Triterpenoids

CONNOLLY, J. D.; Hill, R. A.; Ngadjui, B. T.

doi:10.1039/np9941100467

Cited by 14 publications

(7 citation statements)

References 100 publications

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“…As myricerone 3 was an apparent intermediate to 1 , we next focused on the synthesis of 3 from a readily available compound. Oleanolic acid ( 4 ) has a very close structure to 3 , and all that is required to convert 4 to 3 is oxidation of the 3-hydroxy to the 3-oxo group and hydroxylation of the methyl group at the 27-position. Barton and co-workers reported a synthesis of cincholic acid (3β-hydroxyolean-12-ene-27,28-dioic acid) three decades ago, which started from oleanolic acid ( 4 ) and introduced a hydroxy group at the 27-position by a photochemical reaction known as the Barton reaction …”

Section: Resultsmentioning

confidence: 99%

Practical Partial Synthesis of Myriceric Acid A, an Endothelin Receptor Antagonist, from Oleanolic Acid

et al. 1997

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Myriceric acid A (1) is an oleanane triterpene that is a potent and specific endothelin A receptor antagonist. A practical procedure for large-scale synthesis of myriceric acid A (1) has been developed starting from oleanolic acid 4. The conversion of oleanolic acid 4 to the key intermediate myricerone 3 was achieved in an efficient manner employing a photochemical reaction (the Barton reaction) of nitrite 7. Our synthetic procedure alleviated several difficulties of the original Barton's procedure with regard to yields and large-scale operation. Myricerone 3 afforded Horner−Wadsworth−Emmons (HWE) type phosphonate 2 which has proved to be a versatile precursor of 1. The preparation of phosphonate 2 on a scale of several hundred grams is described. The synthesis was completed by condensation of 2 with 3,4-bis[(diphenylmethyl)oxy]benzaldehyde (21), giving α,β-unsaturated ester 22, which was deprotected to afford 1. The whole synthetic sequence is efficient (14 steps, 31% yield) and requires no chromatographic purification except to obtain the final product 1.

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Section: Resultsmentioning

confidence: 99%

Practical Partial Synthesis of Myriceric Acid A, an Endothelin Receptor Antagonist, from Oleanolic Acid

et al. 1997

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“…Since 1985, Connolly and Hill have regularly reviewed the scientific literature dealing with triterpenoid characterization from natural resources. [239][240][241][242][243][244][245][246][247][248][249][250][251][252][253][254][255][256] Although numerous triterpenoids possessing various scaffolds have been reported, only a small portion of them were explored systematically for their pharmacological activities. Of those so explored, most showed only marginal potency in preliminary screening.…”

Section: Discussionmentioning

confidence: 99%

Plant-derived triterpenoids and analogues as antitumor and anti-HIV agents

et al. 2009

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“…Of these, cycloartenol, eburicane, and several 3,4- seco -lanostane derivatives have all been identified as active compounds . Other interesting groups of tetracyclic triterpenoids and their degraded derivatives include the cucurbitacins (cucurbitanes), dammaranes, limonoids, and quassinoids. ,− Several lanostane derivatives have been identified as anti-inflammatory, antiviral, or anticancer agents; their effects on cell death, either through necrosis or apoptosis, have been partly implicated in their mechanism of action. ,, …”

Section: Introductionmentioning

confidence: 99%

Lanostanoids from Fungi: A Group of Potential Anticancer Compounds

et al. 2012

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Lanostanes are a group of tetracyclic triterpenoids derived from lanosterol. They have relevant biological and pharmacological properties, such as their cytotoxic effects via induction of apoptosis. This review compiles the most relevant lanostanoids studied from 2000 to 2011, principally those isolated from Ganoderma lucidum and other related fungi, such as Poria cocos, Laetiporus sulphureus, Inonotus obliquus, Antrodia camphorata, Daedalea dickinsii, and Elfvingia applanata, which have great potential as anticancer agents because of their cytotoxic or apoptotic effects. The compounds were selected on the basis of their proapoptotic mechanisms, through their ability to modify transcriptional activities via nuclear factors or genes and the activation or inhibition of pro- or antiapoptotic proteins; studies based only on their cytotoxicity were excluded from this review in the absence of complementary studies on their mechanisms of action. A total of 81 compounds from Ganoderma lucidum and other species from this genus are included, as well as 96 compounds isolated from other fungi, principally Poria cocos. Some of these compounds were found to arrest the cell cycle in the G1 phase, increase levels of p53 and Bax, or inhibit the phosphorylation of Erk1/2 or the activation of NF-κB and AP-1. Other lanostanes have inhibitory effects on the growth of androgen prostate carcinoma through increasing the expression of p21, which activates the tumor suppressor protein p53, while other compounds have been shown to selectively inhibit topo II activity without affecting topo I. General considerations concerning the chemical structure-biological activities of these compounds are also discussed.

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Triterpenoids

Cited by 14 publications

References 100 publications

Practical Partial Synthesis of Myriceric Acid A, an Endothelin Receptor Antagonist, from Oleanolic Acid

Practical Partial Synthesis of Myriceric Acid A, an Endothelin Receptor Antagonist, from Oleanolic Acid

Plant-derived triterpenoids and analogues as antitumor and anti-HIV agents

Lanostanoids from Fungi: A Group of Potential Anticancer Compounds

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