Darutoside is a natural component, a rare "ent-pimarane" type diterpenoid extracted from some plants belonging to the Asteraceae family: Siegesbeckia orientalis L. (syn. S.glutinosa WALL.) and Siegesbeckia glabrescens Makino, Siegesbeckia pubescens Makino.

Although slightly toxic, Siegesbeckiae plants have been used in traditional Asian medicine as a remedy for acute arthritis, rheumatism, furunculosis, impetigo, and menstrual disorders (1) wound healing. Other terpenoids have also been isolated from this plant: darutigenol, hythiemoside A, ent-(15R),16,19-trihydroxypimar-8(14)-ene 19-O-beta-D-glucopyranoside (2).

What it is used for and where

Medical

Siegesbeckia pubescens Makino with its active ingredients, can attenuate chemical inflammation, prevent inflammatory cell infiltration and exert good anti-inflammatory and antinociceptive activity (3). Darutoside extracted from Siegesbeckia pubescens has shown inhibitory anticancer activities (4).

Cosmetics

Darutoside is rich in active compounds, including terpenes and flavonoids, with anti-inflammatory and collagen-stimulating properties. It is marketed as an ingredient that can help improve the appearance of ageing skin, in particular by promoting the synthesis of collagen and elastin fibres.

In cosmetics, it is used as an anti-wrinkle for its skin repair and collagen matrix restoration properties.

Skin conditioning agent. It is the mainstay of topical skin treatment as it has the function of restoring, increasing or improving skin tolerance to external factors, including melanocyte tolerance. The most important function of the conditioning agent is to prevent skin dehydration, but the subject is rather complex and involves emollients and humectants that can be added in the formulation.

The most relevant studies on this chemical compound have been selected with a summary of their contents:

Darutoside studies

• Molecular Formula: C₂₆H₄₄O₈
• Molecular Weight: 484.62 g/mol
• CAS: 59219-65-7 
• UNII EG8ODI0780 
• EC Number: 
• DSSTox Substance ID: 
• Beilstein   6542518
• PubChem Substance ID 

Synonyms:

• Darutin
• (2R,3R,4S,5S,6R)-2-[[(2R,4aS,4bR,7S,10aS)-7-[(1R)-1,2-dihydroxyethyl]-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthren-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CHEMBL4105670
• beta-D-Glucopyranoside, 7-(1,2-dihydroxyethyl)-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,1,4a,7-tetramethyl-2-phenanthrenyl

References________________________________________________________________

(1) Selected Medicinal Plants in Vietnam ed. by Le V. T., Science and Technology, Hanoi, 1999, pp. 277—282.

(2) Giang PM, Son PT, Otsuka H. ent-pimarane-type diterpenoids from Siegesbeckia orientalis L. Chem Pharm Bull (Tokyo). 2005 Feb;53(2):232-4. doi: 10.1248/cpb.53.232.

(3) Li YS, Zhang J, Tian GH, Shang HC, Tang HB. Kirenol, darutoside and hesperidin contribute to the anti-inflammatory and analgesic activities of Siegesbeckia pubescens makino by inhibiting COX-2 expression and inflammatory cell infiltration. J Ethnopharmacol. 2021 Mar 25;268:113547. doi: 10.1016/j.jep.2020.113547. 

(4) Wang J, Xie K, Duan H, Wang Y, Ma H, Fu H. Isolation and characterization of diterpene glycosides from Siegesbeckia pubescens. Bioorg Med Chem Lett. 2017 Apr 15;27(8):1815-1819. doi: 10.1016/j.bmcl.2017.02.051. 

Compendium of the most significant studies with reference to properties, intake, effects.

Li YS, Zhang J, Tian GH, Shang HC, Tang HB. Kirenol, darutoside and hesperidin contribute to the anti-inflammatory and analgesic activities of Siegesbeckia pubescens makino by inhibiting COX-2 expression and inflammatory cell infiltration. J Ethnopharmacol. 2021 Mar 25;268:113547. doi: 10.1016/j.jep.2020.113547.

Ou Z, Zhao L, Wang K, Fu H. Chemical constituents of Siegesbeckia pubescens. Zhongguo Zhong Yao Za Zhi. 2009 Nov;34(21):2754-7.

Son PT, Giang PM, Taylor WC. NMR studies of darutoside, a rare ENT-pimarane glucoside. Nat Prod Res. 2005 Jul;19(5):503-7. doi: 10.1080/14786410412331280997.

Kong FY, Hu HH, Han ZB, Xu WY, Feng MX, Ma CH. Study on index components and fingerprints of crude and processed Siegesbeckia Herbs. Zhongguo Zhong Yao Za Zhi. 2014 Aug;39(15):2907-11.

Su T, Yu H, Kwan HY, Ma XQ, Cao HH, Cheng CY, Leung AK, Chan CL, Li WD, Cao H, Fong WF, Yu ZL. Comparisons of the chemical profiles, cytotoxicities and anti-inflammatory effects of raw and rice wine-processed Herba Siegesbeckiae. J Ethnopharmacol. 2014 Oct 28;156:365-9. doi: 10.1016/j.jep.2014.09.038.

Dong XY, Chen M, Jin W, Huang DX, Shen SM, Li HT. Studies on antifertility constituents of Siegesbeckia glabrescens Mak. Yao Xue Xue Bao. 1989;24(11):833-6.

Wang J, Xie K, Duan H, Wang Y, Ma H, Fu H. Isolation and characterization of diterpene glycosides from Siegesbeckia pubescens. Bioorg Med Chem Lett. 2017 Apr 15;27(8):1815-1819. doi: 10.1016/j.bmcl.2017.02.051.

Gao LJ, Xu SF, Li XY, Huang WK, Hao SJ, Ye YP. Diterpenoids as PPARγ agonists from Siegesbeckia pubescens and their anti-inflammatory effects in vitro. Zhongguo Zhong Yao Za Zhi. 2019 Dec;44(23):5191-5197.doi: 10.19540/j.cnki.cjcmm.20190906.204.

 Song XL, Zhang QY, Wang ZM, Fu HZ, Qian RQ. A rapid and simple RP-HPLC method for quantification of kirenol in rat plasma after oral administration and its application to pharmacokinetic study. Biomed Chromatogr. 2011 May;25(5):542-6. doi: 10.1002/bmc.1481.