Three new compounds, (24R,S)-3α-acetoxy-24-hydroxy-5α-lanosta-8,25-dien-21-oic acid, named tsugaric acid C (1); 3α-acetoxy-5α-lanosta-8,24-diene-21-O-β-D-xyloside, named tsugarioside B (2); and 3α-acetoxy-(Z)-24-methyl-5α-lanosta-8,23,25-trien-21-oic acid ester β-D-xyloside, named tsugarioside C (3), and a mixture of two known steroids were isolated from the fruit bodies of Ganoderma tsugae. The structures of 1−3 were determined by spectral and chemical methods. The cytotoxic activity of the lanostanoid constituents of this fungus was evaluated against several different cancer cell lines.

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18	C19	C20	C21	C22	C23
21	bDXylp	102.7	71.9	73.7	69.7	63.7
3	Ac	170.9	21.4
	Subst	30.2	23.3	78.1	36.7	45.3	18.0	26.0	134.0	134.6	36.9	21.0	30.8	44.3	49.9	27.5	29.7	40.6	16.1	19.0	44.9	70.2	30.7	24.7


1H NMR data:
missing...

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CC(=O)O[C@@H]1CC[C@]2(C)C3=C(CC[C@H]2C1(C)C)[C@]1(C)CC[C@H]([C@@H](CCC=C(C)C)CO[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@@]1(C)CC3

616.88 g/mol (C₃₇H₆₀O₇)

Three new compounds, (24R,S)-3α-acetoxy-24-hydroxy-5α-lanosta-8,25-dien-21-oic acid, named tsugaric acid C (1); 3α-acetoxy-5α-lanosta-8,24-diene-21-O-β-D-xyloside, named tsugarioside B (2); and 3α-acetoxy-(Z)-24-methyl-5α-lanosta-8,23,25-trien-21-oic acid ester β-D-xyloside, named tsugarioside C (3), and a mixture of two known steroids were isolated from the fruit bodies of Ganoderma tsugae. The structures of 1−3 were determined by spectral and chemical methods. The cytotoxic activity of the lanostanoid constituents of this fungus was evaluated against several different cancer cell lines.

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18	C19	C20	C21	C22	C23
21	bDXylp	94.5	72.3	75.9	69.5	65.8
3	Ac	170.9	21.4
	Subst	30.4	23.3	78.1	36.7	45.3	18.0	25.9	133.7	134.7	36.9	20.8	30.8	44.3	49.5	27.0	28.9	47.0	16.3	19.0	47.8	175.2	32.9	123.5


1H NMR data:
missing...

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

C=C(C)/C(C)=C/C[C@@H](CO[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](OC(C)=O)C(C)(C)[C@@H]1CC3

628.891 g/mol (C₃₈H₆₀O₇)

Three new compounds, (24R,S)-3α-acetoxy-24-hydroxy-5α-lanosta-8,25-dien-21-oic acid, named tsugaric acid C (1); 3α-acetoxy-5α-lanosta-8,24-diene-21-O-β-D-xyloside, named tsugarioside B (2); and 3α-acetoxy-(Z)-24-methyl-5α-lanosta-8,23,25-trien-21-oic acid ester β-D-xyloside, named tsugarioside C (3), and a mixture of two known steroids were isolated from the fruit bodies of Ganoderma tsugae. The structures of 1−3 were determined by spectral and chemical methods. The cytotoxic activity of the lanostanoid constituents of this fungus was evaluated against several different cancer cell lines.

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CC(=O)O[C@@H]1CC[C@]2(C)C3=C(CC[C@H]2C1(C)C)[C@]1(C)CC[C@H]([C@@H](CCC=C(C)C)C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@]1(C)CC3

660.889 g/mol (C₃₈H₆₀O₉)

Mannosylerythritol lipids (MELs) are natural glycolipid biosurfactants which have potential applications in the fields of food, cosmetic and medicine. In this study, MELs were produced from vegetable oil by Pseudozyma aphidis. Their structural data through LC/MS, GC-MS and NMR analysis revealed that MEL-A with two acetyls was the major compound and the identified homologs of MEL-A contained a length of C8 to C14 fatty acid chains. This glycolipid exhibited a surface tension of 27.69 mN/m at a critical micelle concentration (CMC), self-assembling into particles in the water solution. It was observed to induce cell growth-inhibition and apoptosis of B16 melanoma cells in a dose-dependent manner, as well as cause cell cycle arrest at the S phase. Further quantitative RT-PCR analysis and western blotting revealed an increasing tendency of both mRNA and protein expressions of Caspase-12, CHOP, GRP78 and Caspase-3, and a down-regulation of protein Bcl-2. Combined with the up regulation of signaling IRE1 and ATF6, it can be speculated that MEL-A-induced B16 melanoma cell apoptosis was associated with the endoplasmic reticulum stress (ERS).

glycolipid, biosurfactant, mannosylerythritol lipid, Pseudozyma aphidis, MEL

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
4,2	LIP
4,3	LIP
4,4	Ac	174.5	16.2
4,6	Ac	174.5	16.2
4	bDManp	100.2	69.5	71.6	66.8	73.3	63.2
	xDEry-ol	64.4	72.8	72.0	73.1


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
4,2	LIP
4,3	LIP
4,4	Ac	-	0.8
4,6	Ac	-	0.8
4	bDManp	4.7	5.2	5.0	4.2-4.7	3.6-3.7	4.2
	xDEry-ol	3.6-4.0	3.6-4.0	3.6-4.0	3.6-4.0


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
4,2	LIP
4,3	LIP
4,4	Ac		16.2/0.8
4,6	Ac		16.2/0.8
4	bDManp	100.2/4.7	69.5/5.2	71.6/5.0	66.8/4.2-4.7	73.3/3.6-3.7	63.2/4.2
	xDEry-ol	64.4/3.6-4.0	72.8/3.6-4.0	72.0/3.6-4.0	73.1/3.6-4.0

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

R1 = LIP
[1*]O[C@@H]1[C@H](OC[C@@H](O)[C@@H](O)CO)O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@@H]1O[1*]

366.319 g/mol (C₁₄H₂₂R₂O₁₁, R = residue superclass(es), not counted in mol weight)