نوع مقاله : مقاله پژوهشی
نویسندگان
1 دانشگاه شاهد
2 گروه علوم باغبانی- دانشگاه شاهد
چکیده
پیرتروم (Tanacetum cinerariifolium L.) یکی از مهمترین حشرهکشهای طبیعی شناختهشده است که بهدلیل سمیت انتخابی برای حشرات، تجزیهپذیری سریع در محیط و ایمنی نسبی برای پستانداران، جایگاه ویژهای در کشاورزی پایدار و مدیریت تلفیقی آفات یافته است. ترکیبات فعال پیرتروم شامل شش استر اصلی موسوم به پیرترینها هستند که از نظر ساختار شیمیایی، فعالیت زیستی و پایداری، تفاوتهایی با یکدیگر دارند. هدف از این مقاله مروری، بررسی جامع پیشرفتهای علمی مرتبط با شیمی پیرترینها، مسیرهای بیوسنتز در گیاه، عوامل مؤثر بر تجمع این ترکیبات، روشهای استخراج کلاسیک و نوین و بهویژه روشهای آنالیتیکی معتبر مبتنی بر HPLC، LC–MS/MS و GC–MS است. در این مقاله، دادههای واقعی و منتشرشده مربوط به شرایط کروماتوگرافی، زمانهای نگهداری، حدود تشخیص و کمّیسازی و کاربرد این روشها در کنترل کیفیت عصارههای گیاهی و پایش باقیماندهها در محصولات کشاورزی گردآوری و تحلیل شدهاند. نتایج این مرور نشان میدهد که روشهایLC–MS/MS بهعنوان دقیقترین و اختصاصیترین ابزار برای تفکیک و تعیین جداگانه شش پیرترین شناخته میشوند، در حالی که HPLC-DAD همچنان روشی مقرونبه صرفه و قابل اعتماد برای کنترل کیفیت فرآوردههای گیاهی است. این مقاله میتواند بهعنوان مرجع علمی برای پژوهشگران حوزه گیاهان دارویی، حشرهکشهای گیاهی و آنالیز ترکیبات طبیعی مورد استفاده قرار گیرد.
کلیدواژهها
عنوان مقاله [English]
A Comprehensive Phytochemical Review of the Natural Insecticidal Pyrethrum Flower (Tanacetum cinerariifolium (Trevir.) Sch. Bip., Asteraceae)
نویسندگان [English]
- Fatemeh Bina 1
- Amin panjsotouni 1
- Ayatollah Rezaei 2
1 shahed University
2 تهران - بزرگراه اشرفی اصفهانی- باغ فیض- خ خجسته پور- پلاک 65
چکیده [English]
Introduction
Pyrethrum, derived from Tanacetum cinerariifolium L., is one of the most significant natural insecticides known for its selective toxicity toward insects, rapid environmental degradation, and low mammalian toxicity. These properties have secured its role in sustainable agriculture and integrated pest management (IPM) systems. The insecticidal activity of pyrethrum is primarily attributed to six lipophilic esters collectively known as pyrethrins, which are categorized into Type I (pyrethrin I, cinerin I, jasmolin I) and Type II (pyrethrin II, cinerin II, jasmolin II). Type I pyrethrins exhibit stronger knockdown effects, whereas Type II compounds offer greater stability. Despite its long-standing use and environmental compatibility, the efficacy and quality of pyrethrum-based products are highly variable, influenced by genetic, agronomic, and analytical factors. Therefore, a comprehensive understanding of pyrethrin chemistry, biosynthesis, extraction techniques, and modern analytical methodologies is essential for optimizing its application and ensuring product consistency.
Method
This paper is structured as a systematic literature review. A thorough search was conducted across major international scientific databases including Web of Science, Scopus, PubMed, ScienceDirect, and Google Scholar using key terms such as Pyrethrum, Pyrethrins, Pyrethrin biosynthesis, HPLC analysis of pyrethrins, LC–MS/MS pyrethrins, and botanical insecticides. The search spanned publications from 1970 to 2025, with particular emphasis on analytical advancements in the last decade. Peer-reviewed research articles, review papers, book chapters, and reports from authoritative bodies like the WHO and FAO were critically evaluated. The focus was on integrating current knowledge regarding the chemical profile of pyrethrins, their biosynthetic pathways, the impact of environmental and genetic variables on accumulation, extraction methods (both classical and modern), and validated analytical techniques especially high-performance liquid chromatography (HPLC) and liquid chromatography–tandem mass spectrometry (LC–MS/MS) used for quality control and residue monitoring.
Results and Discussion
The biosynthesis of pyrethrins in T. cinerariifolium involves the convergence of the terpenoid pathway producing chrysanthemic acid and the jasmonic acid pathway yielding rethrolone-type alcohols. Key enzymes such as chrysanthemyl diphosphate synthase (CDS) and transcription factors like TcMYC2 regulate this process in response to developmental and environmental cues, including mechanical stress or insect herbivory. Pyrethrins accumulate predominantly in the glandular tissues of flower heads, especially in the ovaries, with concentrations peaking at full bloom. Extraction techniques have evolved from solvent-intensive classical methods (e.g., Soxhlet with hexane) toward greener, more efficient alternatives such as ultrasound-assisted extraction (UAE) and supercritical CO₂ extraction, which improve yield while minimizing thermal degradation and solvent use. Analytically, HPLC with diode array detection (DAD) remains a cost-effective and reliable method for the simultaneous quantification of all six pyrethrins in botanical extracts, typically using a C18 column and acetonitrile–water mobile phases with detection at 225 nm. However, for complex matrices such as food or environmental samples, LC–MS/MS offers superior sensitivity and selectivity, with detection limits in the nanogram-per-kilogram range via multiple reaction monitoring (MRM) in positive electrospray ionization mode. This technique is critical for compliance with Maximum Residue Limits (MRLs) established by regulatory agencies like the European Commission. Despite its benefits, pyrethrum faces challenges including photodegradation, batch-to-batch variability, and non-selective toxicity to beneficial insects like pollinators. Future research should focus on stabilizing formulations (e.g., nano-encapsulation), breeding high-yielding cultivars through genetic insight, and integrating pyrethrum into ecologically sound IPM frameworks. Overall, pyrethrum remains a cornerstone of natural pest control, and its continued relevance depends on synergizing botanical knowledge on cutting-edge analytical and agronomic innovations.
کلیدواژهها [English]
- pyrethrum active compounds
- pyrethrins
- HPLC
- LC–MS/MS
- herbal insecticide
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