Plant growth activity of guaianolides with C-4 oxygen-containing groups

Kalsi, P. S.; Gupta, D. N.; Dhillon, R. S.; Arora, G. L.; Talwar, K. K.; Wadia, M. S.

doi:10.1016/s0031-9422(00)98526-1

Cited by 11 publications

(3 citation statements)

References 4 publications

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“…Root-promoting action of dehydrocostuslactone (1) was enhanced tremendously with the formation of an epoxy group at C(4) as in compound I [64], and a similar case was reported previously by Kalsi et al [210]. Compound J with an epoxy ring at C(13), as expected [211], was also much more potent than the parent a-methylidene-g-lactone [67].…”

Section: Otherssupporting

confidence: 82%

“…A similar effect of the epoxy group was not observed in the case of eudesmanolides [211]. Moreover, the presence of a OH group at C(4) or C(10), and an oxirane at C(10) had no such effect [210].…”

Section: Othersmentioning

confidence: 53%

“…It has been further established that, only in the case of guaianolides, the presence of a C(4)-epoxy or a C(4)ÀOÀC(10) ether group further enhance the biological activity [210] compared with the parent lactone. A similar effect of the epoxy group was not observed in the case of eudesmanolides [211].…”

Section: Othersmentioning

confidence: 99%

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Secondary Metabolites of Plants from the Genus Saussurea: Chemistry and Biological Activity

Wang

Dong

et al. 2010

Chemistry & Biodiversity

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The Asteraceae family comprises ca. 1000 genera, mainly distributed in Asia and Europe. Saussurea DC., as the largest subgenus of this family, comprises ca. 400 species worldwide, of which ca. 300 species occur in China. Most plants in China grow wild in the alpine zone of the Qingzang Plateau and adjacent regions at elevations of 4000 m. Plants of the genus Saussurea (Asteraceae) are used in both traditional Chinese folk medicine and Tibet folklore medicine, since they are efficacious in relieving internal heat or fever, harmonizing menstruation, invigorating blood circulation, stopping bleeding, alleviating pain, increasing energy, and curing rheumatic arthritis. A large number of biologically active compounds have been isolated from this genus. This review shows the chemotaxonomy of these compounds (215 compounds) such as sesquiterpenoids (101 compounds), flavonoids (19 compounds), phytosterols (15 compounds), triterpenoids (25 compounds), lignans (32 compounds), phenolics (23 compounds), and chlorophylls (11 compounds). Biological activities (anti-inflammatory, anticancer, antitumor, hepatoprotective, anti-ulcer, cholagogic, immunosuppressive, spasmolytic, antimicrobial, antiparasitic, antifeedant, CNS depressant, antioxidant, etc.) of these compounds, including structure-activity relationships, are also discussed.

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Section: Otherssupporting

confidence: 82%

Section: Othersmentioning

confidence: 53%

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Secondary Metabolites of Plants from the Genus Saussurea: Chemistry and Biological Activity

Wang

Dong

et al. 2010

Chemistry & Biodiversity

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Plant Growth Regulatory Substances Both of Microbial and Plant Origin

Gross

1991

Chemistry of Plant Protection

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Inhibition of elongation growth by two sesquiterpene lactones isolated from Helianthus annuus L.

Spring

Hager

1982

Planta

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Two sesquiterpene lactones belonging to the germacranolides were isolated from the leaves and stems of Helianthus annuus L. Their formation in the plant is light-dependent. Both sesquiterpene lactones (SL) strongly inhibit indole-3-acetic acid (IAA)-induced elongation growth of Avena sativa L. coleoptile segments and Helianthus annuus L. hypocotyl segments. Both SL do not, however, inhibit acid-induced growth nor growth triggered by fusicoccin at all. In the presence of dithiothreitol (DTT), the inhibitory effect of SL in the Avena-segment-test can be completely neutralized. This can be attributed to the binding of DTT to both SL. Using thin-layer-chromatography it could be shown that the inhibitors build adducts with SH-rich compounds, e.g., cysteine, glutathione, mercapto-ethanol, and DTT, whose Rf-value significantly differs from those of the primary substances. If the coleoptile segments are first treated with an inhibitor and the inhibitor is subsequently washed out, close to normal elongation growth can be induced by adding an IAA-solution. If the segments are simultaneously treated with inhibitor and IAA, no notable growth can be initiated for an extended amount of time, after the removal of both substances and the anewed addition of IAA. Fusicoccin, however, can immediately neutralize the induced growth inhibition. The same irreversible inhibition is observed when 2,4-dichlorophenoxyacetic acid (2,4-D) is used: If coleoptile segments are treated with an inhibitor plus 2,4-D or an inhibitor plus 3,5-dichlorophenoxyacetic acid (3,5-D), respectively, IAA-induced growth after removal of the substances can only be observed by those coleoptiles which had previously been treated with the non-auxin, 3,5-D plus an inhibitor. Based on these results, a possible mechanism describing how the inhibitor functions is discussed. The binding of an auxin to an auxin receptor sets a SH-group free (possibly due to a change in the conformation of the receptor); a site is given to which the inhibitor can bind irreversibly (via a S-bond). The IAA-receptor-inhibitor-complex is then no longer able to initiate elongation growth. If auxin is not present, no lasting bond between the inhibitor and the receptor can occur, since the essential SH-group remains masked. The inhibitor can be washed out again. Consequently, the SL's have to be able to intervene at the beginning of the IAA-induced reaction sequence, while the following steps remain uninfluenced, i.e. namely, the active excretion of protons into the cell wall compartments, which is directly induced by fusicoccin and causes elongation growth.

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Plant growth activity of guaianolides with C-4 oxygen-containing groups

Cited by 11 publications

References 4 publications

Secondary Metabolites of Plants from the Genus Saussurea: Chemistry and Biological Activity

Secondary Metabolites of Plants from the Genus Saussurea: Chemistry and Biological Activity

Plant Growth Regulatory Substances Both of Microbial and Plant Origin

Inhibition of elongation growth by two sesquiterpene lactones isolated from Helianthus annuus L.

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