Terpenoids. I. The Triterpenes of the Cactus Lemaireocereus Thurberi

Djerassi, Carl; Geller, Leo; Lemin, A. J.

doi:10.1021/ja01105a507

Cited by 31 publications

(6 citation statements)

References 5 publications

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“…Although many investigators have contributed to our knowledge of the chemistry of columnar cacti, two individuals stand out: Carl Djerassi and Henry Kircher. Djerassi's work in the 1950s and 60s includes some of the original chemical descriptions of cactus alkaloids and triterpenes (Djerassi and Lippman, 1955;Djerassi et al, 1953aDjerassi et al, , b, 1954aDjerassi et al, , b, 1955Djerassi et al, , 1957Djerassi et al, , 1958Djerassi et al, , 1962. Kircher was a collaborator of Bill Heed and was specifically involved in the chemistry of the cactus-microorganism-Drosophila model system from its inception in the early 1960s (Kircher, 1977(Kircher, , 1980(Kircher, , 1982Kircher and Bird, 1982).…”

Section: Allelochemistry Of Columnar Cactimentioning

confidence: 99%

Chemical Interactions in the Cactus-Microorganism-Drosophila Model System of the Sonoran Desert1

Fogleman

Danielson

2001

American Zoologist

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SYNOPSIS. The Cactus-Microorganism-Drosophila Model System of the Sonoran Desert represents an excellent paradigm of the role of chemistry in plant-animal interactions. In this system, four species of endemic Drosophila feed and reproduce in necrotic tissue of five species of columnar cacti. Studies over the past 35 yr have characterized a myriad of interactions between the three major components of the model system. The cacti contain a variety of allelochemicals which are primarily responsible for the highly specific pattern of host plant utilization exhibited by the desert Drosophila. Plant chemistry, through its effect on the microbially produced volatile patterns, is further involved in host specificity because the flies use the volatile pattern to cue in on necroses in the appropriate species of cactus. The metabolic activities of microorganisms (bacteria and yeasts) living in the necrosis can affect the substrate chemistry in both positive and negative ways (i.e., acting to increase or to decrease the toxicity of the substrate). Finally, cactus chemistry may affect drosophilid mating behavior since larval rearing substrate has been shown to influence adult hydrocarbon epicuticular composition. In D. mojavensis, adult hydrocarbon profile has been implicated as a determinant of mate choice leading to premating isolation between geographically isolated populations that use chemically different cactus substrates. Current research is focused on the evolution and regulation of genes whose products (cytochrome P450 enzymes) are involved in the specific insect-host plant relationships which exist between the Drosophila species and the cactus species.There are many reasons why investigators choose to focus their research efforts on what are referred to as ''model systems.'' Typically included among these would be the idea that model systems are easier to study because they are less complex than other scientific situations. At the same time, model systems should be representative of more complex, natural systems so that information that is obtained from their study is broadly applicable. For almost a century, the fruit fly, Drosophila melanogaster, has served as a model organism for the study of genetics. As a genetic paradigm, Drosophila is more tractable to scientific investigation than most organisms and has provided important insights into a wide variety of human maladies from alcohol abuse to neurological brain disorders (Bellen, 1998). Similarly, the interrelationships of the columnar cacti and the cactophilic Drosophila species of the Sonoran Desert have, for the past 35 yr, provided an excellent model system with which to study relevant questions in evolution, ecological genetics, and chemical ecology. The intent of this article is to briefly review and characterize the chemical interactions between the plants (cacti) and animals (Drosophila) of this model system, and, in addition, provide some thoughts on possible future directions for integrative approaches in this research area.

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Section: Allelochemistry Of Columnar Cactimentioning

confidence: 99%

Chemical Interactions in the Cactus-Microorganism-Drosophila Model System of the Sonoran Desert1

Fogleman

Danielson

2001

American Zoologist

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“…int. )[M]+ 452(29), [M-Me}+ 437 (5), 409 (5), 367 (9), 354 (4), 233 (11), 219 (11), 205 (37), 187 (12), 41 (100); hreims m/z [M]+ 452.329444 (C30H44O3 requires 452.329045); 1'C nmr see Table 1.…”

Section: Ochraceolidementioning

confidence: 99%

“…Indeed, the mass spectrum of 1 was quite similar to that of thurberogenone [4] (9), a derivative of thurberogenin, previously isolated from the organ pipe cactus (Stenocereus thurberi Buxb.) (10)(11)(12). However, other spectral evidence clearly showed that 1 was not identical to thurberogenone [4],…”

mentioning

confidence: 97%

New Cytotoxic Lupane Lactones from Kokoona ochracea

Ngassapa¹,

Soejarto²,

Che³

et al. 1991

J. Nat. Prod.

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Three new compounds, ochraceolides A, B, and C, were isolated from nonpolar extracts derived from Kokoona ochracea stem bark. Based on spectroscopic data, their structures were determined to be the closely related lupane lactones: 3-oxolup-20(29)-en-30,21 alpha-olide, 20,29-epoxy-3-oxolupan-30,21 alpha-olide, and 3,6-dioxolup-20(29)-en-30,21 alpha-olide. Compounds 1 and 3 exhibited significant cytotoxic activity with cultured P-388 cells (ED50 values of 0.26 and 0.53 microgram/ml, respectively) but were at least tenfold less active with a variety of human tumor cell lines. Compound 2 was weakly active with cultured P-388 and KB-3 cells (ED50 values of 7.8 and 5.2 micrograms/ml, respectively), but no significant activity was observed with other human cancer cell types (ED50 values of more than 20 micrograms/ml).

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“…The first report of a steroidal 3,5-dieno [3,[4][5][6]dithiane appeared in a 1960 publication of Fieser, Yuan, and Goto,1 2in which the structures of a variety of anomalous products from the reactions of cholestenolone acetates with ethanedithiol were deduced mainly through application of the then new nmr techniques. One of these products, formed in approximately 50% yield by reaction of equivalent amounts of 6/3-acetoxy-4-choIesten-3-one and ethanedithiol in the presence of boron trifluoride etherate, was shown to be cholesta-3,5-dieno [3,[4][5]dithiane (la). The only other reports of such dithianes are two papers and a patent of Tomoeda, et al,1 in which it is disclosed that steroidal 4d,5-epoxy-3-ones react with ethanedithiol and polyphosphoric acid in dioxane, yielding 40-50% of the dithianes (Ia-c).…”

mentioning

confidence: 99%

“…When 6/3-chloro-4-en-3-ones were subjected to the thioketalization conditions (at 25°), no 6-chloro-3ethylenethioketals were formed. The only isolable crystalline products were 40-70% of the 3,5-dieno- [3,[4][5][6]dithianes. A general preparative method for the latter consisted in stirring the 6/3-chloro ketone with ethanedithiol and pyridine hydrochloride in methanol for approximately 1 hr.…”

mentioning

confidence: 99%

Synthesis of steroidal 3,5-dieno[3,4-b]dithianes

Karmas¹

1967

J. Org. Chem.

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Terpenoids. I. The Triterpenes of the Cactus Lemaireocereus Thurberi

Cited by 31 publications

References 5 publications

Chemical Interactions in the Cactus-Microorganism-Drosophila Model System of the Sonoran Desert1

Chemical Interactions in the Cactus-Microorganism-Drosophila Model System of the Sonoran Desert1

New Cytotoxic Lupane Lactones from Kokoona ochracea

Synthesis of steroidal 3,5-dieno[3,4-b]dithianes

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