Cicada slough is one of the traditional crude drugs in East Asia. A comprehensive LC-MS analysis was conducted to overview constituents in a commercially purchased cicada slough as a crude drug. It revealed that there were oligomers of N-acetyldopamine with the degree of polymerization of up to 8. High-resolution tandem mass spectrometry could enable a detailed analysis on their structures by uncovering the presumed fragmentation pathways. Additional isolation experiments disclosed the presence of four known compounds: 2,3’,4’-trihydroxyacetophenone, 2-oxo-N-acetyldopamine, protocatechuic acid, and paeonol. The quantified paeonol content for purchased cicada slough ranged from 3 to 290 μg/g dw crude drug, although wild cicada slough did not show the presence of paeonol.
KomatsuK, ShibaharaN, KadowakiM, TohdaC, KonnoK, HattoriM, ZhuS, KazumaK, SakuraiH, WatanabeS, SaikiI, ShimadaY, OhtaS, WatanabeH. (2012) Traditional Medical & Pharmaceutical Database. Division of Pharmacognosy, Department of Medicinal Resources, Institute of Natural Medicine, University of Toyama. http://dentomed.u-toyama.ac.jp/index_en.
2.
NanbaT. (1984) Gensyoku wakanyaku zukan (in Japanese). HOIKUSHA Publishers Co. (Osaka, Japan), 331. ISBN 9784586300570.
3.
Kyokugai shouki shuppan kentoukai (in Japanese). (2016) The Japanese standards for non‐pharmacopoeial crude drugs 2015: bilingual in Japanese and English. YAKUJI NIPPO, 340. ISBN 9784840813730.
NodaN, KubotaS, MiyataY, MiyaharaK. (2000) Optically active N-acetyldopamine dimer of the crude drug “Zentai,” the cast-off shell of the Cicada, Cryptotympana sp. Chemical & Pharmaceutical Bulletin, 48, 1749–1752.
6.
YangL, LiGY, LiQR, WangJH. (2012) Two new N-acetyldopamine tetrapolymers from Periostracum Cicadae. Journal of Asian Natural Products Research, 14, 204–209.
7.
YangL, LiGY, WangHY, ZhangK, ZhuY, ZhaoW, WangH, WangJH. (2016) Five new N-acetyldopamine dimers from Periostracum Cicadae. Phytochemistry Letters, 16, 97–102.
8.
AndersenSO. (2010) Insect cuticular sclerotization: a review. Insect Biochemistry and Molecular Biology, 40, 166–178.
9.
KuwajimaH, ShibanoN, BabaT, TakaishiK, InoueK, ShinguT. (1996) An acetophenone glycoside from Exacum affine. Phytochemistry, 41, 289–292.
10.
TozukaH, OtaM, KofujitaH, TakahashiK. (2005) Synthesis of dihydroxyphenacyl glycosides for biological and medicinal study: β-oxoacteoside from Paulownia tomentosa. Journal of Wood Science, 51, 48–59.
AndersenSO, RoepstorffP. (1978) Phenolic compounds released by mild acid hydrolysis from sclerotized cuticle: purification, structure, and possible origin from cross-links. Insect Biochemistry, 8, 99–104.
13.
HowardRW, JurenkaRA, BlomquistGJ. (1986) Prostaglandin synthetase inhibitors in the defensive secretion of the red flour beetle Tribolium castaneum (Herbst) (Coleoptera:Tenebrionidae). Insect Biochemistry, 16, 757–760.
14.
YunCS, ChoiYG, JeongMY, LeeJH, LimS. (2013) Moutan Cortex Radicis inhibits inflammatory changes of gene expression in lipopolysaccharide-stimulated gingival fibroblasts. Journal of Natural Medicines, 67, 576–589.
15.
OuY, LiQ, WangJ, LiK, ZhouS. (2014) Antitumor and Apoptosis Induction Effects of Paeonol on Mice Bearing EMT6 Breast Carcinoma. Biomolecules & Therapeutics, 22, 341–346.
16.
ZhangL, TaoL, ShiT, ZhangF, ShengX, CaoY, ZhengS, WangA, QianW, JiangL, LuY. (2015) Paeonol inhibits B16F10 melanoma metastasis in vitro and in vivo via disrupting proinflammatory cytokines-mediated NF-kappaB and STAT3 pathways. IUBMB Life, 67, 778–788.
17.
JiaoJ, SunL, GuoZ, HouS, HolystR, LuY, FengX. (2016) Antibacterial and anticancer PDMS surface for mammalian cell growth using the Chinese herb extract paeonol (4-methoxy-2-hydroxyacetophenone). Scientific Reports, 6, 38973.
18.
AbebeAT. (2013) Biochemistry of 1,2-dehydro-n-acetyldopamine derivatives. In Graduate Doctoral Dissertations. Paper 106., University of Massachusetts Boston, 42–48.
19.
AndersenSO, RoepstorffP. (1981) Sclerotization of insect cuticle—II. Isolation and identification of phenolic dimers from sclerotized insect cuticle. Insect Biochemistry, 11, 25–31.
20.
XuH, ZhangN, CasidaJE. (2003) Insecticides in Chinese medicinal plants: survey leading to jacaranone, a neurotoxicant and glutathione-reactive quinol. Journal of Agricultural and Food Chemistry, 51, 2544–2547.
