Abstract
Discovery of novel natural herbicides has become crucial to overcome increasing weed resistance and environmental issues. In this article, we describe the finding that a methanol extract of dry long pepper (Piper longum L.) fruits is phytotoxic to lettuce (Lactuca sativa L.) seedlings. The bioassay-guided fractionation and purification of the crude extract led to isolation of sarmentine (1), a known compound, as the active principle. Phytotoxicity of 1 was examined with a variety of seedlings of field crops and weeds. Results indicated that 1 was a contact herbicide and possessed broad-spectrum herbicidal activity. Moreover, a series of sarmentine analogues were then synthesized to study the structure-activity relationship (SAR). SAR studies suggested that phytotoxicity of sarmentine and its analogues was specific due to chemical structures, i.e., the analogues of the acid moiety of 1 were active, but the amine and its analogues were inactive; the ester analogues and amide analogues with a primary amine of 1 were also inactive. In addition, quantification of 1 from different resources of the dry P. longum fruits using liquid chromatography-mass spectrometry showed a wide variation, ranging from almost zero to 0.57%. This study suggests that 1 has potential as an active lead molecule for synthesized herbicides as well as for bioherbicides derived from natural resources.
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Claims 9
Claim · model-written summary
Long pepper fruit extract was phytotoxic to lettuce seedlings.
- Taxon
- lettuce (Lactuca sativa L.)
Lactuca sativae0 - Treatment
- a methanol extract of dry long pepper (Piper longum L.) fruitse0
- Outcome
- phytotoxice0
Not reportedComparatorDirection
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“a methanol extract of dry long pepper (Piper longum L.) fruits is phytotoxic to lettuce (Lactuca sativa L.) seedlings.”
Claim · model-written summary
Sarmentine was isolated as the phytotoxic principle.
Not reportedTaxon
Verbatim
e0“isolation of sarmentine (1), a known compound, as the active principle.”
Claim · model-written summary
Sarmentine acted as a broad spectrum contact herbicide.
Not reportedTaxonComparatorDirection
Verbatim
e0“1 was a contact herbicide and possessed broad-spectrum herbicidal activity.”
Claim · model-written summary
Acid moiety analogues were phytotoxic.
Not reportedTaxonComparatorDirection
Verbatim
e0“the analogues of the acid moiety of 1 were active”
Claim · model-written summary
The amine and its analogues were inactive.
Not reportedTaxonComparatorDirection
Verbatim
e0“the amine and its analogues were inactive”
Claim · model-written summary
Ester analogues were inactive.
Not reportedTaxonComparatorDirection
Verbatim
e0“the ester analogues and amide analogues with a primary amine of 1 were also inactive”
Claim · model-written summary
Primary amine amide analogues were inactive.
Not reportedTaxonComparatorDirection
Verbatim
e0“the ester analogues and amide analogues with a primary amine of 1 were also inactive”
Claim · model-written summary
Sarmentine content in dry long pepper fruits varied from almost zero to 0.57%.
- Taxon
- P. longum
Piper longume0 - Outcome
- wide variatione0
- Value
- 0.57%e0
- Qualifier
- almost zeroe0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“different resources of the dry P. longum fruits using liquid chromatography-mass spectrometry showed a wide variation, ranging from almost zero to 0.57%.”
Claim · model-written summary
The authors propose sarmentine as a herbicide lead molecule.
- Outcome
- active lead molecule for synthesized herbicides as well as for bioherbicides derived from natural resourcese0
Not reportedTaxon
Verbatim
e0“1 has potential as an active lead molecule for synthesized herbicides as well as for bioherbicides derived from natural resources.”
The same questions in other papers
botanical · crop injury · Lactuca sativa (garden lettuce)Positive and negative results
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See all 21 papers →Claims are grouped by organism, treatment and what was measured or targeted. A paper counts as positive when any of its claims in the group is positive.