, cyclization of the side chain might lead to C30 apo derivatives like grandifoliolenone (22) and azadirachtol (23), whereas degradation of the side chain would give tetra; penta; or hexa-nor tetracyclic triterpenoids…”

Section: Resultsmentioning

confidence: 99%

Tetracyclic Triterpenoids of the Fruit Coats of Azadirachta indica

Siddiqui¹,

Siddiqui²,

Ghiasuddin³

et al. 1991

J. Nat. Prod.

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“…12' 3~,23S,25-Trihydroxytirucall-7-en-24-one (133) occurs in Simaba multlJIora with the known hispidol B (1 34) whose side-chain stereochemistry has now been confirmed by X-ray analysis.lZ8 The C-23 configurations of these compounds were wrongly assigned in the publication. Other tirucallanes include 2 1,23-epoxytirucalla-7,24-dien-3-0ne (135) and the related acetate (136) from Cornus ~apitata,~~~ nimbocinone (1 37)130 and nimbolinone (1 38)131 from Azadiruchta indicu, and lipomelianol, a crystalline mixture of the 3-0-stearate, myristate, palmitate, and laurate of melianol from the fruits of MeIia t o o ~e n d a n . ~~~ Details of the crystal structure analysis of methyl masticadienonate (methyl 3-oxotirucalla-7,24-dien-26-oate) have been published.…”

Section: R5mentioning

confidence: 99%