Megaphone is a

cytotoxic Cytotoxicity is the quality of being toxic to cells. Examples of toxic agents are toxic metals, toxic chemicals, microbe neurotoxins, radiation particles and even specific neurotransmitters when the system is out of balance. Also some types of dr ...

neolignan The lignans are a large group of low molecular weight polyphenols found in plants, particularly seeds, whole grains, and vegetables. The name derives from the Latin word for "wood". Lignans are precursors to phytoestrogens. They may play a role ...

obtained from '' Aniba megaphylla'', a

flowering plant Flowering plants are plants that bear flowers and fruits, and form the clade Angiospermae (). The term angiosperm is derived from the Ancient Greek, Greek words (; 'container, vessel') and (; 'seed'), meaning that the seeds are enclosed with ...

in the

laurel family Lauraceae, or the laurels, is a plant family that includes the true laurel and its closest relatives. This family comprises about 2850 known species in about 45 genera worldwide. They are dicotyledons, and occur mainly in warm temperate and tr ...

which gave the compound its name. Megaphone has also been prepared synthetically. Studies carried out in the 1960s demonstrated that an alcoholic extract of the ground root of ''Aniba megaphylla'' inhibited, ''in vitro'', growth of cells derived from human

carcinoma Carcinoma is a malignancy that develops from epithelial cells. Specifically, a carcinoma is a cancer that begins in a tissue that lines the inner or outer surfaces of the body, and that arises from cells originating in the endodermal, mesoder ...

of the

nasopharynx The pharynx (: pharynges) is the part of the throat behind the mouth and nasal cavity, and above the esophagus and trachea (the tubes going down to the stomach and the lungs respectively). It is found in vertebrates and invertebrates, though its ...

. In 1978, the active components of the extract were isolated using

silica gel Silica gel is an amorphous and porosity, porous form of silicon dioxide (silica), consisting of an irregular three-dimensional framework of alternating silicon and oxygen atoms with nanometer-scale voids and pores. The voids may contain wate ...

chromatography In chemical analysis, chromatography is a laboratory technique for the Separation process, separation of a mixture into its components. The mixture is dissolved in a fluid solvent (gas or liquid) called the ''mobile phase'', which carries it ...

, characterized and named as megaphone (C₂₂H₃₀O₆, solid), megaphone

acetate An acetate is a salt formed by the combination of acetic acid with a base (e.g. alkaline, earthy, metallic, nonmetallic, or radical base). "Acetate" also describes the conjugate base or ion (specifically, the negatively charged ion called ...

(C₂₄H₃₂O₇, oily liquid) and megaphyllone acetate (C₂₃H₂₈O₇, oily liquid). For comparison, megaphone acetate was also produced synthetically by reacting megaphone with

acetic anhydride Acetic anhydride, or ethanoic anhydride, is the chemical compound with the chemical formula, formula . Commonly abbreviated , it is one the simplest organic acid anhydride, anhydrides of a carboxylic acid and is widely used in the production of c ...

at 50 °C for 6 hours. Stirring an alcoholic solution of megaphone (megaphone acetate), with added palladium catalyst, in hydrogen atmosphere, followed by evaporation of the solvent yields tetrahydromegaphone (tetrahydromegaphone acetate) as an oil. Millimeter-sized crystals of megaphone can be grown from an

ether In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R� ...

chloroform Chloroform, or trichloromethane (often abbreviated as TCM), is an organochloride with the formula and a common solvent. It is a volatile, colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to refrigerants and po ...

solution. They have monoclinic symmetry with

space group In mathematics, physics and chemistry, a space group is the symmetry group of a repeating pattern in space, usually in three dimensions. The elements of a space group (its symmetry operations) are the rigid transformations of the pattern that ...

''P''2₁, lattice constants ''a'' = 0.8757 nm, ''b'' = 1.1942 nm and ''c'' = 1.0177 nm and two

formula unit In chemistry, a formula unit is the smallest unit of a non-molecular substance, such as an ionic compound, covalent network solid, or metal. It can also refer to the chemical formula for that unit. Those structures do not consist of discrete mol ...

s per

unit cell In geometry, biology, mineralogy and solid state physics, a unit cell is a repeating unit formed by the vectors spanning the points of a lattice. Despite its suggestive name, the unit cell (unlike a unit vector In mathematics, a unit vector i ...

. Megaphone and megaphone acetate molecules are

chiral Chirality () is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek language, Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is dist ...

and the reported extraction and synthesis procedures yielded their

racemic mixture In chemistry, a racemic mixture or racemate () is a mixture that has equal amounts (50:50) of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as r ...

s. Megaphone acetate was also isolated from the root of ''Endlicheria dysodantha'', another plant of

Laurel family Lauraceae, or the laurels, is a plant family that includes the true laurel and its closest relatives. This family comprises about 2850 known species in about 45 genera worldwide. They are dicotyledons, and occur mainly in warm temperate and tr ...

, using chromatography of ethanolic solution. It showed inhibitory activity against cells of crown gall tumor and human lung, breast and colon carcinomas.

References

{{lignan Lignans O-methylated natural phenols Total synthesis Cyclohexenes Plant toxins