Musk deer (Moschus moschiferus): Reinvestigation of main lipid components from preputial gland secretion

Sokolov, Volodymyr; Kagan, M. Z.; Vasilieva, V. S.; Prihodko, V. I.; Zinkevich, E. P.

doi:10.1007/bf01020352

Cited by 29 publications

(24 citation statements)

References 15 publications

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“…These herbal products were shown to contain ephedrine and its structural analogues such as norephedrine, pseudoephedrine and cathine that would lead to a positive test result if urinary threshold levels are exceeded. Sources and applications of steroid hormone-containing remedies were rarely reported; however, few articles were published particularly concerning the composition6 7 and use of musk pod and its extracts as TCM in cases of health conditions necessitating cardiovascular and/or β-adrenergic stimulation,8 anti-inflammatory therapeutics9 or androgenic hormone intervention 6 7 10. Musk is the dried secretion from the preputial follicles of the male musk deer, which are located in a small sac (resulting from an infolding of the skin) in close proximity to the preputial orifice (figure 1A).…”

Section: Introductionmentioning

confidence: 99%

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Traditional Chinese medicine and sports drug testing: identification of natural steroid administration in doping control urine samples resulting from musk (pod) extracts

et al. 2012

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The administration of musk extract, that is, ingredients obtained by extraction of the liquid secreted from the preputial gland or resulting grains of the male musk deer (eg, Moschus moschiferus), has been recommended in Traditional Chinese Medicine (TCM) applications and was listed in the Japanese pharmacopoeia for various indications requiring cardiovascular stimulation, anti-inflammatory medication or androgenic hormone therapy. Numerous steroidal components including cholesterol, 5α-androstane-3,17-dione, 5β-androstane-3,17-dione, androsterone, etiocholanolone, epiandrosterone, 3β-hydroxy-androst-5-en-17-one, androst-4-ene-3,17-dione and the corresponding urea adduct 3α-ureido-androst-4-en-17-one were characterised as natural ingredients of musk over several decades, implicating an issue concerning doping controls if used for the treatment of elite athletes. In the present study, the impact of musk extract administration on sports drug testing results of five females competing in an international sporting event is reported. In the course of routine doping controls, adverse analytical findings concerning the athletes' steroid profile, corroborated by isotope-ratio mass spectrometry (IRMS) data, were obtained. The athletes' medical advisors admitted the prescription of TCM-based musk pod preparations and provided musk pod samples for comparison purposes to clarify the antidoping rule violation. Steroid profiles, IRMS results, literature data and a musk sample obtained from a living musk deer of a local zoo conclusively demonstrated the use of musk pod extracts in all cases which, however, represented a doping offence as prohibited anabolic-androgenic steroids were administered.

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Section: Introductionmentioning

confidence: 99%

“…Upon removal of moisture, the material converts into small, dark, reddish-brown musk grains. In comprehensive studies,6 7 the lipid constituents of musk were elucidated and numerous steroidal components were characterised as summarised in table 1.…”

Section: Introductionmentioning

confidence: 99%

Traditional Chinese medicine and sports drug testing: identification of natural steroid administration in doping control urine samples resulting from musk (pod) extracts

et al. 2012

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“…In the course of investigations into the characteristic steroids of musk, two androstane alkaloids (1, 2) were newly isolated from a natural source together with eight androstanoids and known cholestanoids, which had already been reported from the musk of M. moschiferus. 5,6) Compounds 1 and 2 were synthetically prepared by reaction of androst-4-ene-3,17-dione and testosterone with urea, although the their structural assignments were only given for protons. 7) We report here the identification of 1 and 2, and assignment of their NMR signals based on two-dimensional NMR analysis ( 1 H-1 H-COSY, HMQC, HMBC, and NOESY).…”

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confidence: 99%

Androstane Alkaloids from Musk of Moschus moschiferus.

