Dependence of activity of cucurbitacin in repression of Botrytis laccase on its structure

Ada Viterbo; Boris Yagen; Robert Rosenthal; Alfred M. Mayer

doi:10.1016/0031-9422(93)85081-2

Dependence of activity of cucurbitacin in repression of Botrytis laccase on its structure

Ada Viterbo^*, Boris Yagen, Robert Rosenthal, Alfred M. Mayer

^*Corresponding author for this work

School of Pharmacy

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

The activity of cucurbitacin D and I in repressing laccase formation by Botrytis cinerea, under inducing conditions was compared with some of their derivatives. The activity of cucurbitacin D and its 25-monoacetate were similar. The 2,16-cucurbitacin D diacetate and 2,16,25-cucurbitacin D triacetate were four and 16 times more effective than the parent compound, while the activity of the 2,16-valproate derivative of cucurbitacin D did not differ significantly from cucurbitacin D itself. The 2-O-β-d-glucopyranosyl-cucurbitacin I was inactive, but its hexaacetate had the same activity as cucurbitacin I. The difference in activity of the compounds may be related to their relative solubilities in cell membranes, which determine to what extent they penetrate to the site of their activity.

Original language	English
Pages (from-to)	1313-1315
Number of pages	3
Journal	Phytochemistry
Volume	33
Issue number	6
DOIs	https://doi.org/10.1016/0031-9422(93)85081-2
State	Published - 12 Aug 1993

Keywords

Botrytis cinerea
cucurbitacins
fungus
laccase
structure-activity.

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10.1016/0031-9422(93)85081-2

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title = "Dependence of activity of cucurbitacin in repression of Botrytis laccase on its structure",

abstract = "The activity of cucurbitacin D and I in repressing laccase formation by Botrytis cinerea, under inducing conditions was compared with some of their derivatives. The activity of cucurbitacin D and its 25-monoacetate were similar. The 2,16-cucurbitacin D diacetate and 2,16,25-cucurbitacin D triacetate were four and 16 times more effective than the parent compound, while the activity of the 2,16-valproate derivative of cucurbitacin D did not differ significantly from cucurbitacin D itself. The 2-O-β-d-glucopyranosyl-cucurbitacin I was inactive, but its hexaacetate had the same activity as cucurbitacin I. The difference in activity of the compounds may be related to their relative solubilities in cell membranes, which determine to what extent they penetrate to the site of their activity.",

keywords = "Botrytis cinerea, cucurbitacins, fungus, laccase, structure-activity.",

author = "Ada Viterbo and Boris Yagen and Robert Rosenthal and Mayer, \{Alfred M.\}",

year = "1993",

month = aug,

day = "12",

doi = "10.1016/0031-9422(93)85081-2",

language = "אנגלית",

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T1 - Dependence of activity of cucurbitacin in repression of Botrytis laccase on its structure

AU - Viterbo, Ada

AU - Yagen, Boris

AU - Rosenthal, Robert

AU - Mayer, Alfred M.

PY - 1993/8/12

Y1 - 1993/8/12

N2 - The activity of cucurbitacin D and I in repressing laccase formation by Botrytis cinerea, under inducing conditions was compared with some of their derivatives. The activity of cucurbitacin D and its 25-monoacetate were similar. The 2,16-cucurbitacin D diacetate and 2,16,25-cucurbitacin D triacetate were four and 16 times more effective than the parent compound, while the activity of the 2,16-valproate derivative of cucurbitacin D did not differ significantly from cucurbitacin D itself. The 2-O-β-d-glucopyranosyl-cucurbitacin I was inactive, but its hexaacetate had the same activity as cucurbitacin I. The difference in activity of the compounds may be related to their relative solubilities in cell membranes, which determine to what extent they penetrate to the site of their activity.

AB - The activity of cucurbitacin D and I in repressing laccase formation by Botrytis cinerea, under inducing conditions was compared with some of their derivatives. The activity of cucurbitacin D and its 25-monoacetate were similar. The 2,16-cucurbitacin D diacetate and 2,16,25-cucurbitacin D triacetate were four and 16 times more effective than the parent compound, while the activity of the 2,16-valproate derivative of cucurbitacin D did not differ significantly from cucurbitacin D itself. The 2-O-β-d-glucopyranosyl-cucurbitacin I was inactive, but its hexaacetate had the same activity as cucurbitacin I. The difference in activity of the compounds may be related to their relative solubilities in cell membranes, which determine to what extent they penetrate to the site of their activity.

KW - Botrytis cinerea

KW - cucurbitacins

KW - fungus

KW - laccase

KW - structure-activity.

UR - http://www.scopus.com/inward/record.url?scp=0009435636&partnerID=8YFLogxK

U2 - 10.1016/0031-9422(93)85081-2

DO - 10.1016/0031-9422(93)85081-2

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AN - SCOPUS:0009435636

SN - 0031-9422

VL - 33

SP - 1313

EP - 1315

JO - Phytochemistry

JF - Phytochemistry

IS - 6

ER -

Dependence of activity of cucurbitacin in repression of Botrytis laccase on its structure

Abstract

Keywords

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