Blechnoside B

CAS Registry Number: 104387-06-6

Taxonomy: Physicochemical and Biological Properties of Phytoecdysteroids – Phytoecdysteroids and Their Conjugates

Biological sources: Asparagus dumosus [1], Blechnum minus [2], Froelichia floridana [3]

C₃₃H₅₄O₁₀: 610.3716

Mp: 218–220°C (EtOAc-MeOH) [2]

IR (KBr) ν_max cm⁻¹: 3440, 1660 [2]

UV λ ^EtOH_max nm (log ε): 243 (4.03) [2]

CD (c, 0.12, EtOH): Δε = −1.28 (253 nm), Δε = +1.35 (330 nm) [2]

DEI m/z: 611 [M + 1] (0.4%); 431 [M + 1-glucose] (10%) [2]

Anal. Calcd. for C₃₃H₅₄O₁₀: C, 63.0; H, 9.0. Found: C, 62.9; H, 8.8 [2]

¹ H NMR (300 MHz, J/Hz, C₅D₅N): 3.86 (br m, J = 10.0, He-3), 2.89 (H-5), 6.19 (br d, J = 2.0, H-7), 3.48 (m, Ha-9), 0.72 (s, CH₃-18), 0.88 (s, CH₃-19), 1.29 (d, J = 6.5, CH₃-21), 4.10 (Hb-22), 1.40 (s, CH₃-26), 1.40 (s, CH₃-27), β-D-Glcp′: 4.90 (d, J = 7.5, H-1) [2]

¹³ C NMR (62.9 MHz, C₅D₅N) [2]:

Table 1

C-1	29.9	C-12	31.8	C-23	25.8
2	29.5	13	48.2	24	42.5
3	72.5	14	84.1	25	69.8
4	27.6	15	31.8	26	30.0
5	51.5	16	26.8	27	30.3
6	203.0	17	48.4	Glc′-1	103.3
7	121.3	18	15.9	2	75.3
8	165.9	19	24.0	3	78.3
9	34.7	20	43.0	4	71.9
10	36.8	21	13.7	5	78.7
11	21.6	22	74.1	6	63.0

Pharm./Biol.: Calliphora bioassay: high active [2], Human DNA Topoisomerase I test: not active [3].