Lee²,

Chang³

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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Musk, a dried preputial gland of the male musk deer (Moschus sp. Moschidae), 1) is one of the most popular and expensive Chinese drugs and has been used for cardiovascular stimulation, antiinflammation, and potentiation of badrenergic activity.2-4) Because all of this crude drug has been imported from other countries, distinguishing it from imitation musks that usually contain synthetic muscones is important in Korea. In the course of investigations into the characteristic steroids of musk, two androstane alkaloids (1, 2) were newly isolated from a natural source together with eight androstanoids and known cholestanoids, which had already been reported from the musk of M. moschiferus. 5,6) Compounds 1 and 2 were synthetically prepared by reaction of androst-4-ene-3,17-dione and testosterone with urea, although the their structural assignments were only given for protons. 7) We report here the identification of 1 and 2, and assignment of their NMR signals based on two-dimensional NMR analysis ( 1 H-1 H-COSY, HMQC, HMBC, and NOESY). Results and DiscussionCompound 1 3) suggested the presence of an amide group. From these 13 C-NMR data, 1 was considered to be a C 19 -ketosteroid having one substituent composed of one amino-, one imino-, and one carbonyl groups (i.e., an ureido group).8) This was further confirmed by two proton signals at d 6.21 and 6.83, which were not correlated with any carbons in the H 1 -detected multiple quantum coherence spectrum (HMQC). The entire structure was established by 1 H-1 H correlation spectroscopy (COSY) and 1 H-detected heteronuclear multiple-bond correlation spectrum (HMBC). In COSY, a multiplet methine proton at d 4.63 showed strong cross peaks with the protons at d 5.47 and 6.83. In HMBC, an NH proton at d 6.83 showed strong correlations with carbons at d 44.5, 120.9, and 159.3, and an olefinic methine proton at d 5.47 showed strong correlations with carbons at d 26.6 and 44.5 (Table 1). These results confirmed that a ureido group was present at the C-3 position of the androstane skeleton. 8,9) Recently, two steroidal alkaloids with the same partial structure of C-2 to C-5 [-CH 2 CH(NH)CHϭC-] were reported. Salignarine E [(20S)-2b-hydroxy-4b-acetoxy-5a,6a-epoxy-20-(dimethylamino)-3b -(tigloylamino)-pregnane], a pregnane-type alkaloid from Sarcococca saligna with a 3b-imino configuration, but NOE interactions between NH and H-2a/b and between H-1a and H-3/NH were not described.10) However, 22E,24R-3a -ureido-ergosta-4,6,8(14),22-tetraene from the fruit body of Chlorophyllum molybdites suggested a 3a-ureido configuration by NOE interaction between NH/H-1a. The stereochemistry of compound 1 at C-3 could be assigned to be the R configuration based on nuclear Overhouser effect spectroscopy (NOESY). The NOE interactions of H-1a at d 1.26 were unambiguously detected with H-9 (d 0.31) and NH (d 6.83), whereas H-3 (d 4.63) showed NOE interactions with H-4 (d 5.47), H-2 (d 1.75, 1.95) and NH (d 6.83), which suggested that the ureido group is a-oriented (Fig. 1). These spectral studies c...

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“…Other typical steroids were identified by comparison with previously published data. [19][20][21] The isolated sterols were identified as 24-methylenecycloartanol 1, cycloeucalenol 2, More recently, 5 the composition of sterols in Bathymodiolus sp. has been reported and typical sterols in mussels have mainly been cholesterol, desmosterol, and 24-methylenecholesterol similar to those of Antarctic krill.…”

Section: Resultsmentioning

confidence: 99%

Sterols from bivalves Calyptogena soyoae and Bathymodiolus septemdierum living in deep sea

et al. 2007

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From the two species of bivalves, Calyptogena soyoae around a cold seep and Bathymodiolus septemdierum near hydrothermal vents in the sea, sterols were isolated using highpressure liquid chromatography analysis of the lipid fraction guided by characteristic 1 H NMR signals of the sterol skeleton. The minor sterol composition of C. soyoae included 24-methylenecycloartanal, cycloeucalenol, and obtusifoliol, which are known phytosterols. From B. septemdierum, lathosterol and cholesterol as main sterols together with more diverse sterols were obtained. The difference between these species and their sterol contents is most likely because of feeding modes and metabolism of nutrients from their habitat.

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Musk deer (Moschus moschiferus): Reinvestigation of main lipid components from preputial gland secretion

Cited by 29 publications

References 15 publications

Traditional Chinese medicine and sports drug testing: identification of natural steroid administration in doping control urine samples resulting from musk (pod) extracts

Traditional Chinese medicine and sports drug testing: identification of natural steroid administration in doping control urine samples resulting from musk (pod) extracts

Androstane Alkaloids from Musk of Moschus moschiferus.

Sterols from bivalves Calyptogena soyoae and Bathymodiolus septemdierum living in deep sea

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