Cosmeceuticals and Active Cosmetics

Raja Sivamani, Jared R. Jagdeo, Peter Elsner, Howard I. Maibach, Raja Sivamani, Jared R. Jagdeo, Peter Elsner, Howard I. Maibach

• Publisher: CRC Press
• Year: 2015
• ISBN:
  9781498782463
• Edition: 3
• Topic: Medicina
• Subtopic: Teoria, pratica e riferimenti medici

Cosmeceuticals and Active Cosmetics discusses the science of nearly two dozen cosmeceuticals used today. This third edition provides ample evidence on specific cosmeceutical substances, their classes of use, skin conditions for which they are used, and points of interest arising from other considerations, such as toxicology and manufacturing. The b

Chapter 1

Bakuchiol: A Retinol-Like Functional Compound, Modulating Multiple Retinol and Non-Retinol Targets

Ratan K. Chaudhuri

Background

Bakuchiol (Figure 1.1; Phenol, 4-[1E, 3S]-3-ethenyl-3, 7-dimethyl-1, 6-octadienyl) was first isolated by Mehta et al. from the Psoralea corylifolia seed in 1973.1 Absolute configuration of bakuchiol was established in the same year by Parakasarao et al.2 Bakuchiol has one asymmetric center and is shown to possess (S)-chirality.3 Mechanistically, both the 4-hydroxystyryl and terpenic moieties of the compound seem to be important for its bioactivity. Total synthesis was also accomplished in 1973.4 Banerji and Chintalwar reported the biosynthesis of bakuchiol and established the pathway by using phenylalanine and mevalonic acid as substrates.5,6

Figure 1.1

Structure of bakuchiol.

Bakuchiol is mainly obtained from the seeds of the plant Psoralea corylifolia, which is widely used in Indian as well as in Chinese medicine to treat a variety of diseases.7 Traditional medicine practitioners in India and China have utilized the plant for centuries. Psoralea corylifolia is known by a wide variety of names, suggesting its widespread use. For example, babchi, baguchi, babachi, Bakchi in Hindi and by many other names depending on the Indian languages; Ravoli in Sri Lanka; Boh-gol zhee in Korea; Buguzhi in Chinese.7 A recent chapter on P. corylifolia describes its botany, phytochemistry, and ethnopharmacology, along with the various pharmacological activities of the plant.8 Bakuchiol has also been isolated from other plants, such as P. grandulosa,9,10 P. drupaceae,11 Ulmus davidiana,12 Otholobium pubescens,13 Piper longum,14 and Aerva sangulnolenta Blum.15

Structurally, bakuchiol (Figure 1.1) belongs to the family of meroterpenes. Meroterpenes are terpenes having an aromatic ring in the chemical structure. The term meroterpenoid was first applied by Cornforth, in 1968, to describe natural products of mixed biosynthetic origin which are partially derived from terpenoids.16 They are typically derived from higher plants though they have also been obtained from fungi17 as well as having been produce...