Santalol

The herbs of Santalum album L.

Medicinal properties of alpha-santalol, a naturally occurring constituent of sandalwood oil: review.[Pubmed:29130352]

Nat Prod Res. 2017 Nov 13:1-17.

Alpha-Santalol is a naturally occurring sesquiterpene that is derived from sandalwood oil. Its wide range of health benefits have been attributed to the modulation of various signalling pathways involved in the development of a particular disease. For example, the antitumour and cancer preventive properties of alpha-Santalol have been shown to involve cell death induction through apoptosis and cell cycle arrest in various cancer models. A marked decrease in inflammatory markers have also been shown with alpha-Santalol administration in skin tissue models. The current review is aimed at bringing the most recent advances of alpha-Santalol against various disease-specific models and highlighting its associated mechanistic details.

The Synthesis of Fragrant Natural Products from Santalum album L.: (+)-(Z)-alpha-Santalol and (-)-(Z)-beta-Santalol.[Pubmed:29289243]

Chimia (Aarau). 2017 Dec 1;71(12):823-835.

The synthetic challenges associated with the selective synthesis of alpha-Santalene (1), (Z)-alpha-Santalol (2), beta-Santalene (3), and most importantly (Z)-beta-Santalol (4) have interested the world's synthetic chemists for decades. These molecules, lovely examples of nature's exquisite creations, have been isolated from East Indian Sandalwood Oil (Santalum album L.) and have stimulated chemists to develop new and efficient methodologies to synthesize them. The synthesis and evolution of various approaches to the [2.2.1]bicycloheptane ring system present in beta-Santalene (3) and the even more challenging selective synthesis of the (Z)-allylic alcohol sidechain present in both (Z)-alpha-Santalol (2) and ((Z)-beta-Santalol (4) will be covered in this review.

Sesquiterpene Variation in West Australian Sandalwood (Santalum spicatum).[Pubmed:28587294]

Molecules. 2017 Jun 6;22(6). pii: molecules22060940.

West Australian sandalwood (Santalum spicatum) has long been exploited for its fragrant, sesquiterpene-rich heartwood; however sandalwood fragrance qualities vary substantially, which is of interest to the sandalwood industry. We investigated metabolite profiles of trees from the arid northern and southeastern and semi-arid southwestern regions of West Australia for patterns in composition and co-occurrence of sesquiterpenes. Total sesquiterpene content was similar across the entire sample collection; however sesquiterpene composition was highly variable. Northern populations contained the highest levels of desirable fragrance compounds, alpha- and beta-Santalol, as did individuals from the southwest. Southeastern populations were higher in E,E-farnesol, an undesired allergenic constituent, and low in Santalols. These trees generally also contained higher levels of alpha-bisabolol. E,E-farnesol co-occurred with dendrolasin. Contrasting alpha-Santalol and E,E-farnesol chemotypes revealed potential for future genetic tree improvement. Although chemical variation was evident both within and among regions, variation was generally lower within regions. Our results showed distinct patterns in chemical diversity of S. spicatum across its natural distribution, consistent with earlier investigations into sandalwood population genetics. These results are relevant for plantation tree improvement and conservation efforts.

Antifungal and Ichthyotoxic Sesquiterpenoids from Santalum album Heartwood.[Pubmed:28698478]

Molecules. 2017 Jul 8;22(7). pii: molecules22071139.

In our continuing study on a survey of biologically active natural products from heartwood of Santalum album (Southwest Indian origin), we newly found potent fish toxic activity of an n-hexane soluble extract upon primary screening using killifish (medaka) and characterized alpha-Santalol and beta-Santalol as the active components. The toxicity (median tolerance limit (TLm) after 24 h at 1.9 ppm) of alpha-Santalol was comparable with that of a positive control, inulavosin (TLm after 24 h at 1.3 ppm). These fish toxic compounds including inulavosin were also found to show a significant antifungal effect against a dermatophytic fungus, Trichophyton rubrum. Based on a similarity of the morphological change of the immobilized Trichophyton hyphae in scanning electron micrographs between treatments with alpha-Santalol and griseofulvin (used as the positive control), inhibitory effect of alpha-Santalol on mitosis (the antifungal mechanism proposed for griseofulvin) was assessed using sea urchin embryos. As a result, alpha-Santalol was revealed to be a potent antimitotic agent induced by interference with microtubule assembly. These data suggested that alpha-Santalol or sandalwood oil would be promising to further practically investigate as therapeutic agent for cancers as well as fungal skin infections.

Genomics-Based Discovery of Plant Genes for Synthetic Biology of Terpenoid Fragrances: A Case Study in Sandalwood oil Biosynthesis.[Pubmed:27480682]

Methods Enzymol. 2016;576:47-67.

