Tumor inhibitors. XLVI. Vernolepin, a novel sesquiterpene dilactone tumor inhibitor from Vernonia hymenolepis

Sm, Kupchan; Rj, Hemingway; Werner, Dieter; Karim, Aziz

doi:10.1021/jo01264a034

Cited by 98 publications

(37 citation statements)

References 3 publications

(4 reference statements)

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“…However, it may still be possible that the activity of 1 can be increased if the acyl moiety is changed to a more hydrophobic group (methacryloyl group) as in the case of 2. 4,15-Dihydrovernodalin (7) and 1,2,2' ,3'-tetrahydrovernodalin (8) showed no significant change in activity compared to that of 1. However, when the .1 11 ,13 double bond of8 was saturated (compound 9), the activity was much less.…”

Section: 3)mentioning

confidence: 90%

Antitumoral and Antimicrobial Activities of Bitter Sesquiterpene Lactones ofVernonia amygdalina, a Possible Medicinal Plant Used by Wild Chimpanzees

Jisaka

Ohigashi²,

Takegawa³

et al. 1993

Bioscience, Biotechnology, and Biochemistry

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Section: 3)mentioning

confidence: 90%

Antitumoral and Antimicrobial Activities of Bitter Sesquiterpene Lactones ofVernonia amygdalina, a Possible Medicinal Plant Used by Wild Chimpanzees

Jisaka

Ohigashi²,

Takegawa³

et al. 1993

Bioscience, Biotechnology, and Biochemistry

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“…Fortunately, it is known that conjugation of one of the double bonds with π-substituents makes [3,3]sigmatropic rearrangements easier. 17 Bearing this idea in mind, we began the synthesis of 1 (Scheme 2) assaying the selective oxidation of the primary alcohol of 5 with different reagents.…”

Section: Resultsmentioning

confidence: 99%

Approaches to the synthesis of 8-epi-vernolepin from germacrolides

Barrero

Oltra²,

Barragán³

et al. 1998

J. Chem. Soc., Perkin Trans. 1

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As part of our program aimed at the synthesis of bioactive products, the enantiospecific synthesis of 8-epi-vernolepin derivatives, starting from accessible germacrolides, was attempted. Synthesis of (ϩ)-8-O-acetyl-1,2,11β,13-tetrahydro-8-epi-vernolepin (23) from (ϩ)-salonitenolide (6) was performed in nine steps with an acceptable overall yield. On the other hand, the synthesis from (ϩ)-stenophyllolide (5) presented several intrinsic difficulties and was discarded. (ϩ)-Salonitenolide provides one of the most useful raw materials for the synthesis of (ϩ)-vernolepin related compounds preserving its functionalization at C-8.

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“…Thus cyclization of dihydrocostunolide 28 affords a mixture of olefins 29'" and Lewis acid-catalyzed cyclization of the corresponding synthetically derived 1(IO)-trans-epoxide (30), several analogs of which occur naturally, yields 31. ':" The stereochemistry of all naturally-occurring eudesmanolides is in accord with this hypothesis and numerous laboratory analogies for both processes exist.…”

Section: Germacranolides and Eudesmanolldesmentioning

confidence: 99%