Synonym name: Lycoricidinol
Catalogue No.: BP0978
Cas No.: 29477-83-6
Formula: C14H13NO7
Mol Weight: 307.258
Botanical Source: Alkaloid from Narcissus incomparabilis, all Narcissus spp. examined, and present in many other Amaryllidaceae spp. Also found in the Texas grasshopper Brachystola magna
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
Narciclasine (CAS No.: 29477-83-6) is a natural product derived from plants of the genus Narciclasine, belonging to the isoquinoline alkaloids. Since its first isolation from Narcissus spp. in the mid-20th century, Narcissus cycline has attracted widespread attention due to its unique biological activity, especially its potential in antitumor treatment. As a plant growth regulator, Narcissandin's ability to regulate the Rho/Rho kinase/LIM kinase/cofilin signaling pathways not only plays an important role in plant physiology, but also provides a molecular basis for its function in cytoskeletal remodeling and cell motility. In recent years, with advances in molecular pharmacology and medicinal chemistry, the antitumor mechanisms of Narcissian Cycline have gradually been revealed. Its targets cover multiple key signaling molecules and transcription factors such as MCL1, BCL2, and STAT3, showing promising prospects for drug development.
This paper will systematically review the chemical structure and physicochemical properties of Narcissusin, plant origin and extraction methods, pharmacological activity and mechanism, druggability evaluation, and pharmacokinetic characteristics, and finally discuss its clinical application potential, aiming to provide comprehensive reference materials for researchers and drug developers in the field of natural product pharmacology.
The molecular formula of Narcissus cycline is C16H15NO5, with a molecular weight of 307.2580. Its structure belongs to the isoquinoline alkaloids, featuring polyhydroxyl-substituted benzene rings and nitrogen-containing heterocycles, with multiple hydroxyl and ketone groups within the molecule, giving it high polarity. The unique chemical structure determines its biological activity and ability to bind to targets.
In terms of physicochemical properties, the LogP value of Narcissus Cycline is about -0.4825, indicating strong hydrophilicity, with a water solubility of 10.2780, indicating good water solubility. Its topological pole surface area (TPSA) is 128.48 Ų, and a higher TPSA value is usually associated with poor cell membrane permeability, which may affect its oral bioavailability. The low permeability of the blood-brain barrier suggests its limited distribution in the central nervous system, which helps reduce the risk of CNS toxicity. The hERG channel inhibition test was negative, indicating a low risk of cardiac toxicity in narcine cycline. The Ames test scored 0.6, indicating a low genotoxicity risk and meeting safety requirements.
Narcissus spp. is mainly found in the bulbs and leaves of plants of the genus Narcissus and is one of the isoquinoline alkaloids unique to this genus. Daffodil plants are widely distributed across Europe, North Africa, and parts of Asia, and have traditionally been used for horticulture and medicinal purposes.
The process for extracting Narcissus cycline typically includes the following steps:
In recent years, with advances in separation technology, supercritical fluid extraction and molecular blotting techniques have also been attempted for efficient extraction and purification of narcissus, significantly improving yield and purity.
Narcissianin exhibits significant pharmacological effects across various biological activities, especially in the antitumor field.
Narcissian exerts anti-tumor effects through multiple targets and pathways, covering various tumor cell lines including breast cancer, lung cancer, liver cancer, colorectal cancer, and brain tumors. Its main manifestations are:
Besides anti-tumor effects, Narcissandin acts as a plant growth regulator, significantly enhancing GTPase RhoA activity by regulating the Rho/Rho kinase/LIM kinase/cofilin signaling pathways, promoting actin stress fiber formation, and affecting cytoskeleton remodeling and cell motility. This mechanism is not only significant for regulating plant cell growth but also provides a molecular basis for its role in tumor cell migration and invasion.
The anti-tumor mechanisms of Narcissian are complex and diverse, mainly achieved through the following key targets and signaling pathways:
Narcissus cycline significantly activates RhoA GTPase, which in turn activates downstream Rho kinase (ROCK) and LIM kinase (LIMK), regulating the phosphorylation state of actin-binding protein cofilin and promoting the formation of actin stress fibers. This process affects cell morphology and motility, inhibiting the migration and invasion of tumor cells.
Narcissipcon downregulates the expression of anti-apoptotic proteins such as MCL1 and BCL2, disrupts mitochondrial membrane potentials, promotes the generation of intracellular reactive oxygen species (ROS), and activates apoptosis signaling pathways.
Narcissandin also affects estrogen receptors (ESR1) and aromatase (CYP19A1), suggesting its potential application value in hormone-dependent tumors such as breast cancer.
The molecular weight of Narcissusian cycline is 307.2580, meeting the molecular weight requirements of the Lipinski rule. Its LogP value is -0.4825, indicating good water solubility, but lower lipid solubility may limit its cell membrane permeability. The TPSA value is 128.48 Ų, and the higher polarity may affect oral absorption and bioavailability. Narcissiptracycline does not inhibit hERG channels, reducing the risk of cardiotoxicity. Ames test results show a low genotoxicity risk and good safety.
Currently, pharmacokinetic research on Narcissus cycline is relatively limited. Previous studies have shown that the oral bioavailability of Narcissus cycline is relatively low, mainly due to its high polarity and pronounced first-pass effect. Its low blood-brain barrier permeability limits its application in central nervous system tumors. Metabolism in the body mainly occurs through the liver enzyme system, and the metabolites still require further identification.
To enhance the pharmacokinetics of Narcissus, researchers have attempted strategies such as nanocarriers, liposome encapsulation, and structural modification to improve its in vivo stability and targeting properties, thereby enhancing its antitumor effect.
As a multi-target antitumor natural product, Narcissandanine has broad clinical development potential. Its unique mechanism of action enables it to show good inhibitory effects across various tumor types, especially showing advantages in refractory and drug-resistant tumors.
Future research directions include:
Moreover, research on Narcissus cycline in plant growth regulation and cytoskeletal regulation has provided new ideas for its applications in agriculture and cell biology.
As a natural product with a unique structure and multi-target mechanism, Narcissandin-Cycline demonstrates significant anti-tumor potential. By regulating the RhoA signaling pathway and various key regulatory factors, it inhibits tumor cell proliferation, migration, and angiogenesis, promoting tumor cell apoptosis. Although its druggability remains challenging, through modern drug delivery technology and structural optimization, Narcine cycline is expected to become an important candidate for the new generation of anti-tumor drugs. In the future, in-depth mechanistic research and clinical development will further advance the drug development of Narcinocycline, bringing new hope to cancer treatment.
