Luciden / Xanthohumol / Hops X factor / Lupulin

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Recently, there has been great interest in studying certain phytochemicals found in hops for their possible anti-inflammatory, anticancer, chemopreventive and estrogenic activities. Two of the phytochemicals found in hops that have been receiving a great deal of attention are xanthohumol for its possible anticancer activity and 8-prenylnaringenin for its phytoestrogenic activity.

Xanthohumol is a prenylated chalcone derived from hops. In hops, the yellow compound is found in high amounts in the lupulin glands of the female inflorescence.

Dr. Langer: Like many dietary antioxidants, Xanthohumol is a flavonoid. In addition to other benefits, flavonoids scavenge and neutralize free radicals. Everything we do creates oxidative stress and metabolic waste. Exercise, digestion and even breathing cause the release of free radicals. Antioxidants help us keep these free radicals in check so that we are not overwhelmed by what many scientists believe to be the underlying cause of aging. Xanthohumol is by far the most promising natural antioxidant flavonoid I've found in scientific literature. Over 198 published studies show Xanthohumol's potential to assist in a variety of biological functions. The most important research shows that Xanthohumol is up to 200 times more powerful than resveratrol. Evidence suggests that not only is Xanthohumol more bioavailable, it's more active so you get greater benefit by taking less.

The hop plant (Humulus lupulus L.) is a dioecious plant, meaning that there are separate male and female hop plants. Only the female hop plant produces the flowers, or, more specifically, the strobiles that are used for brewing or possible medicinal purposes. Male plants have no commercial value but are used to pollinate the female plants. Pollination stimulates higher yields by increasing cone size and seed set, but because brewers prefer seedless hops, males are only grown with otherwise poor-yielding female varieties. Hop seed from a pollinated female is only planted when a cross between the male and female is desired to obtain a new variety.

The term "hop' in a strict sense refers to the hop plant, and the term "hops' refers to the flower cones (""hop cones'' or ""hops''). However, both terms are commonly used interchangeably. The flowers in a female hop plant are arranged in characteristic clusters on stems. The flower cluster is called an inflorescence. The female inflorescences are rich in polyphenolic compounds and acyl phloroglucides that are widely used to preserve beer and give beer its characteristic flavor and aroma.

The hop cones are green, built like pine cones and vary in size. At the base of the leaves (bracts, also called scales) of the cones, are collections of small, yellow spheres called the lupulin glands. The lupulin glands are little sacs of bitter and aromatic acids and oils. In the lupulin glands can be found the alpha-acids and their derivatives, including the iso-alpha-acids and the rho-iso-alpha acids, the beta acids and xanthohumol, among several other compounds. The iso-alpha-acids, including isohumulone, account for the bitter taste of beer. The oils in the hops are mainly responsible for the aroma of beer.

In addition to their role in beer, hops extracts have been used for medicinal reasons. The traditional use of hops as a mild sedative has its origin in the observation that the transfer of hop resin from the hands of hop-pickers to their mouths appeared to cause sleepiness and fatigue in the workers. In Germany, the use of hops is approved for the treatment of restlessness, anxiety and sleep disorders. However, high-quality clinical studies supporting the use of hops as a sedative are few and far between. Thus, the effectiveness of the use of hops for the treatment of sleep disorders is uncertain.

Xanthohumol is secreted as part of the hop resin (lupulin) by glandular trichomes found on the adaxial surfaces of cone bracts. It is also found in the trichomes on the underside of young leaves. The chalcone is found in small amounts in the Chinese traditional medicine plant, Sophora flavescens, extracts of which are used in the treatment a number of diseases, including certain cancers and viral diseases. A chalcone is an aromatic ketone that forms the central core for a variety of biological compounds. Chalcones are the immediate precursors in the biosynthesis of flavonoids, and their structures differ from that of other flavonoids by the inclusion of an open C-ring. (Chalcones are sometimes referred to as open C-ring flavonoids.) Xanthohumol is usually referred to as a prenylflavonoid. It is the precursor of the flavonoid, isoxanthohumol, which belongs to the flavanone subclass of flavonoids. Xanthohumol possesses a free 2′-hydroxy group and can therefore readily isomerize to isoxanthohumol.

Xanthohumol has been found to have broad-spectrum anticancer activity.

However, in contrast to some other phytochemicals in hops, especially 8-prenylnaringenin, xanthohumol per se does not possess phytoestrogenic activity.

Xanthohumol's empirical formula is C21H22O5, its molecular weight is 354.396, and its CAS Registry Number is 6754-58-1. Xanthohumol is described chemically as (E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one. It is also known as (3′-[3,3-dimethylallyl]-2′,4′,4-trihydroxy-6′-methoxychalcone).

In addition to being classified as a prenylated chalcone or prenylchalcone and a prenylflavonoid, xanthohumol can be classified as a terpenophenol and a polyphenol.

Xanthohumol is represented by the following chemical formula:

CHEMICAL STRUCTURE

Xanthohumol

Xanthohumol is a plant secondary metabolite and has broad-spectrum activity against bacteria, viruses and fungi, all of which can cause damage to the plant. The amount of xanthohumol in beer is low (about 0.1 milligram per liter). This is due to the thermal conversion of xanthohumol to isoxanthohumol during the brewing process. Xanthohumol does impart some bitter taste to beer and helps to stabilize the foam.

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