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米拉萨罗文:一种来自潜水甲虫(大理石色热水龟虫)防御性分泌物的隐蔽型20-酮孕烷。

Mirasorvone: a masked 20-ketopregnane from the defensive secretion of a diving beetle (Thermonectus marmoratus).

作者信息

Meinwald J, Huang Q, Vrkoc J, Herath K B, Yang Z C, Schröder F, Attygalle A B, Iyengar V K, Morgan R C, Eisner T

机构信息

Department of Chemistry, Cornell University, Ithaca, NY 14853, USA.

出版信息

Proc Natl Acad Sci U S A. 1998 Mar 17;95(6):2733-7. doi: 10.1073/pnas.95.6.2733.

DOI:10.1073/pnas.95.6.2733
PMID:9501158
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC19637/
Abstract

The sunburst diving beetle, Thermonectus marmoratus, ejects a milky fluid from its prothoracic defensive glands when disturbed. Two major volatile components of this secretion are steroids; cybisterone (structure 7) constitutes about 20% of the volatiles, and a new steroid, mirasorvone, about 50%. Mirasorvone is assigned an 18-oxygenated pregnane structure (structure 9) on the basis of extensive spectroscopic data. Although no 18-oxygenated steroid has been described previously from an insect source, a closely related hormone with mineralocorticoid activity, 18-hydroxydeoxycorticosterone (structure 13), has been isolated from the adrenal glands of rats.

摘要

太阳爆纹潜水甲虫(Thermonectus marmoratus)受到干扰时会从其前胸防御腺中喷出一种乳白色液体。这种分泌物的两种主要挥发性成分是类固醇;环斑甾酮(结构7)约占挥发物的20%,一种新的类固醇,米拉斯沃酮,约占50%。基于广泛的光谱数据,米拉斯沃酮被确定为具有18-氧代孕烷结构(结构9)。尽管此前尚未从昆虫来源描述过18-氧代类固醇,但一种具有盐皮质激素活性的密切相关激素,18-羟基脱氧皮质酮(结构13),已从大鼠肾上腺中分离出来。

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引用本文的文献

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本文引用的文献

1
Inhibition of sunfish feeding by defensive steroids from aquatic beetles: Structure activity relationships.水生甲虫防御性类固醇对太阳鱼摄食的抑制作用:结构活性关系。
J Chem Ecol. 1991 Jul;17(7):1363-70. doi: 10.1007/BF00983769.
2
Rendering the inedible edible: circumvention of a millipede's chemical defense by a predaceous beetle larva.将不可食用之物变为可食用:一种捕食性甲虫幼虫对千足虫化学防御的规避。
Proc Natl Acad Sci U S A. 1998 Feb 3;95(3):1108-13. doi: 10.1073/pnas.95.3.1108.
3
Firefly "femmes fatales" acquire defensive steroids (lucibufagins) from their firefly prey.雌性萤火虫“致命女人”从它们的萤火虫猎物身上获取防御性类固醇(蟾毒色胺)。
Proc Natl Acad Sci U S A. 1997 Sep 2;94(18):9723-8. doi: 10.1073/pnas.94.18.9723.
4
Pregnanes from defensive glands of a belostomatid bug.负子蝽科昆虫防御腺中的孕甾烷类化合物。
Experientia. 1993 Feb 15;49(2):175-6. doi: 10.1007/BF01989425.
5
[On the chemistry of ecdysone. VI. Reactions of ecdysone molecules].[关于蜕皮激素的化学。VI. 蜕皮激素分子的反应]
Chem Ber. 1965 Jul;98(7):2394-402. doi: 10.1002/cber.19650980743.
6
[Cybisteron, a new arthroped steroid].[西比司特龙,一种新型节肢动物类固醇]
Justus Liebigs Ann Chem. 1967 Apr;703:182-9. doi: 10.1002/jlac.19677030122.
7
Defensive steroids from a carrion beetle (Silpha americana).来自一种埋葬虫(美洲埋葬虫)的防御性类固醇。
Experientia. 1985 Apr 15;41(4):516-9. doi: 10.1007/BF01966178.