The structure of 19αH-Lupeol methyl ether from Chionochloa bromoides

Pauptit, RA; Waters, JM; Rowan, DD; Russell, G. B.; Connor, HE; Purdie, AW

doi:10.1071/ch9841341

Cited by 13 publications

(5 citation statements)

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“…2). In addition, none of the following compounds have been detected in our samples: hop-22(29)-en-3β-ol ME (Rowan and Russell, 1992;Paupit et al, 1984), friedelenol ME (Oros and Simoneit, 2001) and serratenol ME (Rowe and Bower, 1965). Table 2 that none of the species cited in the literature affords a range of PTMEs as wide as that encountered in our samples.…”

Section: Biological Sources Of Ptmesmentioning

confidence: 87%

Pentacyclic triterpene methyl ethers in recent lacustrine sediments (Lagoa do Caçó, Brazil)

Jacob

Disnar

Boussafir

et al. 2005

Organic Geochemistry

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The lipid extracts of sediments collected from the Quaternary filling of a tropical lacustrine series (Lagoa do Caçó, Brazil) were investigated by gas chromatography-mass spectrometry (GC-MS). Various pentacyclic triterpene 3-methyl ethers (PTMEs) were present in the neutral fraction. Comparison of retention times and mass spectra with available standards allowed us to certify the presence of olean-12-en-3β-ol ME (β-amyrin ME), olean-18-en-3β-ol ME (miliacin), taraxer-14-en-3β-ol ME (crusgallin), fern-9(11)-en-3β-ol ME (arundoin) and arbor-9(11)-en-3β-ol ME (cylindrin). The following other compounds coud also be tentatively identified from their GC-MS characteristics: urs-12-en-3β-ol ME, bauer-7-en-3β-ol ME and fern-8-en-3β-ol ME. Other compounds such as possible 3α isomers of the PTMEs as well as di-or tri-unsaturated counterparts might be PTME diagenetic derivatives. According to previous chemotaxonomic studies, all these compounds most probably originate from Gramineae that used to colonize the savannas of Northern Brazil at the time of deposition.

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Section: Biological Sources Of Ptmesmentioning

confidence: 87%

Pentacyclic triterpene methyl ethers in recent lacustrine sediments (Lagoa do Caçó, Brazil)

Jacob

Disnar

Boussafir

et al. 2005

Organic Geochemistry

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“…All reactions as well as column chromatography were monitored routinely with the aid of thin layer chromatography with precoated silica gel 60 F256 from Merck. The 3D structures were built using the X-ray structure of 19R-lupeol methyl ether 23 as registered in the Cambridge Structural database. After modifications of the structure to fit with the different derivatives, energy minimization using Chem-X (Chemical Design Ltd., Oxford) and/or Insight (Biosym Technologies Inc., San Diego) was performed.…”

Section: Methodsmentioning

confidence: 99%

“…Methyl 3β-[(Dimethyl-tert-butylsilyl)oxy]lup-20(29)-en-28-oate (23). To a solution of methyl betulinate (1c) (6.5 g, 13.8 mmol) in DMF (165 mL) were added imidazole (2.82 g, 41.4 mmol) and tert-butyldimethylsilyl chloride (4.25 g, 27.6 mmol).…”

Section: N-[3β-hydroxy-28-norlup-20(29)-en-28-oyl]-11-aminoundecanoic...mentioning

confidence: 99%

Betulinic Acid Derivatives: A New Class of Human Immunodeficiency Virus Type 1 Specific Inhibitors with a New Mode of Action

et al. 1996

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A series of omega-undecanoic amides of lup-20(29)-en-28-oic acid derivatives were synthesized and evaluated for activity in CEM 4 and MT-4 cell cultures against human immunodeficiency virus type 1 (HIV-1) strain IIIB/LAI. The potent HIV inhibitors which emerged, compounds 5a, 16a, and 17b, were all derivatives of betulinic acid (3beta-hydroxylup-20(29)-en-28-oic acid). No activity was found against HIV-2 strain ROD. Compound 5a showed no inhibition of HIV-1 reverse transcriptase activity with poly(C).oligo(dG) as template/primer, nor did it inhibit HIV-1 protease. Additional mechanistic studies revealed that this class of compounds interfere with HIV-1 entry in the cells at a postbinding step.

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“…(1967, Martin-Smith etal. (1967,1971, and for Chionochloa in Russell et al (1976), Pauptit et al (1984), and Rowan & Russell (1992).…”

Section: Triterpene Methyl Ethers In Chionochloaand Cortaderia Leaf Waxmentioning

confidence: 99%

Flora of New Zealand ‐ Gramineae supplement I: Danthonioideae

Connor

2004

New Zealand Journal of Botany

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The newly erected grass subfamily Danthonioideae encompasses four New Zealand genera viz Chionochloa, Cortaderia, Pyrrhanthera, and Rytidosperma; 43 endemic species comprise it. In Rytidosperma new chromosome counts confirm earlier reports of diploid and hexaploid species and report tetraploids (2n = 48) as an additional level of ploidy. In Pyrrhanthera 2n = c. 156, which is the highest chromosome number in the subfamily and second highest recorded in the Gramineae. New Zealand species of Cortaderia should not be included in the same clade as South American species according to cladistic analyses of rpoC2 and ITS sequences. Morphologically this separation fails. Monophyletic Chionochloa is generically secure. Earlier data on the triterpene methyl ethers (TMEs) isolated from the epicuticular leaf wax of species of Chionochloa and Cortaderia are interpreted along modern pathways of the biosynthesis of the precursor sterols and triterpenols, and their subsequent methylation. In Chionochloa where 18 taxa in 33 synthesise TMEs mostly as single compounds, dedicated synthases for each of several triterpenoids is indicated. Nonrandomness of TME synthesis is characteristic, but there is no total accord between taxonomic treatment and TME synthesis. Zones of TME-richness lie in the Tararua and Rimutaka Ranges, southern North Island (6 TMEs), and Canterbury, South Island (5 TMEs).

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The structure of 19αH-Lupeol methyl ether from Chionochloa bromoides

Cited by 13 publications

References 0 publications

Pentacyclic triterpene methyl ethers in recent lacustrine sediments (Lagoa do Caçó, Brazil)

Pentacyclic triterpene methyl ethers in recent lacustrine sediments (Lagoa do Caçó, Brazil)

Betulinic Acid Derivatives: A New Class of Human Immunodeficiency Virus Type 1 Specific Inhibitors with a New Mode of Action

Flora of New Zealand ‐ Gramineae supplement I: Danthonioideae

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