Two insecticidal monoterpenes, telfairine and aplysiaterpenoid A, from the red alga Plocamium telfairiae: Structure elucidation, biological activity, and molecular topographical consideration by a semiempirical molecular orbital study

doi:10.1016/0048-3575(90)90134-N

Pesticide Biochemistry and Physiology

Volume 37, Issue 3, July 1990, Pages 275-286

https://doi.org/10.1016/0048-3575(90)90134-N Get rights and content

Abstract

Two insecticidal polyhalogenated monoterpenes, aplysiaterpenoid A and telfairine were isolated from the red alga Plocamium telfairiae. Both compounds showed strong insecticidal activities against the German cockroach (Blatella germanica) and mosquito larvae (Anopheles gambiae). The dieldrin-resistant strain of mosquito larvae (A. gambiae) which exhibited the significant cross-resistance to $(124635)-1,2,3,4,5,6- hexachlorohexane$ (γ-BHC) also revealed weak but definite cross-resistance to aplysiaterpenoid A and telfairine. The electrophysiological symptom that telfairine increases the frequency of spontaneous discharge and prolongs the synaptic after-discharge of the central nervous system of the German cockroach (B. germanica) in the same manner as γ-BHC indicated that telfairine also has some excitatory effect on the central nervous system. The molecular topographical studies by semiempirical molecular orbital calculation about these insecticidal monoterpenes were carried out in terms of their electrostatic similarity to picrotoxinin and extending volumes from the surface of picrotoxinin molecule. The result suggested that the orientations of the steric bulky regions and electronegative centers in aplysiaterpenoid A and telfairine could satisfy the geometrical requirement for interacting with the picrotoxinin receptor as well as γ-BHC, while the large extending volumes of both compounds led to the loose fitting into the receptor. Accordingly, we propose that two insecticidal monoterpenes from marine alga seem to interact with the picrotoxinin receptor, indicating that their mode of action is cyclodiene-type.

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Citation Excerpt :
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^☆: A part of these results was presented at the 16th International Symposium on the Chemistry of Natural Products, IUPAC, Kyoto, Japan,1988.

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Pesticide Biochemistry and Physiology

Abstract

References (24)

A polyhalogenated insecticidal monoterpene from the red alga, Plocamium telfairiae

Phytochemistry

Extension of AM1 to the halogens

Theochem

Pharmacological evidence for a discrete neurotoxic action of dieldrin (HEOD) in the American cockroach, Periplanata americana (L.)

Pestic. Biochem. Physiol

Picrotoxinin receptor in the central nervous system of the American cockroach: Its role in the action of cyclodiene-type insecticides

Pestic. Biochem. Physiol

Neuromuscular action of insecticidal domoic acid on the American cockroach

Pestic. Biochem. Physiol

Chemical and biological aspects of marine monoterpenes

Prog. Chem. Nat. Prod

a new cyclic monoterpene skeleton from a red marine alga

J. Org. Chem

Halogenated alicyclic monoterpene from the red algae Plocamium

J. Org. Chem

Two new polyhalogenated monoterpenes from the sea hare, Aplysia kurodai

Liebigs Ann. Chem

Pyrethroid resistance mechanism in German cockroach, Blattera germanica (Orthoptera: Blattellidae)

Appl. Entomol. Zool

AM1: A new general purpose quantum mechanical molecular model

J. Amer. Chem. Soc

Cited by (40)

Insecticidal effects of natural products in free and encapsulated forms: an overview

Toxic assessment, growth disrupting and neurotoxic effects of red seaweeds’ botanicals against the dengue vector mosquito Aedes aegypti L.

Bioactive compounds in seaweeds: An overview of their biological properties and safety

Larvicidal and oviposition deterrent activity of sesquiterpenes from the red seaweed Laurencia johnstonii against Aedes aegypti

Larvicidal and oviposition deterrent activity of sesquiterpenes from Laurencia johnstonii seaweed against Aedes aegypti

Anti-Inflammatory Halogenated Monoterpenes from the Red Alga Portieria hornemannii

Two insecticidal monoterpenes, telfairine and aplysiaterpenoid A, from the red alga Plocamium telfairiae: Structure elucidation, biological activity, and molecular topographical consideration by a semiempirical molecular orbital study☆

Abstract

Phytochemistry

Theochem

Pestic. Biochem. Physiol

Pestic. Biochem. Physiol

Pestic. Biochem. Physiol

Chemical and biological aspects of marine monoterpenes

Prog. Chem. Nat. Prod

a new cyclic monoterpene skeleton from a red marine alga

J. Org. Chem

Halogenated alicyclic monoterpene from the red algae Plocamium

J. Org. Chem

Two new polyhalogenated monoterpenes from the sea hare, Aplysia kurodai

Liebigs Ann. Chem

Pyrethroid resistance mechanism in German cockroach, Blattera germanica (Orthoptera: Blattellidae)

Appl. Entomol. Zool

AM1: A new general purpose quantum mechanical molecular model

J. Amer. Chem. Soc