Terpenoid fragrances are powerful mediators of ecological interactions in nature and have a long history of traditional and modern industrial applications. Plants produce a great diversity of fragrant terpenoid metabolites, which make them a superb source of biosynthetic genes and enzymes. Advances in fragrance gene discovery have enabled new approaches in synthetic biology of high-value speciality molecules toward applications in the fragrance and flavor, food and beverage, cosmetics, and other industries. Rapid developments in transcriptome and genome sequencing of nonmodel plant species have accelerated the discovery of fragrance biosynthetic pathways. In parallel, advances in metabolic engineering of microbial and plant systems have established platforms for synthetic biology applications of some of the thousands of plant genes that underlie fragrance diversity. While many fragrance molecules (eg, simple monoterpenes) are abundant in readily renewable plant materials, some highly valuable fragrant terpenoids (eg, Santalols, ambroxides) are rare in nature and interesting targets for synthetic biology. As a representative example for genomics/transcriptomics enabled gene and enzyme discovery, we describe a strategy used successfully for elucidation of a complete fragrance biosynthetic pathway in sandalwood (Santalum album) and its reconstruction in yeast (Saccharomyces cerevisiae). We address questions related to the discovery of specific genes within large gene families and recovery of rare gene transcripts that are selectively expressed in recalcitrant tissues. To substantiate the validity of the approaches, we describe the combination of methods used in the gene and enzyme discovery of a cytochrome P450 in the fragrant heartwood of tropical sandalwood, responsible for the fragrance defining, final step in the biosynthesis of (Z)-Santalols.

Fumigant and contact toxicity of 22 wooden essential oils and their major components against Drosophila suzukii (Diptera: Drosophilidae).[Pubmed:27742359]

Pestic Biochem Physiol. 2016 Oct;133:35-43.

Fumigant and contact toxicities of 22 plant essential oils (EOs) from 14 families and their constituents against the adult spotted wing drosophila (SWD), Drosophila suzukii were examined. Analyses by GC, GC-MS, and NMR led to the identification of 2, 16, 13, 4, 6, 9, and 10 compounds from Gaultheria fragrantissima, Croton anistatum, Illicium verum, Liquidamabar orientalis, Cinnamomum cassia, Rosa damasena, and Santalum album, respectively. In fumigant toxicity test, G. fragrantissima, C. anistatum, and I. verum exhibited 100, 93.8, and 95.8, and 100, 70.0, and 80.0% mortalities against the adult male and female SWD at 4.41mg/L air, respectively. LC50 values (mg/L air) of G. fragrantissima, C. anistatum, and I. verum were 3.46, 3.67, and 3.16 against male, and 3.48, 4.31, and 4.01 against female SWD. LC50 values (mg/L air) of methyl salicylate and trans-anethole were 2.17 and 1.75 against male and 2.65 and 3.00 against female SWD, respectively. In contact toxicity tests, L. orientalis, C. cassia, R. damasena, and S. album showed insecticidal activity with LD50 values (mug/fly) of 2.64, 1.84, 3.40 and 2.18 against male SWD and of 3.74, 2.24, 8.91 and 5.61 against female SWD, respectively. 2-Phehy-1-ethanol, 3-phenyl-1-propanol, trans-cinnamaldehyde, trans-cinnamyl alcohol, and alpha-Santalol also exhibited insecticidal activity with LD50 values of 9.79, 5.52, 2.39, 3.02 and 2.37 against male SWD and of 11.77, 7.04, 2.94, 3.32, and 3.99 against female SWD, respectively. trans-Cinnamaldehyde exhibited the highest AChE inhibition but its inhibition is likely due to a non-specific chemical inhibition. Our results indicate that wooden EOs and their components can be used as fumigants or spray-type control agents against SWD.

Chemoprevention of Breast Cancer by Transdermal Delivery of alpha-Santalol through Breast Skin and Mammary Papilla (Nipple).[Pubmed:28589445]

Pharm Res. 2017 Sep;34(9):1897-1907.

PURPOSE: Almost all breast cancers originate from epithelial cells lining the milk ducts in the breast. To this end, the study investigated the feasibility of localized transdermal delivery of alpha-Santalol, a natural chemopreventive agent to the breast. METHODS: Different alpha-Santalol formulations (cream, solution and microemulsion) were developed and the in vitro permeability was studied using excised animal (porcine and rat) and human breast skin/mammary papilla (nipple). The in vivo biodistribution and efficacy studies were conducted in female rats. A chemical carcinogenesis model of breast cancer was used for the efficacy studies. RESULTS: Phospholipid based alpha-Santalol microemulsion showed the highest penetration through the nipple and breast skin. Delivery of alpha-Santalol through the entire breast (breast skin and nipple) in vivo in rats resulted in significantly higher concentration in the mammary gland compared to transdermal delivery through the breast skin or nipple. There was no measurable alpha-Santalol concentration in the blood. Transdermal delivery of alpha-Santalol reduced the tumor incidence and tumor multiplicity. Furthermore, the tumor size was significantly reduced with alpha-Santalol treatment. CONCLUSIONS: The findings from this study demonstrate the feasibility of localized transdermal delivery of alpha-Santalol for chemoprevention of breast cancer.

Santalol is a mixture of α and β-isomer santalol. α-santalol is isolated from sandalwood oil. α-santalol is a promising anti-cancer agent against cancers such as oral, breast, prostate and skin cancer.

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